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Cheap Holiday Villa Deals in Chicago, IL

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    Travellers to Chicago are booking May dates now. Secure your holiday rental today, and have the perfect trip.
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    £1,394
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    1 / 12
    5 of 5 stars (7) Excellent
    1 Bedroom / 3 Bathrooms / Sleeps 2
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    £48
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    1 / 14
    Hyde Park
    1 Bedroom / 1 Bathroom / Sleeps 2
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    £51
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    1 / 31
    2 Bedrooms / 2 Bathrooms / Sleeps 8
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    1 / 14
    4.5 of 5 stars (12) Very good
    Northwest Side
    Studio / 1 Bathroom / Sleeps 2
    travellers have booked this property
    Overview Reviews (12) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Satellite TV
    • DVD Player
    • Grill
    • Dryer
    • Refrigerator
    • Washer
    • Linens Provided
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    The studio is situated in the couch house of the property. It is 300 square feet plus the bathroom. Beautiful decorated and very quiet place with the windows facing the beautiful garden. There is a washer and dryer on side. We are city bee keepers as we learned they are very important for our... View all property information
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    Location Information
    Chicago, Illinois 60618
    3 of 5 stars Reviewed 28 July 2015
    We are a couple in our 60s and our dog. The Good: It is a lovely studio in a garden area. Roomy enough. Well equipped with hot plate, dishes, pots and pans, silverware, etc. Nice...
    5 of 5 stars Reviewed 10 July 2015
    Spacious, very clean and comfortable place, with a very comfy bed. The owners were very accomodating. I recommend.
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    1 / 12
    4.5 of 5 stars (3) Very good
    Northwest Side
    Studio / 1 Bathroom / Sleeps 2
    travellers have booked this property
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    Amenities & Details
    • Fireplace
    • Air Conditioning
    • Ceiling Fans
    • Hairdryer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    This studio is situated in the garden of the property. Very quiet and peaceful setting. It has a Murphy bed and a jacuzzi. View all property information
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    Location Information
    Chicago, Illinois 60618
    5 of 5 stars Reviewed 6 July 2015
    This place was GREAT! We had a wonderful time and Hanne was great to work with! Place was clean, nice and very close to Wrigley Field, which is what we were looking for. We'll...
    5 of 5 stars Reviewed 2 July 2015
    This room has all the amenities of a small condo, and is perfect if you plan to be out sightseeing all day. There is a small kitchenette with a table, but the table gets folded...
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    1 / 11
    2 of 5 stars (1) Poor
    Rogers Park
    2 Bedrooms / 1 Bathroom / Sleeps 6
    travellers have booked this property
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    Amenities & Details
    • Refrigerator
    • Dryer
    • Hot Tub
    • Wi-Fi
    • Linens Provided
    • Patio
    • Air Conditioning
    • Garage
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    The Space Living room and dining room combo. Rooms are nice and cozy, cute and quiet. The unit is located in the East Rogers Park neighborhood of Chicago and border with Edgewater, within walking distance to the CTA Red Line Loyola station, Loyola University, restaurants, coffee shops, Lake... View all property information
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    Location Information
    Chicago, Illinois 60626
    2 of 5 stars Reviewed 6 May 2015
    Place was dark and damp. Bed sheets were clean, but pillows old and flat. Beds are double size. Towels were clean, but bathroom toilet area smelled moldy. Floors not very clean...
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    1 / 15
    4.5 of 5 stars (3) Very good
    Studio / 1 Bathroom / Sleeps 2
    travellers have booked this property
    Overview Reviews (3) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • TV
    • Refrigerator
    • Dryer
    • Washer
    • Elevator/Lift access
    • Wi-Fi
    • Cooker
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
    Furnished Studio. Double bed, full bath, and full kitchen. Unique location. You don't need a car living here. Plenty of transit options. A couple of blocks to Red line train station. Direct express bus to Chicago downtown stops right around the corner. 20 minutes to the city center by public... View all property information
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    Location Information
    Chicago, Illinois 60640
    4 of 5 stars Reviewed 4 September 2014
    Great stay, close to the El train and cheaper than a hotel! Able to stay parked out front for free and take the El where ever we wanted to. If you want a great stuffed pizza...
    5 of 5 stars Reviewed 8 July 2014
    the location of the apartment we stayed was convenient enough:only some min away from the red line train and a min from the bus stop,so getting to downtown is easy.we got a great...
