We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.
We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Holiday Rentals in Chicago, IL

Map
Satellite
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Your filters are still active.
There are no pins in your viewport. Try moving the map or changing your filters.
dd/mm/yyyy dd/mm/yyyy
    There are no pins in your viewport. Try moving the map or changing your filters.
    • {providername} {price}
    {providername} {price}
      {listitems}
    {sold_out_text}
    We can't find prices for this accommodation
    From {rate_price} {rate_periodicity}
    List your property
    Payment Protection
    Use a credit card to book with our Payment Protection.Learn more
    Show Prices
    Change Dates
    Price
    per night
    |||
    |||
    £0
    £120 Average
    £1,000+
    Bedrooms
    Any
    Amenities
    Any
    Neighbourhood
    Any
    Payment
    Book Online
    View Map
    More filters
    loading...
    Travellers to Chicago are booking May dates now. Secure your holiday rental today, and have the perfect trip.
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    1 / 40
    4.5 of 5 stars (2) Very good
    Lakeview
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    1 / 10
    5 of 5 stars (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    1 / 13
    5 of 5 stars (15) Excellent
    Lakeview
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    About this property
    Modern 2 Bedroom Apartment walking distance to Wrigley Field and the Blue Line. Beautiful Place and Great Location! The apartment comes with anything you could want. -A full kitchen, with all brand new appliances. -A brand new queen sized bed with box spring, and an ultra modern bathroom... View all property information
    Location Information
    Chicago, Illinois 60657
    5 of 5 stars Reviewed 16 February 2014
    During our 4 day stay we had nothing but best time here. The appartment was very clean and had everything you need. It was also walking distance from Wrigley stadium and...
    5 of 5 stars Reviewed 16 January 2014
    My stay at this unit lasted a few weeks and I plan on renting again soon when I return to Chicago. The location is perfect. Close to the public transportation, but not only the...
    See all reviews
    1 / 21
    5 of 5 stars (1) Excellent
    Near North Side
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Satellite TV
    • Wi-Fi
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
    Whether you are coming to stay at Raffaello Chicago for business, a romantic getaway, or traveling with your family and friends, we have the perfect accommodation ready and waiting for you. Every Raffaello guest room reflects an upscale European style with soothing accents, subtle earth tones and... View all property information
    Location Information
    Chicago, Illinois 60611
    5 of 5 stars Reviewed 27 February 2015
    We were lucky that we chose this place. It is in a perfectly managed hotel , Raffaello Hotel . Everything was ready to have a nice stay. Thanks
    See all reviews
    1 / 23
    5 of 5 stars (1) Excellent
    DePaul
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
    other traveller has booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Grill
    • Patio
    • Wi-Fi
    • DVD Player
    • Balcony
    • Washer
    • Parking
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Historic cottage in exclusive Lincoln Park neighborhood. 3 bedrooms (1 King and 2 Queens); 2 full and 1 half bath; laundry; full kitchen and family room; media room; 2 car garage; living and dining room; outdoor decks; walking distance to DePaul University, Lincoln Avenue entertainment district,... View all property information
    Location Information
    Chicago, Illinois 60604
    5 of 5 stars Reviewed 2 September 2015
    My friends and I spent the weekend at Paul's house for our fantasy football draft. The house is in walking distance to Wrigley field and lake shore drive. It easily accommodates 6...
    See all reviews
    1 / 56
    5 of 5 stars (28) Excellent
    Northwest Side
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Balcony
    • Air Conditioning
    • Shared Garden
    • Terrace
    • Satellite TV
    • Internet Access
    • Washer
    • 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
    Location Information
    Chicago, Illinois 60618
    5 of 5 stars Reviewed 31 December 2015
    quiet, warm, close to family and friends. Hanne was very friendly, helpful and very responsive to our questions, quick to help with heating. The big dining table was just perfect...
    5 of 5 stars Reviewed 9 December 2015
    Thank you Hanne for making our trip to Chicago a very comfortable experience. My family and I enjoyed staying in your apartment. The location was perfect to all the places we...
