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Chicago

Tours & things to do hand-picked by our insiders

Top 10 Insider's Picks See all

Chicago Grand Half-Day Tour, Chicago

Chicago Grand Half-Day Tour

4 star rating: Recommended 73 Reviews

Chicago, Illinois

From USD $45.00
John Hancock Observatory Admission, Chicago

John Hancock Observatory Admission

4.5 star rating: Recommended 11 Reviews

Chicago, Illinois

From USD $15.50
$18.00 Save $2.50
Chicago Dinner Cruise, Chicago

Chicago Dinner Cruise

4.5 star rating: Recommended 8 Reviews

Chicago, Illinois

From USD $119.54

Sightseeing Tickets & Passes See all
Only Show: Attraction Tickets | Museum Tickets & Passes | Nightclub Passes | Sightseeing & City Passes

Chicago CityPass, Chicago

Chicago CityPass

5 star rating: Highly Recommended 123 Reviews

Chicago, Illinois

From USD $89.00
$173.50 Save $84.50
Skydeck Chicago Admission, Chicago

Skydeck Chicago Admission

4.5 star rating: Recommended 33 Reviews

Chicago, Illinois

From USD $18.00
$23.50 Save $5.50
Go Chicago Card, Chicago

Go Chicago Card

4.5 star rating: Recommended 47 Reviews

Chicago, Illinois

From USD $74.99

Tours & Sightseeing See all
Only Show: Bus & Minivan Tours | Half-day Tours | Hop-on Hop-off Tours | Night Tours | Segway Tours

Chicago Segway Tour, Chicago

Chicago Segway Tour

5 star rating: Highly Recommended 63 Reviews

Chicago, Illinois

From USD $60.00
Chicago City Hop-on Hop-off Tour, Chicago

Chicago City Hop-on Hop-off Tour

4.5 star rating: Recommended 292 Reviews

Chicago, Illinois

From USD $44.99
$54.00 Save $9.01
City Lights at Night Bicycle Tour, Chicago

City Lights at Night Bicycle Tour

4 star rating: Recommended 2 Reviews

Chicago, Illinois

From USD $41.97

Food, Wine & Nightlife See all
Only Show: Dining Experiences | Dinner Theater | Food Tours | Nightlife

Behind-the-Scenes Chicago Pizza Tour, Chicago

Behind-the-Scenes Chicago Pizza Tour

4.5 star rating: Recommended 10 Reviews

Chicago, Illinois

From USD $60.00
Small-Group Chicago Food Tour: Gold Coast and Old Town, Chicago

Small-Group Chicago Food Tour: Gold Coast and Old Town

5 star rating: Highly Recommended 12 Reviews

Chicago, Illinois

From USD $50.00
Small-Group Chicago Food Tour: Wicker Park and Bucktown, Chicago

Small-Group Chicago Food Tour: Wicker Park and Bucktown

5 star rating: Highly Recommended 5 Reviews

Chicago, Illinois

From USD $50.00

Cruises, Sailing & Water Tours See all
Only Show: Day Cruises | Night Cruises

Chicago Architecture River Cruise, Chicago

Chicago Architecture River Cruise

5 star rating: Highly Recommended 55 Reviews

Chicago, Illinois

From USD $25.60
$32.00 Save $6.40
Chicago River Architecture Cruise Including High-Speed Lake Michigan Speedboat Ride, Chicago

Chicago River Architecture Cruise Including High-Speed Lake Michigan ... 

4.5 star rating: Recommended 32 Reviews

Chicago, Illinois

From USD $36.10
Chicago Sunset Dinner Cruise with Buffet, Chicago

Chicago Sunset Dinner Cruise with Buffet

5 star rating: Highly Recommended 15 Reviews

Chicago, Illinois

From USD $95.06

Air, Helicopter & Balloon Tours See all
Only Show: Helicopter Tours

Chicago City Sights Helicopter Tour, Chicago

Chicago City Sights Helicopter Tour

5 star rating: Highly Recommended 3 Reviews

Chicago, Illinois

From USD $198.99
Chicago by Night Helicopter Tour, Chicago

Chicago by Night Helicopter Tour

5 star rating: Highly Recommended 2 Reviews

Chicago, Illinois

From USD $198.99

Transfers & Ground Transport See all
Only Show: Airport & Ground Transfers | Rail Services

