Posted on Tripadvisor  
 
 
 Cathie and Rich 
 
8 September 2026
 
 
  
Neighborhood, Architecture and History Ronnie is personable, knowledgeable and passionate about architecture and Chicago history. It was contagious! Our group totaled 7, all appeared to enjoy as much as my sister and I did. He was concerned about sidewalk safety, made sure we could all hear him, and was open to some spontaneous fun! I highly recommend Ronnie for any tour he gives, he researches what he shares and his app with access to photos was a great addition to what we saw and heard.
  
 
 
 
 
 
 Posted on Tripadvisor  
 
 
 Janet F 
 
7 September 2026
 
 
  
Old Town walking tour Ronnie Frey is a great, knowledgeable, and personable quide. This is the 4th tour I have done with Doorways of Chicago and I have enjoyed every one and learned new things about my favorite city from Ronnie.
  
 
 
 
 
 
 Posted on Tripadvisor  
 
 
 Spoorthi s 
 
7 September 2026
 
 
  
Stop and notice your city with Ronnie! Ronnie is the nicest guide and shows you parts of historic Chicago that you probably breezed past. His tours make you stop and notice your city more. HIGHLY RECOMMEND
  
 
 
 
 
 
 Posted on Tripadvisor  
 
 
 Patty B 
 
7 September 2026
 
 
  
Fun and Informative This is my second tour with Ronnie. Both the Fine Arts Building and Wicker Park tours were wonderful. Ronnie is very knowledgeable and makes learning about the history and architecture fun. Next stop, Old Town!
  
 
 
 
 
 
 Posted on Tripadvisor  
 
 
 Danielle O 
 
6 September 2026
 
 
  
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!
  
 
 
 
 
 
 Posted on Tripadvisor  
 
 
 nancy w 
 
6 September 2026
 
 
  
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.
  
 
 
 
 
 
 Posted on Tripadvisor  
 
 
 Cathy L 
 
3 September 2026
 
 
  
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!
  
 
 
 
 
 
 Posted on Tripadvisor  
 
 
 Travis 
 
23 August 2026
 
 
  
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!
  
 
 
 
 
 
 Posted on Tripadvisor  
 
 
 Danielle O 
 
22 July 2026
 
 
  
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!
  
 
 
 
 
 
 Posted on Tripadvisor  
 
 
 Ryan W 
 
21 July 2026
 
 
  
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!
  
 
 
 
 
 
 Posted on Tripadvisor  
 
 
 Jennifer T 
 
18 July 2026
 
 
  
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.
  
 
 
 
 
 
 Posted on Tripadvisor  
 
 
 Raza S 
 
14 July 2026
 
 
  
A secret worth sharing Such a fun experience! Got a chance to experience history and beauty in one tour! Highly reccomend.
  
 
 
 
 
Load more
 
 
 
 
 Tripadvisor rating score: 5.0 of 5, based on 194 reviews