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Things to Do in Chicago

438 tours and activities · from $24.30 per person · prices in USD

Chicago has 438 tours and activities you can book through Booking Wolf, 98 of them private or group tours priced per vehicle or group. The largest groups are day trips (93), cultural tours (89) and food tours (42). The most-reviewed tour on this page is Chicago Architecture River Cruise on the Historic Chicago River, with 15,769 reviews.

How booking works: these are the same tours sold on Viator, run by the same operators. The price on each card is the Booking Wolf price for two travellers, and a saving is shown only where that tour's price is lower than Viator's. Book with Booking Wolf and we ask the operator for a better price.

Most popular tours in Chicago

Ranked by number of reviews. Prices are per person for two travellers.

Chicago Architecture River Cruise on the Historic Chicago River
Save 10%vs Viator
Boat trips

Chicago Architecture River Cruise on the Historic Chicago River

by Shoreline Sightseeing

★ 4.8 (15,769)1 hour
Free cancellationBest seller
From$39Viator
$35.10per person
via Booking WolfSave 10%
Chicago River 90-Minute Architecture Tour
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Boat trips

Chicago River 90-Minute Architecture Tour

by Wendella Tours & Cruises

★ 4.7 (9,655)1.5 hours
Free cancellationBest seller
From$45Viator
$40.50per person
via Booking WolfSave 10%
Chicago Architecture Center River Cruise aboard First Lady with Expert Docents
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Boat trips

Chicago Architecture Center River Cruise aboard First Lady with Expert Docents

by Chicago Architecture Foundation & Chicago's First Lady Cruises

★ 4.9 (5,536)1.5 hours
Best seller
From$57Viator
$51.30per person
via Booking WolfSave 10%
Chicago Crime and Mob Bus Tour with Stops at Historic Landmarks
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Motorised tours

Chicago Crime and Mob Bus Tour with Stops at Historic Landmarks

by Chicago Crime Tours and Experiences

★ 4.6 (3,206)1.5 hours
Free cancellationBest seller
From$49Viator
$44.10per person
via Booking WolfSave 10%
Chicago River 45-Minute Architecture Boat Tour from Magnificent Mile
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Boat trips

Chicago River 45-Minute Architecture Boat Tour from Magnificent Mile

by Wendella Tours & Cruises

★ 4.7 (2,962)45 min
Free cancellationBest seller
From$28Viator
$25.20per person
via Booking WolfSave 10%
Chicago Lake and River Architecture Tour
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Boat trips

Chicago Lake and River Architecture Tour

by Wendella Tours & Cruises

★ 4.7 (2,308)1.5 hours
Free cancellationBest seller
From$45Viator
$40.50per person
via Booking WolfSave 10%
Chicago Favorites Ultimate Food and Walking Tour with Deep-Dish Pizza, Hot Dog, and Italian Beef
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Food tours

Chicago Favorites Ultimate Food and Walking Tour with Deep-Dish Pizza, Hot Dog, and Italian Beef

by Bobby's Bike, Hike & Food Tours - Chicago

★ 4.9 (1,973)3 hours
Free cancellationBest seller
From$84.99Viator
$76.49per person
via Booking WolfSave 10%
Skydeck Chicago Willis Tower Admission with The Ledge Glass Balcony
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Tickets

Skydeck Chicago Willis Tower Admission with The Ledge Glass Balcony

by Skydeck Chicago

★ 4.3 (1,781)30 min
Free cancellation
From$44Viator
$39.60per person
via Booking WolfSave 10%
Chicago River 90-Minute Architecture Boat Tour including Wrigley Building, Aqua Tower & Chinatown
Save 19%vs Viator
Boat trips

Chicago River 90-Minute Architecture Boat Tour including Wrigley Building, Aqua Tower & Chinatown

by Tours and Boats

★ 4.8 (1,635)1.5 hours
Free cancellationBest seller
From$37Viator
$29.97per person
via Booking WolfSave 19%
Lake Michigan Sunset Cruise in Chicago on Wendella Boats
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Boat trips

Lake Michigan Sunset Cruise in Chicago on Wendella Boats

by Wendella Tours & Cruises

★ 4.5 (1,518)1.5 hours
Free cancellationBest seller
From$45Viator
$40.50per person
via Booking WolfSave 10%
Chicago Architecture Interiors Tour: Dazzling Chicago Board of Trade, Cultural Center & Loop
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Walking tours

Chicago Architecture Interiors Tour: Dazzling Chicago Board of Trade, Cultural Center & Loop

by Inside Chicago Walking Tours

★ 5 (1,512)2 hours
Free cancellationBest seller
From$35Viator
$31.50per person
via Booking WolfSave 10%
Chicago Donut Walking Tour: Delicious Donuts & City Sights in The Loop
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Food tours

Chicago Donut Walking Tour: Delicious Donuts & City Sights in The Loop

by Underground Donut Tour

★ 4.9 (1,391)2 hours
Free cancellationBest seller
From$70Viator
$63per person
via Booking WolfSave 10%
360 Chicago Observation Deck Admission in Chicago
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Tickets

360 Chicago Observation Deck Admission in Chicago

by 360 CHICAGO Observation Deck (Formally John Hancock Center)

★ 3.9 (1,214)1 hour
Free cancellation
From$27Viator
$24.30per person
via Booking WolfSave 10%
Chicago Food, History & Architecture Walking Tour in a Day
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Walking tours

Chicago Food, History & Architecture Walking Tour in a Day

by Intrepid Urban Adventures - USA

★ 4.9 (1,158)4.5 hours
Free cancellationBest seller
From$100.95Viator
$90.86per person
via Booking WolfSave 10%
Medieval Torture Museum Ticket with Audio Guide and Ghost Hunting in Chicago
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Cultural tours

