Chicago Condo Rentals

Compare 1,797 available properties from 27 providers
Chicago
Save up to 26%

Best Vacation Home Deals in Chicago

-26%
e.g. 11/10 - 11/17
Apartment ∙ 5 guests ∙ 2 bedrooms
Ravenswood, Chicago, Illinois, United States
from $106 $144
VRBO
4.7
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-25%
e.g. 1/5 - 1/12
Apartment ∙ 6 guests ∙ 3 bedrooms
Bridgeport, Chicago, Illinois, United States
from $166 $220
VRBO
4.9
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-15%
e.g. 1/5 - 1/12
Apartment ∙ 6 guests ∙ 3 bedrooms
Ravenswood, Chicago, Illinois, United States
from $175 $207
VRBO
4.9
View deal

Compare and find a rental that fits your needs among the 1,797 beautiful properties from several vacation rental websites in Chicago. HomeToGo instantaneously highlights the best offers by comparing all of the listed acommodations in Chicago from 27 different providers.

Recommended Vacation Rentals in Chicago

Rent a vacation accommodation in Chicago: from $35 per night

Apartment ∙ 2 guests ∙ 1 bedroom
Chicago, Cook County, Illinois, United States
from $72
VRBO
4.4
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Apartment ∙ 4 guests ∙ 2 bedrooms
Old Town, Chicago, Illinois, United States
from $157
VRBO
4.5
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House ∙ 4 guests ∙ 2 bedrooms
West Town, Chicago, Illinois, United States
from $193
VRBO
4.9
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Apartment ∙ 4 guests ∙ 1 bedroom
Horner Park, Chicago, Illinois, United States
from $93
VRBO
4.8
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Apartment ∙ 4 guests ∙ 2 bedrooms
Chicago, Cook County, Illinois, United States
from $141
VRBO
4.9
View deal
Apartment ∙ 5 guests ∙ 3 bedrooms
Near West Side, Chicago, Illinois, United States
from $135
VRBO
4.5
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Apartment ∙ 4 guests ∙ 2 bedrooms
Andersonville, Chicago, Illinois, United States
from $228
VRBO
5.0
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Apartment ∙ 2 guests ∙ 1 bedroom
South Loop, Chicago, Illinois, United States
from $249
VRBO
4.0
View deal
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Apartments With a Balcony or Patio

Balcony/Patio
Apartment ∙ 4 guests ∙ 1 bedroom
Near North, Chicago, Illinois, United States
from $146
VRBO
4.9
View deal
Balcony/Patio
Apartment ∙ 4 guests ∙ 1 bedroom
Ravenswood, Chicago, Illinois, United States
from $134
VRBO
4.9
View deal
Balcony/Patio
Apartment ∙ 4 guests
Sheridan Park, Chicago, Illinois, United States
from $110
VRBO
4.7
View deal
Balcony/Patio
Apartment ∙ 6 guests ∙ 3 bedrooms
Rogers Park, Chicago, Illinois, United States
from $189
VRBO
5.0
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Best Dog-Friendly Rentals

Pet-friendly
Apartment ∙ 2 guests ∙ 1 bedroom
Gold Coast, Chicago, Illinois, United States
from $264
VRBO
4.9
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Pet-friendly
Apartment ∙ 6 guests ∙ 2 bedrooms
Rogers Park, Chicago, Illinois, United States
from $169
VRBO
4.8
View deal
Pet-friendly
Apartment ∙ 3 guests ∙ 1 bedroom
River West, Chicago, Illinois, United States
from $229
Booking.com
4.3
View deal
Pet-friendly
Apartment ∙ 2 guests
River West, Chicago, Illinois, United States
from $160
Booking.com
4.4
View deal
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Vacation Rentals With a Fireplace

Fireplace
Apartment ∙ 5 guests ∙ 2 bedrooms
Edgewater, Chicago, Illinois, United States
from $146
VRBO
4.8
View deal
Fireplace
Apartment ∙ 5 guests ∙ 2 bedrooms
Ravenswood, Chicago, Illinois, United States
from $144
VRBO
4.7
View deal
Fireplace
Apartment ∙ 6 guests ∙ 3 bedrooms
Bridgeport, Chicago, Illinois, United States
from $166
VRBO
4.9
View deal
Fireplace
Apartment ∙ 6 guests ∙ 3 bedrooms
Ravenswood, Chicago, Illinois, United States
from $175
VRBO
4.9
View deal
See all offers

