The Ultimate Chicago Bucket List: 50 Things to Do
Welcome to the Windy City! Chicago, a bustling metropolis known for its rich history, stunning architecture, and vibrant culture, offers an endless array of activities and attractions. Whether you’re a local or a first-time visitor, this ultimate Chicago bucket list covers 50 must-do experiences that capture the essence of this iconic city. From exploring world-class museums to savoring deep-dish pizza, each activity promises an unforgettable adventure. Let’s dive in!
1. Explore Millennium Park
Start your Chicago journey at Millennium Park, a 24.5-acre urban park located in the Loop community area. Known for its iconic Cloud Gate sculpture, affectionately known as “The Bean,” this park offers stunning art installations and is a hub for cultural activities. Don’t miss the Crown Fountain and the Jay Pritzker Pavilion for an unforgettable experience.
2. Visit the Art Institute of Chicago
Ranked among the world’s top museums, the Art Institute of Chicago houses an impressive collection spanning centuries. Art enthusiasts will relish masterpieces by Monet, Van Gogh, and Seurat. For an enhanced visit, consider taking a guided tour to delve deeper into the stories behind these iconic works.
3. Stroll Along the Chicago Riverwalk
The Chicago Riverwalk is a pedestrian-friendly promenade that offers stunning views of the city’s architectural marvels. Enjoy a leisurely stroll, dine at riverside restaurants, or take a boat tour to admire Chicago’s skyline from the water. It’s a perfect spot for photography enthusiasts, especially during sunset.
4. Discover the Field Museum
Home to the world-renowned T. rex named Sue, the Field Museum is a treasure trove of natural history. Explore exhibits that span millions of years and cover diverse topics, from ancient civilizations to modern ecosystems. Plan your visit around special exhibitions for a unique experience.
5. Experience Willis Tower Skydeck
For breathtaking panoramic views of Chicago, head to the Willis Tower Skydeck. Step onto The Ledge, a glass balcony extending 1,353 feet above the ground, for a heart-pounding view of the city beneath you. Pro tip: Visit at sunset to see the city transition from day to night.
6. Indulge in Chicago’s Deep-Dish Pizza
No trip to Chicago is complete without sampling its famous deep-dish pizza. Head to renowned spots like Lou Malnati’s, Giordano’s, or Pequod’s to savor this cheesy, hearty delight. Be prepared for a wait, as these popular eateries often draw large crowds.
7. Walk Through Lincoln Park Zoo
One of the last free-admission zoos in the country, Lincoln Park Zoo is home to a diverse range of animals and is situated in a beautiful park setting. Ideal for families, this zoo offers educational programs and events throughout the year.
8. Attend a Chicago Cubs Game at Wrigley Field
Experience America’s favorite pastime at the historic Wrigley Field. Catch a Chicago Cubs game and soak in the electric atmosphere of one of the oldest ballparks in the country. Don’t forget to grab a hot dog or some popcorn to complete the experience.
9. Explore the Museum of Science and Industry
The Museum of Science and Industry is a must-visit for curious minds of all ages. Interactive exhibits, including a full-size replica of a coal mine and a World War II-era German submarine, make learning fun and engaging. It’s a great spot for families and science enthusiasts alike.
10. Wander Through Grant Park
Known as “Chicago’s front yard,” Grant Park offers lush greenery, walking paths, and cultural attractions. Visit Buckingham Fountain, one of the largest fountains in the world, and make sure to check the park’s schedule for free concerts and festivals during the warmer months.
11. Marvel at the Architecture on an Architectural Boat Tour
Chicago is known for its stunning architecture, and an architectural boat tour is the best way to see it. Learn about the history and design of the city’s most famous buildings while cruising along the Chicago River. This tour is both informative and visually captivating.
12. Visit the Shedd Aquarium
The Shedd Aquarium offers a fascinating glimpse into the underwater world with over 32,000 animals. From beluga whales to vibrant coral reefs, this aquarium provides hours of exploration. Check for feeding schedules and special shows to enhance your visit.
13. Experience the Magic at Navy Pier
A trip to Chicago isn’t complete without a visit to Navy Pier. Enjoy rides, shops, and restaurants along this iconic pier. The Centennial Wheel offers stunning views of the city and Lake Michigan, especially enchanting at night when the lights illuminate the skyline.
14. Explore Chicago’s Diverse Neighborhoods
Each of Chicago’s neighborhoods offers a unique cultural experience. From the authentic Mexican cuisine in Pilsen to the vibrant arts scene in Wicker Park, there’s something for everyone. Spend a day exploring these areas to truly appreciate the city’s diversity.
