Is the Windy City calling your name? Get ready for a whirlwind of excitement, culture, and, of course, incredible food. Chicago, the third-largest city in the U.S., is packed with iconic neighborhoods that each have their own unique vibe. Whether you’re walking through the artsy streets of Wicker Park or soaking up the amazing architecture along the Riverwalk, there’s so much to see.
Additionally, no trip to Chicago is complete without sinking your teeth into a slice of the legendary deep-dish pizza. Plus, if you’re lucky enough to visit during one of the city’s world-famous music festivals, like Lollapalooza, you’ll experience the city of Chicago in full force. So, whether you’re in town for a weekend or planning to stay a week, we’ve got you covered on what to do in Chicago.
Visit the Field Museum
If you can only hit one museum in Chicago, make it this one. The Field Museum is one of the largest natural history museums in the world and is packed with over 40 million artifacts and specimens. Check out amazing exhibitions like Egyptian mummies, the infamous man-eating lions of Tsavo, and SUE, the largest and most complete Tyrannosaurus rex ever found.
Eat Chicago pizza
When you’re in Chicago, trying deep-dish pizza is an absolute must. This iconic dish is baked in a deep pan, giving it that high edge that holds loads of gooey cheese and chunky tomato sauce. With hundreds of spots to choose from, you won’t be lacking options. Lou Malnati’s is a fan favorite with over 60 locations, famous for its buttery Buttercrust™. Another gem is George’s Deep Dish, where owner George Bumbaris uses a unique sourdough starter and layers toppings over the sauce instead of under it. You can also check out Giordano’s for their stuffed version and Pequod’s for that crunchy, caramelized crust.
Get tickets for a show on Broadway in Chicago
Who says Broadway is just for New York? Broadway In Chicago brings the excitement of live theater to the Windy City, showcasing a fantastic mix of musicals and plays across five beautiful theaters in the Loop. Annually, over 1.7 million people flock to the Chicago Theatre District for unforgettable performances. The scene is known for pre-Broadway productions, with hits like The Producers, Spamalot, and Kinky Boots. Plus, you can catch long-running favorites like Wicked, The Lion King, and Hamilton.
Go thrifting in Andersonville
If you’re wondering what to do in Chicago, don’t miss Andersonville. This trendy neighborhood is steeped in Swedish heritage, showcasing delightful restaurants, bakeries, and charming boutiques. But what really sets Andersonville apart is its amazing thrift and antique shops. Stroll along North Clark Street, where you’ll find gems like The Brown Elephant, 2nd STREET Andersonville, and Buffalo Exchange for unique second-hand clothing. For music lovers, Rattleback Records is a must-visit, and bookworms will enjoy browsing Uncharted Books.
Listen to blues at Buddy Guy’s Legends
If you’re a blues fan, checking out Buddy Guy’s Legends is a no-brainer. Since opening in 1989, it’s become the spot for live blues in Chicago, with up-and-coming talent and famous acts jamming 7 nights a week. Legends has hosted blues icons like B.B. King and Koko Taylor, plus rock stars like Eric Clapton and The Rolling Stones. The venue features amazing live music, New Orleans-inspired food, and walls packed with blues history – art, records, and rare photos. It’s like a museum, but one where you can drink, dance, and maybe spot a legend or two!
Get your comedy fix at the Laugh Factory
Looking for a good laugh? Head to the Laugh Factory, one of the best comedy clubs around. Originally opening in L.A. in 1979, this world-famous club has a Chicago location that serves up laughs seven days a week. From open mics featuring fresh talent to sets by some of your favorite comedians, you’re guaranteed a fun night. Grab some drinks, sit back, and enjoy the show.
Walk around Navy Pier
Completed in 1916, this iconic 3,300-foot pier stretches into Lake Michigan and is packed with fun activities year-round, especially in the summer when fireworks and live music light up the night. Don’t miss the Centennial Wheel at Pier Park for unbeatable views, or check out the Chicago Children’s Museum if you’re visiting with your kiddos. You can also hop on a boat cruise for a scenic tour of the city from the water.
Enjoy views from Skydeck Chicago
Located on the 103rd floor of Willis Tower, it offers amazing views that stretch across four states. Step onto The Ledge, a glass-floored balcony that extends 4.3 feet outside the building, with just 1.5 inches of glass separating you from the city below. There’s also a small museum where you can dive into Chicago’s history.
Explore Millennium Park
When considering what to do in Chicago, Millennium Park often comes to mind very quickly. This iconic spot is homie to the iconic Cloud Gate (aka The Bean), making it one of the most photographed places in the city. In the summer, Millennium Park offers interactive fountains, lush gardens, public art, rock climbing, and free concerts. Come winter, it transforms into a winter wonderland with ice skating rinks and festive Christmas events.
