StartupStories: Walk This Way! Free Chicago Walking Tours Is Changing The Path of American Tourism

America is the land of opportunity, right? Free opportunity is a language that everyone speaks. Jeff Mikos discovered free-of-charge walking tours while visiting South America, and he just had to bring that concept back to the States. Starting in his hometown of Chicago, Jeff created a free walking tour program that shows tourists parts of the city that they may not have stumbled upon on their own. After a pretty spontaneous start with no real business experience, Jeff was able to roll up his sleeves and master the dirty work of entrepreneurship in order to mold Free Chicago Walking Tours into the successful company it is today, tearing a hole in the financial barrier that surrounds the travel industry.

free chicago walking tours


Free Chicago Walking ToursWhy were you inspired to start Free Chicago Walking Tours?

My wife and I spent 7 months backpacking in South America. While we were in Santiago, Chile we came across a free walking tour. We thought to ourselves “is this for real?” We went to the advertised starting point, met our tour guide, and had one of the most memorable 2.5-hour tours of our entire trip. We continued to seek out these tours. And finally after a free walking tour in Quito, Ecuador we made the decision to bring this concept back to our hometown of Chicago.



How did your business get started?  From the good, bad and ugly, what was your startup process like?

I had never started a business before, which is both good and bad. The good part is that I just went for it. The bad part is I just went for it. I was a bit disorganized in the beginning and got a little caught up in making sure I had a Facebook page, Instagram account, and Twitter all linked to my website – but I didn’t have a strategy for either. Eventually, I had to remove the Twitter feeds because I wasn’t active on that. I probably didn’t do enough research into how Google Business and TripAdvisor work from a registering and compliance perspective so I had to do some backtracking to get those important aspects of my business organized as well. Selecting the tour guides was an adventure. If I look back at who I thought would be a guide at the end of the year vs. who actually is a guide now, it’s two different groups of people.


What niche or hole in the market are you filling with Free Chicago Walking Tours?

Chicago sees about 50 million visitors a year and there is so much to see. We’re hoping to capture the audience that is familiar with these types of tours and also encourage locals to come out and join us. So many people are afraid to be a tourist in their own city. Removing the cost barrier will hopefully encourage them to step out of their box.


How much has your business changed from day one until now?

The most obvious difference was we are busier. I remember constantly checking out bookings in the beginning and smiling when we had a few reservations. Now I smile when we sell out. We went from creating incentives for the guides to manage through the slow period to working with the guides on techniques and strategies of giving tours to large groups of people. We’re using data so much more (peak times and hours) to develop our schedules as well.


free chicago walking toursWhat are your biggest challenges in marketing Free Chicago Walking Tours?

There are so many awesome tour companies in Chicago. Over 150 businesses are listed under the tour category on TripAdvisor. Getting people’s attention with so many operators was really tough in the beginning. We’re much more open to marketing services and help now that we can see the potential than we were in the beginning.


What types of marketing are most effective for your business?

Interestingly, our most effective marketing has been an effective use of SEO and paid Google search. I really thought that we would rely on our TripAdvisor ranking and work with local hostels/hotels. While those are important, SEO and paid search are driving the majority of our traffic. We will continue to focus on content generation and paid keyword search in 2017.


What is the #1 lesson you learned since starting Free Chicago Walking Tours?

It’s hard. It’s a grind. There are constant questions and comments to respond to. The amount of time and effort that this business required in the beginning is much more than I anticipated. It’s helped me create systems and processes to ease the burden. Still, I would do it all over again if given the opportunity.


If you won $50,000, how would you invest it in your business?

I have an idea for a hybrid food tour/tasting business that I would use the money on. Food tours are our #1 requested tour but I don’t like how food tours are done today. There are a few dominant players. Restaurants don’t love bringing in people and typically there isn’t a wonderful theme to these tours. $50,000 would allow me to change how Chicago does food tours.


What advice would you give to someone looking to start their own business?

Start today. Figure out the least expensive path to start and then start. Today. You can get bogged down by thinking about raising money, creating a business plan, and the red tape that is licensing/registering your company. Those all play a role but do not let that hinder you. So many people like to talk about starting a business or imagine what it would be like. Simply go out and do it. You will learn so much more.


What can we expect from Free Chicago Walking Tours in the next year?

We are going to operate more tours and different tours. Our season will start a bit earlier and you’re going to see our marketing materials at a lot more touchpoints in 2017. We’ve partnered with a marketing company that will ensure our presence is felt at a lot of the largest hotels and tourist spots in Chicago. We’re looking for large employers to do work with interns or team-building events and we’re looking to expand to a couple of other cities in 2017.


To learn more about Free Chicago Walking Tours, please visit

Looking to get your own Startup off the ground? Meet StartupSites, our all-in-one digital marketing service for startups and small businesses on a budget. Get started today and you too could be sharing your StartupStory!

Leave a Comment

Start typing and press Enter to search

content marketingWordPress myths