Chicago Condo Rentals - HomeToGo base64Hash Chicago Condo Rentals - HomeToGo

Chicago Condo Rentals

Find 5,331 available offers from 29 partners
Chicago
Anytime
Guests

Choose the perfect vacation rental

Price per night
Up to $100
$100 - $199
From $200
Accommodation types
Apartment
Bed & Breakfast
Private room
Distance to center
Max. 1 km
Max. 2 km
Max. 5 km
Rating
Outstanding: 4.5+
Very Good: 4+
Good: 3.5+

Chicago Condo Rental: Enjoy a Fun and Cultural Trip

The historic city of Chicago boasts a fabulous skyline and a profusion of world-class museums, art galleries, jazz clubs, and playhouses. A walk through downtown Chicago will reveal some of the world's best architectural styles: Gothic, classic, modernist, and more.

The winds that blow across Lake Michigan have earned Chicago a nickname as the Windy City. Check in at your Chicago condo and find out what the fuss is all about.

Show all 5,331 properties
Save up to 59%

Best Vacation Home Deals Chicago

Apartment South Loop
Jan. 14 - Jan. 21
-50%
$700
$352 per night
Apartment ∙ 5 guests ∙ 2 bedrooms
South Loop, Chicago, Illinois, United States
Details
Kasa Living
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Apartment South Loop
Jan. 14 - Jan. 21
-58%
$554
$231 per night
Apartment ∙ 3 guests ∙ 1 bedroom
South Loop, Chicago, Illinois, United States
Details
Kasa Living
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Apartment South Loop
Jan. 14 - Jan. 21
-59%
$581
$239 per night
Apartment ∙ 2 guests ∙ 1 bedroom
South Loop, Chicago, Illinois, United States
Details
Kasa Living
View deal

5,331 wonderful vacation homes from 29 providers, such as Casamundo or Booking.com, are listed in Chicago. By directly analyzing these accommodations, HomeToGo features the best deals and the highest rated vacation homes in Chicago.

Book Vacation Rentals with the Highest User Rating

Top-Rated Offers and Accommodations Chicago

Apartment New East Side
Jun. 25 - Jul. 2
-52%
$2,979
$1,428 per night
Apartment ∙ 8 guests ∙ 3 bedrooms
5.0
"Excellent" (2 ratings)
New East Side, Chicago, Illinois, United States
Details
HomeToGo
View deal

Recommended Vacation Rentals Chicago

Find your perfect vacation rental Chicago: from $47 per night

Apartment South Loop
Jan. 14 - Jan. 21
-50%
$709
$355 per night
Apartment ∙ 5 guests ∙ 2 bedrooms
South Loop, Chicago, Illinois, United States
Details
Kasa Living
View deal
Apartment South Loop
Jan. 14 - Jan. 21
-58%
$554
$233 per night
Apartment ∙ 3 guests ∙ 1 bedroom
South Loop, Chicago, Illinois, United States
Details
Kasa Living
View deal
Apartment Near North
Feb. 4 - Feb. 11
-38%
$433
$268 per night
Apartment ∙ 2 guests ∙ 1 bedroom
Near North, Chicago, Illinois, United States
Details
Kasa Living
View deal
Apartment South Loop
Jan. 14 - Jan. 21
-59%
$591
$242 per night
Apartment ∙ 2 guests ∙ 1 bedroom
South Loop, Chicago, Illinois, United States
Details
Kasa Living
View deal
Apartment Near North
Jan. 14 - Jan. 21
-45%
$438
$243 per night
Apartment ∙ 2 guests ∙ 1 bedroom
Near North, Chicago, Illinois, United States
Details
Kasa Living
View deal
Apartment South Loop
Jan. 14 - Jan. 21
-50%
$497
$248 per night
Apartment ∙ 2 guests ∙ 1 bedroom
3.8
"Good" (73 ratings)
South Loop, Chicago, Illinois, United States
Free cancellation
Details
travelstaytion
View deal
Apartment South Loop
Jan. 14 - Jan. 21
-51%
$598
$293 per night
Apartment ∙ 3 guests ∙ 1 bedroom
South Loop, Chicago, Illinois, United States
Details
Kasa Living
View deal
Apartment Near North
Jan. 14 - Jan. 21
-50%
$528
$265 per night
Apartment ∙ 2 guests ∙ 1 bedroom
Near North, Chicago, Illinois, United States
Details
Kasa Living
View deal
Apartment South Loop
$556 per night
Apartment ∙ 6 guests ∙ 3 bedrooms
South Loop, Chicago, Illinois, United States
Details
Kasa Living
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Vacation rentals with Wi-Fi

