Top Chicago Tours & Sightseeing

Tours & Sightseeing

Only Show: Bike Rentals | Bus & Minivan Tours | City Tours | Classic Car Tours | Escape Games | Half-day Tours | Hop-on Hop-off Tours | Night Tours | Photography Tours | Private Tours | Segway Tours | Self-guided Tours & Rentals | Skip-the-Line Tours | Trolley Tours

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Viator VIP: Willis Tower Skydeck Early Access, Trolley City Tour and Chicago River Cruise

4.5 star rating: Recommended 99 Reviews

See classic Chicago sights with this Viator VIP package that includes early entry to the Skydeck in Willis (formerly Sears) Tower where you'll be greeted and ... 

Location: Chicago, Illinois
Duration: 6 hours

From USD $124.00

Chicago Segway Tour

5 star rating: Highly Recommended 209 Reviews

Hop on the most innovative tour to hit Chicago in years! Gliding around the Windy City on your very own Segway, you'll see all the famous sights - Buckingham ... 

Location: Chicago, Illinois
Duration: Flexible

From USD $70.85

Chicago Crime and Mob Tour

4.5 star rating: Recommended 369 Reviews

Some of the world’s most notorious criminals, mobsters and gangsters bamboozled their way through Chicago. On this Chicago crime tour, escape into the city’s ... 

Location: Chicago, Illinois
Duration: 90 minutes

From USD $39.95

Chicago Grand Tour and Admission to 360 Chicago (formerly John Hancock Observatory)

3.5 star rating: Worth doing 79 Reviews

Take a tour of Chicago and visit the 360 Chicago (John Hancock Observatory)! This comprehensive half-day tour is the perfect introduction to the Windy City. ... 

Location: Chicago, Illinois
Duration: 4 hours

From USD $69.95

Chicago City Hop-on Hop-off Tour

4.5 star rating: Recommended 913 Reviews

Explore Chicago at your own pace during this hop-on hop-off bus trolley of the city. Choose between a 1-, 2-, or 3-day pass depending on your trip time. See ... 

Location: Chicago, Illinois
Duration: Flexible

From USD $30.99
$37.00 Save $6.01

Chicago by Night Helicopter Tour

5 star rating: Highly Recommended 46 Reviews

Watch the Chicago skyline sparkle from the air on this thrilling nighttime helicopter tour! Aboard a heated, state-of-the-art helicopter, soak in amazing views ... 

Location: Chicago, Illinois
Duration: 15 minutes

From USD $149.00

Big Bus Chicago Hop-On Hop-Off Tour

4.5 star rating: Recommended 94 Reviews

The lakeside metropolis of Chicago is famous for its striking skyscrapers, world-class museums and colorful political history. Explore the Windy City at your ... 

Location: Chicago, Illinois
Duration: 1- or 2-days

From USD $29.00

Chicago Explorer Pass

4.5 star rating: Recommended 168 Reviews

Create your own sightseeing itinerary with the Chicago Explorer Pass, saving up to 42% on ticket prices. This multi-attraction pass, valid for 30 days after ... 

Location: Chicago, Illinois
Duration: Varies

From USD $79.00

Chicago City Minibus Tour with Optional Architecture River Cruise

5 star rating: Highly Recommended 93 Reviews

Don’t miss Chicago’s famous sights and fabulous views on this award-winning small-group sightseeing tour of the city. Travel through Chicago with an expert ... 

Location: Chicago, Illinois
Duration: 2 hours

From USD $35.00

Chicago Helicopter Tour Nighttime Experience

5 star rating: Highly Recommended 3 Reviews

Chicago Helicopter Experience provides you the most spectacular, panoramic views of the world’s best skyline from the optimal vantage point.  Your journey ... 

Location: Chicago, Illinois
Duration: 15 minutes

From USD $160.00
$178.00 Save $18.00

Chicago Film Tour

4.5 star rating: Recommended 49 Reviews

Movie buff or not, you’ll see the best of Chicago on this movie tour of the city! Travel by luxury air-conditioned coach through 30 miles (48 km) of Chicago ... 

Location: Chicago, Illinois
Duration: 2 hours

From USD $30.00

Chicago Lakefront and Museum Campus Segway Tour

5 star rating: Highly Recommended 9 Reviews

Looking for fun things to do in Chicago? Look no further - Explore Chicago with one of our professional guides on this scenic 7 or 8 mile Chicago Segway tour. ... 