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    £54
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    1 / 16
    5 of 5 stars (34) Excellent
    Northwest Side
    1 Bedroom / 1 Bathroom / Sleeps 2
    travellers have booked this property
    Overview Reviews (34) Make Enquiry
    Amenities & Details
    • Satellite TV
    • Washer
    • Refrigerator
    • Internet Access
    • Towels Provided
    • Dryer
    • Air Conditioning
    • Linens Provided
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
    A big thank you to my guests for their great reviews. I'm so honored to have earned a 2014 Certificate of Excellence from tripadvisor! Very comfortable, private lower level of duplex. Perfect for a business traveler who doesn't want to be downtown, or a couple visiting the city for pleasure.... View all property information
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    Location Information
    Chicago, Illinois 60625
    5 of 5 stars Reviewed 7 July 2015
    We loved staying here! It is conveniently located near L stops, wonderful restaurants and safe and quiet neighborhood. We were very comfortable each night we stayed and upon...
    5 of 5 stars Reviewed 21 May 2015
    Cheryl made us feel like a guest in her home. She has a gift of hospitality that made our stay there welcoming and enjoyable. There is plenty of room and very clean and...
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    1 / 40
    4.5 of 5 stars (7) Very good
    The Loop
    Studio / 1 Bathroom / Sleeps 2
    travellers have booked this property
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    Amenities & Details
    • Satellite TV
    • Wi-Fi
    • Game Room
    • Staffed Property
    • DVD Player
    • Air Conditioning
    • Pool Table
    • Housekeeping...
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • Smoking allowed
    • Elder access
    • x
    About this property
    888.761.RENT or 312.242.1625 215 W. Washington St. Chicago, IL. 60606 (Washington/Wells in the Loop in Downtown Chicago - Five Blocks West of Michigan Avenue and Millenium Park 'Bean'; In Business/Theater District) Check Availability and Book Online Now: http://reservation.worldweb.com/hotel/1278... View all property information
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    Location Information
    Chicago, Illinois 60661
    5 of 5 stars Reviewed 23 July 2015
    In January 2015 I found out that I needed to get a rental in town for 5 weeks due to a summer program at Joffrey Ballet n which my daughter would be participating. I needed a...
    5 of 5 stars Reviewed 19 July 2014
    Beautiful furnished apartments with kitchennete and in the heart of downtown, just a few blocks away from State st and michigan ave. I had a very pleasant and comfortable stay...
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    £57
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    1 / 6
    4 of 5 stars (1) Very good
    The Loop
    1 Bedroom / 1 Bathroom / Sleeps 3
    Overview Reviews (1) Make Enquiry
    Amenities & Details
    • Dryer
    • Water Views
    • Air Conditioning
    • Hot Tub
    • Satellite TV
    • Internet Access
    • Sauna
    • Washer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    These Vacation Rentals are located in the Chicago LOOP, a mixed-use neighborhood west of Michigan Avenue that includes apartments, homes, businesses and retailers surrounded by magnificent parks that are framed by the Chicago River to the North, Buckingham Fountain to the South, Michigan Avenue to... View all property information
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    Location Information
    Chicago, Illinois 60606
    4 of 5 stars Reviewed 17 September 2014
    Upon arrival we were greeted with a sign on the door saying we could not use the kitchen sink. Room had no iron, dish towels, kitchen utensils, hangers, missing a light bulb in...
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    £58
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    1 / 36
    2 Bedrooms / 1 Bathroom / Sleeps 6
    Overview Make Enquiry
    Amenities & Details
    • Stereo System
    • Washer
    • DVD Player
    • Air Conditioning
    • Dryer
    • Deck
    • Internet Access
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Comfy Rental In A Neighborhood That Has Kept Its Old World Charm With The New! Artsy, Quiet And Comfortable Place Ideal For Value Seekers Looking For A Memorable And Culturally-Diverse Experience In A Quaint Neighborhood That's Also A Convenient Base To Explore Other Fun Sites In Chicago.... View all property information
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    Location Information
    Chicago, Illinois 60625
    From
    £61
    / Night
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    1 / 7
    2 Bedrooms / 1 Bathroom / Sleeps 4
    Overview Make Enquiry
    Amenities & Details
    • Dishwasher
    • Cooker
    • Paper Towels...
    • Refrigerator
    • Freezer
    • Wi-Fi
    • Central Heating
    • Microwave
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    2 Bedroom 1 Bath garden apartment walking distance to green line CTA Green line stop (California) 1 &1/2 city blocks away takes you downtown, to the waterfront/ lake or shopping on Michigan Ave in approx 10 minutes (hint: check out GoRoo), or Chicago's new bike rental service Divvy, we are also 1.5... View all property information
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    Location Information
    Chicago, Illinois 60612
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    £61
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    1 / 10
    5 of 5 stars (1) Excellent
    Lakeview
    1 Bedroom / 1 Bathroom / Sleeps 2
    travellers have booked this property
    Overview Reviews (1) Make Enquiry
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    This is a beautiful garden unit. It comes fully furnished with a queen size bed plus a pull-out couch. Plenty of sitting room, updated bathroom, does not have kitchen but does have small fridge, microwave and coffee maker. The location is ideal, being close to the city and still in a quiet... View all property information
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    Location Information
    Chicago, Illinois 60657
    5 of 5 stars Reviewed 13 October 2014
    My wife and I spent 3 night here in Sept 2014. The owner was very friendly and helpful. This studio is located in a nice quiet neighborhood, close to restaurants and shops, and...
