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Chicago Condo Rentals

Find 9,358 available offers from 12 partners
Chicago
Anytime
Guests

Choose the perfect vacation rental

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+

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 9,365 properties

Best Vacation Home Deals in Chicago

Save up to 45%

Resort Archer Heights
Dec 12 - Dec 19
-29%
$190
$136 per night
Resort ∙ 10 guests ∙ 1 bedroom

Resort in Archer Heights

3.8
Good
Archer Heights, Chicago, Illinois, United States
Details
Agoda
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Apartment McKinley Park
Jan 14 - Jan 21
-45%
$408
$224 per night
Apartment ∙ 2 guests ∙ 1 bedroom

Apartment in Mckinley Park with Yard

McKinley Park, Chicago, Illinois, United States
Free cancellation
Details
HomeToGo
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9,358 wonderful vacation homes from 12 providers, such as Booking.com or Abritel, are listed in Chicago. By directly analyzing these accommodations, HomeToGo features the best deals and the highest rated vacation homes in Chicago.

Top-Rated Offers and Accommodations in Chicago

Book Vacation Rentals with the Highest User Rating

Condo The Gap
$129 per night
Condo ∙ 5 guests ∙ 2 bedrooms

Condo in The Gap

4.8
Outstanding (29 ratings)
The Gap, Chicago, Illinois, United States
Details
Vrbo
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House Palmer Square
$578 per night
House ∙ 10 guests ∙ 5 bedrooms

Wonderful House in Palmer Square with Grill

4.9
Outstanding (6 ratings)
Palmer Square, Chicago, Illinois, United States
Details
Vrbo
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House Fifth City
Jan 6 - Jan 13
-29%
$464
$327 per night
House ∙ 5 guests ∙ 3 bedrooms

Vacation Home in Fifth City with Grill & Yard

5.0
Outstanding (1 rating)
Fifth City, Chicago, Illinois, United States
Details
HomeToGo
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Recommended Vacation Rentals in Chicago

Find your perfect vacation rental in Chicago: from $40 per night

Apartment Washington Park
$141 per night
Apartment ∙ 4 guests ∙ 2 bedrooms

Apartment in Washington Park

Washington Park, Chicago, Illinois, United States
Details
Vrbo
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House North Austin
$438 per night
House ∙ 12 guests ∙ 4 bedrooms

Nice House in North Austin with Yard & Grill

North Austin, Chicago, Illinois, United States
Details
Vrbo
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House Humboldt Park
$225 per night
House ∙ 10 guests ∙ 3 bedrooms

House in Humboldt Park with Pool, Grill & Sauna + Degree Views

Humboldt Park, Chicago, Illinois, United States
Details
Vrbo
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Apartment Ashburn
$106 per night
Apartment ∙ 4 guests ∙ 2 bedrooms

Rental Rental Apartment in Ashburn

Ashburn, Chicago, Illinois, United States
Details
Vrbo
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Apartment West Ridge
$74 per night
Apartment ∙ 2 guests ∙ 1 bedroom

Apartment in West Ridge

West Ridge, Chicago, Illinois, United States
Details
Vrbo
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House Beverly
$308 per night
House ∙ 10 guests ∙ 4 bedrooms

Vacation Home in Beverly with Grill

4.2
Very good (14 ratings)
Beverly, Chicago, Illinois, United States
Details
Vrbo
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House Avalon Park
Dec 16 - Dec 23
$467 per night
House ∙ 15 guests ∙ 4 bedrooms

Nice House in Avalon Park with Grill & Yard

Avalon Park, Chicago, Illinois, United States
Details
HomeToGo
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Apartment East Garfield Park
Dec 16 - Dec 23
$166 per night
Apartment ∙ 6 guests ∙ 1 bedroom

Rental Apartment in East Garfield Park

East Garfield Park, Chicago, Illinois, United States
Free cancellation
Details
Agoda
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Apartment Tri-Taylor
Jan 13 - Jan 20
-59%
$435
$177 per night
Apartment ∙ 4 guests ∙ 2 bedrooms

Apartment in Tri-Taylor

Tri-Taylor, Chicago, Illinois, United States
Free cancellation
Details
Agoda
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Budget-friendly Rentals in Chicago

Find Fantastic yet Inexpensive Rentals

House The Island
$173 per night
House ∙ 8 guests ∙ 3 bedrooms

Wonderful Vacation Home in The Island with Yard

The Island, Chicago, Illinois, United States
Details
Vrbo
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Apartment Tri-Taylor
$226 per night
Apartment ∙ 6 guests ∙ 2 bedrooms

Apartment in Tri-Taylor

Tri-Taylor, Chicago, Illinois, United States
Details
Vrbo
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House Washington Park
$642 per night
House ∙ 8 guests ∙ 3 bedrooms

House in Washington Park with Yard

Washington Park, Chicago, Illinois, United States
Details
Vrbo
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Apartments and vacation rentals with a kitchen

Cook up a feast on your next vacation and book a Chicago rental with full kitchen.

Apartment  North Lawndale
Dec 16 - Dec 23
-39%
$345
$209 per night
Apartment ∙ 4 guests ∙ 2 bedrooms

Apartment in North Lawndale

North Lawndale, Chicago, Illinois, United States
Free cancellation
Kitchen
Details
Agoda
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Apartment  Brighton Park
Dec 16 - Dec 23
-21%
$211
$167 per night
Apartment ∙ 4 guests ∙ 1 bedroom

Charming Rental Apartment in Brighton Park

Brighton Park, Chicago, Illinois, United States
Kitchen
Details
Agoda
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Apartment  North Lawndale
Feb 10 - Feb 17
-27%
$446
$326 per night
Apartment ∙ 11 guests ∙ 5 bedrooms

Rental Apartment in North Lawndale

North Lawndale, Chicago, Illinois, United States
Free cancellation
Kitchen
Details
Agoda
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Vacation rentals and apartments with air conditioning

Keep cool during your trip to Chicago and book a vacation rental with air conditioning.

