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The Best Things to Do in Chicago

By AFAR Editors

Apr 15, 2020

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Learn all about Chicago’s famous buildings on an architecture boat tour.

Photo by Adam Alexander

Learn all about Chicago’s famous buildings on an architecture boat tour.

Architecture boat tours, ballgames at Wrigley Field, sunny beach days on Lake Michigan, and strolls through Millennium Park: here’s what to do in Chicago.

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Are you one of Chicago’s more than 50 million annual visitors with no idea where to start? We get it. The Windy City can overwhelm with its numerous world-class sights, but we’ve cherry-picked the best of the best for you below.

Whether you’re visiting for the architecture, the baseball, or the beaches, you certainly won’t be bored here. Pose for a picture in front of the Bean, hang with the penguins at Lincoln Park Zoo, or take in the skyline from 1,353 feet in the air at Willis Tower. Stroll through massive public gardens, bike down an elevated trail, or catch a concert at a historic venue.

The options for fun are endless. Read on for even more ideas, then check out our separate guide to the best museums in Chicago.

Cruise the river on an architecture tour

There’s no better way to experience the Chicago River and Lake Michigan—and learn about Chicago’s best buildings—than with an architecture boat tour. While there are plenty of cruises available, go with First Lady, which relies on expert docents from the Chicago Architecture Foundation to provide extensive historical, cultural, and stylistic insights (for example, how the design of Willis Tower was based on cigarettes, or how the Monadnock Building on Jackson Boulevard was constructed with 100 different shapes of brick). Tours run every day of the week from May to November and last about 90 minutes.

Snap a selfie at Cloud Gate

Cloud Gate’s reflective surface makes for the perfect photo.

Visitors take their best Chicago portraits in front of the iconic Millennium Park sculpture that is Cloud Gate (known colloquially as the Bean, for its shape). Conceived by British artist Anish Kapoor and constructed from 168 stainless steel plates with no visible seams, the 33-foot-tall sculpture is one giant polished surface, reflecting infinite variations of the Chicago skyline. The work was chosen from among more than 30 others commissioned by the city and was inspired by liquid mercury.

Gain new perspective at Willis Tower

Brave the Ledge at Willis Tower and gaze down at the city from 1,353 feet.

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Willis Tower—originally known as the Sears Tower—was the world’s tallest building for 23 years until it was unseated in 1996 by the Petronas Twin Towers in Kuala Lumpur. Nevertheless, the 110-story skyscraper is mighty impressive, with its “bundled tube” design, inspired by a handful of cigarettes, that forever changed the construction of supertall, wind-resistant buildings around the world. For a real thrill, head up to the 103rd floor, where you can get a bird’s-eye-view of the city from the Skydeck observatory, or venture onto the Ledge, a glass-bottomed box that juts out more than four feet from the side of the building and hovers 1,353 feet above the street.

Root for the home team at Wrigley Field

Catching a baseball game at Wrigley Field is a quintessential Chicago experience.

Steeped in history, loved by many, loathed by some, and always angling for a championship, Wrigley Field is a true cornerstone of the always controversial sporting world. No trip to Chicago is complete without a visit to this monument to baseball. Snag tickets and cheer on the Cubs from the stands, or simply wander the surrounding area and take in the local antics on game day. You’ll be entertained regardless.

Visit the animals at the Lincoln Park Zoo

With its monkeys, penguins, lions, and more, Lincoln Park Zoo is fun for the whole family.

Open year round and always free to enter, the enormous Lincoln Park Zoo is one of Chicago’s single greatest attractions. Visit the monkeys in their house of hilarity, or let the penguins entertain you (and themselves) with slippery antics and tuxedo-clad fun. There are plenty of places to grab a snack along the way, plus a huge gift shop filled with trinkets and memorabilia should you want to bring home a souvenir. In the winter, the zoo also hosts ZooLights, a jaw-dropping display of Edison-esque wizardry that’s guaranteed to impress even the biggest Scrooge.  

Get back to nature at Garfield Park Conservatory

The Palm House at Garfield Park Conservatory is a welcome respite from chilly Chicago winters.

Opened in 1908, Garfield Park Conservatory remains one of the largest and most diverse public gardens in the country. The grounds—designed by renowned landscape architect Jens Jensen—cover 14 acres and feature more than 5,000 rare and exotic plants from around the globe. Start your visit at the Palm House, where you’ll find six dozen varieties of palm trees, ample waterfalls, and koi fish, then head to the Fern Room and check out the plant that’s thought to be more than 300 years old. Be sure to also swing by the gift shop and grab some honey—the conservatory makes its own.  

Bike down the 606

Lined with art, greenery, and cool buildings, the 606 trail is an entertaining place for a bike ride.

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Built from an old industrial rail line and repurposed bridges, The 606 (which takes its name from the common numerals in all Chicago zip codes), is a 2.7-mile elevated park and biking trail that connects some of the city’s coolest neighborhoods. Runners and cyclists alike can access the attraction via 12 entry points (there’s one approximately every quarter mile), then take in lush greenery, city sights, and a collection of temporary and permanent art exhibits along the way. No matter where you exit, you’re bound to end up somewhere good—the path runs through Wicker Park, Bucktown, Logan Square, and Humboldt Park, meaning a post-workout bite at one of the city’s best restaurants is just seconds away.

Get a tan at North Avenue Beach

At North Avenue Beach, you can stroll the sand in view of the Chicago skyline.

Chicago has no shortage of lakefront beaches, but there are few that boast the location, the views, and the recreation of North Avenue. Located just footsteps from the Lincoln Park Zoo and the vibrant shopping and nightlife in Old Town, this prime stretch of sand features a $7 million beach house, an abundance of volleyball courts, and the always-packed Castaways Bar & Grill, where locals and visitors mingle over daiquiris, tacos, and the latest Top 40 tracks. Throw down a towel and soak up Chicago’s summer sun or try your hand at any of the on-site activities, including yoga and stand-up paddleboarding. 

See some live music at Thalia Hall

Around since 1892, Thalia Hall is still one of Chicago’s best spots to see a concert.

You can’t visit Pilsen without a stop at this historic concert hall, a favorite of both national and local musicians—as well as their fans. Allegedly modeled after the Prague State Opera House, the venue opened in 1892 with the aim of bringing arts and entertainment to the surrounding neighborhood and its bohemian community. It remained virtually untouched until 2013, when hospitality group 16” on Center took over, restoring the grand old building to its former glory and bringing in the Michelin-starred Dusek’s, cocktail bar Punch House (which, true to its name, serves some drinks by the punchbowl), and modern-day piano bar Tack Room. 

Take in a play at Court Theatre

See local talent in action at Court Theatre, which hosts five different productions each year.

Located on the University of Chicago’s campus in Hyde Park, the Court Theatre opened back in 1955 and has been drawing crowds ever since with its diverse programming and community outreach. Each season features five productions, which range from familiar shows (My Fair Lady) to lesser-known plays (Pericles) to revivals from the African American theatrical canon to completely original works. Much of the programming is also informed by the university’s mission, resources, and students, giving shows here a uniquely local feel.

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>>Next: Plan your trip with AFAR’s Travel Guide to Chicago

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