Some of the Best City Tours to Take in Chicago

Activities

Our list of city tours in Chicago will elevate your next group adventure like only the Windy City can with history, mystery and Segways!

Visiting friends and relatives in Chicago should include one of the many city tours of the area. What’s different about group tours here is that they all scream Windy City showcasing one-of-a-kind adventures. Sure, Chicago is known for its delicious food scene and water activities. There are so many unique ways to learn what makes this place so desirable.

City tours in Chicago along Lake Michigan at night.

Memorable City Tours in Chicago

As they say, “When in Rome, do as the Romans would do.” Well, here in Chicago, there are so many uniquely Chicago activities, it’s hard to know where to start. Sure, it’s a metropolis known for its deep-dish pizza, beautiful Lake Michigan shores, the Chicago River and home to thousands of loyal sports fans. But you could consider a different approach to sightseeing with your group. From foodies and trekkers to gangsters and speakeasies, consider these city tours for your next group adventure in Chicago:

Inside Chicago Walking Tours

For a fascinating indoor experience, take an Inside Chicago Walking Tour such as The Dazzling Interiors of the Loop. On this journey, groups will explores the internal beauty of the Loop’s finest buildings. The tour provides a history of Chicago’s buildings and details of the architectural designs that often go unnoticed by passersby.

Chicago Segway Night Tour

Eco-friendly options for city tours in Chicago include gliding past landmarks and along the shores of Lake Michigan on a Segway Night Tour. Take off after sunset to experience the city’s beautiful skyscrapers fully illuminated at night. In the “City that doesn’t rest,” view the cityscape as you visit famous Chicago locations such as Buckingham Fountain and Lincoln Park.

Segway tours in Chicago.

Chicago’s Chinatown Food and Walking Tour

Walking city tours offer groups the chance to savor, explore and go at their own pace. A walking tour through Chinatown in Chicago offers delicious insight into how the Chinese culture influenced the city. Visit the many authentic restuarants and sample a variety of ethnic dishes and regional drinks such as dumplings, saki and duck.

The Big Bus Hop-On Hop-Off Tour

For a more relaxed way to see the city, take a Big Bus Hop-On Hop-Off Tour. These buses stop at 13 popular locations around the city, such as the Willis Tower Skydeck, Navy Pier, and Millennium Park. Tour takers can hop off the bus at any of these locations, stay as long as they want, and continue the tour from a later Big Bus.

City tours in Chicago make stops at the Navy Pier for group fun.

Original Chicago Prohibition Tour

If you and your friends are looking for a bar crawl with a unique historical twist, take the Original Chicago Prohibition Tour. This bus tour is one of the best group city tours to take in Chicago. Travel through neighborhoods such as Old Town, Wicker Park, and the Loop to historic speakeasies where you will learn about feuds among gangsters and politicians and the history of prohibition in Chicago.

Tour Historic Chicago By Kayak

There are many guided city tours, but none quite like this. For a more active sightseeing adventure in Chicago, take a kayak tour down the Chicago River’s Main Branch. The kayak tour guides you down the Chicago River for an up-close look at some of the city’s most historic and famous architecture.

Kayaking city tours on the Chicago River on St. Patty’s Day.

Tours are a great way to see all that the city of Chicago has to offer on your next group getaway. Learn about Chicago’s history, culture, and cuisine, all while taking in unique and astonishing sights.

For more great group adventures, city tours and group destinations, subscribe to the current issue of Leisure Group Travel today.

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