Best Things To Do In Chicago

The Windy City has awe-inspiring skyscrapers, hunger-stomping food and culture to match almost any city in the world. But what never ceases to amaze is just how much you can do for free in Chicago. Donations by philanthropists have bestowed the city with superlative museums and more than 700 works of public art, by Picasso, Chagall, Miró – the list is huge. These have turned the skyscraper forest of the Loop and the Millennium Park into one big outdoor gallery. There are free events too, like Taste of Chicago, the largest food festival in the world, and music festivals to honour the city’s enviable music heritage. Chicago is also great to get around on foot, along the Lakefront Trail or the new Riverwalk, or even underground in the sophisticated Pedway system. Let’s explore the best things to do in Chicago.

Best Things To Do In Chicago

1. River and Lake Cruises

11 Best Boat Tours in Chicago | Essential Things to Do in Chicago

Out on Lake Michigan and along the Chicago River you can sit back and give Chicago’s cityscape the attention it deserves.

There’s a selection of cruises, from gentle lake tours to exhilarating speedboat rides.

The Classic Lake Tour is a 40-minute sightseeing trip giving you plenty of time to soak up the sights, and with a recorded commentary for interesting titbits.

At the old Navy Training Center on Navy Pier you can jet off on a speedboat for a 75-Minute Architecture Cruise, starting on the lake and heading upriver as far as the Willis Tower.

The Chicago River Architecture Cruise has a more sedate pace, and gives you a clear view of more than 40 listed landmarks, accompanied by live commentary from an expert guide.

2. Check out trippy paintings come to life at Immersive Van Gogh

The US premier of this international project lands in Chicago’s Germania Club Building for an immersive experience featuring moving images illustrating the works of Vincent Van Gogh now through September 6. The 600,000-cubic-foot experience includes bright flashing lights set to soundtracks in a historic Gold Coast building.

3. Spend an afternoon at Navy Pier

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Chicago’s iconic lakefront destination, Navy Pier plays host to renowned restaurants, shopping opportunities, boat tours, and so much more. The waterfront space was conceived as merely a freight dock, however, its slowly evolved over the last century; today, the must-see destination features exhibits, rides, parks, and unbeatable views of the glistening Lake Michigan.

Countless walking tours pass through the area, which also serves as the main cruise departure point.

4. See it all from the 360 Chicago Observation Deck

Located on the 94th floor of the John Hancock Center, the 360 Chicago Observation Deck offers spectacular views of the city’s crowded skyline (including the Willis Tower) and the shimmering lake Michigan below. From the soaring 1,030-feet-high viewing platform, all four of the nearby states are visible (Illinois, Wisconsin, Indians, and Michigan).

Step outside onto the thrilling tilting platform (TILT), then unwind at the bar and soak in the sunset.

5. Food Tours

If it’s big portions and bold flavours you’re after, Chicago is the town for you.

Chicago may be America’s top food city, and you would be brave to disagree.

The staples are deep-dish pizza, hot dogs piled with seven toppings, Italian beef sandwiches, brownies and beer.

Lou Mitchell’s and Twin Anchors have nationwide fame, but if you want local spots that might escape the attention of out-of-towners, there are a range of tours for hungry visitors.

6. Support Chicago’s Black Community

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Whatever else you do this spring, be sure to do your part and make the community we live in a better place for all its residents. Aid in the fight for racial justice and social equity taking place across the city, while also supporting Chicago’s Black community from nonprofits and community organizations to restaurants and bookstores.

7. Grant Park

Affectionately known as “Chicago’s front yard”, Grant Park fronts the Loop on Lake Michigan and is the city’s prime open space.

These 319 acres contain lots of Chicago’s top attractions like Millennium Park, the Museum Campus Chicago, the Art Institute of Chicago, Maggie Daley Park and the epic Soldier Field, home of the Chicago Bears NFL team.

You could write a whole article on Grant Park and the layers of things to do in its boundaries.

But it’s also worth remembering that the park is a lively place for Chicagoans just to unwind and be active, with baseball diamonds, tennis courts and lush boulevards to wander down.

In July Grant Park hosts the Taste of Chicago Festival, the biggest food event anywhere, and in October is the start and finish line for the Chicago Marathon.