    See all reviews
    1 / 11
    5 of 5 stars (2) Excellent
    Roscoe Village
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Internet Access
    • Air Conditioning
    • Washer
    • Satellite TV
    • Porch
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Make our apartment the perfect home base for your family vacation or romantic getaway to Chicago. There is plenty of room to spread out and enjoy yourselves. The house is beautifully furnished and stocked with all of the essentials. The apartment is an easy walk to multiple bus and train lines,... View all property information
    Location Information
    Chicago, Illinois 60618
    5 of 5 stars Reviewed 7 August 2015
    We needed a place to stay in Chicago close to family. This rental was perfect. There was more than enough room for 5 of us. It was extremely clean and very nicely decorated...
    5 of 5 stars Reviewed 26 September 2014
    My wife and I travel to Chicago 4-6 times per year to visit our daughter and her family. We usually stay with her but this time she hosted her sister and their family which made...
    See all reviews
    Northwest Side
    2 Bedrooms, 2 Bathrooms, Sleeps 12 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Outdoor Dining Area
    • Porch
    • DVD Player
    • Air Conditioning
    • Grill
    • Wi-Fi
    • Washer
    • Balcony
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    The space is fresh and open and can sleep 8 on individual beds and 12 if you double up on the queen mattresses. There are 2 sets of bunk beds in a small 3rd bedroom/bonus room. There are 2 living rooms which makes it easy to get away from your mates when one wants to have some quiet time or giving... View all property information
    Location Information
    Chicago, Illinois 60622
    1 / 16
    5 of 5 stars (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
    other traveller has booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Grill
    • Patio
    • DVD Player
    • Balcony
    • Air Conditioning
    • Wi-Fi
    • Housekeeping...
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    LOCATION,LOCATION, LOCATION!!!! Newly listed amazing home in great location - Luxurious 2 bedroom, 3 bed, 2 bath condo with amazing views in multiple directions, centrally location to every major attraction in the Chicago-land area and easy access to all city transit. There are three bedrooms in... View all property information
    Location Information
    Chicago, Illinois 60605
    5 of 5 stars Reviewed 16 September 2015
    I emailed D (the owner) multiple times and she was so sincere and helpful with our requests... she really went out of her way for our family. She spent over 25 minutes on the...
    See all reviews
    List your property for free!
    List your holiday rental where TripAdvisor travellers can find it.
    Add a Listing
    1 / 7
    4 of 5 stars (7) Very good
    Lincoln Park
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Satellite TV
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Wireless Internet Flat Screen TV in bedroom and living room Cable Clean sheets and towels Silverware, pots & pans Very large bedroom and living room Wall unit AC's in bedroom and living room Washer & Dryer is downstairs on first floor This is an ideal location for visitors. Nice restaurants... View all property information
    Location Information
    Chicago, Illinois 60614
    5 of 5 stars Reviewed 10 August 2015
    Stayed in the LPA location this past weekend and enjoyed the area tremendously. You have a park across the street and zoo just mins. down the road. The apartment itself is a cozy...
    4 of 5 stars Reviewed 13 July 2015
    Located across from Lincoln Park Zoo & Conservatory, this is an ideal location for a couple, or a family of 3. The apartment is on the 4th floor and features a large living room...
    See all reviews
    1 / 10
    5 of 5 stars (2) Excellent
    The Loop
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    This 39-story Chicago hotel is across the river from Magnificent Mile shopping, six blocks from Lake Michigan, and a half-mile from the Loop's theater district and the Art Institute of Chicago. Located on the Magnificent Mile. Industry and creativity converge in Chicago, the birthplace of the... View all property information
    Location Information
    Chicago, Illinois 60601
    5 of 5 stars Reviewed 10 June 2015
    From the time that we checked in to the time that we left, everything was great. The staff and service was first rate. The rooms were clean and well kept. The front desk was very...
    5 of 5 stars Reviewed 2 December 2014
    For downtown Chicago stay, this was fantastic...lots of room and great location! We were a walk away from anything...from Navy Pier to the beach to shopping to family museums. A...
