Must-Dos in the Windy City
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Welcome to the Windy City! With its soaring skyscrapers and famous food, Chicago is the ultimate city getaway. Here’s a bucket list to make sure you experience all that Chicago has to offer!
Willis Tower
One of the most iconic skyscrapers in Chicago is the Willis Tower. As the third tallest building in the Western Hemisphere, the Willis Tower offers some impressive views of the city. Head to the top of the building to experience The Skydeck and The Ledge, a glass balcony extending four feet out from the 103rd floor. Click here for more information on the experience.
John Hancock Tower
The John Hancock Tower, now named 875 North Michigan Avenue, is a 100-story skyscraper that dominates the Chicago skyline. Located on the 94th floor is the 360 Chicago Observatory. If you’re looking for a thrill, take part in the TILT ride in the observatory. You’ll stand by a glass window over 1,000 feet above Magnificent Mile and tilt out from the tower. Learn more about the observatory here.
Architecture Boat Tour
If the weather is good, head out on an architecture boat tour to see Chicago’s beautiful skyline. Once on board, you’ll get to hear about the city’s history and see famous buildings such as Marina City and the Tribune Tower. There are a few different companies that offer architecture boat tours – we recommend this one.
Try iconic Chicago foods
Of course, you can’t visit Chicago without trying some of its most iconic food! The top item you have to try is deep dish pizza. Stop by Lou Malnati’s, Uno Pizzeria, or Giordanos for a slice. You should also add trying a Chicago-style hot dog to your Chicago bucket list! Chicago-style hot dogs have a poppy seed bun and are topped with onions, peppers, and a pickle spear. You can even go on a Chicago food and walking tour.
Navy Pier
Stretching out into Lake Michigan, Navy Pier is one of the top attractions in Chicago. The best thing to do at Navy Pier is catch a ride on the Centennial Wheel where you can get a 360 degree view of Chicago and Lake Michigan. We recommend heading to Navy Pier in the late afternoon and staying there for dinner and sunset.
The Bean and Millennium Park
The Bean is the famous metallic sculpture located in Millennium Park. With its reflective surface, The Bean allows you to see yourself and the Chicago skyline together, making it a great spot for photos. While you’re there, make sure to explore the rest of Millennium Park! Check out the interactive Crown Fountain, listen to live music, or stroll through the Boeing Galleries.
Magnificent Mile
Chicago’s Magnificent Mile is one of the most famous shopping and dining districts in the world. Walk the Magnificent Mile to see beautiful architecture such as the Wrigley Building and flagship stores including Gucci and Burberry.
Starbucks Reserve
Did you know that the largest Starbucks in the world is in Chicago? Located on Michigan Avenue, the Starbucks Reserve Roastery serves up creative coffee drinks and cocktails across five floors. Get there early or prepare to wait in line – it’s one of the most popular destinations in the city!
Museum of Science and Industry
If you enjoy visiting museums, make sure to include the Museum of Science and Industry in your itinerary. This expansive museum is the largest science center in the Western Hemisphere. Check out the flight simulators, science storms, and transportation gallery.
Alder Planetarium
The Adler Planetarium is America’s first planetarium. Dedicated to astronomy and astrophysics, the museum has exhibits on meteors, space exploration, and life beyond Earth. General admission for adults starts at $19. All tickets must be purchased online in advance of your visit.
Field Museum
The Field Museum is one of the top natural history museums in the world, with collections ranging from Egyptian mummies to Sue, the 40-foot-long T-rex. We recommend budgeting about four hours for your visit. Ticket prices vary depending on the day of the week that you go, and there’s discounts for students, teachers, and military personnel.
Art Institute of Chicago
Not too far from Millennium Park is the Art Institute of Chicago. This extensive museum houses famous pieces such as American Gothic, Nighthawks, and A Sunday Afternoon on the Island of La Grande Jatte. Plan to spend two hours to half a day here. General admission for adults is $32.
Wrigley Field
Located on the north side of Chicago is the home of the Chicago Cubs. You can tour the stadium on both game days and non-game days. See this link for more information. While you’re there, make sure to spend some time exploring the sports bars and pubs in the Wrigleyville neighborhood!
Lincoln Park Zoo
Lincoln Park Zoo, spanning 35 acres, is one of the few admission-free zoos in the country. This green oasis is the perfect spot to take kids while in Chicago. Stop by to see lions, penguins, seals, and more!
Catch a Show at One of Chicago’s Iconic Venues
Chicago has no shortage of entertainment options. Stop by the iconic Chicago Theatre for a concert, or head over to Harris Theater in Millennium Park for a night at the ballet. One of the best live shows to see is the Blue Man Group at Briar Street Theatre; check here for upcoming shows.
Disclaimer: All information presented in this post was accurate at the time of our trip. Attractions, availability, circumstances, operating hours, prices, etc. are subject to change and this post may not reflect the most up-to-date information. Readers are advised to do their due diligence in researching the location prior to travel. Hyperlink content may be out-of-date and is not sponsored by or affiliated with Scenic Sites unless otherwise noted.
Posted February 2024
