Chicago, the third largest city in the U.S., is famous for its cuisine, culture, and its exciting landmarks. While visiting the Windy City for these purposes, many people typically schedule a few tours to supplement their vacation. We’ve got you covered if you’re looking for some of the most unique Chicago tours to add to your itinerary!
These tours range from haunted tours that take you through the city streets to running tours to help you stay active as you learn about Chicago history. Below, you’ll find a guide on the top seven unique Chicago tours to check out during your next trip to Illinois!
1. City Running Tours
As mentioned, Chicago Running Tours are a unique way to view the city. These tours, which take you about 5 kilometers, offer a way to combine a favorite sport with exploring different city areas. The intention of the tours is to gather a group of people together who don’t know each other with a chance to meet new people, have fun and get a good workout while seeing the city.
While running, you’ll see some of the famous landmarks like the “Bean,” officially known as Cloud Gate in Millennium Park, Magnificent Mile, and the Chicago River. This tour is meant for runners of all abilities, from beginner to advanced
2. Pizza City USA Tours
You can’t visit Chicago without enjoying a slice or two of pizza, especially its famous deep dish pizza. On this tour, you’ll be led by a James Beard award-winning food critic who’ll take you through some of the best pizza restaurants in the city.
You’ll be guided through downtown Chicago and its well-known foodie neighborhoods on a quest to enjoy Chicago-style pizza. While you will be enjoying a slice or two of deep dish pizza, you’ll also be eating Neopolitan, tavern-style, and other varieties. Bring an empty stomach and an open mind to this fun tour.
3. Urban Kayaks
Kayaking and touring combine in this option to form an unforgettable experience in Chicago. Urban Kayaks tours allow you to view Chicago from Lake Michigan or the Chicago River. During the tour, you’ll paddle through the water between skyscrapers and iconic Chicago architecture. These tours occur throughout the day, allowing you to choose between morning, midday, and evening options. If you want to view fireworks during your tour, elect for an evening kayak excursion.
4. Chicago’s Original Gangster Tours (Untouchable Tours)
One of the best tours in Chicago is the Original Gangster Tour, offering you insight into the city in the 1920s-1930s. During this time, some of the most famous gangsters like Capone, Moran, and Dillinger used Chicago as one of their main hangouts. This tour takes you to famous sites related to these gangsters, like the spot where the St. Valentine’s Day Massacre occurred. This tour is on the darker side, so it’s best for older teenagers and adults.
5. Chicago Architecture Center
Many visitors opt for viewing Chicago’s architectural highlights from the water, which is an excellent option. However, the Chicago Architecture Center now offers a Chicago architecture tour from a different perspective – a ride on the “L” trains. This tour takes you on Chicago public transit starting from the Architecture Center so you can experience an elevated view of the buildings.
If you prefer other touring methods, the Chicago Architecture Center also provides a bus, bike, boat, or walking tour option.
6. Bizarre Bucktown (Chicago) Walking Tours
The Bizarre Bucktown tours are a fun option for those who enjoy learning about quirky or weird history stories. During this tour, you’ll be visiting Bucktown, one of Chicago’s many neighborhoods. Besides learning about Bucktown’s (and Wicker Park’s) history, you’ll also gain knowledge on hauntings, gangster-related activities, neighborhood mysteries, and more. This tour is led by a Chicago native, a magician, and writer, Gordon Meyer. Small group and private tours are available through Bizarre Bucktown Walking Tours.
7. Free Tours by Foot
Free Tours by Foot runs its tours differently than most available tour options. Instead of having a set price for their tours, they have a pay-what-you-can system. After you enjoy a tour, you pay what you think the tour is worth or what’s in your budget. This helps keep Free Tours by Foot affordable for everyone, making it an excellent budget-friendly option.
When taking one of these tours, there are quite a few options. Head to Navy Pier to see the Centennial Wheel, visit Grant Park and the Buckingham Fountain, or explore the Riverwalk with Free Tours by Foot.
Despite its name, Free Tours by Foot also offers bike and bus tours for those who prefer to tour via a different method.
Suppose you still have extra time after working through this unique Chicago tours list. In that case, you can also take a self-guided tour through other popular attractions like the Lincoln Park Zoo, along the Lake Michigan shoreline (at one of the many beaches), or enjoy a river cruise for incredible views of the Chicago skyline.