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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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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$567/ person
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Chicago Haunts and Hooligans Tour
5.0(37)
Nightly Spirits’ Haunts and Hooligans Tour will illustrate Chicago’s haunted history of secret parlors, underground tunnels, murderous movie theaters and supernatural speakeasies. Whether you’re a recent transplant to Chicago or have lived among the Windy City’s ‘others’ for years, you’re about to get a haunted history that may leave you with more memories than you dare to retain. Tours begin at the haunted Harry Caray’s Italian Steakhouse in downtown Chicago. A costumed guide will lead tour goers on a walking journey exploring the creepy past of one of Chicago’s most famous bootleggers, offering glimpses into the past and revealing the stories of long-dead phantoms and specters who still call Chicago home.
From$35/ 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(5,628)
1 tours
Chicago Favorites Ultimate Food and Walking Tour
★4.9(2,017)
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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.
theatre
theatreThe Angel Next Door
North Shore Center For The Performing Arts - Northlight Theatre
Sunday, April 12, 2026 · 2:30 PM
🎟️ 24 tickets
From $10
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comedy
concertsThe Nude Party & Tobacco City
Lincoln Hall
Thursday, April 16, 2026 · 8:00 PM
🎟️ 52 tickets
From $1
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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.
