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Chicago Accommodation

Find 6,362 available offers from 17 partners
Chicago
Anytime
Guests
Save up to 69%

Best holiday rental deals in Chicago

Apartment South Loop
15 Jan - 22 Jan
-69%
$1,189
$369 per night
Apartment ∙ 3 guests ∙ 2 bedrooms
3.7/5.0 "Good"
(43 ratings)
South Loop, Chicago, Illinois, United States
Free cancellation
Details
travelstaytion
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Apartment Near North
15 Jan - 22 Jan
-57%
$1,117
$477 per night
Apartment ∙ 5 guests ∙ 2 bedrooms
3.7/5.0 "Good"
(30 ratings)
Near North, Chicago, Illinois, United States
Free cancellation
Details
travelstaytion
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Apartment South Loop
15 Jan - 22 Jan
-61%
$1,067
$421 per night
Apartment ∙ 5 guests ∙ 2 bedrooms
3.7/5.0 "Good"
(97 ratings)
South Loop, Chicago, Illinois, United States
Free cancellation
Details
travelstaytion
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Explore 15 holiday lettings featured in Chicago and discover a wonderful place for your getaway. Our search engine instantly evaluates all of the properties so you can save up to 69%.

Recommended holiday rentals in Chicago

Rent a holiday home, apartment or cottage in Chicago from just $70 per night

Apartment Chicago Loop
23 Apr - 30 Apr
$157 per night
Apartment ∙ 3 guests ∙ 1 bedroom
Chicago Loop, Chicago, Illinois, United States
Details
e-domizil
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Apartment Near North
25 Jan - 1 Feb
-57%
$1,090
$473 per night
Apartment ∙ 5 guests ∙ 2 bedrooms
3.7/5.0 "Good"
(76 ratings)
Near North, Chicago, Illinois, United States
Free cancellation
Details
travelstaytion
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Apartment South Loop
15 Jan - 22 Jan
-59%
$1,500
$616 per night
Apartment ∙ 6 guests ∙ 3 bedrooms
3.7/5.0 "Good"
(53 ratings)
South Loop, Chicago, Illinois, United States
Free cancellation
Details
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Apartment South Loop
16 Jan - 23 Jan
-59%
$866
$357 per night
Apartment ∙ 3 guests ∙ 1 bedroom
3.7/5.0 "Good"
(17 ratings)
South Loop, Chicago, Illinois, United States
Free cancellation
Details
travelstaytion
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Apartment Near North
12 Jan - 19 Jan
-58%
$668
$279 per night
Apartment ∙ 2 guests ∙ 1 bedroom
3.7/5.0 "Good"
(78 ratings)
Near North, Chicago, Illinois, United States
Free cancellation
Details
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Apartment South Loop
16 Jan - 23 Jan
-59%
$698
$288 per night
Apartment ∙ 2 guests ∙ 1 bedroom
3.7/5.0 "Good"
(12 ratings)
South Loop, Chicago, Illinois, United States
Free cancellation
Details
travelstaytion
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Apartment South Loop
15 Jan - 22 Jan
-57%
$689
$297 per night
Apartment ∙ 2 guests ∙ 1 bedroom
3.7/5.0 "Good"
(32 ratings)
South Loop, Chicago, Illinois, United States
Free cancellation
Details
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Apartment New East Side
15 Jan - 22 Jan
-31%
$1,694
$1,166 per night
Apartment ∙ 8 guests ∙ 3 bedrooms
New East Side, Chicago, Illinois, United States
Free cancellation
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Apartment South Loop
25 Jan - 1 Feb
-56%
$1,007
$443 per night
Apartment ∙ 5 guests ∙ 2 bedrooms
3.7/5.0 "Good"
(41 ratings)
South Loop, Chicago, Illinois, United States
Free cancellation
Details
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Vacation rentals with Wi-Fi

Studio flat Internet Chicago Loop
23 Apr - 30 Apr
$138 per night
Studio flat ∙ 3 guests ∙ 1 bedroom
Chicago Loop, Chicago, Illinois, United States
Internet
Details
your.rentals
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Apartment Internet Near North
15 Jan - 22 Jan
-52%
$967
$469 per night
Apartment ∙ 5 guests ∙ 2 bedrooms
3.7/5.0 "Good"
(33 ratings)
Near North, Chicago, Illinois, United States
Free cancellation
Internet
Details
travelstaytion
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Apartment Internet South Loop
15 Jan - 22 Jan
-52%
$1,285
$620 per night
Apartment ∙ 6 guests ∙ 3 bedrooms
3.7/5.0 "Good"
(12 ratings)
South Loop, Chicago, Illinois, United States
Free cancellation
Internet
Details
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Apartments and vacation rentals with a kitchen

Apartment Kitchen Near North
15 Jan - 22 Jan
-52%
$967
$469 per night
Apartment ∙ 5 guests ∙ 2 bedrooms
3.7/5.0 "Good"
(94 ratings)
Near North, Chicago, Illinois, United States
Free cancellation
Kitchen
Details
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Apartment Kitchen South Loop
15 Jan - 22 Jan
-69%
$945
$291 per night
Apartment ∙ 2 guests ∙ 1 bedroom
3.7/5.0 "Good"
(98 ratings)
South Loop, Chicago, Illinois, United States
Free cancellation
Kitchen
Details
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Apartment Kitchen South Loop
8 Jan - 15 Jan
-67%
$1,171
$388 per night
Apartment ∙ 3 guests ∙ 1 bedroom
3.7/5.0 "Good"
(53 ratings)
South Loop, Chicago, Illinois, United States
Free cancellation
Kitchen
Details
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Vacation rentals and apartments with air conditioning