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    £63
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    1 / 11
    Northwest Side, Wicker Park / Bucktown
    2 Bedrooms / 1 Bathroom / Sleeps 4
    travellers have booked this property
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    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Unique 2 Bedroom apartment with brand new hardwoods floors, updated kitchen and spacious living area. Located in one the trendiest neighborhoods in Chicago, Bucktown has world class restaurants, bars and shops. All are located within walking distance of our home. Bucktown is one of best and... View all property information
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    Location Information
    Chicago, Illinois 60647
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    1 / 14
    5 of 5 stars (15) Excellent
    Northwest Side
    2 Bedrooms / 1 Bathroom / Sleeps 4
    travellers have booked this property
    Overview Reviews (15) Make Enquiry
    Amenities & Details
    • Washer
    • Air Conditioning
    • Refrigerator
    • Dryer
    • Satellite TV
    • Internet Access
    • Fireplace
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    This is a nice place on a quiet street, close to transportation and many restaurants. Very close to I 94. View all property information
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    Location Information
    Chicago, Illinois 60618
    5 of 5 stars Reviewed 30 July 2015
    Everything about our stay was perfect for our family. Hanna's readiness to help, her pet cat, freshly brewed Greek coffee powder, location to Belmont CTA station, #77 bus to and...
    5 of 5 stars Reviewed 14 June 2015
    Clean. Spacious. Comfortable. Well appointed and equipped. Complete kitchen. Two TVs and audio system. Near expressway. Quiet. Safe. On street Parking passes provided. Only way...
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    1 / 7
    5 of 5 stars (1) Excellent
    Northwest Side
    1 Bedroom / 1 Bathroom / Sleeps 2
    travellers have booked this property
    Overview Reviews (1) Make Enquiry
    Amenities & Details
    • Cooker
    • Dryer
    • Air Conditioning
    • Washer
    • Internet Access
    • Refrigerator
    • Satellite TV
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    If you are looking for a private, cozy, and comfortable place then this is just right for you. Here you can relax and lay back in a newly renovated unit with a private entrance for your convenience. Let the travel stress behind you and enjoy your stay in that great City we call HOME, Chicago We... View all property information
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    Location Information
    Chicago, Illinois 60618
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    £64
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    1 / 18
    Near North Side
    Studio / 1 Bathroom / Sleeps 3
    Overview Make Enquiry
    Amenities & Details
    • Linens Provided
    • Refrigerator
    • Dryer
    • Parking
    • Washer
    • Dishwasher
    • Satellite TV
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Old looking building but cozy room to relax , Drop bags and go about your business , convenient location , safe area , a block away from red line train station as well the 151 bus that operates to downtown , taxis are a flag away , surrounded by street side restuarants, very close to boystown and... View all property information
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    Location Information
    Chicago, Illinois 60613
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    1 / 17
    5 of 5 stars (1) Excellent
    Northwest Side
    2 Bedrooms / 1 Bathroom / Sleeps 4
    travellers have booked this property
    Overview Reviews (1) Make Enquiry
    Amenities & Details
    • Central Heating
    • Deck
    • Washer
    • Grill
    • TV
    • DVD Player
    • Dryer
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    1100 sq feet of your own space! Lots of room to stretch out here, two bedrooms with queen-sized beds, an office, living room, den, full kitchen, one bathroom, laundry in unit, back deck, backyard with apple tree (apples!!!), Keurig coffee maker, and parking right out front! Queen sized air... View all property information
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    Location Information
    Chicago, Illinois 60622
    5 of 5 stars Reviewed 8 February 2015
    This is a two bedroom apartment on the first floor on a quiet street two blocks from Humboldt Park. We arrive in two days after the big blizzard, and the sidewalk was nicely...
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    1 / 15
    2.5 of 5 stars (2) Poor
    Rogers Park
    3 Bedrooms / 1 Bathroom / Sleeps 8
    travellers have booked this property
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    Amenities & Details
    • Air Conditioning
    • Internet Access
    • Refrigerator
    • Cooker
    • Patio
    • Balcony
    • Deck
    • TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Perfect Home while visiting Chicago for a few days or longer stays, perfect for family gatherings, vacation, wedding stays, or simply enjoying time in The city. Walking distance to lots and public transportation! THE UNIT Lots of natural light due to the unit being on the top floor of nice and... View all property information
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    Location Information
    Chicago, Illinois 60626
    1 of 5 stars Reviewed 15 April 2015
    My sister was staying with us on (Apr.7) and opened the door and entered, NO HEAT,beds shabby very low to the floor and frumpy.The house was not up to advertised pictures on the...
