50 Fascinating Tours to Explore the Heart of Chicago

Immerse Yourself in Chicago's Architectural Legacy

1. Chicago Architecture Foundation River Cruise (90 minutes)
- Admire over 50 iconic buildings from the unique perspective of the Chicago River.
- Learn about the city's architectural history and its renowned designers.

2. The Willis Tower Skydeck and Ledge (90 minutes)
- Ascend to the 103rd floor of the former Sears Tower for breathtaking panoramic views.
- Step out onto The Ledge, an all-glass enclosed platform extending 4 feet beyond the building.

3. Architecture Center Chicago River Tour (90 minutes)
- Explore the city's architectural heritage and iconic landmarks from the comfort of a boat.
- Led by experienced architects and historians, the tour covers renowned buildings and significant architectural styles.

Discover Chicago's Art and Culture

4. Art Institute of Chicago (2-3 hours)
- Explore one of the world's most renowned art museums, featuring an impressive collection spanning from ancient to contemporary art.
- Witness masterpieces such as Grant Wood's "American Gothic" and Georges Seurat's "A Sunday Afternoon on the Island of La Grande Jatte."

5. The Field Museum (3-4 hours)
- Delve into the world of natural history at the renowned Field Museum.
- Encounter Sue, the largest and most complete Tyrannosaurus rex skeleton ever discovered, and explore exhibits on ancient Egypt, wildlife, and human evolution.

6. The Museum of Science and Industry (3-4 hours)
- Engage in hands-on science demonstrations and interactive exhibits at the Museum of Science and Industry.
- Witness the U-505 submarine, learn about space exploration, and explore the human body through interactive displays.

Indulge in Chicago's Culinary Delights

7. Chicago Food Planet:
- Pizza Tour (3 hours): Savor deep-dish and thin-crust pizzas at iconic pizzerias.
- Chicago Food Tasting Adventure (3 hours): Sample a variety of local specialties, including hot dogs, Italian beef, and Garrett's Popcorn.

8. The Chopping Block Cooking Class (2-3 hours)
- Learn culinary skills in a professional kitchen environment.
- Choose from a variety of class themes, including pasta making, knife skills, and grilling techniques.

9. Windy City Wine Tours (3-4 hours)
- Embark on a guided tour of Chicago's vibrant wine scene.
- Visit local wineries, sample award-winning wines, and learn about the region's viniculture.

Explore Chicago's Neighborhoods and Culture

10. Wicker Park and Bucktown Walking Tour (2 hours)
- Discover the trendy neighborhoods of Wicker Park and Bucktown, known for their vibrant street art, independent boutiques, and lively nightlife.
- Listen to stories of the area's artistic and cultural heritage.

11. Pilsen Neighborhood Art and Food Tour (2 hours)
- Immerse yourself in the vibrant Pilsen neighborhood, renowned for its Mexican and Chicano art.
- Visit murals and galleries, and indulge in authentic Mexican cuisine.

12. Bronzeville Historical and Cultural Walking Tour (2 hours)
- Discover the rich history of Bronzeville, once known as "The Black Metropolis."
- Learn about the area's role in the Great Migration and the contributions of African Americans to Chicago's culture.

Uncover Chicago's Hidden Gems

13. Hidden Gems of the Loop Walking Tour (2 hours)
- Venture off the beaten path in the bustling Loop to uncover hidden architectural details, public art, and historical secrets.
- Experience the city from a fresh perspective.

14. Chicago Cultural Center Highlights Tour (1 hour)
- Explore the stunning Chicago Cultural Center, a historic landmark with free exhibitions on art, history, and music.
- Discover hidden courtyards, ornate architecture, and rotating art installations.

15. Pullman National Historical Park (2 hours)
- Visit Pullman National Historical Park, a former industrial town established by George Pullman, pioneer of the sleeping car.
- Learn about Pullman's innovative manufacturing techniques and its impact on American history.

Experience Chicago's Live Entertainment

16. The Second City Mainstage Show (2 hours)
- Witness the legendary improv comedy troupe, The Second City, at their historic venue in Old Town.
- Enjoy a hilarious and thought-provoking night of sketch comedy and improvisation.

