Our Guides

Our guides are what make Free Chicago Walking Tours special. Each guide prides themselves on creating unique tours infused with their own personalities. Take a little time to read about each guide so that you’re not a complete stranger on the tour.

Hello, I’m Alex. I’m a teacher, writer, food enthusiast and photographer – but most people who know me will tell you I’m a perpetually fascinated reservoir of Chicago facts, trivia and history. I was born in the south suburbs, but my family immigrated to Chicago from places like Croatia, Germany and Slovakia over the last 120 years. In that time, Chicago has seen the most profound changes any city could witness. And I’d like to tell you about them!

Take a stroll with me along Chicago’s idyllic lakefront or through the Loop, and learn to appreciate Chicago’s understated, yet staggering contributions to the modern world. Or if you want to know where to find the best views of the skyline, where Al Capone liked to get his hair cut, the best pan pizza joint, or if Oprah really ate a chicken sandwich on that park bench in 1998, I can tell you that too. Let’s have some fun!

Tours Alex Guides:


Bruno is an artist, designer and general life lover coming from the far way land of Quito, Ecuador. For the past 5 years he has called Chicago his home. He is a recent graduate from the School of the Art Institute of Chicago where he studied graphic design and printmaking. When he isn’t designing posters for bands or hitting the drums you can find him showing off his beautiful city to whoever is in need of some windy city love.

Bruno shares his passion of art and architecture on our Loop Architecture Tour and Magnificent Mile Tour. Make sure you check him out!


Tours Bruno Guides:



Matt Free Chicago Walking ToursHi there, I’m Matt. When I’m not working in my local library or poking around in a dusty archive, I’m writing books and articles on Chicagoland history. I hail from the suburbs of the Chicago, but have had a family connection to Chicago since a Hessian ancestor of mine first settled there in the 1840s to work as a tailor. I want to tell you everything that’s happened since that time and then some; be it why silver was painted white, how not to become the Outfit’s “trunk music”, or where to get the best Chicago-style pizza.

For our Austrian, German and Swiss guests – ich spreche Deutsch, und beiße auch nicht!


Tours Matt Guides:




Jeff Free Chicago Walking TOursHello! I am Jeff – a food & travel enthusiast who loves a well-made Manhattan and soaking in the sun at a daytime Cubs game. I’ve lived in and around Chicago my entire life. Currently I call the Lincoln Park neighborhood home (I guide our Lincoln Park tours). I’m constantly seeking a hidden gem restaurant or watering hole around the city.

I’ve taken plenty of walking tours in cities across the globe and want to give back to visitors of Chicago. Meeting people and hearing their stories is just as exciting as being able to share my hometown.

If I am not giving a tour you will find me trying out the latest food spot, butchering a top 40 hit at some karaoke bar or sitting front row at a stand-up comedy show. I can’t wait to meet you on my tours!

Tours Jeff Guides:


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