15. Catch a Show at the Chicago Theatre
With its iconic marquee, the Chicago Theatre is a historic venue that hosts a variety of performances, from concerts to comedy shows. Check the schedule ahead of your visit to catch a live performance in one of the city’s most beloved venues.
16. Visit the Adler Planetarium
Located on the shores of Lake Michigan, the Adler Planetarium is a leader in space science education. Explore exhibits about the universe, participate in a sky show, or enjoy hands-on activities that bring the wonders of space closer to Earth.
17. Try a Chicago-Style Hot Dog
A trip to Chicago wouldn’t be complete without trying a classic Chicago-style hot dog. Piled high with mustard, onions, relish, a pickle spear, tomatoes, sport peppers, and celery salt, this local favorite is a must-try. Head to Portillo’s or Superdawg for an authentic taste.
18. Visit the Chicago Cultural Center
The Chicago Cultural Center hosts free art exhibitions and performances throughout the year. Marvel at the stunning architecture, including the world’s largest Tiffany stained-glass dome. It’s a great way to experience Chicago’s vibrant arts scene at no cost.
19. Take a Walk on the 606 Trail
The 606 Trail is an elevated greenway built on a former rail line, perfect for walking, jogging, or biking. Spanning 2.7 miles, it connects several neighborhoods and offers a unique perspective of the city. It’s a community favorite for outdoor activities.
20. Enjoy Jazz at the Green Mill
For an authentic Chicago jazz experience, visit the Green Mill Cocktail Lounge. This historic venue has been a jazz hotspot since the 1900s and offers live performances in a cozy, speakeasy-style setting. It’s a must-visit for music lovers.
21. Explore the Garfield Park Conservatory
Known as “landscape art under glass,” the Garfield Park Conservatory is one of the largest and most stunning botanical conservatories in the nation. Explore its lush gardens and seasonal flower shows for a peaceful escape from the urban hustle.
22. Visit the Museum of Contemporary Art
The Museum of Contemporary Art in Chicago showcases the latest in modern art. With frequently changing exhibits and a stunning permanent collection, art lovers will find plenty to explore. Check the event calendar for artist talks and performances.
23. Walk the Lakefront Trail
The Lakefront Trail offers 18 miles of scenic pathways along Lake Michigan. Ideal for walking, biking, or rollerblading, this trail provides breathtaking views of the lake and city skyline. Pack a picnic and enjoy a day by the water.
24. Savor a Meal in Greektown
Experience the flavors of Greece right in Chicago’s Greektown. Enjoy traditional dishes such as moussaka, souvlaki, and baklava at renowned restaurants like Greek Islands and Athena. It’s a culinary journey you won’t want to miss.
25. Discover the Chicago History Museum
Delve into the rich history of Chicago at the Chicago History Museum. From the Great Chicago Fire to the city’s role in the civil rights movement, this museum offers fascinating exhibits that paint a vivid picture of the past.
26. Experience a Dinner Cruise on Lake Michigan
For a unique dining experience, take a dinner cruise on Lake Michigan. Enjoy stunning views of the Chicago skyline while savoring a gourmet meal. Many cruises offer live music and entertainment, making it a memorable evening out.
27. Visit the National Museum of Mexican Art
The National Museum of Mexican Art in Pilsen is home to one of the largest Mexican art collections in the U.S. With exhibits that celebrate Mexican culture and heritage, this museum is a vibrant and educational experience.
28. Explore the Magnificent Mile
No shopping enthusiast should miss the Magnificent Mile. This iconic stretch of Michigan Avenue is lined with high-end boutiques, department stores, and restaurants. It’s a shopper’s paradise with something for every taste and budget.
29. Attend a Festival in Grant Park
Chicago is known for its vibrant festival scene, and Grant Park is often the center of the action. From Lollapalooza to the Chicago Gourmet festival, there’s always something happening. Check the city’s events calendar to catch a festival during your visit.
30. Visit the Oriental Institute Museum
Part of the University of Chicago, the Oriental Institute Museum offers an incredible collection of artifacts from ancient Near Eastern civilizations. Explore exhibits that cover ancient Egypt, Persia, and Mesopotamia for a fascinating historical journey.
31. Enjoy a Comedy Show at Second City
As the birthplace of improv comedy, Second City is a legendary venue known for launching the careers of many famous comedians. Catch a show for a night of laughter and entertainment in Chicago’s vibrant comedy scene.
