doorwaysofchicago.com Reviews

Danielle O 2026.09.06

     

Verified

An absolute masterclass in neighborhood charm! Ronnie is an absolute gem of a tour guide! If you want to experience Chicago history without even a hint of dry textbook boredom, Doorways of Chicago is an absolute must-book. We have done a few of his neighborhood walks now, including Old Town, and every single one is genuinely amazing. Ronnie brings so much life, wit, and vibrant energy to the history of the streets. He has this wonderful gift for making you look past the modern facades and see the neighborhood through a completely different, much more beautiful lens. He really captures the electric pulse and character of these historic blocks, weaving storytelling with architectural appreciation in a way that feels utterly effortless and fun. You walk away not just deeply entertained, but completely inspired to get involved and advocate for protecting these incredible historic homes. If Ronnie is leading a tour, clear your schedule and just go. Five stars does not even cover it, and as a true cherry on top, I also highly recommend picking up his book Doorways of Chicago to keep the magic going at home!

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nancy w 2026.09.06

     

Verified

Discover a Secret Side of Chicago I loved this tour with Ronnie Frey. We saw a side of Chicago new to me. These buildings began as worker's cottages in the 1800's. Now they are charming, elegant private homes and gardens. Ronnie knows his architecture, pointing out specific period details. He fills in historic details too, connecting the past to the present. I am looking forward to checking out his other tours.

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Cathy L 2026.09.03

     

Verified

Look Up! After a day taking two of Ronnie’s tours, Art Deco Madness and the Fine Arts Building, I see Chicago in a whole new light. I have a newfound appreciation for buildings I’ve passed by many times over the years and the beautiful elements of their enduring architecture. These tours are not just for out-of-town visitors, but for those who love their city and want to appreciate its beauty and history in a new way. “Look up,” Ronnie says. You’ll be amazed by what you see and how you take that knowledge with you in every city you visit!

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Travis 2026.08.23

     

Verified

Amazing walking tour in Wicker Park Thoroughly enjoyed the walking tour around Wicker Park with Ronnie. I learned so much about Wicker Park’s history and the buildings were beautiful. Highly recommend this tour!

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Danielle O 2026.07.22

     

Verified

Absolute best walking tours in Chicago hands down Stumbled on his Instagram and immediately booked a tour for the next day, and honestly it was the best decision ever. We did both the Wicker Park and the Graceland Cemetery tours and they were incredible. We’ve since gone on another one and at this point we honestly can’t wait to do the rest of them. He is such an incredible storyteller and without a doubt runs the best walking tours in Chicago. We’ve already recommended him to so many people, and everyone we’ve talked to who has gone says the exact same things. We also ended up buying two copies of his Doorways of Chicago book so we could keep one at home and put one in the office, and the patients are totally obsessed with flipping through it. Truly cannot recommend enough!

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Ryan W 2026.07.21

     

Verified

A Fascinating Journey Through Chicago’s History We’ve now done multiple tours with Ronnie, and once again he delivered an outstanding experience. The Graceland Cemetery tour was fascinating from start to finish. It was incredible to learn about the history of Chicago through the stories of the visionaries, innovators, and influential figures who helped shape the city. Ronnie has a gift for bringing history to life. Every stop had a story that was engaging, meaningful, and full of details we never would have noticed on our own. You can tell he genuinely loves what he does, and that passion makes the experience unforgettable. Whether you’re a lifelong Chicagoan or just visiting, this tour offers a whole new perspective on the city’s history. We left with an even greater appreciation for Chicago and are already looking forward to our next tour with Ronnie. Highly recommend!

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Jennifer T 2026.07.18

     

Verified

Ronnie is a Chicago treasure Ronnie’s passion for architecture and the Fine Arts Building makes this a must see tour. It is obvious he has put so much of his time into making sure every second is full of the most interesting facts about the building and its creative tenants throughout the years. I don’t want to spoil any of it for you, but know that you haven’t lived until you’ve spent time with Ronnie in this building.

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Raza S 2026.07.14

     

Verified

A secret worth sharing Such a fun experience! Got a chance to experience history and beauty in one tour! Highly reccomend.

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Kevin J 2026.07.11

     

Verified

Old Town, New Appreciation Ronnie Frey’s Doorways of Chicago tour through Old Town was a fantastic way to spend an afternoon. The tour was a great reminder to slow down and really look at the details of Chicago’s world-class vernacular architecture, from humble workers’ cottages to the city’s hidden corners that are easy to miss at street level. Seeing the homes of Frederick and Charles Wacker standing next to one another was wild. Ronnie knows his stuff, keeps the history lively, and somehow makes you look at every doorway in Old Town a little differently.

