Compare 5,189 properties available in Chicago and discover a welcoming place to stay for a relaxing holiday. HomeToGo allows you to easily search and compare the prices for each rental from numerous providers to discover the best deal and save up to 60%.
Rent a holiday home, apartment or cottage in Chicago from just £29 per night
Check above for our most commonly selected filters in Chicago and the number of rentals that include them. In Chicago, 5,553 rentals provide Internet. Consequently, if you can't imagine a holiday without internet, use the Internet filter to see this type of accommodation. You could even compare and find properties if you want a rental with a jacuzzi (120 rentals include Hot tub in Chicago) or you plan to go fishing (54 rentals with Fishing).
We analysed price data and summarised them in this graph, which shows holiday letting prices for the next twelve months in Chicago. £397 is the highest price average in the next twelve months. On average, the most interesting prices are in one week in January (14/01 - 21/01), when the average price is only £166 per night.
Our availability graph helps you identify the busiest months in Chicago. It is in June that you will find the week with the fewest available holiday lettings (04/06 - 11/06). Conversely, you will find the highest number of available rentals during one week in October (29/10 - 05/11).
Check out the climate diagram for Chicago. On average, the warmest month is July. However, temperatures can go lower than -7° in Chicago in February. The rainiest month is March, while the driest month is February.
The world comes to Chicago for gastronomical expertise, so indulge those tastebuds! Devon Avenue is the place for Indian delights, which you can eat in or take away to enjoy back at your Chicago holiday apartment. 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 hotdogs 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 accommodation prices are reasonable. Moreover, plenty of cultural activities take place across this part of the calendar. If you intend to visit during summer, book your Chicago accommodation well in advance as this is the most popular visitng season. Chicago can be just as magical in winter, making it a true year-around 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 Centre.
Chicago's ethnic 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 be spoilt for 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 so on. 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 Theatre, 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 Theatre awaits.
Chicago has plenty to keep kids occupied. Right along the lake on Museum Campus lie three institutions in 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.
The year begins with colourful Chinese New Year celebrations and the highly-awaited Chicago Auto Show. April brings the Chicago Improv Festival and C2E2 Chicago Comic & Entertainemt 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 holiday home 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 Centre 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 centre 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.
On average, a Apartment rentals or Bed & Breakfast rentals in Chicago costs £29 per night.
August is the time of year with the highest amount of Apartment rentals and Bed & Breakfast rentals available in Chicago, so you'll find plenty of great holiday deals during this month.
The top three amenities our customers choose for holiday rentals in Chicago are Internet, TV and Pool.
Holidaymakers looking for accommodation in Chicago will be pleased to know that there are 5,191 options on offer, with prices starting from just £29 per night.
Finding accommodation in Chicago for you and your dog is definitely possible, with 1,327 pet-friendly holiday homes available.
Sun lovers should visit Chicago in July and August to enjoy the warmest weather.
You can find great value holiday lets in Chicago with the nightly price of a let beginning at £29 - and HomeToGo has introduced plenty of features that mean it's easy to see the best deals. When considering different dates for a trip, try a search using HomeToGo's flexible dates technology to easily look for low-price timings and see savings of up to 60%. In addition, HomeToGo's 'distance from' filter makes it easy to locate top quality accommodation offers in great value, under-the-radar locales that are just as close to your desired destination, whether that's a beach, lake, ski region or city centre. Start your search as soon as possible to get the benefits of the greatest variety of options and top discounts - and do so without worries by ticking HomeToGo's 'free cancellation' filter when you search.
From serenity away from the crowds to more space to enjoy with your loved ones, holiday homes in Chicago bring a variety of benefits. HomeToGo surfaces real reviews from verified visitors, and searching is secure, simple, and stress-free - so with 5,191 lets from 27 providers in the area, you're guaranteed to uncover the ideal type of accommodation with all of the amenities to suit you in Chicago.
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