Apartment Internet South Loop
Jan. 14 - Jan. 21
-47%
$460
$242 per night
Apartment ∙ 2 guests ∙ 1 bedroom
South Loop, Chicago, Illinois, United States
Internet
Details
Kasa Living
View deal
Apartment Internet South Loop
Jan. 14 - Jan. 21
-50%
$708
$354 per night
Apartment ∙ 5 guests ∙ 2 bedrooms
South Loop, Chicago, Illinois, United States
Internet
Details
Kasa Living
View deal
Apartment Internet South Loop
Jan. 14 - Jan. 21
-59%
$560
$233 per night
Apartment ∙ 3 guests ∙ 1 bedroom
South Loop, Chicago, Illinois, United States
Internet
Details
Kasa Living
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Apartments and vacation rentals with a kitchen

Apartment Kitchen South Loop
Jan. 14 - Jan. 21
-50%
$646
$325 per night
Apartment ∙ 3 guests ∙ 2 bedrooms
3.8
"Good" (27 ratings)
South Loop, Chicago, Illinois, United States
Free cancellation
Kitchen
Details
travelstaytion
View deal
Apartment Kitchen Near North
Feb. 25 - Mar. 4
-17%
$411
$343 per night
Apartment ∙ 3 guests ∙ 1 bedroom
Near North, Chicago, Illinois, United States
Kitchen
Details
Kasa Living
View deal
Apartment Kitchen Near North
Feb. 1 - Feb. 8
-40%
$442
$264 per night
Apartment ∙ 2 guests ∙ 1 bedroom
Near North, Chicago, Illinois, United States
Kitchen
Details
Kasa Living
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Vacation rentals with a fireplace

Apartment Fireplace Streeterville
Jul. 4 - Jul. 11
-54%
$3,015
$1,401 per night
Apartment ∙ 8 guests ∙ 3 bedrooms
3.5
"Good" (19 ratings)
Streeterville, Chicago, Illinois, United States
Fireplace
Details
travelstaytion
View deal
Apartment Fireplace Streeterville
Jul. 4 - Jul. 11
-51%
$2,397
$1,167 per night
Apartment ∙ 6 guests ∙ 2 bedrooms
3.5
"Good" (48 ratings)
Streeterville, Chicago, Illinois, United States
Fireplace
Details
travelstaytion
View deal
Apartment Fireplace New East Side
Jun. 20 - Jun. 27
-55%
$3,284
$1,489 per night
Apartment ∙ 8 guests ∙ 3 bedrooms
3.5
"Good" (60 ratings)
New East Side, Chicago, Illinois, United States
Fireplace
Details
travelstaytion
View deal
See all offers

Popular Rental Amenities Chicago

  • Internet (5,581)
  • Air conditioning (5,071)
  • TV (4,726)
  • No smoking (3,157)
  • Microwave (2,419)
  • Pool (1,787)
  • No pets (1,771)
  • Wheelchair access (1,703)
  • Kitchen (1,661)
  • Crib (1,503)
  • Washer (1,468)
  • Pet allowed (1,227)

If you travel with your pet, you can easily search and find a pet-friendly rental Chicago. Hotel rooms are the most pet-friendly property type in Chicago. Also, a night in a pet-friendly rental there is, on average, $512. There's no need to look only outside the city for a rental, as a few of the pet-friendly vacation rentals are very central (less than 2 kilometres from the city centre).

Price and Availability Index in Chicago

Vacation Rental Price Information Chicago

We analyzed vacation houses, cottages and apartments to display a price graph showing the average price per night Chicago. The most expensive week of the next 12 months is in July (7/23 - 7/30), where prices hit an average of $679 a night. In January (1/14 - 1/21), prices will hit an average low of $268 per night.

