Holiday homes & rentals in Chicago

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 holiday apartment and find out what the fuss is all about.

Getting to your Chicago accommodation

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

What to eat during your Chicago holiday

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.

What weather to expect on your Chicago holiday

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.

What to do and see in Chicago

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 culture in Chicago

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.

Family holidays in Chicago

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.

Regular Events and Festivities

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!

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 Centre 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 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.

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.

Frequently Asked Questions