    4 of 5 stars Reviewed 10 April 2015
    We like the house, it 's bright, lot of windows,it's a charming older home with hardwood floor.Very good location, walking distance to Loyola University and lake Michigan. There...
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    1 / 13
    The Loop
    1 Bedroom / 1 Bathroom / Sleeps 4
    Overview Make Enquiry
    Amenities & Details
    • Towels Provided
    • Linens Provided
    • Wi-Fi
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    One bedroom apt located in south loop Bronzeville area. Close to McCormick convention center. About 15 mins to Sox stadium.Easy access to public transportation cta bus and train. 15 mins drive to downtown. And Chinatown neighborhood.Walking distance to grocery store jewel. Walgreens .next to la... View all property information
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    Location Information
    Chicago, Illinois 60653
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    1 / 18
    Rogers Park
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    travellers have booked this property
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Wi-Fi
    • Linens Provided
    • Washer
    • TV
    • Dryer
    • Dishwasher
    • Refrigerator
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
    Nice and bright 2 bedroom 2 bath condominium two blocks from the lake and one block from train, bus, restaurants and coffee shops. Unit is cozy, spacious and conveniently located on first floor, with washer and dryer. Hardwood floors. LOCATION The unit is located on East Rogers Park, two blocks... View all property information
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    Location Information
    Chicago, Illinois 60626
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    £64
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    1 / 23
    Rogers Park
    3 Bedrooms / 1 Bathroom / Sleeps 8
    travellers have booked this property
    Overview Make Enquiry
    Amenities & Details
    • TV
    • Internet Access
    • Air Conditioning
    • Cooker
    • Linens Provided
    • Refrigerator
    • Deck
    • Patio
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Perfect Home while visiting Chicago for a few days or longer stays, perfect for family gatherings, vacation, wedding stays, or simply enjoying time in The city. Walking distance to lots and public transportation! THE UNIT Lots of natural light due to the unit being on the top floor of nice and... View all property information
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    Location Information
    Chicago, Illinois 60626
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    £64
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    1 / 10
    Gold Coast, Near North Side
    1 Bedroom / 1 Bathroom / Sleeps 3
    Overview Make Enquiry
    Amenities & Details
    • Dryer
    • Hot Tub
    • Water Views
    • Deck
    • Internet Access
    • Satellite TV
    • Air Conditioning
    • Washer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Located in the heart of Chicago, these Corporate Furnished Apartments offer breathtaking views, rooftop deck with poolside service, premier gym, wireless internet lounge, and much more. Overlooking 1,200 acres of glorious Lincoln Park greenery and offering panoramic views of Lake Michigan, our... View all property information
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    Location Information
    Chicago, Illinois 60610
    From
    £66
    / Night
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    1 / 17
    Roscoe Village
    2 Bedrooms / 1 Bathroom / Sleeps 8
    Overview Make Enquiry
    Amenities & Details
    • Washer
    • Satellite TV
    • Stereo System
    • Deck
    • Internet Access
    • Air Conditioning
    • Boat Available
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Beautifully rehabbed with brand new eat-in kitchen and bath. Hardwood floors throughout apartment. All trim and woodwork has been magnificently restored to it's original look. Washer and dryer in unit Central air with individual controls for heat and AC. Guest love the huge outdoor finished space... View all property information
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    Location Information
    Chicago, Illinois 60618
    From
    £67
    / Night
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    1 / 7
    3.5 of 5 stars (7) Average
    Near North Side
    1 Bedroom / 1 Bathroom / Sleeps 4
    Overview Reviews (7) Make Enquiry
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
    Excellent Location: 1 block to the Navy Pier and lakefront 2 blocks to the shopping area on Michigan Ave Just on the other side of the river from Grant Park and Millennium Park (15 min walk) Large Unit: Largest 1bd/1ba floor plan downtown Wrap around windows, corner unit Full size kitchen,... View all property information
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    Location Information
    Chicago, Illinois 60611
    4 of 5 stars Reviewed 16 July 2013
    Our first visit to Chicago and we wanted to stay someplace with a great view--McClurg Court was wonderful for us. The apartment reminded us of a newly employed graduate who can...
    4 of 5 stars Reviewed 18 October 2012
    We stayed here for a week in October. The booking process and everything went well and we were given information relevant to our stay. The unit is in a fantastic location in...
