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Top Things to Do in Chicago

We compared all 142 experiences in Chicago so you can choose in minutes: real prices, verified reviews and our editorial picks.

★4.7 142 experiences from US$ 6 ✓Free cancellation on most experiences

All tours (61–80 of 142)

Chicago: Family Bike & Food Tour with Pizza, Hot Dogs & Lakefront
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Most booked
Chicago: Family Bike & Food Tour with Pizza, Hot Dogs & LakefrontFeel the buzz of Chicago as you bike with your family past Millennium Park, Navy Pier, and the Riverwalk: tasting deep-dish pizza and classic hot dogs. All gear included.
101 reviews
4.81★
Duration
4h
Next departure: 3 Apr 2027Live guide ENFree cancellationfromUS$ 79per person
River North Food Walking Tour Chicago: 5 tastings in 3 hours
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River North Food Walking Tour Chicago: 5 tastings in 3 hoursTaste deep-dish pizza, Rick Bayless Mexican fare and four other stops on a 3-hour guided walk through Chicago's River North.
98 reviews
4.59★
Duration
3h
Fri–Sun
11:00
Season until 29 NovLive guide ENFree cancellationfromUS$ 89per person
Chicago Navy Pier Centennial Wheel: Skip-the-Line Ticket
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Chicago Navy Pier Centennial Wheel: Skip-the-Line TicketSkip the line at Chicago's 200-foot Centennial Wheel with mobile ticket entry. 360-degree views of Lake Michigan and skyline from enclosed gondolas. Year-round access.
96 reviews
4.23★
Duration
15m
Every dayLive guide ENFree cancellationfromUS$ 24per person
Chicago: Perfume Making Class on Magnificent Mile
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Travelers' pick
Chicago: Perfume Making Class on Magnificent MileCreate your own 1oz perfume bottle on the Magnificent Mile. Includes fragrance selection, blending tools, and personalized labeling. Parking validated for 3 hours.
94 reviews
4.88★
Duration
1h 15m
start times · Every day
7
Live guide ENFree cancellationfromUS$ 85per person
Chicago West Loop Food Tour: Donuts, Coffee & Street Art
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Chicago West Loop Food Tour: Donuts, Coffee & Street ArtSpend 1.5 to 2 hours walking Chicago's West Loop with a local guide, tasting donuts at Do-Rite and Voodoo, matcha drinks at Matcha-Cita.
94 reviews
4.97★
Duration
2h
start times · Every day
2
Live guide ENFree cancellationfromUS$ 70per person
Chicago: Private Food Tour with Deep Dish & Beef Sandwich
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Likely to sell out
Chicago: Private Food Tour with Deep Dish & Beef SandwichSavor deep dish pizza, Italian beef, and local treats on a private Chicago food tour through the Loop. Includes foodie guide, lunch, and flexible start times.
88 reviews
4.99★
Duration
3h
start times · Every day
3
Live guide ENFree cancellationfromUS$ 225per person
American Writers Museum Ticket: Interactive Exhibits Chicago
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Best value
American Writers Museum Ticket: Interactive Exhibits ChicagoSpend an hour to several hours exploring American Writers Museum in downtown Chicago with flexible-date entry and a free bookmark.
83 reviews
4.83★
Duration
1h–5h
Every day except Tuesday and WednesdayFree cancellationfromUS$ 16per person
Chicago: Dark Side Ghost & Gangster Walking Tour
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Chicago: Dark Side Ghost & Gangster Walking Tour2-hour Chicago walking tour covering mob history, serial killers, and haunted sites in River North and the Loop. Expert guide, easy pace, under 2 miles.
82 reviews
4.90★
Duration
2h
Thu–Sat
16:00
Live guide ENFree cancellationfromUS$ 35per person
Chicago: Historic Skyscraper Walking Tour & CAC Access
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Chicago: Historic Skyscraper Walking Tour & CAC AccessStep into Chicago’s early skyscrapers, explore the Rookery’s hidden details, and hear stories from a local guide. Includes admission to Chicago Architecture Center.
81 reviews
4.83★
Duration
1h 30m
Wed and Fri
13:00
Live guide ENFree cancellationfromUS$ 35per person
Magnificent Mile Architecture Tour with 360 Chicago Ticket
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Magnificent Mile Architecture Tour with 360 Chicago TicketWalk Chicago's Magnificent Mile with a professional guide past Art Deco landmarks and the world's largest Starbucks.
81 reviews
4.94★
