Chicago Itineraries
Looking for suggestions on how to best spend your time in the Windy City? Check out our Top 10 Don't Miss Tours & Activities in Chicago listed below. For more inspiration, read our blog post - Ode to the Windy City.
All 39 things to do in Chicago »
based on 32 reviews
Duration: Flexible
Departs from: Chicago, Illinois
See 5 of Chicago's most famous attractions for 1 amazing low price! Avoid the queues as you skip the long ticket lines at Shedd Aquarium, Adler Planetarium and Astronomy Museum. Your Chicago CityPass ... More info ›
based on 21 reviews
Duration: Flexible
Departs from: Chicago, Illinois
See all the sights of Chicago at your own pace! With this all day pass you can get off the bus at any scheduled stop to visit Chicago's most popular attractions, then pick up the tour where you left off ... More info ›
based on 5 reviews
Duration: 3 hours (approx.)
Departs from: Chicago, Illinois
Tommy Gun's Garage is an audience interactive speakeasy which offers a musical comedy revue with Gangsters, Flappers and YOU! After dinner join "Vito", "Gloves", da "Mugs" ... More info ›
Duration: 4 hours (approx.)
Departs from: Chicago, Illinois
Why not see Chicago from the water, as you cruise along the skyline in a beautiful streamliner yacht! As well as the business district, the Loop, the exclusive shopping areas and neighborhoods, this tour ... More info ›
based on 4 reviews
Duration: 5.5 hours (approx.)
Departs from: Chicago, Illinois
Experience the rich and fascinating mix of attractions which make Chicago the vibrant center of cultural activity that it is today. This tour captures the best that Chicago has to offer. There you will ... More info ›
based on 2 reviews
Duration: 4 hours (approx.)
Departs from: Chicago, Illinois
After dark, hit two of Chicago's hotspots for the best in blues and late night entertainment. At each club you will be treated to some of the City's popular Blues artists and entertainers. Transportation, ... More info ›
based on 7 reviews
Duration: 3 hours (approx.)
Departs from: 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 Fountain, Navy Pier, Lake Michigan and more. ... More info ›
Duration: 3 hours (approx.)
Departs from: Chicago, Illinois
Accept no imitations! An excellent orientation to all the major sights, city parks, beaches and the North Side of the Chicago River as you cycle through this beautiful city. This 3-hour bicycle tour will ... More info ›
Duration: 2 hours (approx.)
Departs from: Chicago, Illinois
Trace Chicago's invention of the skyscraper and tour the buildings of the famous Loop district. Learn how a group of daring 19th Century architects and engineers revolutionized structural design, developing ... More info ›