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    £67
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    1 / 4
    1 Bedroom / 1 Bathroom / Sleeps 4
    Overview Make Enquiry
    Amenities & Details
    • Ceiling Fans
    • Parking
    • TV
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Welcome to Chicago! Come visit our 1bd/1ba condo. This is a very large unit -- the largest floor plan downtown. Our condo is located in the heart of downtown Chicago. It is 1 block from the Navy Pier where there are shops, restaurants and the lakefront. We are a 5 min walk to the Michigan... View all property information
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    Location Information
    Chicago, Illinois 13456
    From
    £2,051
    / Month
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    1 / 23
    Near North Side
    Studio / 1 Bathroom / Sleeps 2
    Overview Make Enquiry
    Amenities & Details
    • Refrigerator
    • Washer
    • TV
    • DVD Player
    • Cooker
    • Dryer
    • Shared Outdoor Pool...
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    Stunning Space Features wall to wall upgraded plush carpeting, beautiful open kitchen with granite countertops and stainless steel appliances, massive walk in closet with loads of storage space, floor to ceiling windows exposing eastern peak-a-boo lake views, beautifully updated bathroom, and w/d... View all property information
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    Location Information
    Chicago, Illinois 60611
    From
    £2,051
    / Month
    View Details
    1 / 27
    Studio / 1 Bathroom / Sleeps 2
    Overview Make Enquiry
    Amenities & Details
    • Dryer
    • Hot Tub
    • Refrigerator
    • Freezer
    • Cooker
    • Shared Outdoor Pool...
    • Washer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    White quartz countertops, two-tone cabinetry, Frigidaire stainless steel appliances, gas stoves and white glass mosaic tile backsplash Full size washer/dryer Custom designed wide plank flooring throughout Walk in closet Contemporary bath finishes Everything about the building has been considered;... View all property information
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    Location Information
    Chicago, Illinois 60607
    From
    £2,051
    / Month
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    1 / 15
    The Loop
    Studio / 1 Bathroom / Sleeps 2
    Overview Make Enquiry
    Amenities & Details
    • Cooker
    • Refrigerator
    • Freezer
    • Washer
    • Internet Access
    • TV
    • Dryer
    • Shared Indoor Pool
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    Amazing unit features wall to wall espresso hardwood floors, stunning kitchen with quartz countertops and snaidero cabinetry, loads of storage space with professionally organized closets, floor to ceiling windows exposing great Chicago River and city skyline views, beautifully updated marble... View all property information
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    Location Information
    Chicago, Illinois 60601
    From
    £70
    / Night
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    1 / 9
    Northwest Side
    2 Bedrooms / 2 Bathrooms / Sleeps 5
    Overview Make Enquiry
    Amenities & Details
    • Deck
    • Dryer
    • Sauna
    • Internet Access
    • Stereo System
    • Air Conditioning
    • Satellite TV
    • Washer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    This is a 2 bedroom, 2 bathrooms, vintage building that has been rehabbed. This Chicago vacation rental apartment is located on Kedzie Blvd in Chicago, near the blue line. The apartment has washer/dryer in unit, stainless steal appliance, granite counter tops, Beds: 2 Queen Beds View all property information
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    Location Information
    Chicago, Illinois 60647
    From
    £2,115
    / Month
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    1 / 22
    Near North Side
    Studio / 1 Bathroom / Sleeps 2
    Overview Make Enquiry
    Amenities & Details
    • DVD Player
    • Washer
    • Shared Outdoor Pool...