Apartment Aircondition South Loop
22 Jan - 29 Jan
-57%
$1,003
$434 per night
Apartment ∙ 5 guests ∙ 2 bedrooms
3.7/5.0 "Good"
(15 ratings)
South Loop, Chicago, Illinois, United States
Free cancellation
Aircondition
Details
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Apartment Aircondition Near North
15 Jan - 22 Jan
-54%
$644
$299 per night
Apartment ∙ 2 guests ∙ 1 bedroom
3.7/5.0 "Good"
(48 ratings)
Near North, Chicago, Illinois, United States
Free cancellation
Aircondition
Details
travelstaytion
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Apartment Aircondition South Loop
15 Jan - 22 Jan
-69%
$971
$299 per night
Apartment ∙ 2 guests ∙ 1 bedroom
3.7/5.0 "Good"
(83 ratings)
South Loop, Chicago, Illinois, United States
Free cancellation
Aircondition
Details
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Popular holiday rental amenities in Chicago

  • Internet (5,825)
  • No smoking (5,580)
  • Air conditioning (5,357)
  • TV (4,512)
  • Wheelchair access (4,113)
  • Washing machine (2,679)
  • Pet allowed (2,447)
  • Microwave (2,283)
  • No pets (1,818)
  • Kitchen (1,755)
  • Pool (1,718)
  • Cot (1,386)

Use the filters above to search and find an offer fitting your needs among all of the rentals in Chicago. You can easily find a holiday rental matching your criteria in Chicago if you need internet access during your holidays or you want to tune out with some TV time, as a lot of the lettings offer internet or TVs. It is also possible to find a holiday rental if you want a rental with a jacuzzi , as 368 of the lettings there include jacuzzis.

Price and Availability Index in Chicago

Holiday Rental Price Information in Chicago

The graph shows average prices of rental prices in Chicago for the next twelve months. $517 is the highest price average in the next twelve months. Prices decrease in a week of January (08/01 - 15/01), where average prices are $261.

Holiday Home Availability Information in Chicago

Check how busy Chicago is with our availability graph. Be careful if you plan to go to Chicago in July, as it comprises the busiest week of the next 6 months (31/07 - 07/08). On the contrary, you will find the highest number of available rentals in a week of December (18/12 - 25/12).

The weather in Chicago

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-2°
8 days 8
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-7°
7 days 7
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9 days 9
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15°
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22°
12°
8 days 8
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27°
17°
9 days 9
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30°
20°
8 days 8
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28°
19°
8 days 8
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24°
15°
8 days 8
max.
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17°
7 days 7
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8 days 8
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-2°
9 days 9
Jan.
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Mar.
Apr.
May
June
July
Aug.
Sep.
Oct.
Nov.
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- Rainy days

This is the climate diagram in Chicago. In July maximum temperatures go higher than 30°. No heat wave is expected in February, where minimum average temperatures usally hit a -7° low. March is the wettest month.

Accommodation & Apartments in Chicago

Chicago is one of the most fun cities in the world. The City of Broad Shoulders has a blue collar attitude and an artisan’s heart. It’s a robust, thriving city with a multicultural population that lives, works and plays hard. Walking through downtown Chicago is awe-inspiring. The skyscrapers burst from the streets and dominate the skyline. You’ll see it all in downtown Chicago. It isn’t called the Second City for nothing. Only New York City has more to offer a tourist in the United States. Chicago has great theater and authentic, live blues bars that house some of the hottest bands in the world. There are parks, beaches and bars all around Lake Michigan. If you visit in summer, catch a Cubs game at Wrigley Field, the world-famous cathedral to baseball. Don't forget to get a Chicago-style hot dog while you're in town. They're yummy! If you’d rather spend your cash on gifts, daytrips or a nice meal than on an expensive hotel room, you need to scoot on over to the HomeToGo website and find yourself a bargain on a bed and breakfast or apartment. Renting from private owners saves you money and gets you a nicer place to stay, whether it's an apartment in Florence, abed and breakfast in Frankfurt oraccommodation in Glasgow!

Find an apartment on Lake Michigan

You can find apartments in just about any section of Chicago, such as The Loop, which offers easy access to the Miracle Mile of shopping. An apartment downtown invites tourists to wander the city and sample the wonderful restaurants and night clubs. If you want to get an insider’s perspective on the city, rent an apartment from a local who will be able to tell you about all the things that the locals like to do!

Find an amazing bed and breakfast in Chicago

There’s so much to do in Chicago, you could spend two entire days playing and having fun at The Museum of Science and Industry alone. There’s no rule that says a B&B has to be the largest expense of your trip. Rewrite the rules by finding a great bed and breakfast near Lake Michigan with HomeToGo and you could end up paying a fraction of the price of a hotel. You can preview the available facilities in the B&B, get to know the host and save yourself some money. Your bed and breakfast host will cook you a meal every morning and tell you about the best ways to get around town. HomeToGo can find you accommodation from Edinburgh toHamburg!

We list offers from thousands of providers, including:

Booking.com Holiday Rentals in Chicago Vrbo Holiday Rentals in Chicago HomeAway - Stayz Holiday Rentals in Chicago Airbnb Holiday Rentals in Chicago TripAdvisor Holiday Rentals in Chicago VacationRentals.com Holiday Rentals in Chicago HouseTrip Holiday Rentals in Chicago FlipKey Holiday Rentals in Chicago 9flats.com Holiday Rentals in Chicago PerfectPlaces.com Holiday Rentals in Chicago Homestay.com Holiday Rentals in Chicago Only-apartments Holiday Rentals in Chicago Interhome Holiday Rentals in Chicago Bedycasa Holiday Rentals in Chicago Novasol Holiday Rentals in Chicago

Top holiday destinations near Chicago

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