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Chicago Accommodation

Find 10,107 available offers from 21 partners
Chicago
Anytime
Guests
Chicago
Anytime
Guests

Popular Filters to find the Perfect Letting in Chicago

Pets allowed
1 Bedroom
2 Adults
House
4 Adults
Farmhouse
200 m to water

Vacation rentals with Wi-Fi

If it's for remote work or watching your favourite programmes, fast WiFi can be a must-have feature when it comes to selecting a holiday letting. Take a look at HomeToGo's range of holiday homes with internet in Chicago and be sure of a quick and reliable connection during your visit.

Apartment  Tri-Taylor
27 Apr - 4 May
$418 per night
Apartment ∙ 3 guests ∙ 2 bedrooms

Holiday Apartment in Tri-Taylor + City Views

5.0
Outstanding (8 ratings)
Tri-Taylor, Chicago, Illinois, United States
Free cancellation
Internet
Details
Evolve
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Resort  Archer Heights
16 June - 23 June
$156 per night
Resort ∙ 127 guests ∙ 1 bedroom

Resort in Archer Heights

3.7
Good
Archer Heights, Chicago, Illinois, United States
Free cancellation
Internet
Details
Agoda
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Apartment  South Austin
4 Nov - 11 Nov
-48%
$632
$327 per night
Apartment ∙ 6 guests ∙ 3 bedrooms

Flat in South Austin with Garden

5.0
Outstanding (1 rating)
South Austin, Chicago, Illinois, United States
Free cancellation
Internet
Details
Evolve
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Apartments and vacation rentals with a kitchen

Searching for self-catering holiday homes in Chicago? Find the ideal rental for you with our range of Chicago holiday lettings with kitchens. Well furnished with all the needed appliances, these accommodation offers are perfect for self-catered stays.

Apartment  South Austin
4 Nov - 11 Nov
-40%
$544
$329 per night
Apartment ∙ 5 guests ∙ 2 bedrooms

Flat in South Austin

5.0
Outstanding (1 rating)
South Austin, Chicago, Illinois, United States
Free cancellation
Kitchen
Details
Evolve
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House  Fifth City
11 Jan - 18 Jan
-49%
$871
$445 per night
House ∙ 5 guests ∙ 3 bedrooms

House in Fifth City with Barbecue & Garden

5.0
Outstanding (7 ratings)
Fifth City, Chicago, Illinois, United States
Free cancellation
Kitchen
Details
Evolve
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House  Marshall Square
11 Jan - 18 Jan
-48%
$471
$243 per night
House ∙ 6 guests ∙ 2 bedrooms

House in Marshall Square with Barbecue & Garden

Marshall Square, Chicago, Illinois, United States
Free cancellation
Kitchen
Details
HomeToGo
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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  Berwyn
$363 per night
House ∙ 8 guests ∙ 4 bedrooms

Holiday Home in Berwyn with Garden & Terrace

5.0
Outstanding (7 ratings)
Berwyn, Cook County, Illinois, United States
Balcony/Patio
Details
stayz
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House  Heart of Chicago
$1,051 per night
House ∙ 16 guests ∙ 5 bedrooms

House in Heart Of Chicago with Garden & Barbecue

Heart of Chicago, Chicago, Illinois, United States
Balcony/Patio
Details
stayz
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House  Oak Park
$101 per night
House ∙ 4 guests ∙ 2 bedrooms

Charming Holiday Home in Oak Park with Pool, Garden & Barbecue

Oak Park, Oak Park Township, Illinois, United States
Balcony/Patio
Details
stayz
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Best holiday rental deals in Chicago

Save up to 29%

Apartment McKinley Park
11 Jan - 18 Jan
-29%
$397
$281 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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Explore 10,107 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 10%.

Recommended holiday rentals in Chicago

Rent a holiday home, apartment or cottage in Chicago from just $105 per night

Apartment South Austin
18 June - 25 June
$558 per night
Apartment ∙ 6 guests ∙ 3 bedrooms

Charming Holiday Apartment in South Austin

South Austin, Chicago, Illinois, United States
Details
Agoda
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Condo Lake View
$439 per night
Condo ∙ 8 guests ∙ 3 bedrooms

Flat in Lake View with Terrace & Barbecue

Lake View, Chicago, Illinois, United States
Details
stayz
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Apartment Humboldt Park
$182 per night
Apartment ∙ 6 guests ∙ 3 bedrooms

Holiday Apartment in Humboldt Park with Garden & Terrace

4.5
Excellent (64 ratings)
Humboldt Park, Chicago, Illinois, United States
Details
stayz
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House Humboldt Park
$104 per night
House ∙ 6 guests ∙ 2 bedrooms

House in Humboldt Park with Terrace

4.2
Very good (17 ratings)
Humboldt Park, Chicago, Illinois, United States
Details
stayz
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Apartment Brighton Park
$223 per night
Apartment ∙ 8 guests ∙ 3 bedrooms

