Chicago Tours, Things to Do, Day Trips & Sightseeing Tours in Chicago

Chicago CityPass

Absolutely loved it based on 53 traveler reviews

Duration: Flexible

Location: Chicago, Illinois

Chicago CityPass is the best deal in the Windy City, giving you discounted admission to five of the city's premier attractions: Hancock Observatory including ... More info »

Chicago City Hop-on Hop-off Tour

Definitely worth doing based on 32 traveler reviews

Duration: Flexible

Location: Chicago, Illinois

See all the sights of Chicago at your own pace! On a Chicago City Hop-on Hop-off Tour you can get off the bus at any scheduled stop to visit Chicago's most ... More info »

Go Chicago™ Card

Definitely worth doing based on 14 traveler reviews

Duration: 1, 2, 3, 5 or 7 days (approx.)

Location: Chicago, Illinois

The Go Chicago Card is the perfect way to save on your Chicago vacation. You'll get FREE admission to over 25 attractions and tours for one low price! Chicago ... More info »

Tommy Gun's Garage Dinner and Show

Definitely worth doing based on 9 traveler reviews

Duration: 3 hours (approx.)

Location: Chicago, Illinois

Welcome to the only speakeasy dinner show in Chicago – Tommy Gun's Garage! Just say the password and you'll be transported back to the Roaring Twenties. ... More info »

Wicked The Musical in Chicago

Duration: 2 hours and 30 minutes (approx.)

Location: Chicago, Illinois

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Wicked - The Musical, the untold story of the witches of Oz, is now playing in Chicago. Wicked is a true spectacle for the eyes and ears! Wicked - The Musical, ... More info »

Chicago Land and Lake Half-Day Tour

Definitely worth doing based on 4 traveler reviews

Duration: 4 hours (approx.)

Location: Chicago, Illinois

See Chicago from the land and the water on this scenic half-day tour. This comprehensive tour shows you the South Shore business district, the Loop and the ... More info »

Chicago Grand Half-Day Tour

Definitely worth doing based on 7 traveler reviews

Duration: 4 hours (approx.)

Location: Chicago, Illinois

This comprehensive half-day tour is the perfect introduction to the Windy City. From the highlights of the North Side and South Shore, to driving virtually ... More info »

Chicago Segway Morning Tour

Absolutely loved it based on 8 traveler reviews

Duration: 3 hours (approx.)

Location: Chicago, Illinois

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 ... More info »

Chicago Grand Tour and Hancock Observatory

Definitely worth doing based on 5 traveler reviews

Duration: 5.5 hours (approx.)

Location: Chicago, Illinois

Enjoy the Grand Tour of Chicago and a visit to the Hancock Tower! See the sites from one of Chicago's tallest landmarks. It takes the world's fastest elevators ... More info »

Chicago Segway Afternoon Tour

Definitely worth doing based on 4 traveler reviews

Duration: 3 hours (approx.)

Location: Chicago, Illinois

This Segway Tour is perfect for those new to the city as well as Chicago veterans. For the beginners, this 3-hour tour will offer you a fantastic orientation ... More info »

Chicago Hop-on Hop-off Trolley and Upper Decker Tour

Definitely worth doing based on 2 traveler reviews

Duration: Flexible

Location: Chicago, Illinois

Enjoy a scenic tour of Chicago's lake front and downtown area aboard the Trolley buses and the New Upper Deckers! The Hop-on Hop-off Trolley and Upper Decker ... More info »

Medieval Times Dinner and Tournament in Chicago

Duration: Flexible

Location: Chicago, Illinois

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Medieval Times is an adventure unlike any you have ever experienced before. During each live performance, guest enjoy an authentic medieval four-course feast ... More info »

Chicago Dinner Cruise

Duration: 3 hours (approx.)

Location: Chicago, Illinois

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Step aboard the Chicago Dinner Cruise and enjoy a three-hour escape on Lake Michigan. Relaxing in the elegant ambiance that only a true luxury cruising vessel ... More info »

Chicago Segway Night Tour

Absolutely loved it based on 2 traveler reviews

Duration: 2 hours (approx.)

Location: Chicago, Illinois

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! ... More info »

Chicago Architecture Tour and Speedboat Ride on Lake Michigan

Duration: 75 minutes (approx.)

Location: Chicago, Illinois

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Chicago is renowned for its stunning and original architecture – and the most relaxing way to see it is on a cruise on the Chicago River! You'll learn ... More info »