32. Visit the Chicago Botanic Garden
Located just outside the city, the Chicago Botanic Garden offers 385 acres of beautifully landscaped grounds. With 27 gardens and four natural areas, it’s a peaceful retreat that’s perfect for a day trip.
33. Take a Bike Tour of the City
See Chicago from a new perspective on a bike tour. Guided tours offer insights into the city’s history, architecture, and culture while allowing you to cover more ground than on foot. It’s a fun and active way to explore.
34. Explore Chinatown
Chicago’s Chinatown offers a rich cultural experience with authentic cuisine, unique shops, and vibrant architecture. Visit the Chinatown Gate and enjoy a meal at one of the many traditional restaurants for a taste of the East.
35. Visit the Peggy Notebaert Nature Museum
Focused on the environment and conservation, the Peggy Notebaert Nature Museum offers interactive exhibits and a live butterfly house. It’s an educational experience that’s perfect for families and nature enthusiasts.
36. Enjoy Views from the John Hancock Center 360 Chicago
For an unparalleled view of Chicago, visit 360 Chicago at the John Hancock Center. The TILT attraction offers a unique perspective, leaning visitors out over the city for a thrilling experience.
37. Experience the Chicago Jazz Festival
Held annually, the Chicago Jazz Festival is a celebration of jazz music with performances by local and international artists. This free event at Millennium Park attracts jazz lovers from around the world.
38. Visit the Museum of Broadcast Communications
Explore the history of television and radio at the Museum of Broadcast Communications. With exhibits on everything from classic TV shows to presidential debates, it’s a fascinating look at the evolution of media.
39. Take a Class at the Chopping Block
Located in Lincoln Square, The Chopping Block offers cooking classes ranging from knife skills to advanced culinary techniques. It’s a fun and educational way to improve your cooking skills in a hands-on environment.
40. Explore the Smart Museum of Art
Part of the University of Chicago, the Smart Museum of Art offers a diverse collection of art from various cultures and eras. Admission is free, making it an accessible cultural experience for all visitors.
41. Visit the Jane Addams Hull-House Museum
Learn about social reform and the history of Chicago’s immigrant communities at the Jane Addams Hull-House Museum. This historic site offers exhibits and programs that highlight the legacy of Jane Addams and the Hull-House settlement.
42. Enjoy a Day at Montrose Beach
For a relaxing day by the water, head to Montrose Beach. With sandy shores, a dog-friendly area, and opportunities for kayaking and paddleboarding, it’s a popular spot for both locals and visitors.
43. Explore the Pritzker Military Museum & Library
Dedicated to the study of military history, the Pritzker Military Museum & Library offers exhibits and collections that cover a range of military topics. It’s a must-visit for history buffs and those interested in military affairs.
44. Visit the DuSable Museum of African American History
Explore the rich history and culture of African Americans at the DuSable Museum of African American History. With exhibits on art, history, and culture, this museum provides a comprehensive look at African American contributions to society.
45. Experience the Chicago Air and Water Show
One of the largest free events of its kind, the Chicago Air and Water Show features thrilling aerial displays and water stunts. Held annually over Lake Michigan, it’s a spectacular event that draws large crowds.
46. Visit the International Museum of Surgical Science
For a unique museum experience, visit the International Museum of Surgical Science. Explore exhibits on the history of surgery and medical technology in a historic mansion setting.
47. Explore the Pullman National Monument
Visit the Pullman National Monument to learn about Chicago’s industrial past and the role of the Pullman Company in labor history. Guided tours offer insights into this historic community.
48. Take a Ghost Tour
Discover the spooky side of Chicago on a ghost tour. Learn about the city’s haunted history and visit reputedly haunted sites for a thrilling and educational experience.
49. Experience a Chicago Bulls Game
For sports fans, attending a Chicago Bulls game at the United Center is a must. Cheer on the home team and enjoy the energetic atmosphere of an NBA game.
50. Enjoy Ice Skating at Maggie Daley Park
During the winter months, head to Maggie Daley Park for ice skating on the Skating Ribbon. This unique ice path offers a scenic skating experience in the heart of the city.
Conclusion
Chicago is a city that offers something for everyone, from its rich cultural experiences to its stunning natural landscapes. Whether you’re exploring its historic sites, enjoying its culinary delights, or immersing yourself in its vibrant arts scene, there’s no shortage of things to do and see. This ultimate Chicago bucket list is just the beginning of what the city has to offer. So grab your itinerary, lace up your walking shoes, and get ready to explore the Windy City like never before!