    • Refrigerator
    • TV
    • Dryer
    • Balcony
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    Beautiful open floorplan studio with wall to wall bamboo hardwood flooring, open kitchen with tile backsplash, stainless steel appliances, and granite countertops, huge walk-in closet, floor to ceiling windows exposing city views, updated large bathroom with stone surround, and w/d in unit. Great... View all property information
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    Location Information
    Chicago, Illinois 60654
    From
    £70
    / Night
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    1 / 8
    Northwest Side
    1 Bedroom / 1 Bathroom / Sleeps 4
    Overview Make Enquiry
    Amenities & Details
    • Microwave
    • Internet Access
    • Cooker
    • Linens Provided
    • Satellite TV
    • Air Conditioning
    • Refrigerator
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Vintage Mansion on Kedzie Blvd - Vacation Rental License xxxxxx property. This apartment is located on the 3rd floor of a Historic Mansion, overlooking Kedzie Blvd. in the city of Chicago. The apartment is very spacious, approximately 1200 sq ft of space, large living room, dinning and... View all property information
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    Location Information
    Chicago, Illinois 60647
    From
    £71
    / Night
    Payment Protection
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    1 / 16
    The Loop
    1 Bedroom / 1 Bathroom / Sleeps 3
    Overview Make Enquiry
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    This apartment is located in Chicago and comes fully equipped with everything you need to feel at home. Also, our 24/7 virtual concierge service and local hospitality team will be there to ensure you have a great stay. The Space: The place has everything - crisp linen, towels, kitchenware, coffee... View all property information
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    Location Information
    Chicago, Illinois 60615
    From
    £2,179
    / Month
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    1 / 15
    The Loop
    1 Bedroom / 1 Bathroom / Sleeps 2
    Overview Make Enquiry
    Amenities & Details
    • Internet Access
    • Cooker
    • TV
    • Freezer
    • Refrigerator
    • Dryer
    • Washer
    • Shared Indoor Pool
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    A truly beautiful space that features a defined living area with eat in kitchen and separate bedroom space. Unit features wall to wall espresso hardwood floors, stunning kitchen with quartz countertops and snaidero cabinetry, loads of storage space with professionally organized closets, floor to... View all property information
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    Location Information
    Chicago, Illinois 60601
    From
    £74
    / Night
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    1 / 18
    Lincoln Square
    1 Bedroom / 1 Bathroom / Sleeps 2
    Overview Make Enquiry
    Amenities & Details
    • Internet Access
    • Satellite TV
    • Stereo System
    • Air Conditioning
    • Dryer
    • Deck
    • DVD Player
    • Washer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    I live here, but travel frequently! My apartment is a vintage Chicago Brownstone in the trendy, upscale Andersonville Area. It's close to shopping, nightlife, transportation and everything all the cool kids want to see and do! :-) I live on a quiet and very safe street that's easy to access from... View all property information
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    Location Information
    Chicago, Illinois 60625
    From
    £74
    / Night
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    1 / 14
    2 Bedrooms / 2 Bathrooms / Sleeps 10
    Overview Make Enquiry
    Amenities & Details
    • DVD Player
    • Wi-Fi
    • Satellite TV
    • Housekeeping...
    • Refrigerator
    • Stereo System
    • Porch
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Modern 3BD 2Bth Brick-Style Ranch! Sleeps 10!! ASK ABOUT OUR PRICE MATCHING OPTION!! Very affordable home in west suburb that offers easy access to the city. Sleeps up to 10 people. -3 Bedrooms -2 Bathroom -Hardwood Floors -Tiled Bathroom -Centrally controlled Heat and Air -Big back yard... View all property information
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    Location Information
    Chicago, Illinois 60162
    From
    £75
    / Night
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    1 / 22
    Northwest Side, Wicker Park / Bucktown
    3 Bedrooms / 2 Bathrooms / Sleeps 12
    Overview Make Enquiry
    Amenities & Details
    • Internet Access
    • Stereo System
    • Washer
    • Satellite TV
    • Air Conditioning
    • DVD Player
    • Boat Available
    • Dryer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Great location near the 90/94 expressway and the Blue line stop at Western. No cab needed from O'Hare or even Midway airports with easy access from L trains. Meticulous rehab of classic Chicago apartment. All woodwork and maple floors have been refinished. Brick exterior with beautiful limestone... View all property information
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    Location Information
    Chicago, Illinois 60647
    From
    £76
    / Night
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    1 / 8
    5 of 5 stars (1) Excellent
    Near North Side
    Studio / 1 Bathroom / Sleeps 3
    travellers have booked this property
    Overview Reviews (1) Make Enquiry
    Amenities & Details
    • Satellite TV
    • Refrigerator
    • Fireplace
    • Dryer
    • DVD Player
    • Washer
    • Wi-Fi
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
    Experience our amazing, over sized, fully furnished “Old Town Chicago” studio with private balcony designed by famous Chicago artist Edgar Miller (The Chicago Renaissance Man) with Flat Panel HDTVs, Fireplaces, All Utilities, All Major Appliances, WiFi, Internet, Cable, Queen Size Tempur-Pedic... View all property information
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    Location Information
    Chicago, Illinois 60610
    5 of 5 stars Reviewed 7 June 2015
    This was our first time renting instead of booking a hotel, but John was extremely helpful with this experience. I especially appreciated his timeliness in answering any questions...
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    From
    £77
    / Night
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    1 / 6
    1 Bedroom / 1 Bathroom / Sleeps 3
    Overview Make Enquiry
    Amenities & Details
    • Refrigerator
    • Dishwasher
    • Air Conditioning
    • Cooker
    • Wi-Fi
    • Freezer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Popular and convenient WEST TOWN 1 Bedroom 1 Bath Garden apartment nestled right in between Wicker Park, Ukrainian Village and trendy West Loop areas, steps away from the hottest new restaurants on Randolph Street. FOODIE HEAVEN w/ Subzero fridge, new granite kitchen stainless steel double oven!... View all property information
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    Location Information
    Chicago, Illinois 60642
    From
    £2,307
    / Month
    View Details
    1 / 22
    Near North Side
    Studio / 1 Bathroom / Sleeps 2
    Overview Make Enquiry
    Amenities & Details
    • Washer
    • Refrigerator
    • Dishwasher
    • Cooker
    • TV
    • Shared Outdoor Pool...
