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Top things to do in Chicago

See all 99 things to do in Chicago

Things To Do In Chicago

Coming up: Chicago! You're excited to point your compass in a different direction. Perpetually prepared for inventive ways to get inspired and have an eye-opening adventure, you're prepared to explore an exciting destination from top to bottom. Find and book your activities today, and all you'll have left to do is pack your suitcase and prepare to have fun, because Expedia Canada can connect you with tons of things to do.

  • The activities in Chicago are not only perfect for you, but they won't bust your budget. We have 99 things to do here, and you can reserve them starting at just C$10 . Get your favourite tour on Expedia Canada for a great price, and you'll still have enough cash for a top hotel or luxurious dinner while you're travelling.
  • Chicago is a favourite among inquisitive minds. In fact, many travellers have been visiting Chicago to learn about local culture and find the top activities, and a good portion of them can't wait to return. The most loved activities can earn the curiosity of even seasoned travellers, and that includes savvy visitors like you. Our activities includes a wide range of historically based outings and opportunities for excitement. With unequalled ways to see the best this area has to give like a Guided Tour of Legendary Chicago Sports Venues to one-of-a kind ways to see the best this area has to give like a Hop-On Hop-Off City Tour, there are plenty of opportunities to choose from when you browse through all the options for fun available here at Expedia Canada.

Our activities are the ideal way to organize your trip. It takes an expert itinerary to really get the most out of Chicago, especially when you long to pack in trips to museums and outdoor activities. And it's evident that you're itching to explore every avenue—you are excited to get out and take it all in. You can hardly wait to cover the best activities around, and a quiet day exploring local neighbourhoods is a perfect way to spend an afternoon. Book guided tours on Expedia Canada, and you'll learn all about the city's history along the way.

People head to the Windy City for more than just pizza , as they should. In the summer you can claim part of the Lake Michigan shoreline, and when temperatures dip Millennium Park opens up an ice skating rink. From fine dining to world-class shopping , there are plenty of fun things to do in Chicago, Illinois. Of course, the Chicago art and culture scene is also quite the draw, bringing in all types of travelers from around the globe. You’re bound to leave Chicago with a full stomach and lots to talk about.

Areas & Neighborhoods

Chicago is a city of diverse neighborhoods, each with its own flavor. The heartland sure isn’t bland and cookie-cutter, at least in The Windy City. No, Chicago is teeming with cultures from around the globe and plenty of food to please any palate.

Chinatown — On the south side of Chicago, Chinatown serves up authentic gastronomy and landmarks in near equal measure. This cultural haven is among the top attractions in Chicago; once you enter through the eye-catching Chinatown Gate, savor the sights and sounds of this bustling area and examine the tile mosaic art.

Hyde Park — Hyde Park hosted the Chicago World’s Fair in 1893, and it has been welcoming visitors with open arms (and a bounty of good eats) ever since. The historically significant neighborhood is home to architecture designed by Frank Lloyd Wright and the University of Chicago.

Lincoln Park — This north-side neighborhood is a favorite for shoppers and outdoor enthusiasts. Armitage Avenue is characterized by small boutiques, but you can still find upscale stores right around the corner. The area of Lincoln Park also has an actual park by the same name, where you can stroll through the free zoo or picnic somewhere on the 1,200-acre space.

Streeterville — This waterfront is best known as the home of Navy Pier, where you can partake in amusement rides and more. The area has more to offer than the pier, however, so it’s also a good stop if you want to indulge in fine dining or stop by a contemporary art museum.

What to See in Chicago

If you trekked to Chicago with camera in hand, there are plenty of things to see in Chicago. The Willis Tower Skydeck offers stunning views of the city from the glass-bottomed ledge of its 103rd floor. Iconic buildings like the John Hancock Center and Tribune Tower are also worth a photo or two. More than 200 theaters are littered throughout Chicago, including The Chicago Theatre and The Second City comedy club, so you can take in a show any night of the week.

Things to Do & Attractions in Chicago

From hang-gliding to diving into a Chicago-style pizza , you will never run out of things to do in Chicago. The Magnificent Mile is an impressive stretch of nearly 500 stores and hundreds of restaurants, so you can easily fill a day here. When weather permits, hit the links at local greens like the Jackson Park Golf Course. From the evening until the wee hours of the morning, night owls can burn plenty of calories on the dancefloors of downtown nightclubs. You should also embark on one of the many Chicago tours, which help you see the city by Segway®, bicycle, boat tour, or foot.