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Chicago Condo Rentals

Find 10,106 available offers from 21 partners
Chicago
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Chicago
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2 Adults
1 Bedroom
4 Adults
Pets allowed
Pool
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Internet

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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Vacation rentals with Wi-Fi

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

Apartment  Tri-Taylor
Apr 27 - May 4
-20%
$505
$406 per night
Apartment ∙ 3 guests ∙ 2 bedrooms

Rental Apartment in Tri-Taylor + City Views

5.0
Outstanding (8 ratings)
Tri-Taylor, Chicago, Illinois, United States
Free cancellation
Internet
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Apartment  South Austin
Jan 4 - Jan 11
-44%
$613
$341 per night
Apartment ∙ 6 guests ∙ 3 bedrooms

Apartment in South Austin with Yard

5.0
Outstanding (1 rating)
South Austin, Chicago, Illinois, United States
Free cancellation
Internet
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Resort  Archer Heights
Jun 8 - Jun 15
$153 per night
Resort ∙ 127 guests ∙ 1 bedroom

Resort in Archer Heights

3.7
Good
Archer Heights, Chicago, Illinois, United States
Free cancellation
Internet
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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  South Austin
Dec 3 - Dec 10
-35%
$525
$340 per night
Apartment ∙ 5 guests ∙ 2 bedrooms

Apartment in South Austin

5.0
Outstanding (1 rating)
South Austin, Chicago, Illinois, United States
Free cancellation
Kitchen
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House  Fifth City
Jan 11 - Jan 18
-49%
$745
$380 per night
House ∙ 5 guests ∙ 3 bedrooms

Vacation Home in Fifth City with Grill & Yard

5.0
Outstanding (7 ratings)
Fifth City, Chicago, Illinois, United States
Free cancellation
Kitchen
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House  Marshall Square
Jan 11 - Jan 18
-53%
$471
$221 per night
House ∙ 6 guests ∙ 2 bedrooms

Vacation Home in Marshall Square with Grill & Yard

Marshall Square, Chicago, Illinois, United States
Free cancellation
Kitchen
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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  Brighton Park
Jul 1 - Jul 8
$184 per night
Apartment ∙ 4 guests ∙ 1 bedroom

Apartment in Brighton Park

Brighton Park, Chicago, Illinois, United States
Free cancellation
Air conditioning
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Apartment  Tri-Taylor
Jun 24 - Jul 1
$457 per night
Apartment ∙ 6 guests ∙ 2 bedrooms

Wonderful Rental Apartment in Tri-Taylor

Tri-Taylor, Chicago, Illinois, United States
Free cancellation
Air conditioning
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House  Fifth City
Jul 2 - Jul 9
$696 per night
House ∙ 5 guests ∙ 3 bedrooms

Vacation Home in Fifth City

Fifth City, Chicago, Illinois, United States
Free cancellation
Air conditioning
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Best Vacation Home Deals in Chicago

Save up to 47%

Apartment South Austin
Jul 1 - Jul 8
-17%
$654
$545 per night
Apartment ∙ 6 guests ∙ 3 bedrooms

Charming Rental Apartment in South Austin

South Austin, Chicago, Illinois, United States
Free cancellation
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Apartment McKinley Park
Jan 11 - Jan 18
-26%
$347
$256 per night
Apartment ∙ 2 guests ∙ 1 bedroom

Apartment in Mckinley Park with Yard

McKinley Park, Chicago, Illinois, United States
Free cancellation
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House Oak Park
Jun 4 - Jun 11
-47%
$536
$287 per night
House ∙ 7 guests ∙ 3 bedrooms

House in Oak Park with Yard

Oak Park, Oak Park Township, Illinois, United States
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10,106 beautiful vacation rentals from 21 vacation rental websites, including Booking.com and Vrbo, are available in Chicago. Using HomeToGo you can directly search and compare the prices of each listed property to find the best deal and save up to 45%.

Recommended Vacation Rentals in Chicago

Find your perfect vacation rental in Chicago: from $114 per night

Condo Lake View
$400 per night
Condo ∙ 8 guests ∙ 3 bedrooms

Condo in Lake View with Patio & Grill

Lake View, Chicago, Illinois, United States
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House Humboldt Park
$95 per night
House ∙ 6 guests ∙ 2 bedrooms

House in Humboldt Park with Patio

4.2
Very good (17 ratings)
Humboldt Park, Chicago, Illinois, United States
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House North Lawndale
Sept 26 - Oct 3
$870 per night
House ∙ 16 guests ∙ 5 bedrooms

House in North Lawndale

North Lawndale, Chicago, Illinois, United States
Free cancellation
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House Humboldt Park
$584 per night
House ∙ 10 guests ∙ 3 bedrooms

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

5.0
Outstanding (6 ratings)
Humboldt Park, Chicago, Illinois, United States
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Apartment Logan Square
$154 per night
Apartment ∙ 4 guests ∙ 3 bedrooms

Beautiful Apartment in Logan Square

5.0
Outstanding (2 ratings)
Logan Square, Chicago, Illinois, United States
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Apartment Humboldt Park
$166 per night
Apartment ∙ 6 guests ∙ 3 bedrooms

Apartment in Humboldt Park with Yard & Patio

4.5
Excellent (64 ratings)
Humboldt Park, Chicago, Illinois, United States
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House West Loop
$218 per night
House ∙ 9 guests ∙ 3 bedrooms

Vacation Home in West Loop with Private Balcony

4.6
Excellent (59 ratings)
West Loop, Chicago, Illinois, United States
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House Grand Boulevard
$286 per night
House ∙ 6 guests ∙ 3 bedrooms

