5,331 wonderful vacation homes from 29 providers, such as Casamundo or Booking.com, are listed in Chicago. By directly analyzing these accommodations, HomeToGo features the best deals and the highest rated vacation homes in Chicago.
Find your perfect vacation rental Chicago: from $47 per night
If you travel with your pet, you can easily search and find a pet-friendly rental Chicago. Hotel rooms are the most pet-friendly property type in Chicago. Also, a night in a pet-friendly rental there is, on average, $512. There's no need to look only outside the city for a rental, as a few of the pet-friendly vacation rentals are very central (less than 2 kilometres from the city centre).
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 July (7/23 - 7/30), where prices hit an average of $679 a night. In January (1/14 - 1/21), prices will hit an average low of $268 per night.
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 June (6/4 - 6/11), where only 24% rentals are available. Conversely, you will find the highest percentage of available offers Chicago in October (10/29 - 11/5).
Above are the weather conditions for Chicago. In July maximum temperatures go higher than 30°. On the contrary, the coolest month is February. February is the driest month.
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.
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.
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 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.
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.
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 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.
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.
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.
The starting price for Apartment rentals or Bed & Breakfast rentals Chicago is $47 per night.
October has the highest availability of Apartment rentals Chicago, so you can expect plenty of selection, even for last-minute bookings.
When looking to book a vacation home Chicago, the most requested amenities include Internet, TV, and Pool.
Chicago has 5,326 Apartment rentals and Bed & Breakfast rentals available to book.
Yes, there are 1,350 pet-friendly vacation rentals Chicago, with an average nightly price of $512.
The warmest time of year Chicago is July and August, with the nightly price of a vacation home starting at $47.
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