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lisadorenfest 2026.07.05

     

Verified

Wonderful Wicker Park Decided to take Ronnie's Wicker Park tour after enjoying his Old Town Tour and savoring his book "Doorways of Chicago". The Wicker Park tour was informative and eye catching. Ronnie was knowledgable and entertaining as always. It was great to drill deeper into Wicker Park history and to have Ronnie's detailed iPhone guide to refer to during and after the tour. Delighted in lunch at Doves Luncheonette after the tour.

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lisadorenfest 2026.07.04

     

Verified

Old Town With New Eyes Ronnie was a knowledgeable, energetic, and very entertaining guide. Loved seeing Old Town through his eyes and learning the history of my hometown. This tour was a perfect way to reconnect with my beloved Chicago after many years away, and to share the city with my partner and my friend. Cant wait to do another tour with Ronnie.

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Ryan W 2026.07.04

     

Verified

We Thought We Knew Wicker Park… We Were Wrong We came across Ronnie’s Instagram and decided to book his Wicker Park walking tour for the very next day on a whim. It ended up being one of the best spontaneous decisions we’ve made. We walk these streets almost every day, but Ronnie gave us an entirely new perspective. It was amazing to learn the history behind the neighborhood and discover all of the unique architectural details we had unknowingly walked past countless times. The tour made us slow down, stop, look up, and appreciate the smaller details that are so easy to overlook. Ronnie is incredibly knowledgeable, engaging, and clearly passionate about Wicker Park and its history. If you live in the neighborhood or are just visiting, I highly recommend taking this tour. You’ll leave with a much deeper appreciation for one of Chicago’s most interesting neighborhoods.

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lisadorenfest 2026.06.21

     

Verified

Old Town With New Eyes Ronnie was a knowledgeable, energetic, and very entertaining guide. Loved seeing Old Town through his eyes and learning the history of my hometown. This tour was a perfect way to reconnect with my beloved Chicago after many years away, and to share the city with my partner and my friend. A true insider’s perspective. Can’t wait to do another tour with Ronnie.

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Jean G 2026.06.20

     

Verified

Excellent day in the city! Excellent information, beautiful day, engaging tour guide. Overall excellent day in the city! Thanks 😊

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Amy V 2026.06.20

     

Verified

Lovely and informative walking tour Thoroughly enjoyed this tour of the beautiful and historic Old Town Triangle! We learned a lot about the architecture, history, and personalities of the neighborhood. Ronnie is a friendly, knowledgeable, and enthusiastic guide. Highly recommended for both Chicagoans and visitors!

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Passport41814633006 2026.05.31

     

Verified

hidden gems This won’t be by last tour by Ronnie, he is personable, informative and friendly. He takes you on a peaceful tour, while giving you architectural fun facts. I can’t wait to book a different tour through him.

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Ryan C 2026.05.15

     

Verified

Travel guide that wasn’t dry at all Ronnie is the best. Insightful and funny - worth it!

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UrbanTeacher 2026.05.04

     

Verified

Another fabulous tour by Ronnie Frey! My friend and I took Ronnie's tour of the Fine Arts building. I'd never been there before, and since we had such a great time on his tour of Wicker Park workers' cottages, we thought we'd try this one as well. Unsurprisingly it was just as fun and informative as the Wicker Park tour. Ronnie pointed out many surprising things about the building, from interesting architectural choices to the lives and careers of people who had artists' studios in the past. Plus, we got to ride on the last elevator in Chicago which still had an operator! The tour was a bit more than two hours, and was entirely indoors, so it was perfect for a winter day. We told Ronnie at the end of the tour that we'll definitely be joining him for another tour once the weather cooperates. Highly recommended for anyone 10 or older. The tour was also very reasonably priced (about $35 per person) for what you get, which is a very in-depth look at an architectural jewel.

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Aline Viana 2026.04.30

     

Verified

Agende esse tour! É maravilhoso! Chicago sempre foi meu sonho de cidade por causa da Arquitetura e nas minhas pesquisas encontrei os tours do Ronnie e não me decepcionei. Ele tem tours muito autorais e tem um conhecimento muito profundo sobre tudo que nos mostra ao longo do passeio. Além de ser uma pessoa muito divertida que você vai adorar estar por perto!

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Gabby Z 2026.04.27

     

Verified

Book the tour! Ronnie gave such a great tour during the Old Town Workers Cottage walking tour! Having lived in the area for several years, he shared so much fascinating history in addition to pointing out all the different architectural elements found amongst the various historic buildings and homes. I would encourage anyone to take this tour — locals or tourists. Such a great afternoon spent outside learning more about our city!

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