Top Chicago Tours & Sightseeing

Tours & Sightseeing

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

4.5 star rating: Recommended 100 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 210 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 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 $65.00

Chicago Grand Half-Day Tour

4 star rating: Recommended 333 Reviews

This comprehensive half-day tour of Chicago is the perfect introduction to the Windy City! Discover the highlights of Chicago’s North Side and South Side and ... 

Location: Chicago, Illinois
Duration: 4 hours

From USD $49.95

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 96 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: Varies

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 $75.00

Chicago Crime and Mob Tour

4.5 star rating: Recommended 370 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 City Minibus Tour with Optional Architecture River Cruise

5 star rating: Highly Recommended 95 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 $37.00

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 City Hop-on Hop-off Tour

4.5 star rating: Recommended 918 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

Chicago Helicopter Tour

5 star rating: Highly Recommended 7 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

Chicago Lakefront and Museum Campus Segway Tour

5 star rating: Highly Recommended 10 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

Gangsters and Ghosts Tour in Chicago

4.5 star rating: Recommended 5 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 86 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

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

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 30 minutes

From USD $58.27
$64.75 Save $6.48

Chicago Night Crimes Tour

5 star rating: Highly Recommended 3 Reviews

Enjoy a fun night of learning about Chicago's crime history on this 2-2.5-hour bus tour that includes stops on and off the bus.

Location: Chicago, Illinois
Duration: 2 to 2.5 hrs

From USD $42.75
$45.00 Save $2.25

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

Big Bus Chicago Night Tour

4.5 star rating: Recommended 3 Reviews

Enjoy a panoramic night-time sightseeing bus tour and be dazzled by the bright lights of Chicago. See the entire skyline lit up from the Museum Campus, ... 

Location: Chicago, Illinois
Duration: 75 minutes

From USD $29.00

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

City Sightseeing Chicago Hop On Hop Off Tour

5 star rating: Highly Recommended 3 Reviews

Hop-on to a City Sightseeing Chicago bus tour and discover the many amazing, popular landmarks and attractions that are located here. With a 1, 2 or 3 day bus ... 

Location: Chicago, Illinois
Duration: 1 to 3 days

From USD $37.00

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

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
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