Chicago's Best Offbeat City Tours

When braving the winter in Chicago—or the morning commute any time of year—you need a go-to pick-me-up, so many residents rely on a hot cup of coffee. For a taste of some local favorites, sign up for the Joe on the Go Coffee Tour. During this three-hour trolley-and-walking tour, Joel Krause of La Colombe talks through the making of the perfect cup of coffee with some tasters along the way. Participants will even join a cupping demo, during which they’ll learn to experience the flavors and aromas as the coffee masters do. Tickets are $30 for Chicago History Museum members and $40 for non-members.

It wouldn’t be a trip to Chicago without partaking in some deep dish, and Chicago Pizza Tours ensures their clients get the best of the best. Visit well-known, lesser-known, and little-known eateries throughout the city, and experience several Chicago neighborhoods while enjoying a variety of pizza types and toppings. The guides are local pizza aficionados with a wealth of knowledge on the city, as well as its residents’ favorite meal. The original three-and-a-half-hour tour costs $60 for adults and $36 for kids. If a pizza just isn’t as good without a cold alcoholic beverage, opt for the 21-and-older Pizza & Cocktails Tour for $80 per person.

Chicagoans are proud of the many distinct and diverse neighborhoods that comprise their city. Most locals know a little something about each one, but truly immersing yourself in the individual cultures and histories is a big task. Chicago for Chicagoans intends to help with that. Tourists and locals alike can join the two-hour walking tour, which explores a different neighborhood each month. Tour guides collaborate with residents and local businesses to provide a truly authentic experience. The pay-what-you-can model makes this excursion accessible to most, and each tour ends at a local restaurant. Upcoming tours include East Pilsen and Wicker Park.

Underground Donut Tour is Chicago’s only doughnut tour, and they pack a lot into the two hours. The Saturday tour starts in West Loop’s French Market (which is worth a wander) and Sunday starts at Do-Rite Donuts in Streeterville. For $30, a doughnut-loving guide will take participants to three additional shops, where everyone will enjoy a doughnut and take in some of Chicago’s best sights along the way.

If food is your thing, this is your tour. The guides—chefs, chef/owners, or mixologists, each native Chicagoans with upward of 10 years food-serve experience—will lead you to the eateries that chefs love most. There are a variety of tours in different neighborhoods ranging from $135-$150. For the most adventurous, try the Omakase tour, but beware that it comes with a disclaimer: “Please note: this tour is for truly adventurous culinarians with no dietary restrictions or fears.” Most other tours can be amended for vegetarians. Those with other restrictions should inquire.

For a new perspective on Chicago’s classic architecture, try the two-hour Elevated Architecture tour. In addition to seeing some of the more well-known buildings, participants also learn about and ride the elevated train, also called the “L” train, which has a fascinating history all its own. Learn about the symbiotic relationship between the “L” and the city’s development, and see architectural details up close with an appreciation you just can’t get from 20 feet below. For $20 per person, it’s a bargain.

The appropriately named Weird Chicago tours brings you the Al Capone Daydrinker’s Pub Crawl for a bit of drunk history. Visit the sites of Chicago’s most notorious prohibition bars, including the bar run by one of the most infamous gangsters in American history and head of the Chicago mafia outfit, Al Capone, who didn’t much try to hide his illegal activities. The 21-and-older tour runs in June, July, and August and is $35 per person. As these spots tend to get more crowded at night, this afternoon tour offers a chance to really explore the buildings and history.