    • Freezer
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    Amazing unit features wall to wall cherry hardwood floors, stunning kitchen with quartz countertops and snaidero cabinetry, loads of storage space with professionally organized closets, floor to ceiling windows exposing great Chicago River and city skyline views, beautifully updated marble... View all property information
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    Location Information
    Chicago, Illinois 60601
    From
    £2,307
    / Month
    View Details
    1 / 29
    Near North Side
    1 Bedroom / 1 Bathroom / Sleeps 2
    Overview Make Enquiry
    Amenities & Details
    • Cooker
    • Linens Provided
    • Refrigerator
    • Washer
    • Shared Outdoor Pool...
    • Dryer
    • TV
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Beautifully updated studio unit features a large open layout with loads of closet space. Unit features wall to wall dark hardwood floors, updated upgraded kitchen with espresso cabinetry and beautiful granite countertops, large windows exposing beautiful skyline views, huge closet space, and w/d in... View all property information
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    Location Information
    Chicago, Illinois 60654
    From
    £2,307
    / Month
    View Details
    1 / 4
    The Loop
    1 Bedroom / 1 Bathroom / Sleeps 2
    Overview Make Enquiry
    Amenities & Details
    • Dryer
    • Freezer
    • Refrigerator
    • Internet Access
    • TV
    • Washer
    • Cooker
    • Shared Indoor Pool
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    A truly beautiful space that features a defined living area and bedroom space. Unit features wall to wall espresso hardwood floors, stunning kitchen with quartz countertops and snaidero cabinetry, loads of storage space with professionally organized closets, floor to ceiling windows exposing great... View all property information
    Make Enquiry
    Location Information
    Chicago, Illinois 60601
    From
    £77
    / Night
    Payment Protection
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    1 / 6
    3.5 of 5 stars (3) Average
    1 Bedroom / 1 Bathroom / Sleeps 2
    travellers have booked this property
    Overview Reviews (3) Make Enquiry
    Amenities & Details
    • Dryer
    • Hot Tub
    • Air Conditioning
    • Cooker
    • Refrigerator
    • Satellite TV
    • Washer
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Charming, roomy one bedroom , with open kitchen and living space. This recently refurbished loft-style apartment gives visitors to Chicago a chance to visit and explore whist enjoying the comforts of modern living. Hardwood floor, and ceramic tiles in kitchen and bathroom. Plenty of sitting... View all property information
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    Location Information
    Chicago, Illinois 60618
    4 of 5 stars Reviewed 17 September 2014
    The accommodations were not real fancy but well suited for a busy stay in Chicago! Excellent location for the price. Wrigley and other top sites are easily accessible. If you are...
    3 of 5 stars Reviewed 16 June 2014
    Ok so if you're expecting a pretty little getaway in Chicago with views and a location then this place isn't for you. The apartment is located atop of a commercial building that's...
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    From
    £547
    / Week
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    1 / 11
    The Loop
    1 Bedroom / 1 Bathroom / Sleeps 4
    Overview Make Enquiry
    Amenities & Details
    • Satellite TV
    • Air Conditioning
    • Dryer
    • Wi-Fi
    • DVD Player
    • Elevator/Lift access
    • Patio
    • Washer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Enjoy stunning city views from your apartment and walk to work from this centrally located West Loop apartment. In your free time enjoy Michigan Avenue for shopping, as well as museums, restaurants and nightlife at your doorstep. The train, taxis, and buses are all accessible on the same block for... View all property information
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    Location Information
    Chicago, Illinois 60661
    From
    £83
    / Night
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    1 / 40
    5 of 5 stars (1) Excellent
    Lakeview
    1 Bedroom / 1 Bathroom / Sleeps 4
    Overview Reviews (1) Make Enquiry
    Amenities & Details
    • Watersports Nearby
    • Wi-Fi
    • Stereo System
    • Air Conditioning
    • Satellite TV
    • There Are Tennis...
    • DVD Player
    • Elevator/Lift access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Located in Chicago's East Lakeview Neighborhood (home of Wrigleyville and Boystown), our Junior 1-Bedroom Apartment provides peace & quiet while only minutes away from Chicago's best attractions. Steps from Lake Michigan and Belmont Harbor; with easy access to the lakefront, nightlife, dining,... View all property information
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    Location Information
    Chicago, Illinois 60657
    5 of 5 stars Reviewed 16 July 2015
    This was my first time using FlipKey to find a vacation rental online. I was planning a surprise weekend getaway for my husband's 40th birthday and our 9th wedding anniversary...
