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Cloud Gate in Millennium Park | © jmcmichael/Flickr
Cloud Gate in Millennium Park | © jmcmichael/Flickr
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20 Must-Visit Attractions in Chicago

Picture of Liz Behler
Updated: 7 December 2018
With so many things to see and do in Chicago, planning your vacation here can feel overwhelming. With that in mind, we did some legwork and came up with a list of 20 destinations not to be missed. From architecture tours to must-try local dishes, here are the places to visit on your next Chicago vacation.

Cloud Gate

Lovingly referred to as “the Bean” by locals, staring at your reflection (and taking a selfie) at Cloud Gate is a must.

Take a boat tour

Get a different perspective on the city, and learn more about its incredible architecture, by taking a river cruise with the Chicago Architecture Foundation.

Green Mill

Listen to some of the city’s best jazz musicians at this iconic club that was once a haunt of Al Capone.

Wrigley Field

See where the Cubs broke their 108-year curse by (finally) winning the World Series in 2016.

Chicago Water Tower

One of the few building to survive the Great Chicago Fire, this castle-like structure now serves as a miniature art gallery.

Chicago Water Tower | © Mobilus In Mobili / Flickr
Chicago Water Tower | © Mobilus In Mobili / Flickr

Hancock Tower

Head to the observation deck, or to the bar on the 96th floor, to get a bird’s-eye view of the birthplace of the skyscraper.

See a show at Second City

Take in a show at the place that launched the careers of Tina Fey, Steve Carrell and countless other comedy legends.

Ride the L

More than just public transportation, the L (short for “elevated”) is an icon of the city, and one of the best ways to see the Loop.


Stroll past cafes, fountains and floating gardens on the recently opened pathway along the Chicago River.

Millenium Park

The city’s premiere green space—and gathering spot—is full of public art and free concerts.

A concert at the Jay Pritzker Pavilion in Millennium Park | © Connie Ma/Flickr
A concert at the Jay Pritzker Pavilion in Millennium Park | © Connie Ma/Flickr

Art Institute of Chicago

With more than 300,000 works in its permanent collection, you could easily spend days here (or, make a beeline for “American Gothic” and “Nighthawks,” two of the museum’s most famous pieces).

Hit the beach

Chicago may be far from the ocean, but Lake Michigan more than makes up for it with 26 mi. (42 km) of shoreline, and 26 distinct lakefront beaches.

Magnificent Mile

Even if you don’t have a wallet full of cash to spend shopping, it’s worth a stroll down the Mag Mile (aka Michigan Avenue) to take in some of the city’s most famous buildings—the Hancock Tower, Tribune Tower, Chicago Water Tower, and Wrigley Building are all found here.

Take a Frank Lloyd Wright tour

Learn more about one of the most important and influential architects in American history with a tour of his home and studio in Oak Park, or check out his prairie-style masterpiece, the Robie House, on the University of Chicago campus.

Go for a bike ride

Stretching 18 mi. (29km) along Lake Michigan, the Chicago Lakefront Trail is the ideal place to take a scenic summertime bike ride. Divvy, the city’s popular bike-share system, makes renting a bike easy and affordable.

Chicago Lakefront Trail | Courtesy of Liz Behler
Chicago Lakefront Trail | Courtesy of Liz Behler


Make reservations in advance to dine at chef Grant Achatz’s temple to molecular gastronomy, often topping lists as one of the best restaurants in the world.

National Museum of Mexican Art

Situated in the heart of Chicago’s Mexican community, Pilsen, the National Museum of Mexican Art is a showcase for 9,000 seminal artworks spanning from ancient Mexico to present day. Afterwards, explore the neighborhood’s taquerias and street art scene.

Field Museum

Come face to face with Sue, the world’s largest T. Rex at the Field Museum, founded in 1893 as part of the Chicago World’s Fair.

Eat like a local

No trip to Chicago is complete without trying a Chicago-style hot dog (an all-beef dog on a poppy seed bun, topped with yellow mustard, neon green relish, onions, a dill pickle spear, tomatoes, pickled sport peppers and celery salt) and deep-dish pizza (head to Lou Malnati’s and order the Chicago Classic—you can thank us later).

Lincoln Park Zoo

One of the nation’s oldest zoos is also completely free. (Plus, they have penguins!)