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Chicago Accommodation

Find 2,503 available holiday rentals from 10 partners
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Guests
Anytime
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Top 15 Recommended holiday rentals in Chicago

Rent a holiday home, apartment or cottage in Chicago from just $44 per night!

House Oak Park
-59%
29 Apr - 6 May
House ∙ 9 guests ∙ 3 bedrooms

139 m² House

Oak Park, Oak Park Township, Illinois, United States
$673$277
per night
HomeToGo
$673$277
per night
View deal
HomeToGo
House Des Plaines
-44%
26 Apr - 3 May
House ∙ 6 guests ∙ 3 bedrooms

68 m² House

Des Plaines, Maine Township, Illinois, United States
$623$346
per night
Outstanding(1 rating)
HomeToGo
$623$346
per night
View deal
HomeToGo
Motel Worth
-27%
24 Apr - 1 May
Motel ∙ 4 guests ∙ 1 bedroom

Stone Creek Inn

Worth, Palos Township, Illinois, United States
$135$98
per night
Very good
Agoda
$135$98
per night
View deal
Agoda
Apartment Blue Island
-51%
26 Apr - 3 May
Apartment ∙ 7 guests ∙ 3 bedrooms

196 m² Apartment

Blue Island, Cook County, Illinois, United States
$747$368
per night
HomeToGo
$747$368
per night
View deal
HomeToGo
House Oak Park
14 June - 21 June
Free cancellation
House ∙ 9 guests ∙ 3 bedrooms

139 m² House

Oak Park, Oak Park Township, Illinois, United States
$442
per night
Agoda
$442
per night
View deal
Agoda
House Forest Park
House ∙ 9 guests ∙ 4 bedrooms

93 m² House

Forest Park, Proviso Township, Illinois, United States
from $283
per night
stayz
from $283
per night
View deal
stayz
Apartment Oak Park
Apartment ∙ 6 guests ∙ 3 bedrooms

Apartment

Oak Park, Oak Park Township, Illinois, United States
from $313
per night
Outstanding(106 ratings)
stayz
from $313
per night
View deal
stayz
House Chicago Ridge
House ∙ 5 guests ∙ 3 bedrooms

House

Chicago Ridge, Worth Township, Illinois, United States
from $211
per night
Outstanding(13 ratings)
stayz
from $211
per night
View deal
stayz
House Burbank
House ∙ 8 guests ∙ 4 bedrooms

107 m² House

Burbank, Stickney Township, Illinois, United States
from $465
per night
Very good(5 ratings)
stayz
from $465
per night
View deal
stayz
House Des Plaines
House ∙ 8 guests ∙ 4 bedrooms

186 m² House

Des Plaines, Maine Township, Illinois, United States
from $554
per night
Outstanding(5 ratings)
stayz
from $554
per night
View deal
stayz
Apartment Oak Park
Apartment ∙ 3 guests ∙ 2 bedrooms

Apartment

Oak Park, Oak Park Township, Illinois, United States
from $224
per night
Excellent(52 ratings)
stayz
from $224
per night
View deal
stayz
House Oak Park
House ∙ 10 guests ∙ 4 bedrooms

308 m² House

Oak Park, Oak Park Township, Illinois, United States
from $704
per night
Very good(5 ratings)
stayz
from $704
per night
View deal
stayz
House Elmhurst
House ∙ 10 guests ∙ 4 bedrooms

House

Elmhurst, Addison Township, Illinois, United States
from $490
per night
Outstanding(8 ratings)
stayz
from $490
per night
View deal
stayz
House Evergreen Park
House ∙ 6 guests ∙ 3 bedrooms

190 m² House

Evergreen Park, Worth Township, Illinois, United States
from $249
per night
stayz
from $249
per night
View deal
stayz
Apartment Oak Park
Apartment ∙ 5 guests ∙ 2 bedrooms

112 m² Apartment

Oak Park, Oak Park Township, Illinois, United States
from $217
per night
Excellent(22 ratings)
stayz
from $217
per night
View deal
stayz

Vacation rentals and apartments with air conditioning

Condo  Oak Park
from $277 per night
Condo ∙ 11 guests ∙ 3 bedrooms

121 m² Condo

5.0
Outstanding(1 rating)
Oak Park, Oak Park Township, Illinois, United States
Air conditioning
stayz
View deal
Apartment  Stickney
from $241 per night
4 guests ∙ 2 bedrooms

Apartment

4.1
Very good(13 ratings)
Stickney, Stickney Township, Illinois, United States
Air conditioning
stayz
View deal
House  Oak Park
from $628 per night
House ∙ 8 guests ∙ 4 bedrooms

82 m² House

4.8
Outstanding(13 ratings)
Oak Park, Oak Park Township, Illinois, United States
Air conditioning
stayz
View deal
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Vacation homes and cottages with a garden

Apartment  Berwyn
from $218 per night
Apartment ∙ 6 guests ∙ 2 bedrooms

112 m² Apartment

5.0
Outstanding(17 ratings)
Berwyn, Cook County, Illinois, United States
Yard
stayz
View deal
House  Oak Park
from $354 per night
House ∙ 9 guests ∙ 5 bedrooms