Duration
2h
start times · Every day
6
Live guide ENFree cancellationfromUS$ 235per person
Chicago Food Tour: 3-Hour Walk with Deep Dish & Market
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Chicago Food Tour: 3-Hour Walk with Deep Dish & MarketThree hours walking downtown Chicago's holiday landmarks (Millennium Park, the Christkindlmarket, State Street) sampling deep-dish pizza, Italian beef.
81 reviews
4.91★
Duration
3h
Every day
11:30
Live guide ENFree cancellationfromUS$ 85per person
Chicago: Chicago Fire TV Set Tour, Lottie's Pub & Millennium Park
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Chicago: Chicago Fire TV Set Tour, Lottie's Pub & Millennium ParkStep into Chicago Fire’s world: see Firehouse 51, snap photos at Lottie’s Pub, explore Millennium Park & the Cultural Center. Includes hotel pickup & local guide.
80 reviews
4.89★
Duration
2h
start times · Every day
3
Live guide ENHotel pickupFree cancellationfromUS$ 315per group
Private Sailing on Lake Michigan: Navy Pier, Chicago
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Likely to sell out
Private Sailing on Lake Michigan: Navy Pier, ChicagoSail Lake Michigan from Navy Pier with a US Coast Guard licensed captain for up to six people. Choose your route, your music, your pace.
73 reviews
5.00★
Duration
2h
Next departure: 29 May 2027Live guide ENFree cancellationfromUS$ 567per group
Chicago Theatre: Behind-the-Scenes Tour & Stage Access
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Likely to sell out
Chicago Theatre: Behind-the-Scenes Tour & Stage Access60-75 minute guided tour of Chicago Theatre's lobby, auditorium and stage. See signatures from Frank Sinatra and Dolly Parton. Wheelchair accessible, includes Wi-Fi.
59 reviews
4.02★
Duration
1h–1h 15m
Fri–Sun
12:00
Live guide ENfromUS$ 32per person
Field Museum Chicago: Early Access SUE T. Rex & Private Tour
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Field Museum Chicago: Early Access SUE T. Rex & Private TourBeat the crowds at Chicago's Field Museum with 8am early access, private docent tour of SUE the T. rex, and Evolving Planet before public opening. Groups limited to 20.
59 reviews
4.54★
Duration
2h–4h
Every day
08:00
Live guide ENFree cancellationfromUS$ 73per person
Chicago Loop Walking Tour: Architecture & Art in 2 Hours
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Chicago Loop Walking Tour: Architecture & Art in 2 HoursWalk the Loop with a local guide through downtown Chicago's architectural landmarks, including the Chicago Cultural Center and its world-famous Tiffany.
57 reviews
4.86★
Duration
2h
Mon, Wed and Fri
11:00
Live guide ENFree cancellationfromUS$ 60per person
Chicago: Architecture River Cruise & 48-Hour Hop-on Hop-off Bus
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Chicago: Architecture River Cruise & 48-Hour Hop-on Hop-off Bus48-hour hop-on hop-off bus plus 75-minute river architecture cruise in Chicago. Expert guides, 40+ landmarks, open-top double-decker. Save 20% on the bundle.
53 reviews
4.08★
Duration
2h
start times · Every day
24
Live guide ENFree cancellationfromUS$ 99per person
Chicago Segway Tour: Mob Stories & Hidden History
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Chicago Segway Tour: Mob Stories & Hidden HistoryTwo-hour Segway tour of Chicago's lakefront and downtown with live guide covering mob history, political intrigue and forgotten stories.
52 reviews
4.90★
Duration
2h
Next departure: 29 Apr 2027Live guide ENFree cancellationfromUS$ 72per person
Chicago: Adults-Only Ghost Tour & Haunted History
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Chicago: Adults-Only Ghost Tour & Haunted HistoryAdults-only ghost tour through Chicago's darkest history: Iroquois Theatre tragedy, haunted hotels, Al Capone's ghost. Local guide, 2+ hours, wheelchair accessible.
48 reviews
4.25★
Duration
1h 30m
Every day
20:30
Season until 28 NovLive guide ENFree cancellationfromUS$ 35per person
Chicago: Willis Tower & Cloud Gate Half-Day Architecture Tour
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Chicago: Willis Tower & Cloud Gate Half-Day Architecture TourHalf-day Chicago architecture tour covering Willis Tower, Marina City, Cloud Gate & Millennium Park. Small groups, expert guide, bottled water included. Starts 9am downtown.
46 reviews
4.96★
Duration
2h 30m
start times · Tue–Sun
2
Live guide ENHotel pickupFree cancellationfromUS$ 48per person
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