Chicago Condo Rentals - HomeToGo base64Hash Chicago Condo Rentals - HomeToGo

Chicago Condo Rentals

Find 8,804 available offers from 10 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.

Show all 8,727 properties
Save up to 62%

Best Vacation Home Deals Chicago

Apartment Near North
Feb. 4 - Feb. 11
-62%
$511
$197 per night
Apartment ∙ 3 guests ∙ 1 bedroom
Apartment in Near North with On-Site Parking, Close to John Hancock Center
5.0
"Excellent" (2 ratings)
Near North, Chicago, Illinois, United States
Details
Vrbo
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Apartment Near North
Feb. 4 - Feb. 11
-62%
$442
$169 per night
Apartment ∙ 2 guests ∙ 1 bedroom
Lovely Apartment in Near North with On-Site Parking, Next to John Hancock Center
Near North, Chicago, Illinois, United States
Details
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House Woodlawn
Feb. 4 - Feb. 11
-38%
$204
$127 per night
House ∙ 4 guests ∙ 2 bedrooms
Pleasant Vacation Home in Woodlawn with Free Parking
4.9
"Excellent" (25 ratings)
Woodlawn, Chicago, Illinois, United States
Details
Vrbo
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8,804 wonderful vacation homes from 10 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 Logan Square
Jul. 22 - Jul. 29
-22%
$271
$211 per night
Apartment ∙ 4 guests ∙ 2 bedrooms
Pleasant Rental Apartment in Logan Square with Yard
4.7
"Outstanding" (58 ratings)
Logan Square, Chicago, Illinois, United States
Details
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House West Loop
Jul. 22 - Jul. 29
$534 per night
House ∙ 9 guests ∙ 3 bedrooms
Vacation Home in West Loop with Private Balcony
4.8
"Excellent" (31 ratings)
West Loop, Chicago, Illinois, United States
Details
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Apartment Printer's Row
Mar. 18 - Mar. 25
$402 per night
Apartment ∙ 7 guests ∙ 1 bedroom
Rental Apartment in Printer\'s Row with Cheap Parking, Near Willis Tower + Cityscape View
5.0
"Excellent" (7 ratings)
Printer's Row, Chicago, Illinois, United States
Details
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Recommended Vacation Rentals Chicago

Find your perfect vacation rental Chicago: from $89 per night

Apartment Logan Square
Mar. 3 - Mar. 10
$142 per night
Apartment ∙ 2 guests ∙ 1 bedroom
Nice Apartment in Logan Square
5.0
"Excellent" (32 ratings)
Logan Square, Chicago, Illinois, United States
Details
Vrbo
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Apartment Near North
Jul. 1 - Jul. 8
$453 per night
Apartment ∙ 3 guests ∙ 1 bedroom
Pleasant Apartment in Near North with On-Site Parking, Next to John Hancock Center
Near North, Chicago, Illinois, United States
Details
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House Belmont Heights
Jun. 10 - Jun. 17
$250 per night
House ∙ 4 guests ∙ 2 bedrooms
Vacation Home in Belmont Heights with Yard
5.0
"Excellent" (12 ratings)
Belmont Heights, Chicago, Illinois, United States
Details
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Apartment Near North
Jul. 22 - Jul. 29
$770 per night
Apartment ∙ 5 guests ∙ 2 bedrooms
Charming Apartment in Near North with On-Site Parking, Next to John Hancock Center
Near North, Chicago, Illinois, United States
Details
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Condo West Town
Jul. 22 - Jul. 29
$383 per night
Condo ∙ 5 guests ∙ 2 bedrooms
Condo in West Town
5.0
"Excellent" (9 ratings)
West Town, Chicago, Illinois, United States
Details
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Condo Tri-Taylor
Feb. 25 - Mar. 4
-37%
$404
$256 per night
Condo ∙ 3 guests ∙ 2 bedrooms
Rental Apartment in Tri-Taylor + City Views
5.0
"Excellent" (6 ratings)
Tri-Taylor, Chicago, Illinois, United States
Details
Evolve
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Apartment Berwyn
Mar. 3 - Mar. 10
$217 per night
Apartment ∙ 6 guests ∙ 2 bedrooms
Beautiful Apartment in Berwyn
5.0
"Excellent" (32 ratings)
Berwyn, Cook County, Illinois, United States
Details
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House Clearing
Mar. 18 - Mar. 25
-40%
$300
$180 per night
House ∙ 5 guests ∙ 2 bedrooms
Vacation Home in Clearing
4.2
"Very good" (12 ratings)
Clearing, Chicago, Illinois, United States
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Apartment Heart of Italy
Feb. 4 - Feb. 11
$409 per night
Apartment ∙ 4 guests ∙ 2 bedrooms
Beautiful Rental Apartment in Heart Of Italy
5.0
"Excellent" (41 ratings)
Heart of Italy, Chicago, Illinois, United States
Details
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Find Fantastic yet Inexpensive Rentals