    See all reviews
    1 / 24
    5 of 5 stars (1) Excellent
    Lakeview
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Patio
    • Outdoor Dining Area
    • Air Conditioning
    • Grill
    • Wi-Fi
    • Satellite TV
    • DVD Player
    • Shared Garden
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    An irresistibly charming apartment! Good things do come in small packages! CHICAGO GUEST HOUSE Tripadvisor Certificate of Excellence 2015 5.0 of 5 stars --160 Reviews on Tripadvisor Ranked #1 of 55 Specialty Lodging in Chicago! Walk in to the home and the first thing you notice is nothing,... View all property information
    Location Information
    Chicago, Illinois 60657
    5 of 5 stars Reviewed 15 June 2015
    We were very happy finding this vacation rental. The location was accommodating to our interest. The apartment was excellent. We were able to stay altogether and enjoy the...
    See all reviews
    1 / 11
    4 of 5 stars (4) Very good
    Lakeview
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Internet Access
    • Air Conditioning
    • Satellite TV
    • Shared Garden
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Spacious, elegantly appointed and furnished Lakeview vacation/executive two bedroom, one bathroom apartment. First floor on a quiet tree-lined street, the entire apartment features; either oak floors or ceramic tiles, all solid oak doors and windows and oriental rugs. You will find our... View all property information
    Location Information
    Chicago, Illinois 60657
    5 of 5 stars Reviewed 4 February 2015
    Good value for the money. We enjoyed the player piano. Beds were comfortable and everything was clean.
    4 of 5 stars Reviewed 28 July 2014
    Close to transit & grocery. Lots of space. Communication with Andy was great. He answered any questions we had before the trip in a timely manner. Easy check in and out...
    See all reviews
    2 Bedrooms, 1 Bathroom, Sleeps 7 | Quick View
    other traveller has booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Internet Access
    • DVD Player
    • Satellite TV
    • Washer
    • Parking
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
    This historic turn of the century home has been recently remodeled while paying homage to original and period details like crown moldings and stained glass. Fresh, clean and sparkling with drop dead mid century décor. Both comfortable, roomy and stylish. There is a large fully stocked kitchen with... View all property information
    Location Information
    Chicago, Illinois 60625
    1 / 18
    4 of 5 stars (2) Very good
    3 Bedrooms, 1 Bathroom, Sleeps 9 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Air Conditioning
    • Private Garden
    • Patio
    • Outdoor Dining Area
    • DVD Player
    • Internet Access
    • Washer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Welcome! Welcome!Our single family brick house is located in a rare semi-private block about 5 miles West of Downtown Chicago. It has 3 Bedrooms, 1 Bathroom, Living Room, Dining Room and Full Kitchen, Washer/Dryer. If you enjoy a quiet home with free parking, newer beds, clean sheets and towels,... View all property information
    Location Information
    Chicago, Illinois 60644
    5 of 5 stars Reviewed 18 July 2014
    Nice location. Everyone got their own beds. Easy to downtown. Kitchen and free laundry. Free Tide detergent too (not expected). Will stay again.
    3 of 5 stars Reviewed 7 May 2014
    The location of this property was great. It was about 12-15 minutes from downtown, which is where we wanted to be. There was plenty of on-street parking right in front of the...
    See all reviews
    1 / 19
    5 of 5 stars (1) Excellent
    Lakeview
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Porch
    • Wi-Fi
    • Patio
    • Satellite TV
    • DVD Player
    • Washer
    • Grill
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    CHICAGO GUEST HOUSE Tripadvisor Certificate of Excellence 2015 5.0 of 5 stars --187 Reviews Beautifully furnished and fully equipped--guaranteed a unique and unforgettable experience for you, your family and friends. AMAZING LOCATION! Approximately 4 Miles North of the Heart of Downtown right... View all property information
    Location Information
    Chicago, Illinois 60613
    5 of 5 stars Reviewed 28 April 2015
    I traveled to Chicago for a Baptism, meeting family from LA and Boston. We stayed in the Lakeview suite. Teri allowed us to enter the apt. early on the day of our arrival. The...
    See all reviews
    The Loop
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Shared Outdoor Pool...