Flat in Brighton Park with Hassle-Free Parking

4.6
Excellent (18 ratings)
Brighton Park, Chicago, Illinois, United States
Details
stayz
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Apartment Logan Square
$171 per night
Apartment ∙ 4 guests ∙ 3 bedrooms

Beautiful Holiday Apartment in Logan Square

5.0
Outstanding (2 ratings)
Logan Square, Chicago, Illinois, United States
Details
stayz
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House Grand Boulevard
$314 per night
House ∙ 6 guests ∙ 3 bedrooms

House in Grand Boulevard

5.0
Outstanding (7 ratings)
Grand Boulevard, Chicago, Illinois, United States
Details
stayz
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Apartment Tri-Taylor
8 July - 15 July
$549 per night
Apartment ∙ 6 guests ∙ 2 bedrooms

Wonderful Holiday Apartment in Tri-Taylor

Tri-Taylor, Chicago, Illinois, United States
Free cancellation
Details
Agoda
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House Humboldt Park
$640 per night
House ∙ 10 guests ∙ 3 bedrooms

Holiday Home in Humboldt Park with Terrace, Pool & Barbecue + Degree Views

5.0
Outstanding (6 ratings)
Humboldt Park, Chicago, Illinois, United States
Details
stayz
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Budget-friendly Accommodation in Chicago

Find Fantastic yet Inexpensive Accommodation

House West Loop
$238 per night
House ∙ 9 guests ∙ 3 bedrooms

Holiday Home in West Loop with Private Balcony

4.6
Excellent (59 ratings)
West Loop, Chicago, Illinois, United States
Details
stayz
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Apartment Rogers Park
$278 per night
Apartment ∙ 5 guests ∙ 2 bedrooms

Flat in Rogers Park with Large Patio + Lake Views

5.0
Outstanding (32 ratings)
Rogers Park, Chicago, Illinois, United States
Details
stayz
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Apartment East Albany Park
$236 per night
Apartment ∙ 6 guests ∙ 3 bedrooms

Flat in East Albany Park with Garden

5.0
Outstanding (3 ratings)
East Albany Park, Chicago, Illinois, United States
Details
stayz
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Top-Rated Accommodation in Chicago

Book Holiday Offers with the Highest User Rating

Apartment Grand Boulevard
$164 per night
Apartment ∙ 8 guests ∙ 2 bedrooms

Charming Holiday Apartment in Grand Boulevard

4.9
Outstanding (94 ratings)
Grand Boulevard, Chicago, Illinois, United States
Details
stayz
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Condo West Loop
$455 per night
Condo ∙ 6 guests ∙ 2 bedrooms

Flat in West Loop

4.9
Outstanding (16 ratings)
West Loop, Chicago, Illinois, United States
Details
stayz
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Apartment Streeterville
$567 per night
Apartment ∙ 6 guests ∙ 3 bedrooms

Holiday Apartment in Streeterville with Terrace, Close to John Hancock Center + Degree Views

4.9
Outstanding (16 ratings)
Streeterville, Chicago, Illinois, United States
Details
stayz
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Popular holiday rental amenities in Chicago

  • Kitchen (5,463)
  • Washing machine (5,174)
  • WiFi (9,508)
  • Air conditioning (9,663)
  • TV (9,267)
  • Parking (1,601)
  • Fireplace (1,342)
  • Pet-friendly (2,309)
  • No smoking (9,312)
  • Dishwasher (3,521)
  • Cot (2,578)
  • Balcony/patio (2,413)

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. $822 is the highest price average in the next twelve months. Prices decrease in a week of March (15/03 – 22/03), where average prices are $292.

Rental availability information in Chicago

Check how busy Chicago is with our availability graph. Be careful if you plan to go to Chicago in April, as it comprises the busiest week of the next 6 months (26/04 – 03/05). On the contrary, you will find the highest number of available rentals in a week of June (29/06 – 06/07).

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°
8 days 8
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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, 18 May
27°
26°

0%

4 h

12 km/h

Sun, 19 May
23°
20°

0%

5 h

12 km/h

Mon, 20 May
28°
27°

10%

1 h

21 km/h

Tue, 21 May
31°
29°

10%

5 h

25 km/h

Wed, 22 May
22°
21°

15%

2 h

14 km/h

Thu, 23 May
16°
16°

0%

6 h

11 km/h

Fri, 24 May
16°
16°

0%

5 h

14 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 10,107 rentals
🌙 Nightly prices from $105
⭐ Popular amenities Kitchen, Washing machine and Internet
🐾 Pet friendly lettings 2,309 properties
🏊 Holiday rentals with pools 2,420 properties
9 reviews
Chicago holiday lettings have an average rating of 4.4/5 across 9 reviews left by travellers.

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 $105 per night.

How many holiday accommodation offers will I find in Chicago?

Visit Chicago in June 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 10,107 holiday rental offers in Chicago, with plenty of Apartment rental and House rental available.

Are pets permitted in holiday accommodation in Chicago?

There are 2,309 pet-friendly holiday accommodation offers in Chicago, costing $660 per night on average.

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