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Chicago Accommodation

Find 9,371 available offers from 12 partners
Chicago
Anytime
Guests

Choose the perfect holiday letting

Price per night
Up to $100
$100 - $199
From $200
Accommodation types
Apartment
House
Bed and breakfast
Distance to center
1 km
2 km
5 km
Rating
4.5+
4+

Best holiday rental deals in Chicago

Save up to 43%

Resort Archer Heights
12 Dec - 19 Dec
-23%
$210
$162 per night
Resort ∙ 10 guests ∙ 1 bedroom

Resort in Archer Heights

3.8
Good
Archer Heights, Chicago, Illinois, United States
Free cancellation
Details
Agoda
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Apartment McKinley Park
6 Jan - 13 Jan
-43%
$451
$259 per night
Apartment ∙ 2 guests ∙ 1 bedroom

Holiday Apartment in Mckinley Park with Garden

McKinley Park, Chicago, Illinois, United States
Free cancellation
Details
Evolve
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Apartment Tri-Taylor
9 Dec - 16 Dec
-21%
$221
$175 per night
Apartment ∙ 4 guests ∙ 2 bedrooms

Holiday Apartment in Tri-Taylor

Tri-Taylor, Chicago, Illinois, United States
Free cancellation
Details
Agoda
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Explore 9,371 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 43%.

Top-Rated Accommodation in Chicago

Book Holiday Offers with the Highest User Rating

Apartment Irving Park East
$126 per night
Apartment ∙ 4 guests ∙ 1 bedroom

Holiday Apartment in Irving Park East with Barbecue

5.0
Outstanding (4 ratings)
Irving Park East, Chicago, Illinois, United States
Details
stayz
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Recommended holiday rentals in Chicago

Rent a holiday home, apartment or cottage in Chicago from just $67 per night

Apartment Washington Park
$156 per night
Apartment ∙ 4 guests ∙ 2 bedrooms

Holiday Apartment in Washington Park

Washington Park, Chicago, Illinois, United States
Details
stayz
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House North Austin
$471 per night
House ∙ 12 guests ∙ 4 bedrooms

Nice House in North Austin with Garden & Barbecue

North Austin, Chicago, Illinois, United States
Details
stayz
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Apartment Ashburn
$118 per night
Apartment ∙ 4 guests ∙ 2 bedrooms

Rental Flat in Ashburn

Ashburn, Chicago, Illinois, United States
Details
stayz
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Apartment Tri-Taylor
$255 per night
Apartment ∙ 6 guests ∙ 2 bedrooms

Holiday Apartment in Tri-Taylor

Tri-Taylor, Chicago, Illinois, United States
Details
stayz
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House West Town
$388 per night
House ∙ 10 guests ∙ 3 bedrooms

House in West Town with Barbecue, Queen Sofabed

4.8
Outstanding (48 ratings)
West Town, Chicago, Illinois, United States
Details
stayz
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Apartment West Ridge
$74 per night
Apartment ∙ 2 guests ∙ 1 bedroom

Flat in West Ridge

West Ridge, Chicago, Illinois, United States
Details
stayz
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House Palmer Square
$714 per night
House ∙ 10 guests ∙ 5 bedrooms

Wonderful House in Palmer Square with Barbecue

3.4
(6 ratings)
Palmer Square, Chicago, Illinois, United States
Details
stayz
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House The Island
$226 per night
House ∙ 8 guests ∙ 3 bedrooms

Wonderful Holiday Home in The Island with Garden

4.7
Excellent (24 ratings)
The Island, Chicago, Illinois, United States
Details
stayz
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Budget-friendly Accommodation in Chicago

Find Fantastic yet Inexpensive Accommodation

Apartment Tri-Taylor
9 Dec - 16 Dec
$300 per night
Apartment ∙ 4 guests ∙ 2 bedrooms

Lovely Holiday Apartment in Tri-Taylor

Tri-Taylor, Chicago, Illinois, United States
Details
Agoda
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Apartment Tri-Taylor
3 Feb - 10 Feb
-21%
$412
$326 per night
Apartment ∙ 6 guests ∙ 2 bedrooms

Flat in Tri-Taylor

Tri-Taylor, Chicago, Illinois, United States
Free cancellation
Details
Agoda
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Apartment North Lawndale
9 Dec - 16 Dec
-47%
$381
$203 per night
Apartment ∙ 4 guests ∙ 2 bedrooms

Flat in North Lawndale

North Lawndale, Chicago, Illinois, United States
Free cancellation
Details
Agoda
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Best holiday homes with a patio or terrace

Want to enjoy even more amazing views in Chicago? Take a look at our top Chicago holiday rentals with patios and balconies.