    • Hot Tub
    • Washer
    • Air Conditioning
    • Internet Access
    • Sauna
    • Satellite TV
    • Patio
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • Smoking allowed
    • Elder access
    • ?
    About this property
    Unit not available for daily rental in July 4th Holiday ! 1 week minimum *Prices may vary depending on the season. Premium months are between April and September. *Prices negotiable based on length of stay. Please inquire and we will provide a direct quote for your stay. Lakeshore East,... View all property information
    Location Information
    Chicago, Illinois 60601
    1 / 21
    5 of 5 stars (1) Excellent
    Northwest Side
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Wi-Fi
    • Porch
    • Air Conditioning
    • Washer
    • Patio
    • DVD Player
    • Grill
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Our 3 bedroom cozy house feels like a cottage in the middle of the popular Avondale Neighborhood. It's perfect place for a family up to 8, we are a block from a park, Target and the river. Enjoy restaurants and a craft brewery all within in 3 blocks. Entire house with 2 bedrooms and bath... View all property information
    Location Information
    Chicago, Illinois 60618
    5 of 5 stars Reviewed 3 October 2015
    This 4 bedroom 2 full bath was very clean, well stocked, in a good neighborhood, had a very nice park for our grand children to play at within a block, great restaurants within...
    See all reviews
    1 / 11
    1 of 5 stars (1) Terrible
    2 Bedrooms, Sleeps 6 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Internet Access
    • Washer
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Stay in the heart of Chicago A fitness centre and apartments with a full kitchen are featured at the Ginosi Chicago Suites. The Chicago property is 350 metres from 360 Chicago and 300 metres from Loyola University Museum of Art. Free WiFi access is provided. The apartment will provide you with a... View all property information
    Location Information
    Chicago, Illinois 60611
    Get the List
    1 / 9
    3.5 of 5 stars (4) Average
    3 Bedrooms, 1 Bathroom, Sleeps 8 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Air Conditioning
    • Wi-Fi
    • Washer
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Quick Summary: This apartment is in a very desirable neighborhood of Chicago called Andersonville on the 'North Side' of the City. The average new home cost over $1million here. Our home is over 100 years old but it has new energy rated windows, copper water lines, central heating system, hardwood... View all property information
    Location Information
    Chicago, Illinois 60640
    4 of 5 stars Reviewed 16 June 2015
    Nothing fancy...but just what we were looking for. Enough room for all of us. Great location...1 block from the bus to go to Wrigley. 5 blocks from the lake for a Sunday morning...
    4 of 5 stars Reviewed 11 July 2014
    I really enjoyed staying here. A great property. The sink did break while we were there but Jackie was right on getting it fixed for us! Great place, big enough for our group!
    See all reviews
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Hot Tub
    • Internet Access
    • Washer
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Large, roomy two bedroom loft like apartment tastefully appointed and furnished. Hardwood floors and ceramic tiles in kitchen and bathroom. Plenty of sitting room with large screen TV, fireplace and free WiFi. Two full bedrooms, one with a king sized and the other with a queen sized bed. You... View all property information
    Location Information
    Chicago, Illinois 60618
    1 / 18
    4 of 5 stars (1) Very good
    Near North Side
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
    other traveller has booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Shared Outdoor Pool...
