Unique Ways to Explore Chicago
Looking for a new perspective on the Windy City? Chicago offers a wide variety of tours that go beyond the typical bus-and-headset experience. Whether you prefer to be on the water, walking through historic neighborhoods, or gliding on two wheels, there’s a guided excursion for every interest. Here are some of our favorite tours to help you discover a different side of Chicago.
Chicago Tours by Water: River and Lake Adventures
Architectural and Historical Cruises
A cruise on the Chicago River is one of the best ways to experience the city’s stunning skyline. Chicago Line Cruises offers a 90-minute Architectural and Historical tour, developed in partnership with the Chicago History Museum. You’ll learn fascinating facts, from the city’s countless movable bridges to the history of the 1893 World’s Columbian Exposition.
Kayak Tours for an Up-Close View
For a more active tour, Kayak Chicago provides guided paddles on both the lake and the river. Their Lake Paddle offers incredible skyline views, while the Architecture Tour on the Chicago River gives you a unique, water-level perspective on the city’s history and iconic buildings. It’s a great way to get a workout while exploring the outdoors.
Sail on a Historic Tall Ship
Feel like a true explorer on a Tall Ship Windy tour. This 148-foot schooner offers a variety of 75-minute cruises, including the “Rum Runners” tour, which reveals how ships like the Windy were used to smuggle alcohol during Prohibition. Departing from Navy Pier, it’s a memorable sailing experience with a historical twist.
Chicago Walking Tours: Neighborhood and Thematic Adventures
Explore by Foot with Chicago Architecture Foundation
The Chicago Architecture Foundation offers a chance to dive into the city’s diverse neighborhoods. Their popular tours go beyond downtown, with options like “Beverly: A Castle, Mansions, and More” for a look at the historic South Side, or the “Lakeview Pub Crawl” for a boozy exploration of a popular North Side neighborhood.
Frank Lloyd Wright Tours
The Frank Lloyd Wright Preservation Trust allows you to step into the world of the famed Prairie School architect. The organization provides regular tours of his Home and Studio in Oak Park, as well as iconic buildings in Chicago like the Robie House and the Rookery. These tours are a must for any architecture enthusiast.
Chicago Tours on Wheels: Segway and Bike Explorations
Glide Through History on a Segway
For a fun and unique way to get around, an Absolutely Chicago Segway tour is a great option. In addition to standard architecture tours, they offer popular themed excursions. The “Gangster” tour takes you to the speakeasies and crime scenes of legendary mobsters like Al Capone, while the “Haunted” tour adds a spooky twist to the city’s history, visiting sites of the Eastland Disaster and Fort Dearborn Massacre.
Pedal Your Way Through the City on a Bike
Bike and Roll offers four different guided bike tours to help you see the city. The “Amazing Lakefront” tour provides great views of Millennium Park, Navy Pier, and Lake Michigan. If you’re interested in presidential history, the “Presidential” tour takes cyclists through Barack Obama’s old neighborhood of Kenwood and Hyde Park, offering a glimpse into the history of the University of Chicago and the Museum of Science and Industry.
