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Chicago Condo Rentals

Find 8,338 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 & Breakfast
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.

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Save up to 34%

Best Vacation Home Deals Chicago

Apartment Tri-Taylor
Jun. 17 - Jun. 24
-22%
$886
$694 per night
Apartment ∙ 4 guests ∙ 3 bedrooms
Pleasant Apartment in Tri-Taylor
Tri-Taylor, Chicago, Illinois, United States
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Condo Tri-Taylor
Sep. 9 - Sep. 16
-30%
$736
$516 per night
Condo ∙ 6 guests ∙ 2 bedrooms
Condo in Tri-Taylor
4.9
"Excellent" (69 ratings)
Tri-Taylor, Chicago, Illinois, United States
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Apartment Tri-Taylor
Oct. 21 - Oct. 28
-34%
$605
$400 per night
Apartment ∙ 4 guests ∙ 2 bedrooms
Charming Rental Apartment in Tri-Taylor
4.0
"Very good" (7 ratings)
Tri-Taylor, Chicago, Illinois, United States
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8,338 wonderful vacation homes from 12 providers, such as Booking.com or HomeToGo, 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 University Village / Little Italy
$408 per night
Apartment ∙ 8 guests ∙ 4 bedrooms
Apartment in University Village / Little Italy
5.0
"Excellent" (242 ratings)
University Village / Little Italy, Chicago, Illinois, United States
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Condo West Town
$511 per night
Condo ∙ 9 guests ∙ 2 bedrooms
Condo in West Town with Private Terrace + Skyline View
5.0
"Excellent" (187 ratings)
West Town, Chicago, Illinois, United States
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Condo Buena Park
$222 per night
Condo ∙ 6 guests ∙ 3 bedrooms
Condo in Buena Park
4.9
"Excellent" (162 ratings)
Buena Park, Chicago, Illinois, United States
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Recommended Vacation Rentals Chicago

Find your perfect vacation rental Chicago: from $60 per night

Aparthotel Near North
$888 per night
Aparthotel ∙ 8 guests ∙ 3 bedrooms
Aparthotel in Near North with Grill, Pool & Sauna, Near John Hancock Center
4.9
"Excellent" (137 ratings)
Near North, Chicago, Illinois, United States
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Condo West Town
$516 per night
Condo ∙ 9 guests ∙ 2 bedrooms
Condo in West Town with Private Terrace + Skyline View
5.0
"Excellent" (187 ratings)
West Town, Chicago, Illinois, United States
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Apartment University Village / Little Italy
$417 per night
Apartment ∙ 8 guests ∙ 4 bedrooms
Apartment in University Village / Little Italy
5.0
"Excellent" (241 ratings)
University Village / Little Italy, Chicago, Illinois, United States
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Condo Buena Park
$224 per night
Condo ∙ 6 guests ∙ 3 bedrooms
Condo in Buena Park
4.9
"Excellent" (162 ratings)
Buena Park, Chicago, Illinois, United States
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House Avondale
$243 per night
House ∙ 4 guests ∙ 2 bedrooms
House in Avondale with Grill & Yard
5.0
"Excellent" (66 ratings)
Avondale, Chicago, Illinois, United States
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House Old Town Triangle
$231 per night
House ∙ 4 guests ∙ 1 bedroom
Vacation Home in Old Town Triangle with Yard
4.7
"Outstanding" (49 ratings)
Old Town Triangle, Chicago, Illinois, United States
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Apartment Roscoe Village
$176 per night
Apartment ∙ 4 guests ∙ 2 bedrooms
Family Friendly Rental Apartment in Roscoe Village with Grill & Yard
5.0
"Excellent" (156 ratings)
Roscoe Village, Chicago, Illinois, United States
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Apartment West Ridge
$137 per night
Apartment ∙ 4 guests ∙ 2 bedrooms
Family Friendly Modern Rental Apartment in West Ridge with Free Parking
West Ridge, Chicago, Illinois, United States
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Apartment West Town
$234 per night
Apartment ∙ 4 guests ∙ 4 bedrooms
Spacious Apartment in West Town with Yard
4.9
"Excellent" (23 ratings)
West Town, Chicago, Illinois, United States
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Find Fantastic yet Inexpensive Rentals

Budget-friendly Rentals Chicago

House Avondale
$241 per night
House ∙ 4 guests ∙ 2 bedrooms
House in Avondale with Grill & Yard
5.0
"Excellent" (67 ratings)
Avondale, Chicago, Illinois, United States
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House Old Town Triangle
$229 per night
House ∙ 4 guests ∙ 1 bedroom
Vacation Home in Old Town Triangle with Yard
4.7
"Outstanding" (49 ratings)
Old Town Triangle, Chicago, Illinois, United States
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Apartment Roscoe Village
$175 per night
Apartment ∙ 4 guests ∙ 2 bedrooms
Family Friendly Rental Apartment in Roscoe Village with Grill & Yard
5.0
"Excellent" (157 ratings)
Roscoe Village, Chicago, Illinois, United States
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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 Air conditioning Heart of Chicago
$260 per night
Apartment ∙ 4 guests ∙ 2 bedrooms
Apartment in Heart Of Chicago
4.8
"Excellent" (90 ratings)
Heart of Chicago, Chicago, Illinois, United States
Air conditioning
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Apartment Air conditioning Marshall Square
$207 per night
Apartment ∙ 4 guests ∙ 1 bedroom
Apartment in Marshall Square with Grill
Marshall Square, Chicago, Illinois, United States
Air conditioning
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Apartment Air conditioning Oak Park
$190 per night
Apartment ∙ 4 guests ∙ 2 bedrooms
Nice Apartment in Oak Park
4.8
"Excellent" (39 ratings)
Oak Park, Oak Park Township, Illinois, United States
Air conditioning
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Apartments with a balcony or patio