Rental Availability Information Chicago

This graph shows the vacation rental availability rate for the next twelve months. The busiest time to book a rental Chicago so far is in June (6/4 - 6/11), where only 24% rentals are available. Conversely, you will find the highest percentage of available offers Chicago in October (10/29 - 11/5).

The Weather Chicago

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8 days 8
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-6°
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Jan.
Feb.
Mar.
Apr.
May
June
July
Aug.
Sep.
Oct.
Nov.
Dec.
- Rainy days

Above are the weather conditions for Chicago. In July maximum temperatures go higher than 30°. On the contrary, the coolest month is February. February is the driest month.

7-Day Weather Forecast Chicago

Sat., 28 May
24°
13°

5%

10 h

8 km/h

Sun., 29 May
29°
18°

15%

7 h

23 km/h

Mon., 30 May
30°
21°

0%

7 h

23 km/h

Tue., 31 May
30°
23°

15%

4 h

19 km/h

Wed., 1 Jun.
17°
12°

15%

0 h

10 km/h

Thu., 2 Jun.
19°
12°

15%

8 h

9 km/h

Fri., 3 Jun.
24°
15°

0%

15 h

6 km/h

Where to find the best food Chicago?

Chicago Cuisine

The world comes to Chicago for gastronomical expertise, so indulge those taste buds! Devon Avenue is the place for Indian delights, and a mix of everything is served in Uptown, including American, Ghanaian, Nigerian, Japanese, and even Swedish delicacies.

Don't miss the world-famous Chicago-style deep-dish pizza, and devour some iconic Chicago hot dogs at Vienna Beef Factory Deli and Portillo's. Chicago is a drinking city that is home to a record number of dive bars, lounges, and breweries, the best of them found in the Logan Square and Bucktown areas.

What is the weather like Chicago?

A Good Time to Visit

The best time to visit Chicago is in spring and fall, when the weather is pleasant and prices of vacation rentals are reasonable. Moreover, plenty of cultural activities take place in those seasons. If you intend to visit during summer, book your accommodation well in advance, as this is the most popular visiting season. Chicago can be just as magical in winter, making it a true year-round city.

What are the top sights Chicago?

Things to Do and See

The city's most popular attraction is the Lincoln Park Zoo, which houses African apes and other interesting species. Trivia lovers will be impressed to learn that Chicago is home to three out of America's five tallest buildings: the Sears Tower, Trump Tower, and the Aon Center.

Chicago's international neighborhoods are so true-to-life, you'd be forgiven for thinking you were genuinely in another country. There's Chinatown, the Korean community in Lawrence Avenue, the Swedish settlement at Andersonville, Little Italy, Greektown, and several other international pockets. The Polish Cathedrals of St. Mary of the Angels in Bucktown and St. Hyacinth Basilica in Avondale are exquisite. Experience the different facets of the city with guided architecture walks or a river boat tour.

What are the best places to discover the arts and culture of Chicago?

Art and Culture in the City

Art and history enthusiasts will have plenty of choice with the variety of art galleries and museums scattered across the city. The Art Institute of Chicago in the Loop district houses priceless Impressionist and Modernist works, and there's also the National Museum of Mexican Art in Pilsen, the Museum of Photography, the Polish Museum of America in Wicker Park, the International Museum of Surgical Science, and more. Buy the Chicago CityPASS to save money if you plan on visiting several attractions in a short span of time.

For improvisational comedy and performance art, catch a show at The Annoyance Theater, I.O., or the Playground. Steppenwolf in Lincoln Park is more serious, having hosted the likes of John Malkovich. Visit the Auditorium in the Loop for its architecture and brilliant use of performance space. For rock, blues, jazz, and spoken-word performances, the Chicago Theater awaits.

What are the best activities for families Chicago?

Special Tips for Activities with Children

There's no shortage of options to entertain your family if you're visiting Chicago with kids who love animals. Shedd Aquarium is both exciting and educational for kids, with fun interactive displays, live shows, play zones, and exhibits on marine life around the world. Brookfield Zoo is a vast, 216-acre nature park in Chicagoland that's home to hundreds of different animals, a fun motor safari tram, a huge butterfly world, and the Family Play Zoo where you can dress up as zookeepers or furry friends. Closer to downtown, historic Lincoln Park Zoo has exotic creatures like red pandas, snow monkeys, leopards, a classic carousel, and other fun rides.

