Chicago Meeting Professionals Guide - 2025
See Chicago in 24 hours
2024-12-26 10:05:15
Tack some leisure time onto your business trip and plan for a fun extended stay in Chicago. Check out our exciting one-day itinerary for a whirlwind tour of the city’s must-see attractions.
MORNING
Start your day with a walk, run, or bike ride along Chicago’s scenic Lakefront Trail, with the beautiful waters of vast Lake Michigan on one side and the city’s spectacular skyline on the other. You’ll pass picturesque harbors with bobbing boats, lush green parks, and miles of sandy beaches. Rent a set of wheels and pedal off on your own or join a guided bicycle tour with Bobby’s Bike Hike Chicago or Bike and Roll Chicago.
Nearby is Millennium Park, the city’s glorious oasis of greenery in the heart of the Loop. Make your first stop the shiny Cloud Gate sculpture (affectionately known as “The Bean”) and snap the quintessential Chicago selfie. If the weather is warm, dip your toes in the multimedia Crown Fountain, which features video images of everyday Chicagoans. Be sure to stroll the flower-filled path of the all-seasons Lurie Garden. In the evening you can catch a free concert on the lawn of the architecturally stunning Jay Pritzker Pavilion.
Next, head indoors to the worldrenowned Art Institute of Chicago. You can easily spend hours exploring the galleries of this famed art museum that holds the largest collection of Impressionist paintings outside of France. And be sure to see the Modern Wing, with works by greats like Andy Warhol and Pablo Picasso. Join a free daily Gallery Tour to see iconic pieces and lesser-known art treasures with a knowledgeable guide.
Or spend your morning exploring the storied Hyde Park neighborhood, home of the lauded University of Chicago. Get handson at the massive Griffin Museum of Science and Industry, home to hundreds of interactive exhibits that include an actual World War II U-505 German submarine that you can walk through, plus the five-story wraparound Giant Dome Theater. Nearby, tour the magnificent Frederick C. Robie House with a docent from the Frank Lloyd Wright Trust. This UNESCO World Heritage Site is one of the best examples of Wright’s signature Prairie style, which sparked a revolution in residential architecture when it was built in the early 1900s.
AFTERNOON
Learn how Chicago rose from the ashes of the Great Chicago Fire to become the groundbreaking architecture powerhouse it is today at the Chicago Architecture Center. Wander two floors of galleries that feature exhibits such as the dynamic Chicago City Model Experience, which showcases more than 4,000 buildings to illustrate fascinating stories of the city. On the Chicago River just steps away, board the award-winning Chicago Architecture Center River Cruise Aboard Chicago’s First Lady and see more than 50 of the city’s architectural gems on a 90-minute tour narrated by trained local volunteers.
Then, spend some time along the postcard-perfect Chicago Riverwalk. See attractions like the McCormick Bridgehouse & Chicago River Museum and the Vietnam Veterans Memorial, shop for artisan goods at the Community Marketplace, and grab a bite to eat paired with a glass of wine or locally brewed beer at one of the charming waterfront cafes. There are also plenty of ways to get on the water, from renting a kayak or captaining your own Chicago Electric Boat Company boat (including the unique hot tub boat) to boarding a cruise with one of the many tour companies docked at the Riverwalk. At night see the dazzling Art on THE MART, the largest permanent digital art projection in the world.
Get a breathtaking bird’s-eye view of the city at one of Chicago’s awesome observatories. On the lower level of the Willis Tower begin with The Skydeck Experience, an interactive museum of Chicago history that playfully touches on everything from Chicago foods to famous Chicagoans. Afterwards, you’ll be whisked up to the 103rdfloor Skydeck Chicago, the highest observation deck in the U.S. The star of the show is The Ledge, a series of glassenclosed observation boxes that jut out from the side of the Willis Tower, offering Instagram-worthy city views.
Or head over to The Magnificent Mile and take a speedy elevator ride up to the 94th-floor 360 CHICAGO. Here you’ll be treated to incredible views of the city, Lake Michigan, and up to four surrounding states on a clear day. If you dare, step onto the TILT thrill ride that slowly tilts standing riders out from the observatory, hovering 1,030 feet above Michigan Avenue for a truly dizzying view. Afterwards, grab a drink at 360 CHICAGO’s CloudBar, the highest bar in Chicago.
EVENING
Catch a Broadway In Chicago show performed at one of the city’s historic downtown theatres. Some of the country’s best touring plays and musicals are presented on five different stages year-round. Or watch up-and-coming comedy stars ply their craft at The Second City, Chicago’s famed improv club. Superstars like Bill Murray, Tina Fey, and Steve Carell have all trained at the legendary Old Town theatre. See a show any night of the week.
Listen to some live Chicago blues music while you’re in town. Buddy Guy’s Legends books the blues world’s biggest musicians, and Grammy-winning Buddy Guy himself performs a slate of shows here every January. Or check out Kingston Mines, a Lincoln Park blues club staple since 1968. Two stages — which have been graced by the likes of Koko Taylor and Junior Wells — keep the music and dancing going into the wee hours Thursday through Sunday nights.
Toast your trip with a craft cocktail at Offshore Rooftop, perched three stories up at Navy Pier. The world’s largest rooftop bar offers chic indoor and outdoor spaces with amazing views of Lake Michigan and the city skyline. And it offers a front-row seat to Navy Pier’s free fireworks shows, lighting up the sky throughout the summer on Wednesday and Saturday evenings.
Check out the Chicago Visitors Guide for even more great ideas.
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