Popular Rental Amenities in Chicago

  • Internet (1,338)
  • AC (1,264)
  • Kitchen (1,230)
  • TV (1,225)
  • No smoking (1,184)
  • Microwave (1,097)
  • Washer (1,075)
  • Dishwasher (903)
  • Parking (748)
  • Balcony/Patio (515)
  • Grill (496)
  • No pets (491)
Use filters to search and find an offer matching your criteria among the 1,797 rentals in Chicago. In Chicago, 1,267 properties provide "TVs". Consequently, if you want to tune out with some TV time, select the TVs filter to compare these accommodations. Not as many accommodations in Chicago are available if you want to go fishing or if you want to sweat it out in a sauna as "saunas" and "fishing" are not often available in this destination.

Price and Availability Index Chicago

Vacation Rental Price Information in Chicago

This graph displays average prices of the vacation rentals and holiday apartments located in Chicago. $347 is the highest price average in the next twelve months. On the other hand, in January you will find the cheapest prices (1/5 - 1/12). Prices this week are on average $289 a night.

Rental Availability Information in Chicago

Check how busy Chicago is with our availability graph. So far, the week with the least available rentals in Chicago is in September (9/8 - 9/15). People tend to travel less to Chicago during a week in October (10/27 - 11/3) when only 14% of the rentals are booked.

The Weather in Chicago

39°
28°
34°
19°
48°
32°
59°
41°
72°
54°
81°
63°
86°
68°
82°
66°
75°
59°
63°
46°
48°
34°
41°
28°
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 86°. No heat wave is expected in February, where minimum average temperatures usally hit a 19° low. The month of September has nice weather with only 9 rainy days.

In Chicago, many of the 1,797 property types are apartment rentals, which represent 68.14% of its accommodations being offered. Additionally, the average nightly price of apartment rentals in Chicago is $422, and the median size is 1,260 ft². Moreover, the majority of apartment rentals in Chicago can host 6 people, which makes it a wonderful vacation spot for medium-sized groups and families. Hotel rooms are the other most frequent property type in Chicago. These properties cost $325 per night on average and have an average size of 480 ft².

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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Getting There

Flying into Chicago

The city is served by two major airports, O'Hare International and Midway Airport. Taxis will take you to your Chicago vacation rental or condo quickly; you could also catch the CTA train to get from the airport into the city.

Food & Drinks

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.

Weather & Climate

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.

Attractions

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.

Art & Culture

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.

Family Activities

Activities with Children

Chicago has plenty to keep kids occupied. Right along the lake on Museum Campus lie three institutions within walking distance of each other. The Adler Planetarium has the coolest astronomy shows and exhibits, while the Shedd Aquarium features majestic sharks, dolphins, whales, and other superb marine life. The kids will love the giant Tyrannosaurus Rex skeleton in the Field Museum of Natural History. How about a picnic on the clean shores of Lake Michigan to finish up? The waters are safe and excellent for swimming.

Local Events

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!

Sights & things to do 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.

We compare more than 300 providers, including:

Booking.com Vacation Rentals in Chicago VRBO Vacation Rentals in Chicago HomeAway Vacation Rentals in Chicago TripAdvisor Vacation Rentals in Chicago VacationRentals.com Vacation Rentals in Chicago HouseTrip Vacation Rentals in Chicago FlipKey Vacation Rentals in Chicago Wimdu Vacation Rentals in Chicago 9flats.com Vacation Rentals in Chicago VaycayHero Vacation Rentals in Chicago PerfectPlaces.com Vacation Rentals in Chicago Homestay.com Vacation Rentals in Chicago only-apartments Vacation Rentals in Chicago Interhome Vacation Rentals in Chicago Bedycasa Vacation Rentals in Chicago Novasol Vacation Rentals in Chicago HomeEscape Vacation Rentals in Chicago

Inspiration for Your Chicago Vacation

Things to See and Do in Chicago

Vacation Destinations Near Chicago