A ride for kids of all ages is the Navy Pier's Centennial Wheel, which gives fantastic city views topped only by heading up to 360 Chicago on the 94th floor of the John Hancock Tower on Michigan Avenue. For a different perspective of Chicago, hop on board the Tall Ship Windy at Navy Pier and enjoy great city views from Lake Michigan aboard an authentic 4-mast schooner. Kids can even join in and hoist the sails themselves!

The world-class Chicago Children's Museum has hands-on, interactive displays and exhibits, including the popular ""Dinosaur Expedition"" where kids can join an archaeological dig and explore a real fossil pit. The Adler Planetarium lets kids have the feeling of going to outer space without even leaving Chicago, and LEGOLAND Chicago is a toy wonderland with life-sized LEGO displays, interactive areas, and a 4D theatre.

What are the best events and festivals Chicago?

Regular Events and Festivities

The year begins with colorful Chinese New Year celebrations and the highly-awaited Chicago Auto Show. April brings the Chicago Improv Festival and C2E2 Chicago Comic & Entertainment Expo. The summer months are chock-full with events, including the Puerto Rican Parade & Festival, Chicago Blues Festival, and Chicago Pride Fest in June, followed by the Square Roots Festival in July, and Lollapalooza and the Chicago Jazz Festival in August.

Film lovers and athletes should watch out for the Chicago International Film Festival and the Chicago Marathon in October. The year ends on a whimsical note with Christkindlmarket, the Magnificent Mile Lights Festival, and the Winter WonderFest at Navy Pier, where the entire city is adorned with lights.

Book a Chicago condo rental for an unforgettable time in the Windy City!

What are the must-see attractions Chicago?

Chicago: Culture in the Windy City

360 Chicago Observation Deck

What better to way to see the city than from above? Travel up to the 94th floor of the John Hancock Center for stunning views of the city and over Lake Michigan.

Museum of Science and Industry

At this interactive museum you'll find a life-size replica coal mine and recreated historic Chicago streets with functional shops.

Cloud Gate

One of the most iconic pieces of art in the United States, Cloud Gate was created by Anish Kapoor. This beautiful reflective sculpture is nicknamed 'The Bean' due to its shape.

Millennium Park

This urban park in the center of Chicago is a great place to wile away an afternoon amidst a tranquil backdrop. Concerts, local fairs, and fun events are held regularly at the park.

Art Institute of Chicago

As one of the oldest and largest galleries in the country, this impressive museum showcases over 300,000 artworks. Modern art, photography, ancient sculptures, and more feature.

Frequently Asked Questions

What is the typical price of a vacation home Chicago?

The starting price for Apartment rentals or Bed & Breakfast rentals Chicago is $47 per night.

What is the typical availability of Apartment rentals Chicago?

October has the highest availability of Apartment rentals Chicago, so you can expect plenty of selection, even for last-minute bookings.

What are the most popular vacation home amenities Chicago?

When looking to book a vacation home Chicago, the most requested amenities include Internet, TV, and Pool.

How many Apartment rentals and Bed & Breakfast rentals can I find Chicago?

Chicago has 5,326 Apartment rentals and Bed & Breakfast rentals available to book.

Are there pet-friendly vacation rentals Chicago?

Yes, there are 1,350 pet-friendly vacation rentals Chicago, with an average nightly price of $512.

What's the best month to visit Chicago?

The warmest time of year Chicago is July and August, with the nightly price of a vacation home starting at $47.

We list offers from thousands of providers, including:

Booking.com Vacation Rentals Chicago TripAdvisor Vacation Rentals Chicago Vrbo Vacation Rentals Chicago Novasol Vacation Rentals Chicago Inter Chalet Vacation Rentals Chicago EveryStay Vacation Rentals Chicago Interhome Vacation Rentals Chicago 9flats.com Vacation Rentals Chicago HouseTrip Vacation Rentals Chicago Belvilla Vacation Rentals Chicago Sykes Cottages Vacation Rentals Chicago Homestay.com Vacation Rentals Chicago Ski Planet Vacation Rentals Chicago Only-apartments Vacation Rentals Chicago James Villa Holidays Vacation Rentals Chicago

Vacation Destinations Near Chicago

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