Best Vacation Home Deals in Chicago
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
Apartments With a Balcony or Patio
Best Dog-Friendly Rentals
Vacation Rentals With a Fireplace
Popular Rental Amenities in Chicago
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
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.
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.
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.
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.
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.
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 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.
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.
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!
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.
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.
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: