Top Guided Tours

There are so many great places to visit in Chicago and each has a story that helps to build the history and character of our wonderful city.  Guided tours are a great way to learn and experience these places. Whether its architecture, history, or food, tours provide a deeper understanding in a fun group setting.  Here are some of our favorite tours that you should check out on your next visit in Chicago.

The Chicago Architectural Foundation is best known for their informative river cruise boat tour, which is a must when visiting Chicago. This 90 minute tour interprets more than 50 buildings along the Chicago River which help to create a time line of how Chicago grew from a small settlement into one of the world’s largest cities.  If you prefer to explore by land, we also highly recommend the CAF Open House which takes place twice a year.  There are over 250 landmark locations that open their doors to the public with guided tours of architectural treasures.

Free Chicago Walking Tours is another great way to learn about the rich history, architecture and culture that our diverse city has to offer.  And best of all, it’s FREE!  They offer FREE 2 hour tours with different themes such as Chicago Crime & Gangster Tour which takes you on an incredible journey through Chicago’s storied past, Chicago Loop & Public Art Tour that explores some of Chicago 500+ pieces of public art, and new as of this month Chicago Haunted – Millennium Park, Loop & River Night Tour that will introduce you to some of the paranormal characters that haunt Chicago today some friendly – others not so much.

If you want to learn more about the Wicker Park/Bucktown neighborhood, then we recommend the Bizarre Wicker Park Walking Tour.  The tour begins in a Victorian parlor inside the landmark (and haunted) Flat Iron Arts Building. From there, the group will explore Beer Baron’s Row, the bustling “Polish Downtown” shopping district, and the park from which the neighborhood takes its name. You’ll make over15 stops on the one mile tour, all with a special emphasis on forgotten history, strange mysteries, and ghost stories.

But what would Chicago be without its food?  Our diverse neighborhoods and culture have given rise to one of the most exciting food cities in the US.  From street food to Michelin star, Chicago is as a culinary mecca.  And one of the best ways to explore our culinary city is with a guided food tour.  Chicago Food Planet offers 3 hour neighborhood tours that allows you to taste the diverse food and drink of Chicago.  But if pizza is all you’re interested in, check out Pizza City, USA hosted by Chicago’s very own food critic, Steve Dolinsky. Guests sample 4 different styles of pizza and get to decide which is best: deep-dish or thin crust?