Private Arrival Transfer: Chicago Airport to Downtown Chicago, Chicago

Private Arrival Transfer: Chicago Airport to Downtown Chicago

3.5 star rating: Worth doing 12 Reviews

Chicago, Illinois

From USD $15.05
Chicago Airport Roundtrip Transfer, Chicago

Chicago Airport Roundtrip Transfer

4.5 star rating: Recommended 51 Reviews

Chicago, Illinois

From USD $39.25
Luxury Overnight Train Journey: Chicago to New Orleans, Chicago

Luxury Overnight Train Journey: Chicago to New Orleans

Chicago, Illinois

From USD $400.00
$500.00 Save $100.00

Walking & Biking Tours See all
Only Show: Bike & Mountain Bike Tours | Walking Tours

Chicago Pedway Walking Tour, Chicago

Chicago Pedway Walking Tour

4.5 star rating: Recommended 14 Reviews

Chicago, Illinois

From USD $20.00
Tastes of Chicago Bike Tour: Chicago-Style Pizza, Beer, Cupcakes and Hot Dogs, Chicago

Tastes of Chicago Bike Tour: Chicago-Style Pizza, Beer, Cupcakes and ... 

5 star rating: Highly Recommended 3 Reviews

Chicago, Illinois

From USD $70.69
Chicago Walking Tour: Art Deco Architecture, Chicago

Chicago Walking Tour: Art Deco Architecture

5 star rating: Highly Recommended 9 Reviews

Chicago, Illinois

From USD $14.99

Cultural & Theme Tours See all
Only Show: Ghost & Vampire Tours | Historical & Heritage Tours | Literary, Art & Music Tours | Movie & TV Tours

Chicago Movie Tour, Chicago

Chicago Movie Tour

4.5 star rating: Recommended 10 Reviews

Chicago, Illinois

From USD $30.00
Chicago Walking Tour: Tiffany Art Glass Landmarks, Chicago

Chicago Walking Tour: Tiffany Art Glass Landmarks

4.5 star rating: Recommended 10 Reviews

Chicago, Illinois

From USD $21.99
Chicago Walking Tour: Historic Loop Skyscrapers, Chicago

Chicago Walking Tour: Historic Loop Skyscrapers

5 star rating: Highly Recommended 7 Reviews

Chicago, Illinois

From USD $14.99

Water Sports See all
Only Show: Jet Boats & Speed Boats

Chicago River Architecture Cruise Including High-Speed Lake Michigan Speedboat Ride, Chicago

Chicago River Architecture Cruise Including High-Speed Lake Michigan ... 

4.5 star rating: Recommended 32 Reviews

Chicago, Illinois

From USD $36.10
Lake Michigan Speedboat Ride, Chicago

Lake Michigan Speedboat Ride

5 star rating: Highly Recommended 7 Reviews

Chicago, Illinois

From USD $24.80

Shows, Concerts & Sports See all
Only Show: Dinner Packages | Theater, Shows & Musicals

Tommy Gun's Garage Dinner and Show, Chicago

Tommy Gun's Garage Dinner and Show

4.5 star rating: Recommended 64 Reviews

Chicago, Illinois

From USD $59.99
Blue Man Group at the Briar Street Theater in Chicago, Chicago

Blue Man Group at the Briar Street Theater in Chicago

5 star rating: Highly Recommended 19 Reviews

Chicago, Illinois

From USD $54.00
$69.00 Save $15.00

Multi-day & Extended Tours See all
Only Show: Multi-day Rail Tours | Overnight Tours

Luxury Overnight Train Journey: Chicago to New Orleans, Chicago

Luxury Overnight Train Journey: Chicago to New Orleans

Chicago, Illinois

From USD $400.00
$500.00 Save $100.00

Theme Parks See all
Only Show: Theme Park Tickets & Tours

LEGOLAND Discovery Center Chicago, Chicago

LEGOLAND Discovery Center Chicago

Chicago, Illinois

From USD $17.89
$19.95 Save $2.06
See all things to do in Chicago
Insider's Guide to Chicago

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