Top 10 things to do in Chicago

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The next time you blow into the Windy City, consider this list of our top 10 favorite things to do

Whether you’re looking to soak up some soul drifting out of brick-walled jazz clubs, examine the masterpieces of the world’s greatest artists, or test the merits of a blustery nickname while standing on the shores of Lake Michigan, Chicago packs something for everyone between its skyscraper-lined streets.

1. People-watch in picture-perfect parks: Explore the legacy of forward-thinking Chicagoans who decided to make the city’s official motto Urbs en horto, or “City in a garden,” back in 1830. Strolling along the waters of Lake Michigan in the 1,200-acre Lincoln Park or look for your reflection in Millennium Park’s legume-like modern art, nicknamed “The Bean.”

2. Examine exceptional exhibitions: Meet Sue—the most complete T-rex skeleton in the world—at the Field Museum, check out everything from a replica coal mine to a German U-boat at the Museum of Science and Industry, or ponder the secrets of the universe at the Adler Planetarium.

3. Retreat to the river: Snaking between glass-and-steel skyscrapers, the Chicago River offers a unique perspective of the Windy City. Scope out iconic landmarks like the Willis Tower on an entertaining cruise, get an active start to your day with a kayak rental, or follow the bends on foot with an experienced guide.

4. Meet the music: As the birthplace of some of the most innovative jazz and blues movements in the world, Chicago’s soul is found in its historic clubs and landmark venues. Catch a live show at institutions like the Marquee Theater, take a behind-the-scenes look at the most happening joints in town, or grab dinner with a show as you explore the city’s musical character.

5. Eat your way to Italy: With its strong Italian heritage, Chicago is one of the best places in the country to pick up some classic fare from the old country, and it doesn’t shy away from its reputation for specialties like deep dish pizza at Lou Malnati’s or the pepper-laden beef sandwiches at Portillo’s. But that doesn’t mean that resident foodies are growing stagnant. From innovative craft brews to creative cupcakes, there’s plenty to keep your palate occupied.

6. Cheer on the home team: From the eternally hopeful Cubs to the championship-chugging Blackhawks, there’s no shortage of things to see for sports lovers. Grab a seat above the ivy-covered outfield walls at historic Wrigley Field, get an insider’s look at the city’s beloved stadiums, or catch a pickup game of volleyball on the sands of Oak Street Beach.

7. Watch the curtain rise: Head to the Chicago Shakespeare Theater to see updated performances and remixes of your favorite tales, tickle your ribs with an improv act at Second City—where comedic greats like Steve Carrell got their start—or catch Broadway performances in the Theater District.

8. Brush up on culture: Browse the works of impressionist masters at the second-largest art museum in the country, see Picasso’s metallic Cubist sculpture at the Daley Center, or scope out the rotating—and often experimental—exhibits at the Museum of Contemporary Art.

9. Crane your neck to the sky: When the World’s Columbian Exposition hit the city in 1893, it catalyzed an architectural revolution just two decades after the Great Fire in 1871. From the neo-Gothic style of Tribune Tower to the once-record-breaking Willis Tower, this Midwestern metropolis is filled with skyscraping legends. Catch the most notable features with a walk down the Magnificent Mile, or team up with a local to learn about the turn-of-the-century architects who helped make it all possible.

10. Lounge on the lake: Over a hundred miles wide and more than 300 long, Lake Michigan acts more like a small sea than a big lake, which means you can look forward to soaking up some sun on golden sand beaches, taking elegant cruises in open water, or bundling up to watch storms roll in toward the city’s waterfront parks.

Where will the wind take you next time you’re in Chicago?

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Expedia Local Expert

Our articles are designed to make sure you spend more time having fun, exploring, and living like a local and less time trying to figure out the logistics on the go. We share our pointers for maximizing your time and stretching your dollar, offering ideas and advice for attractions, things to do, and itineraries. Our writers are lovers of travel and are eager to share their know-how with you. Read on, and travel better!

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One thought on “Top 10 things to do in Chicago”

  1. re: #1- I hope the City of Chicago didn’t waste any public tax money on this sculpture. It doesn’t look anything like a “BEAN”.

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