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Chicago, IL condos

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All 231 Rentals in Chicago
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£89
Per Night
1 / 19
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Gold Coast, Near North Side
Studio, 1 Bathroom, Sleeps 3
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Details Reviews (1) Make Enquiry
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£101
Per Night
1 / 11
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Roscoe Village
2 Bedrooms, 1 Bathroom, Sleeps 6
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£127
Per Night
1 / 9
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Near North Side
1 Bedroom, 1 Bathroom, Sleeps 2
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Details Reviews (1) Make Enquiry
Also consider
Terrific Lincoln Park apartment
3 Bedrooms, sleeps 8
£118 - £166 / night
Quick & Easy walk to the 'L' train...SLEEPS 3
2 Bedrooms, sleeps 3
£112 / night
Condo-quality short term furnished 1750 sq ft apt
3 Bedrooms, sleeps 4
£143 / night
Luxury Guesthouse in Roscoe Village
2 Bedrooms, sleeps 6
£92 - £159 / night
From
£77
Per Night
1 / 26
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Gold Coast, Near North Side
Studio, 1 Bathroom, Sleeps 2
Bookings
Details Reviews (8) Make Enquiry
5 of 5 stars Reviewed 16 November 2014
We had a wonderful time at Brooks's "Urban Oasis". It is well located to see everything around Chicago city. Friendly helpful doormen/women, secure access, great facilities...
5 of 5 stars Reviewed 16 November 2014
Why was staying at Brook's make your trip to Chicago so special: * Immaculate condo with all your comfort needs *Close to everything -Really! *We felt so very comfortable and...
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£54
Per Night
1 / 14
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Northwest Side
2 Bedrooms, 1 Bathroom, Sleeps 4
Bookings
Details Reviews (6) Make Enquiry
5 of 5 stars Reviewed 20 September 2014
Hanne was very easy to work with and extremely nice. Nice roomy apt and pretty close to everything. I would definitely stay here again when traveling to Chicago. Very quiet...
5 of 5 stars Reviewed 11 September 2014
Roomy 2 bedroom was in walking distance to great bars and restaurants and was a ten minute drive to many "Lincoln Park" area attractions such as the zoo, aquarium and...
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£63
Per Night
1 / 28
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Rogers Park
2 Bedrooms, 1 Bathroom, Sleeps 7
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4 of 5 stars Reviewed 3 October 2014
Three of us stayed at at Devon property and were thrilled with the accommodations. The location to the local bus and train stops were very convenient. The hosts, Lisa and...
4 of 5 stars Reviewed 3 September 2014
Stayed here with a few friends for the weekend. Had a great time, The location is perfect, its close to everything, yet still residential. Lisa was the main contact, she was...
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£57
Per Night
1 / 40
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The Loop
Studio, 1 Bathroom, Sleeps 2
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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...
5 of 5 stars Reviewed 7 May 2014
The location is so convenient, the blue line train from O'hare airport takes you right to the stop of which is about 5 minutes walk to the building. The unit is clean and with...
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£48
Per Night
1 / 16
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Northwest Side
1 Bedroom, 1 Bathroom, Sleeps 2
Bookings
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5 of 5 stars Reviewed 14 November 2014
My husband and I rented the apartment for 5 days in early November. I was attending a Conference downtown and did not want to pay the high price hotel. This place was perfect...
5 of 5 stars Reviewed 7 November 2014
I visit my son often and have stayed in other condos and hotels all throughout the city and this by far is the best. With dorm style amenities and generous snacks, it's better...
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From
£51
Per Night
1 / 14
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Studio, 1 Bathroom, Sleeps 2
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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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£128
Per Night
1 / 19
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Near North Side
1 Bedroom, 1 Bathroom, Sleeps 2
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5 of 5 stars Reviewed 29 July 2014
Beautiful condo with all the amenities. Gym, pool, whirlpool, and a fantastic infinity hot tub on the roof. Great views. Wonderful host. Concierge very friendly and helpful...
4 of 5 stars Reviewed 12 June 2014
The 19th floor condo was clean, serviceable and quiet. Everything works and the washer/dryer were a nice plus. The views from the floor to ceiling windows are not impressive, but...
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£86
Per Night
1 / 37
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Near North Side
2 Bedrooms, 2 Bathrooms, Sleeps 5
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4 of 5 stars Reviewed 18 August 2014
Very strategic location near to major attractions. Very spacious and quiet. The best coffee is just down the building! The only thing was the wifi was extremely slow, me and my...
3 of 5 stars Reviewed 1 July 2014
security was not aware of our check in and had to call and verify. kitchen is not adequately stocked for those who may use knives, forks and wine glasses. it was, however...