House  South Shore
9 Dec - 16 Dec
-16%
$336
$281 per night
House ∙ 4 guests ∙ 2 bedrooms

Holiday Home in South Shore with Barbecue & Garden

South Shore, Chicago, Illinois, United States
Balcony/Patio
Details
Evolve
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House  Wicker Park
20 Jan - 27 Jan
-70%
$2,360
$708 per night
House ∙ 10 guests ∙ 6 bedrooms

Holiday Home in Wicker Park with Garden

Wicker Park, Chicago, Illinois, United States
Free cancellation
Balcony/Patio
Details
RedAwning
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Apartment  Chicago Loop
9 Dec - 16 Dec
$484 per night
Apartment ∙ 2 guests ∙ 1 bedroom

Wonderful Flat in Chicago Loop with Terrace, Next to Cloud Gate

Chicago Loop, Chicago, Illinois, United States
Balcony/Patio
Details
HousingAnywhere
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Vacation homes and cottages with a garden

Looking to enjoy time outdoors during your holiday in Chicago? Find an accommodation offer with a garden for your visit. Browse HomeToGo's range of holiday rentals with gardens and find the perfect let today!

Condo  South Austin
$265 per night
Condo ∙ 7 guests ∙ 3 bedrooms

Flat in South Austin with Garden

South Austin, Chicago, Illinois, United States
Yard
Details
stayz
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Apartment  Stickney
$254 per night
Apartment ∙ 4 guests ∙ 2 bedrooms

Holiday Apartment in Stickney with Garden & Barbecue

5.0
Outstanding (2 ratings)
Stickney, Stickney Township, Illinois, United States
Yard
Details
stayz
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Apartment  Brighton Park
$116 per night
Apartment ∙ 6 guests ∙ 2 bedrooms

Holiday Apartment in Brighton Park with Garden

4.6
Excellent (7 ratings)
Brighton Park, Chicago, Illinois, United States
Yard
Details
stayz
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Popular holiday rental amenities in Chicago

  • Kitchen (5,139)
  • Washing machine (5,087)
  • WiFi (9,014)
  • Air conditioning (8,440)
  • TV (8,685)
  • Parking (1,604)
  • Fireplace (1,284)
  • Pet-friendly (2,110)
  • No smoking (5,293)
  • Dishwasher (3,471)
  • Cot (1,859)
  • Balcony/patio (1,839)

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 never miss an episode of your favourite show, as a lot of the lettings offer Kitchen or Washing machine. It is also possible to find a holiday rental if you think grilling is essential for a great holiday , as 695 of the lettings there include No pets allowed.

Price and Availability Index in Chicago

Click on any bar to see price and availability information

Holiday Rental Price Information in Chicago

The graph shows average prices of rental prices in Chicago for the next twelve months. $1,011 is the highest price average in the next twelve months. Prices decrease in a week of February (03/02 – 10/02), where average prices are $329.

Rental availability information in Chicago

Check how busy Chicago is with our availability graph. Be careful if you plan to go to Chicago in October, as it comprises the busiest week of the next 6 months (26/10 – 02/11). On the contrary, you will find the highest number of available rentals in a week of December (30/12 – 06/01).

The weather in Chicago

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-8°
8 days 8
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-7°
7 days 7
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-2°
9 days 9
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15°
9 days 9
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21°
10°
8 days 8
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27°
16°
9 days 9
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29°
18°
8 days 8
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29°
18°
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24°
13°
8 days 8
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18°
7 days 7
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8 days 8
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-6°
9 days 9
Jan.
Feb.
Mar.
Apr.
May
June
July
Aug.
Sep.
Oct.
Nov.
Dec.
- Rainy days

This is the climate diagram in Chicago. In July maximum temperatures go higher than 29°. No heat wave is expected in January, where minimum average temperatures usally hit a -8° low. March is the wettest month.

7-Day Weather Forecast in Chicago

Sat, 2 Dec

30%

0 h

11 km/h

Sun, 3 Dec

5%

0 h

16 km/h

Mon, 4 Dec

10%

1 h

9 km/h

Tue, 5 Dec

15%

0 h

16 km/h

Wed, 6 Dec

10%

3 h

6 km/h

Thu, 7 Dec

0%

1 h

24 km/h

Fri, 8 Dec

0%

5 h

18 km/h

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!

Information about holiday rentals in Chicago

🏡 Holiday rentals available 9,378 properties
💳 Discounts available up to 42%
🌙 Nightly prices from $45
⭐ Popular amenities Kitchen, Washing machine and Internet
🐾 Pet friendly lettings 2,086 properties
🏊 Holiday rentals with pools 2,371 properties

Frequently Asked Questions

How much should I expect to pay for a holiday letting in Chicago?

When visiting Chicago, you can find holiday rentals from as little as $45 per night.

How many holiday accommodation offers will I find in Chicago?

Visit Chicago in December for the greatest choice of accommodation. This is the month during which the largest amount of Apartment rental and House rental are available.

What holiday rental amenities do people typically look for when visiting Chicago?

The top accommodation priorities for visitors to Chicago are Kitchen, Washing machine and Internet.

How many accommodation offers are there in Chicago?

There are 9,378 holiday rental offers in Chicago, with plenty of Apartment rental and House rental available.

Are pets permitted in holiday accommodation in Chicago?

There are 2,086 pet-friendly holiday accommodation offers in Chicago, costing $514 per night on average.

Top holiday destinations near Chicago

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Top Holiday Ideas

Top cities to visit

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