Best Chicago Tours & Attractions: River Cruises, Food Tours, and Must-See City Experiences
1. Chicago River 90-Minute Architecture Tour
Discover Chicago’s world-famous skyline from the best vantage point—the water! This 90-minute architecture tour takes you along the Chicago River as expert guides share the fascinating stories behind the city’s most iconic buildings and landmarks.
2. Chicago River 45-Minute Architecture Tour from Magnificent Mile
Perfect for those short on time, this 45-minute tour offers a condensed yet captivating look at Chicago’s architectural wonders. Departing from the Magnificent Mile, enjoy expert narration as you cruise through the heart of the city.
3. Flyover in Chicago
Experience Chicago like never before with Flyover, an immersive attraction that uses state-of-the-art flight simulation technology. Soar above the city’s landmarks and breathtaking landscapes from a thrilling new perspective.
4. Chicago Architecture River Cruise
Step aboard for one of Chicago’s must-do experiences! This river cruise offers in-depth commentary on the city’s architectural evolution while gliding past towering skyscrapers and historic landmarks.
5. Chicago CityPASS®
Save big on Chicago’s top attractions with CityPASS®. Gain discounted entry to iconic sites like Shedd Aquarium, Field Museum, Skydeck Chicago, and more, all in one convenient ticket.
6. 360 CHICAGO Observation Deck Admission
Take in sweeping views of Chicago’s skyline, Lake Michigan, and even four neighboring states from the 94th floor of the John Hancock Center. Add the TILT experience for an adrenaline rush!
7. Lake Michigan Sunset Cruise in Chicago
Set sail on Lake Michigan for a magical evening. Watch the sun dip below the Chicago skyline while enjoying drinks and music aboard a comfortable cruise vessel.
8. Skydeck Chicago Admission Ticket
Step onto the Ledge at Skydeck Chicago, a glass balcony 1,353 feet in the air! Enjoy jaw-dropping views from the top of the Willis Tower, one of the city’s most famous landmarks.
9. Chicago Favorites Ultimate Food and Walking Tour
Taste your way through Chicago’s culinary scene on this guided food tour. Sample deep-dish pizza, Chicago-style hot dogs, and other iconic bites while learning about the city’s rich food culture.
10. Lake Michigan Skyline Cruise in Chicago
Marvel at Chicago’s dramatic skyline on this relaxing Lake Michigan cruise. Perfect for photos and sightseeing, it’s a great way to appreciate the city from a different perspective.
11. Big Bus Chicago: Hop-On Hop-Off Sightseeing Tour, 24/48/72hr Pass
Explore Chicago at your own pace with Big Bus’ hop-on hop-off service. With flexible passes, you can visit top attractions while enjoying informative onboard narration.
12. Lake Michigan Fireworks Cruise in Chicago
Enjoy an unforgettable night on Lake Michigan as dazzling fireworks light up the Chicago skyline. This cruise pairs breathtaking views with a lively atmosphere.
13. Chicago Crime and Mob Bus Tour
Dive into Chicago’s colorful past on this guided bus tour exploring infamous mobsters, crime scenes, and Prohibition-era history.
14. Chicago River 90-Minute Architecture Boat Tour
This extended river tour lets you fully appreciate Chicago’s stunning architecture. Learn from expert guides as you pass over 50 of the city’s most famous buildings.
15. Chicago Architecture Center River Cruise aboard First Lady
Partnering with the Chicago Architecture Center, this cruise delivers unparalleled insight into the city’s design and history aboard the elegant First Lady vessel.
16. Chicago Architecture and True Crime History Tour
Combine two fascinating worlds: Chicago’s architectural gems and its darker crime history. Walk or cruise through the city as your guide weaves captivating stories together.
17. Chicago Creepy Cruise
Board this spooky-themed cruise to hear chilling tales of ghosts, legends, and mysterious events along Chicago’s riverfront.
18. Chicago By Night River & Lake Cruise
See Chicago sparkle at night on this serene cruise that takes you from the river out to Lake Michigan for breathtaking evening skyline views.
19. Chicago Lake and River Architecture Tour
This combination tour covers the best of both worlds—explore the Chicago River and Lake Michigan to get the ultimate view of the city’s architecture.
20. Chicago in a Day: Explore Food, History, and Iconic Architecture
Spend a full day uncovering Chicago’s highlights with a guide. Enjoy food tastings, architectural landmarks, and historical stops in one comprehensive tour.
21. Chicago's Fireworks Show aboard Tall Ship Windy!
Step aboard the majestic Tall Ship Windy for a unique sailing adventure featuring Chicago’s spectacular fireworks display from the best seat in the house.
22. Chicago's Chinatown Food and Walking Tour
Experience the vibrant culture of Chinatown on a guided food tour. Taste authentic dishes from family-owned eateries while exploring the neighborhood’s history.
23. Chicago Sightseeing River and Lake Cruise
See the Windy City from all angles on this scenic cruise that covers both the river and Lake Michigan. It’s a complete way to take in Chicago’s beauty.
24. Chicago 3D Fireworks Cruise
Watch fireworks burst over Chicago’s skyline in 3D! Special glasses enhance the colorful display on this one-of-a-kind evening cruise.
Discover Chicago from every angle – start planning your trip now!