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

House Balcony/Patio Fifth City
$296 per night
House ∙ 5 guests ∙ 3 bedrooms
Charming Vacation Home in Fifth City with Grill & Yard
5.0
"Excellent" (4 ratings)
Fifth City, Chicago, Illinois, United States
Balcony/Patio
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House Balcony/Patio Berwyn
$315 per night
House ∙ 8 guests ∙ 4 bedrooms
House in Berwyn with Yard
5.0
"Excellent" (2 ratings)
Berwyn, Cook County, Illinois, United States
Balcony/Patio
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House Balcony/Patio North Lawndale
$645 per night
House ∙ 4 guests ∙ 5 bedrooms
Family Friendly Vacation Home in North Lawndale with Grill & Yard
4.0
"Very good" (1 rating)
North Lawndale, Chicago, Illinois, United States
Balcony/Patio
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Vacation homes and cottages with a garden

Looking for vacation homes with a little extra outdoor space? Check out these accommodations Chicago with private yards.

Apartment Yard Berwyn
$207 per night
Apartment ∙ 6 guests ∙ 2 bedrooms
Beautiful Apartment in Berwyn with Yard
5.0
"Excellent" (41 ratings)
Berwyn, Cook County, Illinois, United States
Yard
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Apartment Yard Little Village
$119 per night
Apartment ∙ 4 guests ∙ 2 bedrooms
Rental Apartment in Little Village with Yard
Little Village, Chicago, Illinois, United States
Yard
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House Yard The Island
$174 per night
House ∙ 8 guests ∙ 3 bedrooms
Wonderful Vacation Home in The Island with Yard
4.5
"Outstanding" (4 ratings)
The Island, Chicago, Illinois, United States
Yard
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Popular Rental Amenities Chicago

  • Internet (8,247)
  • Pool (2,355)
  • Kitchen (4,076)
  • TV (7,787)
  • Air conditioning (7,530)
  • Parking (1,549)
  • Washer (4,385)
  • Pets allowed (2,030)
  • Balcony/Patio (1,722)
  • Microwave (4,615)
  • Dishwasher (2,926)
  • No smoking (5,027)

If you travel with your pet, you can easily search and find a pet-friendly rental Chicago. Apartment rentals are the most pet-friendly property type in Chicago. Also, a night in a pet-friendly rental there is, on average, $537. There's no need to look only outside the city for a rental, as nearly a quarter 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 September (9/30 - 10/7), where prices hit an average of $766 a night. In January (1/6 - 1/13), prices will hit an average low of $288 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 May (5/25 - 6/1), where only 22% rentals are available. Conversely, you will find the highest percentage of available offers Chicago in September (9/23 - 9/30).

The Weather Chicago

max.
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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

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 Chicago

Sun., 4 Jun.
25°
18°

0%

14 h

17 km/h

Mon., 5 Jun.
25°
15°

0%

11 h

8 km/h

Tue., 6 Jun.
21°
16°

10%

1 h

9 km/h

Wed., 7 Jun.
22°
16°

10%

8 h

10 km/h

Thu., 8 Jun.
21°
14°

10%

15 h

12 km/h

Fri., 9 Jun.
23°
16°

0%

14 h

10 km/h

Sat., 10 Jun.
26°
18°

15%

8 h

13 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.

Information about vacation rentals Chicago

🏡 Vacation rentals available 8,294 properties
💳 Discounts available up to 34%
🌙 Price per night from $117
⭐ Popular amenities Internet, Pool and Kitchen
🐾 Pet friendly accommodation options 1,963 properties
🏊 Vacation rentals with pools 2,290 properties

Frequently Asked Questions

What is the typical price of a vacation home Chicago?

The starting price for Apartment rentals or House rental Chicago is $117 per night.

What is the typical availability of Apartment rentals Chicago?

September 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, Pool, and Kitchen.

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

Chicago has 8,294 Apartment rentals and House rental available to book.

Are there pet-friendly vacation rentals Chicago?

Yes, there are 1,963 pet-friendly vacation rentals Chicago, with an average nightly price of $537.

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 $117.

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 Interhome Vacation Rentals Chicago HouseTrip Vacation Rentals Chicago Belvilla Vacation Rentals Chicago Homestay.com Vacation Rentals Chicago Ski Planet Vacation Rentals Chicago Only-apartments Vacation Rentals Chicago James Villa Holidays Vacation Rentals Chicago

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