Explore the History of the Second City With the Best Chicago Tours

Play Tourist in Your Own City with These Chicago Tours

A Cubs game, the Sears Tower, the Art Institute, crashing a parade in the middle of the Loop… pretty casual activities if you’re Ferris Bueller running around the city for a day.

For those of you who need some karaoke practice before belting out “Danke Schoen” in the middle of the city, we’ve got you covered with how to get a taste of Chicago life in a day.


These are the best Chicago tours to participate in.

Underground Donut Tour

chicago tours
Photo Credit: Underground Donut Tours

Start your day with a breakfast fit for a champion: donuts! This Chicago tour features tastings from four donut shops around Chicago, including Beavers Coffee + Donuts in the Chicago French Market, Do-Rite Donuts, and Stan’s Donuts & Coffee. Saturday tours also get to try Firecakes, while Sunday tours sample treats behind the blue door at Doughnut Vault.


Chicago Architecture Foundation River Cruise Tour

chicago tours
Photo Credit: Chicago Architecture Foundation

All aboard Chicago’s First Lady Cruises. Chicago architecture river boat tours begin for the season in March. This Chicago tour is a great opportunity to admire the beauty you may take for granted during your typical morning commute.

Gangsters and Ghosts Tour

chicago tours
Photo Credit: Chicago Gangsters and Ghosts Tour

Fan of true crime and you believe in the paranormal? This is the Chicago tour for you. Explore Chicago’s rich gangster history through the Chicago Loop and follow along with the ghosts of their past during the Gangsters and Ghosts Tour. Notable sites on this tour in Chicago include the Congress Hotel, Death Alley, and the Palmer House.


Original Chicago Pizza Tour

chicago tours
Photo Credit: Pizano’s via Instagram

What’s a day in Chicago without some pizza? For lunch take the Chicago pizza tour.

From the burnt cheese caramelized crust pizza at Pequod’s in Lincoln Park to thin crust with Polish and Italian influences at Flo & Santos in the South Loop, this Chicago tour will fill you up. Tours start at Pizano’s Pizza and Pasta and run for about three and a half hours. Stops can also include Coalfire, Piece Pizza, Lou Malnati’s, Macello, Bella Bacino’s, Spacca Napoli, and Exchequer.


Chicago Crime Tour

chicago tours
Photo Credit: Chicago Crime Tours

Al Capone, H. H. Holmes, the St. Valentine’s Day Massacre. Okay, so you may not hear residents bragging about everything you’ll learn on this tour in Chicago the way we brag about our pizza, but after spending about two hours on the Chicago Crime Tour, you’ll know a lot more about the city’s history.

Chicago Prohibition Tour

chicago tours
Photo Credit: Prohibition Tours

End your day of tours with a nightcap! Enjoy “a sip of history” and visit speakeasies throughout the city. Drinks are not included in the tour, but there are plenty of opportunities to try new cocktails along the way.



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