Unusual Tours in Chicago


There’s no shortage of tour options in Chicago, with tours available for nearly any combination of interest, budget, mode of transport and length of time. While most everyone knows about the boat tours of the Chicago River and Lake Michigan, the bike and segway tours of the city, and the open-topped double-decker bus tours, there are plenty of lesser-known tours of the city available. Here are a few of these smaller, more niche-focused tours.

Foodie tours

Second City Pizza Tours
Deep-dish pizza is a staple of the Chicago diet….well, the term diet being used loosely, seeing as a single slice of deep dish pizza can have more than 800 calories! If you’re ready to indulge and want to sample deep-dish pizza at several of Chicago’s best locations, join this tour, which stops at five restaurants. Guests get a slice at each one (that’s five slices!) while learning about the history of this unique Chicago food.  Tours are 2.5 hours and cost $36 for adults.

Vienna Beef Factory Tours
Another Chicago food staple, the Chicago-style hot dog, isn’t complete without a Vienna Beef hot dog between the bun. To see how these prized sausages are made, make reservations (far in advance) for the Vienna Beef factory tour. Tours are free and offered on Wednesdays at 10am and 11am, but they fill up far in advance, so make your plans early.

Chicago Dine Around
For $85, guests on the Chicago Dine Around tour receive a full meal over the course of several hours. Appetizers are served at the first stop, followed by the main course and dessert at two additional stops. Alcohol is not included.

Chicago Food Planet
Chicago Food Planet tours focus on some of Chicago’s distinctive neighborhoods, like Near North, Bucktown, and Wicker Park. Tours last 3 hours, cost $42 each, and include seven stops at some of the ‘hood’s best restaurants.

Chicago Chocolate Tours
Chicago Chocolate Tours visit some of the city’s tastiest bakeries and sweet shops. Tours cost $40, last about 3 hours, and visit chocolate shops in Lakeview, South Loop, and the Magnificent Mile.

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Weird and scary tours

Weird Chicago Tours
Visiting Chicago’s haunted locations, crime spots and weird places, Chicago Weird Tours cost $30 and last 3 hours. Specialized tours are also available, including serial killer tours, red light district tours, gangster tours and “Devil in the White City” tours.

Untouchables
The Untouchables tour explores Chicago’s gangster history, providing both entertainment and information about some of Chicago’s most notorious bad boys. Tours are about 2 hours and cost $28.

Musical tours

Chicago Blues Tour
The Chicago Blues Tour offers a Blues Shuttle, which includes transportation and all admissions to 3 clubs, as well as 2 drinks and a free collection of Chicago Blues Records downloads. Offered Thursday through Sunday evenings, the private tour requires an advance reservation of 14 days and a minimum of 5 persons. Prices start at $75 per person.

Historical tours and neighborhood tours

Boystown Tour
Chicago Elevated offers a walking tour of Lakeviews’s “gayborhood,” the area along Halsted known as Boystown. Learn about the history of the area and check out some of the wonderful gay-owned and gay-friendly restaurants, bars, shops and other businesses. Tours are about 90 minutes and cost $20.

Board of Trade Tour
Want to feel like Ferris Bueller, watching the action on the trading floor at the Chicago Board of Trade? The only way to do it is with the Chicago Architecture Foundation Board of Trade tour, which takes you through the lobby and up to the observation deck. The one hour tour costs $10 and no does not require reservations.

Women of Influence Cemetery Tour
Celebrate the influential women who help shape Chicago. The Graceland Cemetery tour explores the lives of women like early settlers Juliette Kinzie and Mary Jane Richardson Jones, an African-American pioneer in civil rights; social reform leader Louise deKoven Bowen, one of the guiding forces behind Jane Addams’ Hull House; and Ruth Page and Marion Mahony Griffin, advocates for art and culture. The tour is $15 and lasts 2 hours.

Federal Reserve Money Museum Tour
Guided tours of Chicago’s Federal Reserve Money Museum last about 45 minutes and are available at 1 p.m. Monday through Friday. Tours include a guided walk through the museum, a short video about the operations of the Chicago Fed, and a Q&A session afterwards.

Wrigley Field Tours
Wrigley Field offers tours on select dates for $25 per person. The one hour tour takes guest behind the scenes, with visits to the dugout, the locker rooms, the press box, the bleachers and the field. Along the way you’ll learn about the history of baseball, Wrigley Field, and the Cubs, plus plenty of trivia to impress your friends.

Photo by southie3