Budget-friendly Rentals Chicago

Apartment South Loop
Oct. 28 - Nov. 4
-44%
$427
$241 per night
Apartment ∙ 2 guests ∙ 1 bedroom
Nice Rental Apartment in South Loop with Grill, Next to Flamingo
South Loop, Chicago, Illinois, United States
Details
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Apartment Near North
Feb. 4 - Feb. 11
-63%
$442
$165 per night
Apartment ∙ 2 guests ∙ 1 bedroom
Apartment in Near North with On-Site Parking, Near John Hancock Center
Near North, Chicago, Illinois, United States
Details
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Apartment Near North
Jul. 1 - Jul. 8
$773 per night
Apartment ∙ 5 guests ∙ 2 bedrooms
Apartment in Near North with Grill, Near John Hancock Center
4.9
"Excellent" (21 ratings)
Near North, Chicago, Illinois, United States
Details
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Vacation rentals with Wi-Fi

Stay connected while traveling and book a Chicago accommodation with high-speed internet.

Condo Internet Tri-Taylor
$242 per night
Condo ∙ 6 guests ∙ 2 bedrooms
Condo in Tri-Taylor
4.9
"Excellent" (64 ratings)
Tri-Taylor, Chicago, Illinois, United States
Internet
Details
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House Internet Clearing
$90 per night
House ∙ 5 guests ∙ 2 bedrooms
Vacation Home in Clearing
4.2
"Very good" (12 ratings)
Clearing, Chicago, Illinois, United States
Internet
Details
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House Internet Berwyn
$344 per night
House ∙ 8 guests ∙ 4 bedrooms
House in Berwyn with Yard
5.0
"Excellent" (1 rating)
Berwyn, Cook County, Illinois, United States
Internet
Details
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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.

House Kitchen Berwyn
$271 per night
House ∙ 6 guests ∙ 2 bedrooms
House in Berwyn with Yard
4.8
"Excellent" (8 ratings)
Berwyn, Cook County, Illinois, United States
Kitchen
Details
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House Kitchen Homan Square
$224 per night
House ∙ 8 guests ∙ 3 bedrooms
Vacation Home in Homan Square
4.5
"Outstanding" (147 ratings)
Homan Square, Chicago, Illinois, United States
Kitchen
Details
Vrbo
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Apartment Kitchen Berwyn
$119 per night
Apartment ∙ 5 guests ∙ 1 bedroom
Apartment in Berwyn with Free Parking
5.0
"Excellent" (6 ratings)
Berwyn, Cook County, Illinois, United States
Kitchen
Details
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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 Aircondition Brighton Park
$196 per night
Apartment ∙ 8 guests ∙ 3 bedrooms
Apartment in Brighton Park with Yard
4.7
"Outstanding" (7 ratings)
Brighton Park, Chicago, Illinois, United States
Aircondition
Details
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Apartment Aircondition Heart of Italy
$282 per night
Apartment ∙ 4 guests ∙ 2 bedrooms
Beautiful Rental Apartment in Heart Of Italy
5.0
"Excellent" (41 ratings)
Heart of Italy, Chicago, Illinois, United States
Aircondition
Details
Vrbo
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Apartment Aircondition Berwyn
$89 per night
Apartment ∙ 4 guests ∙ 2 bedrooms
Rental Apartment in Berwyn with Grill & Yard
4.2
"Very good" (10 ratings)
Berwyn, Cook County, Illinois, United States
Aircondition
Details
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Popular Rental Amenities Chicago

  • Internet (6,893)
  • Air conditioning (6,581)
  • TV (6,515)
  • No smoking (4,480)
  • Microwave (4,156)
  • Kitchen (3,636)
  • No pets (2,968)
  • Dishwasher (2,881)
  • Washer (2,821)
  • Pool (1,987)
  • Pet allowed (1,926)
  • Crib (1,531)

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, $450. There's no need to look only outside the city for a rental, as more than 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 May (5/27 - 6/3), where prices hit an average of $594 a night. In February (2/4 - 2/11), prices will hit an average low of $248 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 January (1/20 - 1/27), where only 37% rentals are available. Conversely, you will find the highest percentage of available offers Chicago in August (8/26 - 9/2).

The Weather Chicago

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8 days 8
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-7°
7 days 7
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9 days 9
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29°
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24°
13°
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7 days 7
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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

Thu., 2 Feb.
-2°
-10°

15%

6 h

15 km/h

Fri., 3 Feb.
-10°
-16°

0%

8 h

8 km/h

Sat., 4 Feb.
-7°

0%

6 h

17 km/h

Sun., 5 Feb.

15%

1 h

11 km/h

Mon., 6 Feb.
-1°

0%

1 h

8 km/h

Tue., 7 Feb.
10°

15%

0 h

24 km/h

Wed., 8 Feb.
-2°

0%

9 h

11 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 House rentals Chicago is $89 per night.

What is the typical availability of Apartment rentals Chicago?

August 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 House rentals can I find Chicago?

Chicago has 8,727 Apartment rentals and House rentals available to book.

Are there pet-friendly vacation rentals Chicago?

Yes, there are 1,974 pet-friendly vacation rentals Chicago, with an average nightly price of $450.

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 $89.

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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