    • Shared Garden
    • Outdoor Dining Area
    • Air Conditioning
    • Patio
    • DVD Player
    • Grill
    • Washer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
    This Cozy Studio is in the heart of the prestigious River North neighborhood in downtown Chicago. The new 50 story high rise is surrounded with great shopping, numerous restaurants and exciting night life. Getting anywhere is easy because building located few blocks away from the CTA-Grand Red Line... View all property information
    Location Information
    Chicago, Illinois 60654
    Near North Side
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    Show Prices
    Payment Protection
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    High-end, furnished condo downtown Chicago will be available for vacation rental. 52nd Floor HUGE 2 Bedrooms 2 FULL Bathroom with 3 Queen Beds. Laundry In the Unit The Space The condo is fully furnished with modern design pieces - sectional leather sofas, memory foam on both beds, and feather... View all property information
    Location Information
    Chicago, Illinois 60601
    The Loop
    2 Bedrooms, 1 Bathroom, Sleeps 8 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Washer
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
    This is a one bedroom loft with the living-room converted into a second bedroom. It has two beds in the bedroom and the living-room has a bunk bed. 800 square feet 32″ Flat-screen TV Wireless Internet-5 MPBS This luxury condominium is conveniently located one block to McCormick Place with easy... View all property information
    Location Information
    Chicago, Illinois 60616
    Northwest Side
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Wi-Fi
    • Satellite TV
    • Grill
    • Parking
    • Patio
    • Washer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Thank you viewing this listing. I am offering a fully furnished two bedroom, one bathroom apartment. The apartment is located in the city's far West side. Conveniently located nearby is a Metra train station which travels to Chicago Union Station, located in the Loop (downtown). Another travel... View all property information
    Location Information
    Chicago, Illinois 60707
    Lincoln Square
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    Show Prices
    Payment Protection
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    The Space Beautiful 2 Floor Duplexapartment near Foster and Damen on the North Side of Chicago. •3 bedrooms 2 Full Bathrooms •Full modern kitchen •Wireless internet •Cable with Smart TV have access to your Netflix and Hulu Accounts • Large Outdoor Deck w/ BBQ •Laundry in Unit The apartment... View all property information
    Location Information
    Chicago, Illinois 60625
    1 / 9
    5 of 5 stars (1) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Parking
    • Satellite TV
    • Air Conditioning
    • DVD Player
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Come one Come all Enjoy yourself at my beautiful 2 level condo. This modern beauty features granite, 2 full bathrooms, jet tub, 3 bedrooms, 2 sitting rooms. Enjoy cable tv in every room. The modern decor is absolutely gorgeous. If you need to bring the family, or if you are in town for business,... View all property information
    Location Information
    Chicago, Illinois 60620
    5 of 5 stars Reviewed 21 October 2015
    We were a bit worried about renting in the Southside due to things we had heard. We loved the condo and the neighbor's were friendly and welcoming. We never felt threatened or in...
    See all reviews
    Lincoln Park
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Internet Access
    • Washer
    • Air Conditioning
    • DVD Player
    • Satellite TV
    • Patio
    • Housekeeping...
    • Grill
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
    This house is ideal for a weekend visit or long stay. Every amenity is at your fingertips and every Chicago site is steps or a train away. Great modern space with eat-in chefs kitchen updated comfortable bathrooms and spacious city backyard. Perfect location for a Chicago getaway!!! Heart of... View all property information
    Location Information
    Chicago, Illinois 60614
    1 / 30
    5 of 5 stars (1) Excellent
    Lakeview
    4 Bedrooms, 4 Bathrooms, Sleeps 14 | Quick View
    Show Prices
    Amenities & Details
    • Air Conditioning
    • Grill
    • Washer
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    License#2314739 This is a luxury property consistent of two units one above the other. Book one or both to accommodate the size of your group. A total of 4 bedroom 4 bath brand new construction luxury condos. We are a licensed vacation rental property with the City of Chicago... View all property information
    Location Information
    Chicago, Illinois 60613
    5 of 5 stars Reviewed 26 May 2015
    This rental was absolutely amazing. The owners were very easy to get a hold of & the place was very clean, updated, and accommodated our group of 13 perfectly. The location was...