Apartment  East Garfield Park
Dec 30 - Jan 6
$393 per night
Apartment ∙ 4 guests ∙ 2 bedrooms

Wonderful Apartment in East Garfield Park

East Garfield Park, Chicago, Illinois, United States
Air conditioning
Details
Agoda
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Apartment  North Lawndale
Mar 9 - Mar 16
$229 per night
Apartment ∙ 8 guests ∙ 3 bedrooms

Charming Apartment in North Lawndale

North Lawndale, Chicago, Illinois, United States
Free cancellation
Air conditioning
Details
Agoda
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Apartment  Tri-Taylor
Jan 20 - Jan 27
$272 per night
Apartment ∙ 4 guests ∙ 2 bedrooms

Lovely Rental Apartment in Tri-Taylor

Tri-Taylor, Chicago, Illinois, United States
Free cancellation
Air conditioning
Details
Agoda
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Apartments with a balcony or patio

Looking for a home with a balcony? Check out these vacation homes in Chicago with their own private patios and balconies.

House  South Shore
Dec 16 - Dec 23
-16%
$301
$254 per night
House ∙ 4 guests ∙ 2 bedrooms

House in South Shore with Grill & Yard

South Shore, Chicago, Illinois, United States
Balcony/Patio
Details
HomeToGo
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House  Wicker Park
Jan 25 - Feb 1
-72%
$2,159
$616 per night
House ∙ 10 guests ∙ 6 bedrooms

House in Wicker Park with Yard

Wicker Park, Chicago, Illinois, United States
Free cancellation
Balcony/Patio
Details
HomeToGo
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Apartment  Chicago Loop
Dec 16 - Dec 23
$436 per night
Apartment ∙ 2 guests ∙ 1 bedroom

Wonderful Apartment in Chicago Loop with Patio, Next to Cloud Gate

Chicago Loop, Chicago, Illinois, United States
Balcony/Patio
Details
HousingAnywhere
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Popular Rental Amenities in Chicago

  • WiFi (9,005)
  • Pool (2,350)
  • Kitchen (5,131)
  • TV (8,684)
  • Air conditioning (8,452)
  • Parking (1,604)
  • Washing machine (5,135)
  • Pet-friendly (2,101)
  • Balcony/patio (1,841)
  • Microwave (5,232)
  • Dishwasher (3,466)
  • No smoking (5,264)

If you travel with your pet, you can easily search and find a pet-friendly rental in Chicago. Apartment rental are the most pet-friendly property type in Chicago. Also, a night in a pet-friendly rental there is, on average, $459. There's no need to look only outside the city for a rental, as more than a fifth of the pet-friendly vacation rentals are very central (less than 2 kilometres from the city centre).

Price and Availability Index in Chicago

Click on any bar to see price and availability information

Vacation Rental Price Information in Chicago

We analyzed vacation houses, cottages and apartments to display a price graph showing the average price per night in Chicago. The most expensive week of the next 12 months is in October (10/5 – 10/12), where prices hit an average of $811 a night. In January (1/27 – 2/3), prices will hit an average low of $278 per night.

Rental availability information in Chicago

This graph shows the vacation rental availability rate for the next twelve months. The busiest time to book a rental in Chicago so far is in November (11/30 – 12/7), where only 27% rentals are available. Conversely, you will find the highest percentage of available offers in Chicago in February (2/24 – 3/2).

The Weather in Chicago

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Aug.
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- Rainy days

Above are the weather conditions for Chicago. In July maximum temperatures go higher than 29°. On the contrary, the coolest month is January. February is the driest month.

7-Day Weather Forecast in Chicago

Sun., 10 Dec.
-1°

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15 km/h

Mon., 11 Dec.
-2°

0%

4 h

8 km/h

Tue., 12 Dec.

10%

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13 km/h

Wed., 13 Dec.

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5 h

5 km/h

Thu., 14 Dec.

0%

5 h

7 km/h

Fri., 15 Dec.

15%

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Sat., 16 Dec.

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5 km/h

Where to find the best food in 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 in 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 in 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 in 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 in 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 in 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.

Information about vacation rentals in Chicago

🏡 Vacation rentals available 9,365 homes
💳 Possible discounts up to 45%
🌙 Nightly prices starting at $40
⭐ Popular amenities Internet, Pool and Kitchen
🐾 Pet friendly homes 2,093 homes
🏊 Vacation rentals with pools 2,355 homes

Frequently Asked Questions

What is the typical price of a vacation home in Chicago?

The starting price for Apartment rental or House rental in Chicago is $40 per night.

What is the typical availability of Apartment rental in Chicago?

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

What are the most popular vacation home amenities in Chicago?

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

How many Apartment rental and House rental can I find in Chicago?

Chicago has 9,365 Apartment rental and House rental available to book.

Are there pet-friendly vacation rentals in Chicago?

Yes, there are 2,093 pet-friendly vacation rentals in Chicago, with an average nightly price of $459.

What's the best month to visit Chicago?

The warmest time of year in Chicago is July and August, with the nightly price of a vacation home starting at $40.

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