139 m² House

3.1
(4 ratings)
Oak Park, Oak Park Township, Illinois, United States
Yard
stayz
View deal
House  Cicero
from $248 per night
House ∙ 4 guests ∙ 2 bedrooms

84 m² House

Cicero, Cicero Township, Illinois, United States
Yard
stayz
View deal
See all offers

Most popular holiday houses with a fireplace

House  Maywood
21 Feb - 28 Feb
-46%
$836
$455 per night
House ∙ 6 guests ∙ 3 bedrooms

185 m² House

5.0
Outstanding(3 ratings)
Maywood, Proviso Township, Illinois, United States
Free cancellation
Fireplace
HomeToGo
View deal
House  Oak Park
8 Oct - 15 Oct
$1,276 per night
House ∙ 8 guests ∙ 4 bedrooms

165 m² House

Oak Park, Oak Park Township, Illinois, United States
Free cancellation
Fireplace
Agoda
View deal
House  Maywood
6 Aug - 13 Aug
-44%
$811
$458 per night
House ∙ 6 guests ∙ 3 bedrooms

186 m² House

Maywood, Proviso Township, Illinois, United States
Free cancellation
Fireplace
Agoda
View deal
See all offers

Best holiday rental deals in Chicago

Save up to 63%

House Cicero
5 May - 12 May
-63%
$1,412
$517 per night
House ∙ 6 guests ∙ 2 bedrooms

125 m² House

Cicero, Cicero Township, Illinois, United States
Agoda
View deal

Explore 2,503 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 63%.

Budget-friendly Accommodation in Chicago

Find Fantastic yet Inexpensive Accommodation

House Worth
from $407 per night
House ∙ 10 guests ∙ 4 bedrooms

167 m² House

4.8
Outstanding(71 ratings)
Worth, Palos Township, Illinois, United States
stayz
View deal
Apartment Rosemont
from $227 per night
Apartment ∙ 8 guests ∙ 4 bedrooms

84 m² Apartment

4.4
Very good(19 ratings)
Rosemont, Leyden Township, Illinois, United States
stayz
View deal
Apartment Oak Park
from $373 per night
Apartment ∙ 8 guests ∙ 3 bedrooms

130 m² Apartment

5.0
Outstanding(133 ratings)
Oak Park, Oak Park Township, Illinois, United States
stayz
View deal

Top-Rated Accommodation in Chicago

Book Holiday Offers with the Highest User Rating

House Forest Park
from $287 per night
6 guests ∙ 3 bedrooms

House

5.0
Outstanding(138 ratings)
Forest Park, Proviso Township, Illinois, United States
stayz
View deal
Condo Oak Park
from $198 per night
Condo ∙ 5 guests ∙ 3 bedrooms

223 m² Condo

4.8
Outstanding(65 ratings)
Oak Park, Oak Park Township, Illinois, United States
stayz
View deal
House Oak Park
from $608 per night
House ∙ 8 guests ∙ 6 bedrooms

165 m² House

4.5
Excellent(37 ratings)
Oak Park, Oak Park Township, Illinois, United States
stayz
View deal

Why choose HomeToGo?

Securely pay and stay your way

Securely pay and stay your way

Choose local, trusted payment methods, plus trip insurance and add-on services.

Award-winning customer service

Award-winning customer service

Experience seamless, hands-on support for any booking questions or concerns.

Verified reviews

Verified reviews

Trust in the quality and comfort of your stay with verified guest reviews.

Price clarity, no surprises

Price clarity, no surprises

Spend your budget exactly as planned by comparing thousands of providers.

Smart search made simple

Smart search made simple

Transform holiday planning into a joy with advanced, AI-powered search tools.

Find your dream stay

Find your dream stay

Explore 15 million+ rentals, the world’s biggest selection of holiday homes.

Popular holiday rental amenities in Chicago

  • Kitchen (841)
  • Washing machine (1,099)
  • WiFi (2,380)
  • Air conditioning (2,401)
  • TV (2,080)
  • Parking (102)
  • Fireplace (307)
  • Pet-friendly (903)
  • No smoking (2,325)
  • Dishwasher (346)
  • Cot (682)
  • Balcony/patio (433)

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 enjoy soaking in the hot tub , as 67 of the lettings there include Jacuzzi.

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. $446 is the highest price average in the next twelve months. Prices decrease in a week of May (03/05 – 10/05), where average prices are $384.

Rental availability information in Chicago

Check how busy Chicago is with our availability graph. Be careful if you plan to go to Chicago in December, as it comprises the busiest week of the next 6 months (06/12 – 13/12). On the contrary, you will find the highest number of available rentals in a week of May (24/05 – 31/05).

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!

1,179,821 reviews
Chicago holiday lettings have an average rating of 4/5 across 1,179,821 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 $44 per night.

How many holiday accommodation offers will I find in Chicago?

Visit Chicago in July 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 15 holiday rental offers in Chicago, with plenty of Apartment rental and House rental available.

Are pets permitted in holiday accommodation in Chicago?

There are 0 pet-friendly holiday accommodation offers in Chicago, costing $0 per night on average.

Top holiday destinations in Chicago

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