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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Chicago Crime and Mob Tour

4.5 star rating: Recommended 362 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 $37.95

Chicago Segway Tour

5 star rating: Highly Recommended 208 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 City Hop-on Hop-off Tour

4.5 star rating: Recommended 906 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 Grand Half-Day Tour

4 star rating: Recommended 329 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 $48.00

Chicago by Night Helicopter Tour

5 star rating: Highly Recommended 44 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 89 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 $36.00

Chicago Explorer Pass

4.5 star rating: Recommended 165 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 City Tour with Optional Architecture River Cruise

5 star rating: Highly Recommended 91 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 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 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

City Sightseeing Chicago Hop On Hop Off Tour

5 star rating: Highly Recommended 3 Reviews

With entertaining, live, guided commentary, this tour offers passengers an insight into the sights, tastes, and views of the wonderful city of Chicago. You ... 

Location: Chicago, Illinois
Duration: 2 hours 30 minutes

From USD $33.00

Chicago Sports Tour

3 star rating: Worth doing 3 Reviews

If you are a sports fanatic, this tour is for you! This tour shuttle you and your friends to the top sports parks in Chicago for the ultimate photo op! You ... 

Location: Chicago, Illinois
Duration: 2 hours 30 minutes

From USD $40.00

Chicago Architectural Aficionados Bus Tour

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

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

Bank Heist Escape Room in Schaumburg

You found yourself in hard times and joined notorious crime syndicate. You need to prove yourself to the team, so your mob boss wants you to rob a bank. Try to ... 

Location: Schaumburg, Illinois
Duration: 60 minutes

From USD $29.00

Chicago South Side Tour with Optional River Cruise

4 star rating: Recommended 7 Reviews

Experience the beauty of Chicago on a tour full of history and excitement. See all of the city’s highlights, such as Grant Park, the Adler Planetarium and the ... 

Location: Chicago, Illinois
Duration: 2 hours

From USD $29.00

Chicago Holiday Lights Tour by Segway

5 star rating: Highly Recommended 1 Review

See Chicago all decked out in holiday lights on a Segway sightseeing tour of the Windy City’s sparkling downtown. Get into the Christmas spirit as you ride ... 

Location: Chicago, Illinois
Duration: 2 hours

From USD $70.40

Sorcerer's Secret Escape Room in Schaumburg

Gather a team and enter the magic shop to experience this exciting escape room. Work together to unravel the Sorcerer's Secret in under 60 minutes. Find ... 

Location: Schaumburg, Illinois
Duration: 60 minutes

From USD $29.00

Chicago North Side Tour

5 star rating: Highly Recommended 3 Reviews

Experience the vitality and excitement of Chicago on this sightseeing tour! Explore Chicago's main business district, one of the financial epicenters of the ... 

Location: Chicago, Illinois
Duration: 2 hours

From USD $29.00

Chicago River Walking Tour

5 star rating: Highly Recommended 1 Review

This walking tour along the Chicago river is sure to educate and entertain. You'll learn why the river is referred to as Chicago's lifeblood and an engineering ... 

Location: Chicago, Illinois
Duration: 2 hours

From USD $30.00

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

Electric Bikes at Night 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 $65.47
$72.75 Save $7.28

Chicago Loop Walking Tour

5 star rating: Highly Recommended 2 Reviews

The Loop is the heartbeat of downtown Chicago! This walking tour will take you through the Loop and educate you on the various buildings, businesses, history, ... 

Location: Chicago, Illinois
Duration: 2 hours 30 minutes

From USD $30.00

Chicago Bike Rental

5 star rating: Highly Recommended 1 Review

Explore Chicago at your own pace on an independent bike tour. With your full-day bike rental, pedal along Lake Michigan and visit top Chicago attractions such ... 

Location: Chicago, Illinois
Duration: Flexible

From USD $20.55
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