House in Grand Boulevard

5.0
Outstanding (7 ratings)
Grand Boulevard, Chicago, Illinois, United States
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Apartment Rogers Park
$254 per night
Apartment ∙ 5 guests ∙ 2 bedrooms

Apartment in Rogers Park with Large Patio + Lake Views

5.0
Outstanding (32 ratings)
Rogers Park, Chicago, Illinois, United States
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Budget-friendly Rentals in Chicago

Find Fantastic yet Inexpensive Rentals

Apartment Brighton Park
$203 per night
Apartment ∙ 8 guests ∙ 3 bedrooms

Apartment in Brighton Park with Hassle-Free Parking

4.6
Excellent (18 ratings)
Brighton Park, Chicago, Illinois, United States
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Apartment South Austin
$162 per night
Apartment ∙ 6 guests ∙ 3 bedrooms

Apartment in South Austin

South Austin, Chicago, Illinois, United States
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Condo West Loop
$415 per night
Condo ∙ 6 guests ∙ 2 bedrooms

Condo in West Loop

4.9
Outstanding (16 ratings)
West Loop, Chicago, Illinois, United States
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Top-Rated Offers and Accommodations in Chicago

Book Vacation Rentals with the Highest User Rating

Apartment Grand Boulevard
$150 per night
Apartment ∙ 8 guests ∙ 2 bedrooms

Charming Rental Apartment in Grand Boulevard

4.9
Outstanding (94 ratings)
Grand Boulevard, Chicago, Illinois, United States
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Condo Old Town
$417 per night
Condo ∙ 10 guests ∙ 3 bedrooms

Condo in Old Town with Patio & Grill

4.9
Outstanding (61 ratings)
Old Town, Chicago, Illinois, United States
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Apartment East Albany Park
$217 per night
Apartment ∙ 6 guests ∙ 3 bedrooms

Rental Apartment in East Albany Park with Yard

5.0
Outstanding (3 ratings)
East Albany Park, Chicago, Illinois, United States
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Popular Rental Amenities in Chicago

  • WiFi (9,069)
  • Pool (2,338)
  • Kitchen (5,368)
  • TV (8,847)
  • Air conditioning (9,183)
  • Parking (1,540)
  • Washing machine (5,126)
  • Pet-friendly (2,297)
  • Balcony/patio (2,338)
  • Microwave (5,200)
  • Dishwasher (3,488)
  • No smoking (8,894)

Chicago is a wonderful vacation spot if you want an accommodation with a pool, as 24% of the vacation rentals there have one. Interestingly, our data shows that more hotel room have a pool than apartment rental. Additionally, they can welcome 7 vacationers, on average, while apartment rental with pools can host an average of 3 people. two-thirds of Chicago's vacation homes including a pool are located within two kilometres of water, choose between some pool time or waterfront moments.

Price and Availability Index in Chicago

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Vacation Rental Price Information in Chicago

We analyzed vacation homes, cottages and apartments to display a price graph showing the average price per night in Chicago. The week with the highest average prices is in October (10/5 – 10/12). During this week, a night will cost on average $746. Prices decrease in a week of March (3/15 – 3/22), where average prices are $265.

Rental availability information in Chicago

Have a look at the above graph to see the global availability of vacation rentals in Chicago. The week with the highest booking rate is in April (4/26 – 5/3). Only 4% of the rentals are still available. On the other hand, the week with the most available offers is in June (6/29 – 7/6).

The Weather in Chicago

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- Rainy days

Find the Chicago climate diagram. The highest average temperatures are in the month of July. Conversely, January is the coolest month in Chicago, with temperatures going under -8° The wettest month is March with 9 rainy days on average. On the contrary, there is an average of only 7 rainy days in February, which is the driest month.

7-Day Weather Forecast in Chicago

Wed., 22 May
24°
21°

0%

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25 km/h

Thu., 23 May
27°
26°

0%

6 h

12 km/h

Fri., 24 May
28°
24°

15%

1 h

22 km/h

Sat., 25 May
21°
20°

10%

4 h

8 km/h

Sun., 26 May
13°
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15%

0 h

20 km/h

Mon., 27 May
16°
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10 km/h

Tue., 28 May
17°
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0%

1 h

21 km/h

Accommodations for your vacation in Chicago

1,987 out of the 10,106 vacation accommodations in Chicago are apartment rental. They account for many of the accommodation types in this destination (64.35%). In addition, the average nightly cost of vacation rentals in Chicago is $502, and the median size is 82 m². Moreover, if you are going in a group of 4, vacation rentals are an excellent accommodation type in Chicago, as they usually welcome this exact group size. Users who prefer another type of acommodation can also compare many house rental, which are the other most popular accommodation option in Chicago. Our data shows that the median price of vacation homes is $909 per night for an area of 148 m².
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 10,106 rentals
💳 Possible discounts up to 45%
🌙 Nightly prices starting at $114
⭐ Popular amenities Internet, Pool and Kitchen
🐾 Pet friendly homes 2,309 homes
🏊 Vacation rentals with pools 2,420 homes
9 reviews
Chicago vacation rentals have an average rating of 4.4/5 on 9 reviews left by travelers.

Frequently Asked Questions

What is the typical availability of vacation rentals in Chicago?

At the moment, there are 10,106 vacation homes from 21 different providers in Chicago.

What are the most popular vacation home amenities in Chicago?

Many travellers are searching for Internet, Pool, and Kitchen when booking a vacation home in Chicago.

Are there pet-friendly vacation rentals in Chicago?

If you're travelling with a dog, over 23% of vacation rentals in Chicago are pet-friendly.

What's the best month to visit Chicago?

When booking a vacation rental in Chicago, remember that the rainiest months are usually March and April, with February often being the sunniest.

Find the perfect Chicago home to match your style

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