Location: Chicago, Illinois
Duration: 2 hours

From USD $68.67

Chicago Helicopter Tour

5 star rating: Highly Recommended 6 Reviews

Chicago Helicopter Experience provides you the most spectacular, panoramic views of the world’s best skyline from the optimal vantage point.    Your journey ... 

Location: Chicago, Illinois
Duration: 15 minutes

From USD $142.00
$158.00 Save $16.00

Gangsters and Ghosts Tour in Chicago

5 star rating: Highly Recommended 3 Reviews

Interested in exploring Chicago from the perspective of ghosts and gangsters? Want to really immerse yourself in the history of this great American city, ... 

Location: Chicago, Illinois
Duration: 2 hours

From USD $27.00

Chicago City Tour and Chicago River Cruise

4 star rating: Recommended 83 Reviews

Discover Chicago from both land and water on this scenic half-day tour. Take a narrated tour through the city’s South Side and see highlights including Grant ... 

Location: Chicago, Illinois
Duration: 4 hours

From USD $73.95

Chicago Night Crimes Tour

5 star rating: Highly Recommended 3 Reviews

Enjoy a fun night of learning about Chicago's crime history on this 2.5-hour bus tour that also stops at historic bars such as The Burwood Tap and Harry ... 

Location: Chicago, Illinois
Duration: 2 hours 30 minutes

From USD $42.75

Prison Break Escape Room in Chicago

Can you escape our hardest game? Located in River North just two blocks away from Michigan Ave, The Escape Game offers an escape from ordinary life and allows ... 

Location: Chicago, Illinois
Duration: 60 minutes

From USD $38.14

Amazing Lakefront Segway in Chicago

5 star rating: Highly Recommended 17 Reviews

Segways are amazingly fun, and Chicago's lakefront, parks, and skyline are absolutely gorgeous! Add our smart, entertaining tour guides to the mix, and you ... 

Location: Chicago, Illinois
Duration: 2 hours 30 minutes

From USD $75.00

Chicago Craft Brewery Barrel Bus Tour

5 star rating: Highly Recommended 2 Reviews

There’s never been a better time to be a beer drinker — and Chicago, with its thriving brewery scene and many destination-worthy beer bars, is the perfect ... 

Location: Chicago, Illinois
Duration: 3 hours 30 minutes

From USD $78.40

Chicago Segway Night Tour

5 star rating: Highly Recommended 37 Reviews

Hop on the most innovative tour to hit Chicago in years! Gliding through the Windy City on an eco-friendly Segway is the coolest ride of the 21st century! Far ... 

Location: Chicago, Illinois
Duration: 2 hours

From USD $70.85

Private Chicago Craft Beer and Pizza Tour

Pair craft beer tastings at three of Chicago's finest breweries with a pizza dinner on this 4-hour tour in the Windy City. A guide leads your small group on a ... 

Location: Chicago, Illinois
Duration: 4 hours

From USD $129.00

The Heist Escape Room in Chicago

Come experience the thrill of a heist! Located in River North just two blocks away from Michigan Ave, The Escape Game offers an escape from ordinary life and ... 

Location: Chicago, Illinois
Duration: 60 minutes

From USD $38.14

Electric Bikes at Night Bicycle Tour in Chicago

4.5 star rating: Recommended 6 Reviews

E-Bike through Chicago’s most attractive hotspots at night! Like a party on wheels, you’ll cruise through downtown to see the architecturally stunning ... 

Location: Chicago, Illinois
Duration: 2 hours

From USD $58.27
$64.75 Save $6.48

Chicago Evening Express Segway Tour

5 star rating: Highly Recommended 2 Reviews

Meet your guide and small group at a central location in the South Loop of Downtown Chicago. Start your tour with a 30-minute training sessions so you feel ... 

Location: Chicago, Illinois
Duration: 90 minutes

From USD $54.50

Chicago Architectural Aficionados Bus Tour

3 star rating: Worth doing 1 Review

Discover the exciting diversity of Chicago architecture on this wide-ranging odyssey, which traces the city’s development from its founding through the very ... 

Location: Chicago, Illinois
Duration: 3 hours 30 minutes

From USD $45.00
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