Katie Sagal

Ultimate Chicago Bucket List

With such a diversity of cultures, attractions, cuisines, and neighborhoods, Chicago is just bursting with exciting things to do for locals and visitors. Whether you’re a long-time Chicagoan or a newbie trying out the ropes, we’ve pulled together our favorite things to do in this marvelous city. This ultimate Chicago bucket list isn’t completely exhaustive but it’s a good start for those who hope to enjoy the best and most unique things that the Windy City has to offer. In no particular order, please consider:

Chicago Bucket List 1-10

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  1. Visit the Lions at the Art Institute. One of the best art museums in the world, Michigan Ave. entrance to the Art Institute of Chicago is also guarded by some of the most famous lions.
  2. Go ice-skating at Maggie Daley Park. With their own modest ice-skating ribbon, Maggie Daley Park is a great winter destination for families.
  3. Ride the Centennial Wheel. This Navy Pier icon is perfect for dates or entertaining the kids. Check out the new rooftop bar while you’re at it.
  4. See the summer fireworks at Navy Pier. You can take a cruise to see them closer, but the views from the Pier itself are pretty good, too.
  5. Compare the views. Chicago boasts two main observation decks—SkyDeck Chicago and 360 CHICAGO. Try them both to see which you like best.
  6. Savor deep-dish pizza. One of Chicago’s most famous culinary exports, deep-dish pizza is a must. Try Gino’s East (just off Michigan Ave.) for some authentic options.
  7. Snap your photo with the world’s most famous dinosaur. SUE the T. Rex, at the Field Museum, is the largest and most complete T. Rex skeleton in the world. Get a selfie with it to soak up the celebrity vibes.
  8. Tour Wrigley Field. Or cheer on the Cubs. Either way, the world-famous Wrigley Field is a must-see for all Chicago visitors.
  9. Go shopping. Chicago is a shopping capital of the country, with options ranging from luxe Oak Street to eclectic Wicker Park.
  10. Take a cruise on Lake Michigan. If you’ve never enjoyed an excursion out on a lake so big that it has tides, this Lake Michigan cruise is perfect.

Chicago Bucket List 11-20

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  1. Sample craft brews. Chicagoland has more breweries than any other metro area in the country, and many of them don’t export. Snag that rare Forbidden Root IPA while you can.
  2. See some Frank Lloyd Wright architecture. This iconic American architect called Chicago home for many years, with great examples of his Prairie Style architecture like the Robie House still around to explore.
  3. Enjoy the nightlife. With bars that close at 4 AM and a selection of venues offering everything from expensive champagne to dollar beers, the Chicago nightlife scene is unbeatable.
  4. Put the kids on a historic carousel. The Lincoln Park Zoo boasts an endangered species carousel comprised of 48 artisan-made wooden animals—an artistic marvel in the age of all things plastic.
  5. Take an architecture tour. Even locals love the chance to explore the city’s multi-faceted architectural history. Options include architecture cruises, bus tours, walking tours, or even Segway tours.
  6. Dine at the Walnut Room. Located in Macy’s on State Street, this iconic restaurant is most popular at Christmastime when you can see their annual tree.
  7. Roam Millennium Park. This massive urban park includes landmarks like the Pritzker Pavilion (home to free concerts in the summer) and public art like “Cloud Gate” (also known as The Bean) and the official Chicago Christmas Tree in the winter.
  8. Tour the historic Chicago Theatre. Boasting one of the most iconic marquee signs in the city, the Chicago Theatre also has a lot to offer inside. Take a tour to see it all.
  9. Explore the Chicago Riverwalk. This revitalized area is a hip place to dine, sip cool drinks, or go on a river cruise.
  10. Bike, walk or run along the lakefront trail. It’s one of the nation’s most beautiful and longest waterfront trails. Rent a bike if you weren’t able to bring your own.

Chicago Bucket List 21-25

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  1. Go on a date at a planetarium. The Adler Planetarium offers monthly Adler After Dark events with music, entertainment, and, of course, star-gazing.
  2. Take in a show. Chicago’s theatre scene easily rivals that of New York City, with more theatres, more shows, and more indie productions than Broadway.
  3. Soak up artistic inspiration. The Museum of Contemporary Art offers an eclectic mix of the most innovative and provocative art being produced around the world. They also have a restaurant, Marisol, which is helmed by one of the city’s top chefs.
  4. Party at a music festival. Lollapalooza is one of the biggest and most diverse music festivals in the United States, as well as one of the most long-running.
  5. Commune with nature. The Garfield Park Observatory is an oasis in the middle of the city, bursting with greenery and lush indoor gardens that visitors can enjoy for free year-round.
Save on Chicago Bucket List Ideas Many of these ultimate Chicago bucket list ideas are included on the Go Chicago pass. This convenient digital pass provides up to 55% on combined admission prices to the city’s best attractions and activities. Share Your Adventure with Us Tag @GoCity or use the hashtag #GoCityPass in your vacation photos and we'll feature you on our page. Follow the Go City Instagram and Facebook pages for competitions, special offers, and events and inspiration for your chosen destination, too!
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