8 min 38 sec

Hit the Streets With These Chicago Walking Tours

A trip to South America inspired this pet supplies manager to launch his own “free” walking tour company.
Customer Service Low Startup Potential Service Tourism

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What It's About

The tours are "free," but this creative Chicago guide still earns $2,500/month from them.

Business Model
Skills Required
Communication & Location Knowledge
Profit Potential

Words of Wisdom

Jeff has found his ‘free’ business model to be more beneficial than tours that charge per person. However, he stressed the need to maintain a five-star rating and grow his reviews. This is critical. Just like he was skeptical on his first walking tour, some people question his service’s legitimacy because it advertises as free. The rating assures guests that he’s a legit business.

Fun Fact

There's a lot of interesting (albeit sordid) history in Chicago, and Jeff’s Free Chicago Walking Tours takes advantage of that with his Chicago Crime & Gangster Tour. On this tour, you'll learn how the Chicago mafia came to power as well as take you to some lesser known, infamous Chicago mob hangouts!

Notes from Chris

Episode 643
Jeff Mikos has been the manager of a pet care business for a large grocery cooperative. He’s also dabbled in real estate, with two rental properties, including one he manages himself.

A few years back, Jeff and his wife had an experience while traveling that ended up turning into an accidental side hustle. On an extended trip through South America, they stumbled upon a free city walking tour in Santiago, Chile. They were skeptical at first—how good could a free tour be?—but they decided to try it out. They ended up enjoying it so much that they sought the tours out in every city they visited.

While on a tour in Quito, Ecuador, Jeff’s idea sprouted legs and took a walk of its own. He thought that implementing this model in his hometown of Chicago might have a walking chance. Jeff did some research and discovered this model had a low barrier to entry. “Who wouldn’t want a free walking tour?”

Jeff got to work!

He and his wife spent an entire weekend passing out brochures to every hotel and hostel in the area. Jeff racked up more steps than his pedometer knew what to do with but said it was hard to determine the ROI because there was no way to track it. (There weren’t any coupon codes or anything else that separated signups from one source versus any other.)

Once his site was published, people began signing up. He remembers looking at his wife and thinking, “Huh, we’ve got guests!”

Since its creation, Free Chicago Walking Tours went from nothing to a 5 star TripAdvisor tour company with hundreds of reviews. Jeff has maintained that five-star rating, earning a Certificate of Excellence from TripAdvisor. They walk a fine line!

So far, they’ve led more than 15,000 guests on the tours, and it’s regularly bringing in more than $2,500/month in extra income. It’s not a ton of money, but at this point, the business is low-maintenance—not completely passive income, but close.

He’d like to expand his operations to include additional cities in the midwest. He supplements his income with the private tours and hopes to be running even more tours next year.



Inspiration is good; inspiration combined with action is better. Now get back to work!

Yours in the revolution,


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Quote of the Day
"Time’s up. Stop reading the blogs. Quit talking about it to your friends and family. Put down the books... You’re going to learn and have better questions the books and blogs can help answer once you start doing something."
—Jeff Mikos #SideHustleSchool

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