Medieval Torture Museum Ticket with Audio Guide and Ghost Hunting in Chicago

by Medieval Torture Museum

★ 4.9 (981)1.5 hours
Free cancellationBest seller
From$35.83Viator
$32.25per person
via Booking WolfSave 10%
Lake Michigan Skyline Cruise with Pre-Recorded Commentary in Chicago
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Boat trips

Lake Michigan Skyline Cruise with Pre-Recorded Commentary in Chicago

by Shoreline Sightseeing

★ 4.4 (898)30 min
Free cancellation
From$34Viator
$30.60per person
via Booking WolfSave 10%
Chicago Architectural River Cruise with Live Commentary and Beverages
Save 10%vs Viator
Boat trips

Chicago Architectural River Cruise with Live Commentary and Beverages

by Chicago Line Cruises

★ 4.7 (804)1.5 hours
Free cancellationBest seller
From$50Viator
$45per person
via Booking WolfSave 10%
Chicago Bike & Classic Food Tour: Bikes, Bites & Views for Adults
Save 10%vs Viator
Food tours

Chicago Bike & Classic Food Tour: Bikes, Bites & Views for Adults

by Bobby's Bike, Hike & Food Tours - Chicago

★ 5 (732)4.5 hours
Free cancellationBest seller
From$89Viator
$80.10per person
via Booking WolfSave 10%
Chicago 2-Hour Murder Mystery Walking Tour with Souvenir Mugshot Photos
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Day trips

Chicago 2-Hour Murder Mystery Walking Tour with Souvenir Mugshot Photos

by Magnifico Tours

★ 5 (724)2 hours
Free cancellationBest seller
From$35Viator
$31.50per person
via Booking WolfSave 10%
Chicago City Tour with Optional Architecture River Cruise
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Boat trips

Chicago City Tour with Optional Architecture River Cruise

by See it All Chicago Tours

★ 4.8 (706)2 hours
Free cancellationBest seller
From$49.95Viator
$44.96per person
via Booking WolfSave 10%
Chicago Chinatown 3-Hour Walking Food Tour with Dim Sum, Szechuan, Xi’an Flatbread & Portuguese Egg Tarts
Save 10%vs Viator
Food tours

Chicago Chinatown 3-Hour Walking Food Tour with Dim Sum, Szechuan, Xi’an Flatbread & Portuguese Egg Tarts

by Bobby's Bike, Hike & Food Tours - Chicago

★ 4.9 (604)3 hours
Free cancellationBest seller
From$79.99Viator
$71.99per person
via Booking WolfSave 10%
Chicago 90-Minute River and Lake Sightseeing Cruise
Save 10%vs Viator
Boat trips

Chicago 90-Minute River and Lake Sightseeing Cruise

by First Lady

★ 4.7 (560)1.5 hours
Free cancellationBest seller
From$46Viator
$41.40per person
via Booking WolfSave 10%
Chicago City Minibus Tour with The Rookery, Museum Campus & Buckingham Fountain
Save 10%vs Viator
Day trips

Chicago City Minibus Tour with The Rookery, Museum Campus & Buckingham Fountain

by See it All Chicago Tours

★ 4.9 (522)2 hours
Free cancellationBest seller
From$49.95Viator
$44.96per person
via Booking WolfSave 10%
Chicago CityPASS® - Admission to 5 Top Attractions Including Aquarium and Skydeck Chicago
Save 10%vs Viator
Boat trips

Chicago CityPASS® - Admission to 5 Top Attractions Including Aquarium and Skydeck Chicago

by CityPASS

★ 4.4 (521)9 days
From$144Viator
$129.60per person
via Booking WolfSave 10%

Private and group tours in Chicago

Priced for the whole vehicle or group, not per person.

Chicago Private Custom City Tour with Hotel Pickup
Save 10%vs Viator
Day trips

Chicago Private Custom City Tour with Hotel Pickup

by Chicago Private Tours

★ 4.9 (201)3 hours
Free cancellationBest seller
From$539Viator
$485.10per vehicle, up to 5 guests
via Booking WolfSave 10%
Private Arrival Transfer from Chicago Airports (ORD) (MDW)
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Transport

Private Arrival Transfer from Chicago Airports (ORD) (MDW)

by Carmel Car & Limousine Service

★ 3.7 (196)1 hour
Free cancellation
From$89.60Viator
$80.64per group, up to 3 guests
via Booking WolfSave 10%
Chicago 45-Minute Private Helicopter Tour of Skyline with Live Commentary
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Air & flight

Chicago 45-Minute Private Helicopter Tour of Skyline with Live Commentary

by Heli Chicago

★ 4.8 (127)45 min
Free cancellationBest seller
From$849Viator
$764.10per aircraft, up to 3 guests
via Booking WolfSave 10%

What there is to do in Chicago

Questions about tours in Chicago

How much do tours in Chicago cost?

Per-person prices on this page run from $24.30 to $129.60, based on two travellers; the middle of that range is about $41. Private and group tours are priced for the whole group instead, from $80.64. Prices were checked on 2026-10-19 and change, so the tour page always shows today's price.

Are these the same tours as on Viator?

Yes. Every tour on this page is also sold on Viator, run by the same operator. The price on each card is what you pay with Booking Wolf; where that is below Viator's price, the card shows the saving for that tour.

Can Booking Wolf get a better price?

When you book with Booking Wolf we ask the operator for a better price. If they agree, you pay less than the price shown.

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Other destinations

Prices checked 2026-10-19 in USD for two travellers and shown after Booking Wolf's discount where one applies. Tour counts include every bookable Viator and Hotelbeds listing for Chicago.