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£89
Per Night
1 / 49
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Southwest Side
3 Bedrooms, 2 Bathrooms, Sleeps 6
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5 of 5 stars Reviewed 13 November 2014
Our family of four had an excellent time at this apartment. Bob was very easy to deal with and extremely helpful. Key code access to the apartment was very convenient. A garage...
4 of 5 stars Reviewed 27 September 2014
We were very pleased with our stay at this facility. It isn't in the typical touristy area which we liked as it made our urban experience feel more authentic and any neighbors we...
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From
£57
Per Night
1 / 7
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Northwest Side
1 Bedroom, 1 Bathroom, Sleeps 2
Bookings
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From
£102
Per Night
1 / 48
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Southwest Side
2 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
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5 of 5 stars Reviewed 7 April 2014
Our family of four (two teens) spent 5 days here during spring break and had an excellent experience. We went downtown every day by catching the red line train at the 35th/Sox...
5 of 5 stars Reviewed 2 May 2012
We couldn’t be more pleased with our stay, everyone had a fantastic time. Our visit took place April 12-15 and there were six of us; my parents (early 50’s), younger brother and...
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£127
Per Night
1 / 15
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Near North Side
1 Bedroom, 1 Bathroom, Sleeps 2
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4 of 5 stars Reviewed 21 September 2012
We rented a one-bedroom apartment in this six-apartment building for the entire summer, so we could experience Chicago without exhausting ourselves. Cozy apartment, comfortably...
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£63
Per Night
1 / 20
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1 Bedroom, 1 Bathroom, Sleeps 6
Bookings
Details Reviews (4) Make Enquiry
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...
5 of 5 stars Reviewed 12 November 2013
From start to finish this rental was perfect. I was hesitant to rent from a private party, however great communication early on helped put me at ease. As a solo traveling female I...
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From
£118
Per Night
1 / 32
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The Loop
1 Bedroom, 1 Bathroom, Sleeps 4
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5 of 5 stars Reviewed 6 November 2014
The apartment was great! The hosts were very easy to contact when needed. Even the neighbours were friendly. Good location, away from the busy city Central but still close enough...
5 of 5 stars Reviewed 30 October 2014
21st and Michigan, right on the bus route to go to the Downtown core and to get to the museums. Just blocks away from Chinatown. Market just across the street for meat and eggs...
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From
£126
Per Night
1 / 7
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Northwest Side
2 Bedrooms, 2 Bathrooms, Sleeps 8
Booking
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From
£61
Per Night
1 / 11
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Lincoln Square
1 Bedroom, 1 Bathroom, Sleeps 3
Bookings
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5 of 5 stars Reviewed 24 October 2014
We loved it! Great location, we came into town for a concert series at the Metro (about a 10 minute ride away), there were great restaurants nearby and downtown was also easily...
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From
£50
Per Night
1 / 14
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Northwest Side
Studio, 1 Bathroom, Sleeps 2
Bookings
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5 of 5 stars Reviewed 20 September 2014
The place is immaculate. Super clean and fully equipped. The location is great. You have the subway blue line (to downtown) in a short walk from the house to the station. The...
5 of 5 stars Reviewed 1 September 2014
I enjoyed my stay here and the hosts are warm, friendly and welcoming people. Hanne is just the sweetest person and I feel as if I have known her for many years. She always made...
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From
£159
Per Night
1 / 15
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Lakeview
2 Bedrooms, 1 Bathroom, Sleeps 6
Booking
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From
£61
Per Night
1 / 10
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Lakeview
1 Bedroom, 1 Bathroom, Sleeps 2
Bookings
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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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From
£159
Per Night
1 / 23
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Near North Side
1 Bedroom, 1 Bathroom, Sleeps 4
Bookings
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5 of 5 stars Reviewed 21 September 2014
The apartment is in a great location and very well appointed with facilities and access to the rooftop spa area. We thoroughly enjoyed it. Paul is a good guy.
5 of 5 stars Reviewed 8 September 2014
We spent 7 nights at unit in floor 25. The building is very fancy and has very nice services: full gym, pool, spa, hot tub at rooftop, 4 high speed elevators, nice view, etc. The...
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From
£128
