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See Chicago in 24 hours

In town for business? Meet the real Chicago. Tacking on some leisure time to your business trip allows you to plan for a fun extended stay and get a taste of everything our great city has to offer. Check out this exciting one-day itinerary for a whirlwind tour of the city’s must-see attractions.

Morning

Friends bike on Chicago's Lakefront Trail
Chicago’s Lakefront Trail; photo by Abel Arciniega, @tequilagraphics

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 waterfront restaurants, lush green parks, and miles of sandy beaches.

Rent a set of wheels and pedal off on your own or join a guided 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 iconic Cloud Gate sculpture (known locally as “The Bean”) and snap the quintessential Chicago selfie.

Next, head to the world-renowned Art Institute of Chicago, right next door to Millennium Park. 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 check out the Modern Wing, with works by greats like Andy Warhol and Pablo Picasso.

Alternatively, you could spend your morning exploring the storied Hyde Park neighborhood, home to the lauded University of Chicago. Get hands-on at the massive Griffin Museum of Science and Industry, the largest science museum in the Western hemisphere. Nearby, tour the magnificent Frederick C. Robie House. This UNESCO World Heritage Site is one of the best examples of Frank Lloyd Wright’s signature Prairie style.

Afternoon

Chicago First Lady boat cruises

Learn how this city rose from the ashes of the Great Chicago Fire to become the birthplace of the skyscraper at the Chicago Architecture Center. Afterward, hop on a scenic architecture boat cruise to hear the fascinating stories behind more than 50 of the city’s architectural icons from an expert docent.

Then, spend some time wandering the postcard-perfect Chicago Riverwalk. This award-winning pedestrian pathway is dotted with museums, public art, bustling cafes, and alfresco restaurants. Grab a bite to eat paired with a glass of wine or a locally brewed beer and enjoy panoramic city views.

If you’re looking for more ways to get out on the water, rent a kayak or join a guided tour from Urban Kayak‘s Chicago Riverwalk location. Or check out Chicago Boat Company to captain your own boat for the day.

Next, enjoy a breathtaking bird’s-eye view of the city from one of Chicago’s soaring observation decks. Skydeck Chicago, located in one of the tallest buildings on the planet, offers visitors the chance to see four states from the 103rd floor. The star of the show is The Ledge, an all-glass balcony that allows you to step outside the building more than 1,000 feet above ground.

Or head over to The Magnificent Mile and take a ride up to the 94th-floor 360 CHICAGO. You’ll be treated to incredible views of the city and Lake Michigan, which you can enjoy from the on-site CloudBar. If you dare, step onto the TILT thrill ride that hovers riders out over Michigan Avenue for a truly heart-pounding view.

Evening

LH Rooftop, ©Adam Alexander Photography 2019

Catch a Broadway in Chicago show performed at one of the city’s historic downtown theatres. Some of the country’s top touring plays and exciting premieres are presented on five unique stages year-round. Or catch up-and-coming comedy stars hone their craft at The Second City, Chicago’s legendary improv club.

Listen to live Chicago blues music at Buddy Guy’s Legends, an authentic Blues bar that books the world’s biggest musicians (including owner Buddy Guy himself). Or check out Kingston Mines, a Lincoln Park blues club since 1968. Two stages, graced by the likes of Koko Taylor and Junior Wells, keep the music going until the early hours of the morning.

Finally, toast to your trip from one of Chicago’s stunning rooftop bars. Spots like Offshore Rooftop, LH Rooftop, and Cindy’s all offer sweeping views and the perfect vantage point of the Navy Pier summer fireworks along Chicago’s lakefront. It’s the perfect way to wrap up a busy day experiencing the best of Chicago.

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