    See all reviews
    Roscoe Village
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
    other traveller has booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • DVD Player
    • Porch
    • Outdoor Dining Area
    • Washer
    • Air Conditioning
    • Grill
    • Internet Access
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Welcome to your home away from home nestled in the Village within the City – Roscoe Village in Chicago, IL. Roscoe Village is a very family friendly neighborhood. This warm and welcoming first floor unit features a high end kitchen equipped with stainless appliances & granite countertops, 1 King... View all property information
    Location Information
    Chicago, Illinois 60618
    Lakeview
    5 Bedrooms, 3 Bathrooms, Sleeps 14 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Wi-Fi
    • Washer
    • Terrace
    • Satellite TV
    • Balcony
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    This 5 bedroom apartment sleeps 14, an oasis in the midst of all the excitement that Wrigleyville and Chicago have to offer! Walk to Wrigley Field, CTA Red Line, nightlife, bars, restaurants, and lots more! Perfect for families and large groups! Lots of space in an awesome location - and a... View all property information
    Location Information
    Chicago, Illinois 60613
    1 / 27
    4.5 of 5 stars (6) Very good
    The Loop
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    About this property
    1 KING SIZE Bed in the masteroom and 1 full size bed in the second and air-mattress available for more than 5 people 1600 square feet Sleeps 6 2 Flatscreen TVs Clean freshly-washed white sheets and white Towels waiting for you. Coffee maker now available. Private garage parking in the... View all property information
    Location Information
    Chicago, Illinois 60605
    4 of 5 stars Reviewed 29 May 2015
    I actually rented this place for the "bike the drive" cycle ride over Memorial Day. The pictures are accurate. Tee was always available for questions, checking in, etc. a short...
    5 of 5 stars Reviewed 7 November 2014
    The Condo was a great place for rest and relaxation between all the excitement we found in Chicago. Outstanding views of the Chicago skyline, great location, comfortable beds and...
    See all reviews
    3 Bedrooms, 1 Bathroom, Sleeps 7 | Quick View
    other traveller has booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Internet Access
    • Air Conditioning
    • Parking
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Have a great time in a rarely found 3 bedroom in this area. Leave the car and walk to the great restaurants and bars scene on Madison St. Only a 15 minute drive (or hop on the nearby Green Line subway station) and explore all Chicago has to offer!! You will have access to the whole first floor of... View all property information
    Location Information
    Chicago, Illinois 60130
    1 / 15
    5 of 5 stars (2) Excellent
    Lakeview
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • DVD Player
    • Satellite TV
    • Air Conditioning
    • Washer
    • Waterfront
    • Patio
    • Grill
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Our vintage apartment is located in the beautiful Chicago neighborhood of Lakeview with many ethnic restaurants and clubs with-in walking distance. Try a different ethnic specialty every night of the week. The apartment is in an ideal location to come and explore Chicago. Stroll 2 blocks through... View all property information
    Location Information
    Chicago, Illinois 60657
    5 of 5 stars Reviewed 12 December 2013
    My husband and I and our dog, Mazie, had the best week during the week of thanksgiving. The house was so comfortable and homey and the neighborhood was a great place to walk a...
    5 of 5 stars Reviewed 3 November 2013
    Our family highly recommends "the Ginko Place". What a wonderful place! Where in Chicago can you stay and have a garden/patio BBQ in the middle of the City! Not only is a home...
    See all reviews
    Northwest Side
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Patio
    • Wi-Fi
    • Grill
    • DVD Player
    • Washer
    • Balcony
    • Air Conditioning
    • Outdoor Dining Area
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Three floors of customized beauty on Cortland in the vibrant Bucktown neighborhood! One block from Blue Line, this highly-upgraded condo is 15 minutes from the Loop with easy access to airports, suburbs and all of downtown Chicago! The building is quiet and can easily accommodate any size group... View all property information
    Location Information
    Chicago, Illinois 60647
    1 / 22
    Near North Side
    Studio, 1 Bathroom, Sleeps 2 | Quick View
    Show Prices
    Amenities & Details
    • Terrace
    • Internet Access
    • Washer
    • Balcony
    • DVD Player
    • Shared Outdoor Pool...
