The history of Chicago is immense. Whether you’re interested in mobsters, ghosts, or architecture — or a combination of all three — chances are there’s a historic tour, or two, for you. Here are five of the best of the best tour companies in the city, whether you’re looking to drive around tour, or discover the history of the beautiful Windy City by foot.

(Photo Credit: Weird Chicago Tours's Facebook)

(Photo Credit: Weird Chicago Tours’s Facebook)

Weird Chicago Tours
600 N. Clark St.
Chicago, IL 60654
(217) 791-7859

There’s a lot of weird history and lore in the Windy City, and Windy Chicago Tours covers it all. They cover so much in fact that chances are you’ll take one tour, and you’ll go back for another. Discover the most haunted spots in the city — with plenty of stories for the history buff too — with their Haunted History tour. For the history of the mob and legendary crime spots, hop on the bus for the Blood, Guns, and Valentines Crime Tour. Have you read Devil in the White City? They’ve got a historical tour all about that too. For a full listing of options, visit their site. They offer both public and private tours.

Chicago Architecture Foundation
224 S. Michigan Ave.
Chicago, IL 60604
(312) 922-3432

Established in 1966, the Chicago Architecture Foundation (CAF) is a non-profit designed to educate people about architecture and engineering… and a big part of that are the 85 tours they offer that talk all about the history of the many skyscrapers of Chicago, as well as the Frank Lloyd Wright homes. The CAF has personally trained each of the volunteer docents all about the buildings and history of the city, and they’ll impart that wisdom to those who take their tours.

(Photo Credit:

(Photo Credit:

Inside Chicago Walking Tours
109 S. Michigan Ave.
Chicago, IL 60603
(312) 799-0164

Just as the name implies, get an inside look into the Chicago you always wanted to know about with these fun and informational tours. Or as they like to say, the “second side” of the Second City. The tours focus on the different neighborhoods in and around the loop, and delve into things such as architecture as well as the art, like stunning Tiffany glass mosaics. In addition to two-hour tours, they also offer power hours for those who don’t have as much time, but still want to see the hidden gems.

Related: Best Brewery Tours In Chicago

Chicago Detours
30 E. Adams St.
Chicago, IL 60603
(312) 350-1131

Discover the forgotten history of Chicago with a tour company that says they offers tours for curious people. Their public and private tours offer a variety of themes, from the World’s Fair 1893 to the history of Chicago Blues, or even all about Old Polonia (with food). In other words, there’s a tour for everyone interested in learning about Chicago’s long and storied history.

Untouchable Tours
600 N. Clark St.
Chicago, IL 60654
(773) 881-1195

Journey into the past, when gangsters ruled the city during the 1920s and 1930s, with the fabulous tour from the Untouchable Tours. The tour takes you around the city via a minibus, and stops at old mob hotspots, and places frequented by the likes of Capone, Dillinger, and many more. Not only will you learn a ton about Chicago during the Prohibition era, but you’ll have a ton of fun with the guides who keep the tour entertaining too.

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Liz SanFilippo Hall is a freelance writer, who enjoys trying new foods from all over the world. But her favorite city for culinary treats will always be Chicago. When not blogging about food, she’s working part-time at a culinary vacation company, The International Kitchen, based in the Windy City, as well as repping Younique cosmetics and skincare products. Some of her writing can be found at