With ghosts, gangsters, donuts, and architecture, Chicago is a vibrant city teeming with excitement and entertainment. But how to narrow it down? We’ve created an itinerary that’ll send you to every corner of the city to indulge in local culinary delights and to experience music and art — and yes, baseball is an art to many. We’ve packed in some steps and pedals between meals to keep you moving, so rest up before you head out to Chi-Town, because you won’t want to miss a beat.
With just 48 hours in Chicago, you’ll want to start your day early and with a hearty breakfast. Grab a seat at Lou Mitchell’s on Jackson Boulevard, where you’ll find a menu brimming with southern comfort foods — a happy indicator of Chicago’s rich and complex culture. Locals recommend the buttermilk biscuits and country-style sausage gravy, or the Belgium malted pecan and bacon waffle. Either way, you’ll have a deliriously delicious start to your day.
Grab a half-day bike rental and pedal your way to one of Chicago’s urban parks — cultural hubs that are home to a ton of the city’s top attractions. First head over to Millennium Park, home to the iconic Cloud Gate sculpture also known as “The Bean” — cloud or bean, it makes a great Insta backdrop. Once you’ve snapped your pics, hop back on your bike and head over to the Chicago History Museum. This megastructure is chock full of relics from the World’s Columbian Exposition, exhibitions dedicated to the city’s art and fashion history, and an original L train car. There’s even a giant interactive Chicago-style hot dog. If you ask us, that’s worth the price of admission.
Join in on the Chicago-style vs. New York-style debate that has divided pizza lovers for decades. Decide for yourself at Burt’s Place in Morton Grove. The slices here are arguably the best in the city. Famed culinary expert and world traveler Anthony Bourdain claimed “Burt’s was the only deep-dish pizza I ever loved.” With a crispy caramelized crust loaded with cheese and tomato sauce, you just might end up agreeing with Tony.
When you’ve finished chowing down on pizza, pop on over to the Loop District for an entertaining and history-focused tour of Chicago’s ghosts and its gangsters. The 2-hour walking tour gives you the lowdown on some of the most exciting characters from Chicago’s 1920s and 1930s, including The Big Fella himself, Al Capone.
If you’re ready for some fresh air and views, make your way over to DuSable Bridge and hop on a riverboat for a late-afternoon Chicago River Architecture Tour. Book ahead of time to skip the ticket line. Once onboard grab a drink and hunker down for your guided tour. The guide will take you through over 130 years of architectural history as you motor along the Chicago River and Lake Michigan.
To get a bird’s-eye view of the skyline and let the lessons from your architecture tour soak in, mosey on over to the Streeterville neighborhood. Here, you can zoom up 94 floors in about 40 seconds to reach an observation deck that overlooks the city. Admire the cityscape, Lake Michigan, the Chicago River, and even the four states adjacent to Illinois. If you want to add a little adrenaline rush to your visit, give the TILT a whirl. The TILT is an unparalleled experience that’ll have you leaning out over the city a thousand feet above the ground.
After walking, cycling, boating, and tilting over Chicago, head over to Buddy Guy’s Legends for authentic blues music in a cozy atmosphere. For a century, Chicago’s been home to the most talented, pioneering Blues musicians in history, including Muddy Waters, Sonny Boy Williamson, and Howlin’ Wolf. Their spirits live on at Buddy Guy’s, where you can enjoy dinner and a show. For an unforgettable dinner, try the classic Damn Right Burger, the Catfish Po-Boy, or the Red, Hot & Blue Chicken Sandwich. When the waitress asks if you want to add a cup of gumbo, just say “yes” and be glad you arrived hungry.
Start the second of your 2 days in Chicago, by dragging yourself out of bed early to take a peaceful stroll along Chicago’s Riverwalk. Enjoy the public art that’s found all along the pedestrian trail. Walking along this outdoor art gallery is a great way to work up your appetite for your next morning excursion.
At this point during your 48 hours in Chicago, you donut want to miss out on a 2-hour long Chicago Underground Donut Tour. Sample these sweet treats from 4 different shops and enhance your appreciation for this dessert-for-breakfast confectionary by learning about its historic place in Chicago’s foodie past.
No visit to Chicago is complete without catching a Cubs game at the iconic Wrigley Field. If you’ve timed your visit well, you may even be able to see a game showcasing the notorious Route 66 Rivalry — the Chicago Cubs vs. the St. Louis Cardinals. If you’re ready for another slice of pizza, grab a piece of Giordano’s stuffed deep dish. If not, a beer-can chicken sandwich is a decadent alternative. Whatever you choose, make sure to root, root, root for the home team between bites.
When the game is over, round out your cultural experience by scooting over to the Art Institute of Chicago and spend some time perusing the more-than 300,000 pieces of artwork. The Art Institution of Chicago is one of the largest art museums in the country, second only to the Metropolitan Museum of Art in New York. It’ll be a smooth end to an exciting day.
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