17. Blue Man Group Chicago (1 hour)
- Be mesmerized by the iconic Blue Man Group performance at the Briar Street Theatre.
- Immerse yourself in a mesmerizing blend of music, comedy, and visual art.

18. Shakespeare in the Park by Chicago Shakespeare Theater (2 hours)
- Experience classic Shakespearean plays under the stars at the iconic Navy Pier.
- Enjoy free performances in a beautiful outdoor setting.

Explore Chicago with Kids

19. Shedd Aquarium (2-3 hours)
- Discover a fascinating underwater world at the Shedd Aquarium.
- Behold beluga whales, penguins, and over 1,500 other marine animals.

20. Lincoln Park Zoo (2-3 hours)
- Visit one of the oldest and largest free zoos in the United States.
- Get up close to lions, gorillas, monkeys, and other exotic animals.

21. LEGOLAND Discovery Center Chicago (2-3 hours)
- Unleash your kids' creativity at LEGOLAND Discovery Center.
- Build and play with millions of LEGO bricks, explore interactive rides, and immerse themselves in the world of LEGO.

Step Back in Time in Chicago

22. Chicago History Museum (2-3 hours)
- Delve into Chicago's rich past at the Chicago History Museum.
- Explore exhibits on the Great Fire, the Columbian Exposition, and the city's industrial and cultural legacy.

23. Glessner House Museum (1 hour)
- Step inside the beautifully preserved Glessner House, a landmark designed by renowned architect H.H. Richardson.
- Admire the Victorian era architecture and learn about the Glessner family's influential role in Chicago's history.

24. Hull House Museum (1 hour)
- Visit the historic Jane Addams Hull House, a former settlement house that played a pivotal role in the city's social reform movement.
- Explore exhibits on immigration, labor, and the women's suffrage movement.

Stroll Through Chicago's Beautiful Parks

25. Millennium Park (2 hours)
- Admire the iconic "Cloud Gate" sculpture, commonly known as "The Bean," at Millennium Park.
- Stroll through the Lurie Garden, relax by the Crown Fountain, and enjoy live performances at the Jay Pritzker Pavilion.

26. Lincoln Park (2-3 hours)
- Escape the hustle and bustle in the sprawling Lincoln Park.
- Explore the Lincoln Park Zoo, visit the Peggy Notebaert Nature Museum, and take a leisurely walk or bike ride along the lakefront trail.

27. The 606 (2 hours)
- Discover the elevated parkland known as The 606, stretching from the Logan Square to the Bloomingdale neighborhoods.
- Admire street art, enjoy scenic views, and connect with nature in the heart of the city.

Indulge in Chicago's Nightlife

28. River North Rooftop Tours (2 hours)
- Embark on a guided tour of River North's rooftop scene.
- Sip cocktails, enjoy panoramic city views, and learn about the history and architecture of the area.

29. Wrigleyville Nightlife District (2-3 hours)
- Experience the electric atmosphere of Wrigleyville, known for its baseball atmosphere and lively nightlife.
- Visit iconic bars, cheer on the Cubs at Wrigley Field, or catch a live show at a local music venue.

30. Green Door Tavern (1 hour)
- Step into a piece of Chicago history at the legendary Green Door Tavern.
- Enjoy a drink in the same spot where Al Capone and his crew once gathered.

Delve into Chicago's Sports Scene

31. Wrigley Field Tour (1 hour)
- Take a guided tour of the iconic Wrigley Field, home of the Chicago Cubs.
- Explore the park's history, watch batting practice, and learn about the team's legendary players.

32. United Center Stadium Tour (1 hour)
- Embark on a behind-the-scenes tour of the United Center, home to the Chicago Bulls and Chicago Blackhawks.
- Visit the players' locker rooms, press box, and sit on the actual court or ice.

33. Guaranteed Rate Field Tour (1 hour)
- Discover the home stadium of the Chicago White Sox, Guaranteed Rate Field.
- Learn about the team's rich history, explore the field and dugouts, and stand in the batter's box.

Embark on a Unique Chicago Experience

34. Chop Shop
- Witness a thrilling live demonstration of Chicago's culinary scene at The Chop Shop.
- Watch experienced chefs create mouthwatering dishes and learn about the art of cooking.

35. Willis Tower Thrill Ride (30 minutes)
- Experience a heart