    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
    Location Information
    Chicago, Illinois 60654
    Northwest Side
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Parking
    • Wi-Fi
    • Patio
    • Air Conditioning
    • Satellite TV
    • Grill
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Thank you viewing this listing. I am offering a fully furnished two bedroom, one bathroom apartment. The apartment is located in the city's far West side. Conveniently located nearby is a Metra train station which travels to Chicago Union Station, located in the Loop (downtown). Another travel... View all property information
    Location Information
    Chicago, Illinois 60707
    1 / 15
    The Loop
    Studio, 1 Bathroom, Sleeps 2 | Quick View
    Show Prices
    Amenities & Details
    • Shared Indoor Pool
    • Internet Access
    • Washer
    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
    Location Information
    Chicago, Illinois 60601
    1 / 7
    5 of 5 stars (1) Excellent
    Near North Side
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Wi-Fi
    • Parking
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    It is a great location in Downtown Chicago. It is close to everywhere. Opposite side is Northwestern Memorial Hospital , following building is Ann Lurie Children's Hospital. It is walking distance to Magnificent Mile (Michigan Ave.) , Navy Pier. There are restaurants , markets all around. Welcome... View all property information
    Location Information
    Chicago, Illinois 60611
    5 of 5 stars Reviewed 22 June 2015
    The apartment is in a very good position. I found it clean and with all the services working perfectly.
    See all reviews
    Lakeview
    6 Bedrooms, 2 Bathrooms, Sleeps 16 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Terrace
    • Wi-Fi
    • Satellite TV
    • Balcony
    • Washer
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Lots of space in an awesome location - ONE BLOCK FROM WRIGLEY FIELD AND THE CHICAGO CUBS! This apartment sleeps 16 GUESTS over TWO FLOORS! It offers five queen beds and one double bed in their own bedrooms, plus in the semi-private alcoves in common spaces we have two queen beds, as well as two... View all property information
    Location Information
    Chicago, Illinois 60613
    1 / 14
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
    Show Prices
    Amenities & Details
    • Satellite TV
    • DVD Player
    • Internet Access
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    **W**O**W** Actually in Times Square. Minutes to everything in NYC. - Times Square - Rockefeller Center - Empire State Building - Park Ave - 5th Ave Shopping - Central Park - Broadways shows and theaters We would love to help make your trip to New York a special one.... View all property information
    Location Information
    Chicago, Illinois 60611
    1 / 51
    2 of 5 stars (1) Poor
    Near North Side
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Satellite TV
    • Wi-Fi
    • DVD Player
    • Air Conditioning
    • Washer
    • Terrace
    • Balcony
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Included is a 3-bedroom fully furnished “Old Town Chicago” condo with TWO PRIVATE BALCONIES, Flat Panel HDTVs, Fireplaces, All Utilities, All Major Appliances, WiFi, Internet, Cable, Queen Size Mattresses, Cleaning Service upon Vacating Included, Complimentary Laundry, and all of the atmosphere... View all property information
    Location Information
    Chicago, Illinois 60610
    1 / 37
    4 of 5 stars (5) Very good
    1 Bedroom, 1 Bathroom, Sleeps 6 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Internet Access
    • Washer
    • Parking
    • Outdoor Dining Area
    • Patio
    • Air Conditioning
    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
    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 3 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...
    See all reviews
    1 / 7
    The Loop
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
    Show Prices
    Amenities & Details
    • Washer
    • Air Conditioning
    • Parking
    • Hot Tub
    • Satellite TV
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    , overlooking city, Lake Michigan and the Chicago River. Fully furnished 2 bedroom/2 bath. Building amenities include work-out room, swimming pool, hot tub, parking, dry cleaners on-site, food market on-site. Beds: 1 Queen Bed, 1 Double Bed View all property information
    Location Information
    Chicago, Illinois 60601
    1 / 23
    5 of 5 stars (1) Excellent
    Northwest Side
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
    Show Prices
    Amenities & Details
    • Satellite TV
    • Washer
    • Patio
    • Grill
    • DVD Player
    • Air Conditioning
    • Parking
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Gorgeous, Luxury Oak Park area Townhome…corner unit…completely furnished….close proximity (2 min.) to the historic Oak Park area…home of Frank Lloyd Wright and Ernest Hemingway! Beautiful landscaping, total 2,000 sq. ft. , alarm system, central air. Stunning designer furnishings in every... View all property information
    Location Information
    Chicago, Illinois 60707
    5 of 5 stars Reviewed 24 October 2014
    We recently stayed at this property for a ladies weekend in the Chicago area. There were 6 of us and the townhouse was just the perfect choice for us. We had plenty of room and...