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    From
    £2,467
    / Month
    View Details
    1 / 29
    1 Bedroom / 1 Bathroom / Sleeps 2
    Overview Make Enquiry
    Amenities & Details
    • Dryer
    • Refrigerator
    • Hot Tub
    • Cooker
    • Washer
    • Freezer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    This beautiful unit features Eastern views of the Chicago skyline, including Willis (Sears) Tower. White quartz countertops, two-tone cabinetry, Frigidaire stainless steel appliances, gas stoves and white glass mosaic tile backsplash Full size washer/dryer Custom designed wide plank flooring... View all property information
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    Location Information
    Chicago, Illinois 60607
    From
    £83
    / Night
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    1 / 24
    2 of 5 stars (1) Poor
    Northwest Side, Wicker Park / Bucktown
    1 Bedroom / 1 Bathroom / Sleeps 2
    Overview Reviews (1) Make Enquiry
    Amenities & Details
    • Deck
    • Parking
    • Dishwasher
    • Linens Provided
    • Air Conditioning
    • Refrigerator
    • Fireplace
    • Balcony
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Near restaurants, cafés & bars in vibrant Wicker Park, this tucked away, free standing, 1 bedroom Coach House could be your Chicago oasis! The space includes, an outfitted kitchen as well as a private bathroom, deck & entrance. Located off a quiet tree-lined street near 19th century mansions built... View all property information
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    Location Information
    Chicago, Illinois 60622
    2 of 5 stars Reviewed 3 June 2015
    The carriage house is quaint and convenient to the hipster neighborhood of Wicker Park, but the owners appear to be struggling to keep it going. There is no Wi-Fi, practically in...
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    £83
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    1 / 20
    4 of 5 stars (5) Very good
    1 Bedroom / 1 Bathroom / Sleeps 6
    travellers have booked this property
    Overview Reviews (5) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Parking
    • Dryer
    • Refrigerator
    • Washer
    • Internet Access
    • Patio
    • Linens Provided
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Plenty of free street parking is available on our block. This is the first floor of our home so we expect all guests to be QUIET & respectful. If you love to party, stomp around and yell then this is not the place for you. No parties, no loud music & no stumbling in drunk at 2 am. We are old &... View all property information
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    Location Information
    Chicago, Illinois 60609
    3 of 5 stars Reviewed 12 June 2015
    The rental was okay, very quiet and not exactly handicap accessible; as indicated in the specs - but made it work. Other than that the duration of the stay worked out.
    4 of 5 stars Reviewed 4 September 2014
    This was my first experience using Trip Advisor and renting a private home to stay in. The weekend was great. The apartment was located in a safe neighborhood to walk around in...
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    From
    £577
    / Week
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    1 / 15
    Lincoln Park
    1 Bedroom / 1 Bathroom / Sleeps 2
    Overview Make Enquiry
    Amenities & Details
    • Washer
    • TV
    • Gym
    • Staffed Property
    • Housekeeping...
    • Deck
    • Air Conditioning
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • Smoking allowed
    • Elder access
    • ?
    About this property
    800 square feet 1 bedroom, 9 ft. ceilings, bathroom with Jacuzzi tub, queen size bed and laundry on site. Rooftop deck, 24 hour concierge, 24 hour gym, directly across the street from Lincoln Park and Lincoln Park Zoo. Right in the heart of Lincoln Park, walking distance to Walgreens, Trader... View all property information
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    Location Information
    Chicago, Illinois 60614
    From
    £83
    / Night
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    1 / 13
    5 of 5 stars (2) Excellent
    Lakeview
    1 Bedroom / 1 Bathroom / Sleeps 4
    travellers have booked this property
    Overview Reviews (2) Make Enquiry
    Amenities & Details
    • Washer
    • DVD Player
    • Dryer
    • Air Conditioning
    • Refrigerator
    • Watersports Nearby
    • Wi-Fi
    • TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    This beautifully updated 1 Bedroom, 1 Bathroom loft in Lakeview has all you'll need during your stay in Chicago! Conveniently located only 1 block from the lake shore, only 3 blocks from Wrigley Field, & close downtown, shopping, dining and more! Lakeview is one of the hearts of Chicago. The unit... View all property information
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    Location Information
    Chicago, Illinois 60613
    5 of 5 stars Reviewed 30 June 2015
    I've rented several properties across the nation and this was one of the best - close to everything in Lakeview, surprisingly quiet for a garden level apartment, super clean...
    5 of 5 stars Reviewed 11 April 2015
    Beautifully decorated with a nice location for the baseball game. The owner Lisa, does an excellent job communicating . I look forward to staying again.
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