Fun Things To Do In Chicago, IL

Among the great cities of the world, Chicago’s got something for everybody: foodie to sports fanatic, nature lover to theater obsessive, sunrise-worshipper to night owl. And you sure won’t find a better perch from which to enjoy all that the Windy City has to offer than Hotel Chicago, offering luxurious (and geographically strategic) accommodations in the iconic Marina City complex of River North on the Near North Side.

Here are just a few classic Chicago activities to try out during your next getaway(s) here at our Autograph Collection hotel in the heart of town!

Cruise the Chicago River & Learn About the Cityscape Along the Way

There are many ways to enjoy the Chicago River—strolling and sipping along the Riverwalk, going kayaking or stand-up paddleboarding—but an architecture cruise aboard Chicago’s First Lady has become among the signature ones.

Courtesy of the Chicago Architecture Center and multilingual narration, you’ll get the lowdown on the history and design of better than 50 Chicago buildings as you slide along the city’s heartblood flow.

Attend a Second City Show

To say that the Second City, Chicago’s homegrown improv comedy outfit, has made a major mark upon the world of comedy is putting it mildly. The troupe where everyone from John Candy, Gilda Radner, and Bill Murray to Amy Poehler, Tina Fey, and Jordan Peele cut their teeth is still an absolute blast to take in via a live show, which could range from a comedy competition to fully improvised musicals, sitcoms, and murder mysteries.

And hey, if you feel inspired (and brave), you could even take a Second City improv class…

Visit Wrigley Field

Whether you’re taking a guided tour or actually attending a Cubs home game, it’s pretty darn magical to visit Wrigley Field: aka “the Friendly Confines,” one of the oldest and most flat-out iconic ballparks in Major League Baseball.

Enjoy Free Fireworks at Navy Pier

Among the fixtures of Chicago’s Lake Michigan waterfront, Navy Pier serves up many all-ages delights, and one of the trademark summertime ones is the free fireworks show that goes down every Wednesday and Saturday night through Labor Day weekend.

Stroll the Year-round Gardenscapes of a Chicago Conservatory

The Windy City lays claim to some of the most impressive and historic greenhouse botanical gardens in the country. Whether it’s the height of summer or the depths of winter, you’ll always get to recharge with some lush greenery at Chicago’s famous conservatories, free to enjoy with a reservation.

Wander the Palm House, Orchid House, Show House, and Fern Room at the Lincoln Park Conservatory near the lakefront, or relish the famous “landscape art under glass” presented amid the eight indoor display gardens of the Garfield Park Conservatory. (Both have seasonal outdoor gardens to enjoy as well!)

Windy City Fun on a Hotel Chicago Escape

From selfies in front of Cloud Gate (aka “the Bean”) in Millennium Park to beach-hopping along Lake Michigan—not to mention exploring one of the nation’s best food scenes—we’re obviously leaving out oodles of must-do Chicago activities. But hopefully we’ve whetted your appetite for your next stay at Hotel Chicago, springboard for experiencing the best of the Windy City!


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