Per Night
1 / 8
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Northwest Side
2 Bedrooms, 2 Bathrooms, Sleeps 5
Bookings
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5 of 5 stars Reviewed 18 August 2014
Nice apartment for up to 6 people, around $20 taxi ride from the Airport. Close to a large park, bus, and train stations. We purchased 7 days CTS passes for $33 each with...
4 of 5 stars Reviewed 29 March 2014
Bed was a little uncomfortable and broke often. Parking was difficult. Clean apartment, ideal for a large family
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From
£143
Per Night
1 / 11
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Lakeview
2 Bedrooms, 1 Bathroom, Sleeps 5
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4 of 5 stars Reviewed 29 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...
4 of 5 stars Reviewed 3 July 2014
The house was great, clean and comfortable with everything we needed. The neighborhood was great and walking distance to Wrigley Field. The train was close as well. The only down...
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£57
Per Night
1 / 6
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1 Bedroom, 1 Bathroom, Sleeps 2
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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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£127
Per Night
1 / 14
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West Town
3 Bedrooms, 2 Bathrooms, Sleeps 5
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3 of 5 stars Reviewed 17 September 2014
Nice place, only one bed and couldn't use the garage as advertised. Parking is a bit tricky, had to park several blocks away on Hubbard, but when rush hour ends it is good. No...
4 of 5 stars Reviewed 10 July 2014
This was a beautiful condo in a great location in Chicago. We rented the condo for one day for a video shoot and the couple renting it to us were so helpful and flexible with our...
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From
£73
Per Night
1 / 23
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Northwest Side, Wicker Park / Bucktown
2 Bedrooms, 1 Bathroom, Sleeps 4
Bookings
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2 of 5 stars Reviewed 14 October 2014
I felt like I was being punked! When I booked this place it advertised access to the spa at the bath house. When we arrived the curt "receptionist" said access was only for one...
3 of 5 stars Reviewed 15 June 2014
This apartment in Wicker Park is enormous and very nice! It's in a pretty sweet location above a bathhouse and next to a great breakfast place called Milk & Honey. The el is about...
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From
£105
Per Night
1 / 22
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Lincoln Square
3 Bedrooms, 2 Bathrooms, Sleeps 6
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From
£70
Per Night
1 / 7
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Northwest Side
2 Bedrooms, 1 Bathroom, Sleeps 4
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From
£159
Per Night
1 / 17
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Near North Side
2 Bedrooms, 1 Bathroom, Sleeps 4
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From
£175
Per Night
1 / 9
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DePaul
2 Bedrooms, 1 Bathroom, Sleeps 5
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From
£191
Per Night
1 / 50
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Near North Side
2 Bedrooms, 2 Bathrooms, Sleeps 4
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From
£223
Per Night
1 / 33
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The Loop
2 Bedrooms, 2 Bathrooms, Sleeps 5
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From
£118
Per Night
1 / 26
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Near North Side
1 Bedroom, 1 Bathroom, Sleeps 3
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From
£77
Per Night
1 / 23
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Northwest Side
2 Bedrooms, 1 Bathroom, Sleeps 4
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From
£106
Per Night
1 / 13
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Northwest Side
2 Bedrooms, 1 Bathroom, Sleeps 4
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From
£638
Per Week
1 / 7
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Northwest Side
2 Bedrooms, 1 Bathroom, Sleeps 3
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From
£229
Per Night
1 / 31
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The Loop
2 Bedrooms, 2 Bathrooms, Sleeps 6
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From
£191
Per Night
1 / 26
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The Loop
2 Bedrooms, 1 Bathroom, Sleeps 5
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Neighbourhood

  • All (231)
  • DePaul (10)
  • East Side (0)
  • Gold Coast (11)
  • Hyde Park (0)
  • Lakeview (24)
  • Lincoln Park (3)
  • Lincoln Square (3)
  • Near North Side (58)
  • Near South Side (0)
  • Northwest Side (21)
  • O'Hare (0)
  • Pilsen (1)
  • Rogers Park (7)
  • Roscoe Village (8)
  • Southwest Side (2)
  • The Loop (55)
  • University Village / Little Italy (0)
  • West Town (4)
  • Wicker Park / Bucktown (4)
Learn about Chicago neighbourhoods

Suitability

  • Wheelchair access (58)
  • Elder access (103)
  • Suitable for children (108)
  • Pet friendly (53)
  • Smoking allowed (2)

Amenities

  • Air Conditioning (139)
  • Internet (136)
  • Other outdoor space (100)
  • Washer/Dryer (92)
  • Parking (65)
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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.