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Chicago’s greatest hits: The Second City’s top attractions

Discover all that the Windy City has to offer, from towering skyscrapers to local deep-dish delicacies to parks, museums and more.

chicago skyline
Credit: Illinois Office of Tourism

Every city has its must-dos and have-to-visit spots, and Chicago’s are second to none. There’s the skyline, the lakefront, the Mag Mile, the Bean, countless places to get Chicago-style pizza, hot dogs, and so many other local favorites. Check out our curated list of where to go when you go to Chicago.

Day 1

Chicago is a fantastic, multi-faceted city to explore with attractions that’ll appeal to all ages and interests. Focusing on the city’s most well-known top spots, there’s plenty to keep all entertained. Start your day exploring Millennium Park and take a selfie at Cloud Gate. World-famous museums are up next. The Art Institute of Chicago, Field Museum, Museum of Science & Industry and more. Select one you know you’ll love or branch out to discover something new. For a bite, savor delish Chicago-style deep dish at Giordano’s or Lou Malnati’s.

Day 2

Time to get a different perspective on Chicago’s impressive skyline and historic architecture. But first, coffee. Stop into the Starbucks Roastery on Michigan Avenue—the largest in the world—and then head over to the Chicago Architecture Center. Set sail on an Architecture Boat Cruise, a great way to see some of the city’s most famous structures while learning their history from knowledgeable guides. For a top-tier experience, head to Skydeck Chicago or 360 Chicago to see the city from above. There’s plenty of shopping nearby on the Magnificent Mile and Portillo’s is a great option for a Chicago dog.

If you’d like to stay central but take a break from downtown, beaches and sprawling lakefront trails are a great way to spend the afternoon. Or, head out into one of 77 neighborhoods that make up the city, each diverse and unique in their own way. Many offer neighborhood tours, the perfect way to explore the communities with a local lens.

Day 3

Grab an iconic Chicago snack while you explore the city. Visit Illinois Made Maker Garrett Popcorn Shop for a taste of their famous Chicago mix—a delicious blend of cheese and caramel popcorn. While there’s plenty to keep you entertained downtown, exploring further north you’ll find the impressive (and free) Lincoln Park Zoo. Sports fans should continue to Wrigley Field for a pic with the iconic marquee or head to the United Center for the Michael Jordan statue.