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Curated Experiences
Things to Do in Chicago
Chicago's architecture boat tours are consistently the highest-rated tour experience in America. Beyond the river, the city delivers world-class deep dish pizza tours, improv comedy at Second City, stunning Lake Michigan views, and Millennium Park — all compact enough to explore in a long weekend.
ArchitectureFood ToursComedyLake MichiganMuseumsWalking Tours
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Small-Group Sightseeing Boat Tour in Chicago
5.0(95)
The ultimate custom sightseeing experience in Chicago! Enjoy the City from great vantage points and photograph the world-famous skyline. We zip you to many sights around the local waterways including the Navy Pier, Soldier Field, Fort Dearborn, Vietnam Memorial, Wolf Point, Shedd Aquarium, and many others. Come aboard our safe and seaworthy US NAVY built Rigid Inflatable Boat (RIB), and experience a unique & personal tour of the City!
From$89/ person
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Private Sailing on Beautiful Lake Michigan - Navy Pier, Chicago
5.0(70)
Enjoy a private two-hour sailing experience for up to six people along Chicago’s beautiful lakefront. Kick back, relax, and let the US Coast Guard licensed captain treat you to stunning views of Chicago’s spectacular skyline. Make the experience your own. The flexibility of a private charter allows customization of virtually any aspect of the sailing adventure from guest list to music selection to sailing route. Three departure times offered daily. This experience is not meant to be an in-depth guided tour; however, our captain is always happy to point out interesting sights with anecdotes and historical information. Just ask you captain. Looking for a sunset sail, see our other product listing "Come Sailing with us at Navy Pier - Sunset Sail on Lake Michigan". Looking to watch the Navy Pier Fireworks from a private sailing charter, see our other product listing "Come Sailing with us at Navy Pier - Saturday Fireworks Sail". All charters are NON-SMOKING experiences.
From$508/ person
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Top Attractions in Chicago
Popular landmarks and sights with bookable tours and activities
1 tours
Chicago Architecture Center River Cruise aboard First Lady
★4.9(5,941)
1 tours
Chicago Favorites Ultimate Food and Walking Tour
★4.9(2,088)
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Insider Tips for Chicago
1
Architecture boat tours from the Chicago Riverwalk run March through November. Spring and fall have the best light and smallest crowds.
2
Deep dish takes 45 minutes to bake — order before you're hungry, or do a food tour that pre-arranges tastings at multiple spots.
3
Second City improv shows sell out on Friday and Saturday nights. Wednesday and Thursday shows are the same performers with more intimate audiences.
Tickets in Chicago
Live inventoryBroadway, sports, concerts and more — with real-time availability and pricing.
performing-artsChicago Symphony Orchestra: Ravel, Strauss & Brahms
Chicago Symphony Center
Friday, May 29, 2026 · 1:30 PM
🎟️ 196 tickets
From $2
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concertsotherconcertsconcertsFrequently Asked Questions
What is the most popular tour in Chicago?
The Chicago Architecture Foundation river cruise is the #1 rated tour — it covers over 50 buildings along the Chicago River with expert docent narration. Book the 90-minute version for the complete experience. Morning departures have the best light for photography.
What is the best food experience in Chicago?
Food tours covering deep dish pizza, Chicago-style hot dogs, and Italian beef are the most popular. The best ones cover 4-6 stops across neighborhoods like Wicker Park, Pilsen, or the Loop. Guided tours include samples at each stop — arrive hungry.
Explore Chicago
Experiences powered by Viator, a Tripadvisor company. Prices shown are starting prices per person.
