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5 Unique Walking Tours That Will Show You the Different Sides of Chicago

By / August 30, 2018

In Chicago, there’s so much to do that sightseeing can suddenly feel like a Herculean task, and lose all its fun. But it doesn’t have to be that way. A number of tours allow you to zip across the city without sacrificing substance. The options are endless, but only a few provide the intimate nature of getting to know the city better than a local. Here are the tours that get you up close and personal with Chicago—where even if you have lived in the city your whole life, you’re bound to discover something new.

For the history buff: Saints & Sinners

On the surface, the Gold Coast is a ritzy neighborhood with designer shops, imported cars, and the occasional celebrity sighting. But beneath its glossy veneer is the remnants of bootleggers and the people who gave rise to them. The prohibition-era tour is curated by the Driehaus Museum, which focuses on preserving the culture and art of the Gilded Age. Guests are taken on a walk of the surrounding area which includes an array of churches and bars. The Saints & Sinners tour runs from now until October 26. Drinks will be served along the way for a ticket cost of $50 per person. Teetotalers receive a $20 discount.

For the socially conscious: My Block, My Hood, My City

Some areas of the city get more love than others. That’s no secret. However, Jahmal Cole, founder of My Block, My Hood, My City, a non-profit promoting curiosity and community ownership, is hoping to change that with its youth-led tours of North Lawndale, an area often in the news in association with crime and violence. Cole and teens from his program are working to shift the narrative of the Southwest side of the city. They’re encouraging people to leave the Loop, leading tours and welcoming curious explorers to the streets where they live and play. Guests will have a chance to hear directly from the teens who reside in the area and the $25 ticket cost benefits the organization. Tours run every Saturday in July and August.


For the know-it-all: Chicago Elevated

The pedway is a mystery to many locals and tourists alike. The estimated five miles of tunnels run under the Loop’s highly trafficked area and connects several landmark buildings such as the Chicago Cultural Center and Thompson Center. It might not be the most scenic setting, but knowing how to access and navigate it is sure to come in handy when extreme conditions hit — a common occurrence in the Windy City. Join Margaret Hicks of Chicago Elevated through the 40 blocks of underground passage, and leave with knowledge that’s sure to impress any resident or visitor.

For the pizza aficionado: Pizza City U.S.A.

What better way to experience the culture of a city than by eating your way through it? None, except if your menu is curated by Steve Dolinsky, food reporter for ABC Chicago, 13-time James Beard award-winning journalist and co-host of The Feed Podcast with Chef Rick Bayless. On the search for the best pizza in the city, Dolinsky taste-tested more than 150 pizzas, which led to the creation of his soon-to-be-released book “Pizza City, USA: 101 Reasons Why Chicago Is America’s Greatest Pizza Town.” Pizza City U.S.A. tours is a spin-off of his book in which guests can choose from a walking tour of the cheesy good stuff in West Town, West Loop, Wicker Park/Bucktown or a bus tour through all three. Price per person is $49 and includes ‘za from four different locations. Walking tours end the weekend before Halloween. However, the bus tour continues through the winter.

For the feminist: Badass Bitches

The Art Institute holds a wide array of treasures that every visit can feel unique and different each time. However, if you’re looking for a new perspective on the art, consider the Badass Bitches Tour by Museum Hack. The two-hour walk through the art house spotlights women artists through the ages—a group still in the minority. Of course, Georgia O’Keefe is on the agenda but expect to learn more about lesser-known artists, and their contribution to the industry. Ticket cost is $59 per person and tours run year round.

Want more? Check out these 5 Chicago music venues where the food is as good as the acts on stage.


Ximena N. Larkin is a Chicago based writer on the hunt for adventures. She’s written for Food & Wine, Munchies, Tasting Table, Forbes, and Refinery29. You can find her at @ximenalarkin and

More articles by Ximena Larkin



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