    See all reviews
    1 / 12
    5 of 5 stars (6) Excellent
    Northwest Side
    Studio, 1 Bathroom, Sleeps 2 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Grill
    • Private Garden
    • DVD Player
    • Wi-Fi
    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
    Location Information
    Chicago, Illinois 60618
    5 of 5 stars Reviewed 22 August 2015
    this place is really nice. its really clean and comfortable, the room is just perfect. The owner is such a nice person. I will definitely be booking again on my next trip to...
    5 of 5 stars Reviewed 17 August 2015
    This studio apartment in north Chicago is the best place I have stayed in Chicago, considering location and value for the price. Hanne is a great host. The apartment is located...
    See all reviews
    1 / 17
    1 of 5 stars (2) Terrible
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Central Heating
    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), bicycles available, we are also 1.5 blocks away from the... View all property information
    Location Information
    Chicago, Illinois 60612
    1 / 17
    Roscoe Village
    2 Bedrooms, 1 Bathroom, Sleeps 8 | Quick View
    Show Prices
    Amenities & Details
    • Parking
    • Satellite TV
    • Washer
    • Grill
    • Internet Access
    • Air Conditioning
    • Patio
    • 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
    Location Information
    Chicago, Illinois 60618
    West Town
    3 Bedrooms, 5 Bathrooms, Sleeps 8 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Patio
    • Air Conditioning
    • DVD Player
    • Balcony
    • Secure Parking
    • Washer
    • Wi-Fi
    • Outdoor Dining Area
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    NOT YOUR AVERAGE VACATION RENTAL! This home is a true luxury oasis in the heart of the big city. If you're looking for space to enjoy and relax with all the comforts of home, search no further, the Hubbard Townhouse is for you and your group! Strategically located in between West Loop, Fulton... View all property information
    Location Information
    Chicago, Illinois 60642
    Chicago Holiday Rentals

    Located on the shores of Lake Michigan, Chicago is a stunning city bursting with attractions. Accommodation can be pricey, but choosing a rental property rather than a hotel is the ideal way to save money. Whether you prefer a spacious apartment in the city centre or a family house in a quieter area, you will feel relaxed and be able to organise your schedule as it suits you. You will of course find a host of restaurants catering to all tastes, but when you are tired of eating out, you can prepare your own food in a fully equipped kitchen.

    Chicago attractions

    You might not know where to begin seeing the sights of Chicago, so take a trolley tour to give you and your family an overview. A Wellenda Boat tour along the Chicago River and Lake Michigan is another wonderful way to see the city's architecture. Don't miss the Magnificent Mile, where the John Hancock Observatory offers spectacular views of the skyscrapers and Lake Michigan beyond. Art lovers should make a beeline for the Art Institute of Chicago, with its world-class collections of French and American Impressionists and Dutch Masters. The whole family will enjoy a visit to Millennium Park, where the star attractions are the Crown Fountain and the Chicago Bean, an enormous silver sculpture. You can try out the restaurant there, and you might be lucky enough to catch a music festival as well.

    Chicago holiday rentals for families

    Animal lovers must find time to visit Lincoln Park Zoo, where the Regenstein African Ape Centre, the Kovler Lion House and the Primate House will impress. The youngest members of the family will find the sea lions and penguins especially entertaining to watch. Before you leave Lincoln Park, children will love a visit to Adams Playground. If the weather calls for an indoor activity, head for Chicago Children's Museum at Navy Pier with its interactive exhibits. When you feel like a break from the city, spend some time on one of Lake Michigan's beaches, where you can swim, sunbathe, or go kayaking or canoeing.

    Budget holiday rentals in Chicago

    For a holiday in a vibrant city, Chicago is hard to beat. Hotels can be expensive, but renting your accommodation is the ideal low-cost alternative. Decide whether you would rather be in the city centre within walking distance of the attractions or in the quieter suburbs. Then have a look at our range of apartments and houses and choose the one that suits you best. It's worth reading through our unbiased customer reviews to help you. After that, you can look forward to what promises to be a holiday to remember in Chicago.