Oldtown Triangle Tour: Explore Historic Chicago Cottages
42 Ratings
Step back in time and explore the historic cottages of Oldtown Triangle in Chicago. Discover the unique architectural styles and learn about the city's fascinating history. Book your tour now!
Duration: 1 hour, 45 minutes
Cancellation: 1 day learn more
  • Old Town Triangle - This tour will show you 40-50 of these delightful workers’ cottages and the different styles they were designed and constructed in. Also, you will see some very rare instances where there are several in a row or in one case, an entire block of cottages on both sides of the street! This is what Chicago looked like in the late 1800’s and prior to the Great Fire of 1871. Many of my photos of these cottages have been featured on the Bob Vila website as well as many major architectural accounts on Instagram and other Chicago based “things to do and see” websites.

Plus you will see many other notable historic properties and hear about some fascinating Chicago history that dates back 150 years and beyond!

What's Included
  • Guided walking tour
Additional Information

This excursion introduces you to various charming cottages, showcasing their diverse architectural styles and constructions. It also imparts knowledge about their historical significance and their distinct contribution to Chicago’s development. In addition, you’ll explore intriguing historical facets of Chicago that trace back over a century and a half! The Oldtown Triangle, one of the city’s oldest and most picturesque neighborhoods, is a spot cherished by many Chicagoans. It creates an ambiance that takes you away from the city’s hustle and allows you to travel back in time, specifically to the late 19th century!

164 W Eugenie St
West Eugenie Street
You can find me on the sidewalk in front of the amazing rowhouses at our starting address
Cancellation Policy

For a full refund, cancel at least 24 hours before the scheduled departure time.

Customer Ratings
(42 Ratings)
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May 5, 2024
Excellent walking tour - Excellent walking tour with Ronnie!! He is obviously very knowledgeable and passionate about design and architecture. He helped me see my neighborhood in a new light! The tour moved at a comfortable pace and was very informative.
Review provided by Tripadvisor
Apr 22, 2024
Deep dive into Old Town Cottages - This has been on my list to do for a long time and it did not disappoint. The content was really thorough and interesting. The guide chose the perfect streets to visit and his knowledge was deep.
Review provided by Tripadvisor
Apr 22, 2024
Fun & Informative - So fun, so informative. Learned so much about an area in my own city that I had no idea about. Will take another tour from this group again.
Review provided by Tripadvisor
Apr 4, 2024
The magnificent workers cottages of Chicago. - I loved everything about the tour. The historical information was amazing! It transported me back in time. Loved the views of the entire tour. I would highly recommend you to do tours with Doorways of Chicago wether your a local or visiting Chicago.
Review provided by Tripadvisor
Mar 15, 2024
Fun, informative and full of surprises. - The name of Chicago brings to mind many images. Busy, noisy streets; lots of tall buildings; maybe a murder or two. But one thing which you probably wouldn’t expect to find in Chicago are cute little cottages. There are a lot of tall buildings here too, including a building which was once the tallest building in the USA. Ronnie also showed us inside and it truly is magnificent. The oldest tavern in Chicago is also in this area. The cottages, however, are the focal point of the tour and they are fascinating. They are known as the Workers Cottages and were built because a lot of people came to work in Chicago and needed homes. The cottages display a wide range of styles and colours, some of them designed by prominent architects. They really are lovely to look at, all of them different. In addition to showing us the cottages, Ronnie also gave a history of Chicago and how it grew from its small population of the 1800s to the big, thriving city it is today. Many well-known people have lived in this area, including a General who was involved in a very famous battle, a graphic artist who designed for a couple of well-known products and a German who was very active in the LGBTQIA+ community. Other famous people have pretended to live in this area – a couple of the cottages have featured in a film. Ronnie clearly has a lot of enthusiasm for the workers cottages and it was very special to see the house that first inspired its interest. Ronnie has clearly put a lot into creating a tour which is fun, informative and full of surprises.
Review provided by Tripadvisor
Mar 14, 2024
Wonderful experience! - Fantastic tour! I learned a lot about the Chicago area and the workers’ cottages. Such beautiful homes! It was like stepping into the past for a little bit. I loved it!
Review provided by Tripadvisor
Sep 7, 2023
Highly Recommend!!! - This was my second tour with Ronnie! Old Town is truly an amazing neighborhood in the city. Ronnie does a wonderful job. He provides great information about Chicago history and architecture.
Review provided by Tripadvisor
Sep 2, 2023
Workers cottages of Old Town - time traveling on a Saturday afternoon. - This is very special part of Chicago, and you feel transported in time. Ronnie is very knowledgeable and enthusiastic about architecture and history. I learned new information about the original owners of some of these beautiful homes. The pictures turned out great and I left feeling inspired by this great neighborhood.
Review provided by Tripadvisor
May 13, 2023
Fantastic Tour! - A fantastic tour! Listening to Ronnie's knowledge, passion and love for the city and its architecture was so wonderful and informative-the time flew by. I can hardly wait until I can go on another one!
Review provided by Tripadvisor
Apr 30, 2023
Amazing Gem of a Tour - Ronnie was such an amazing tour guide! I've lived in Chicago most of my life and it was such a treat to learn about this part of the city that is literally right outside our back door! Ronnie's knowledge and enthusiasm for the tour made it a genuine delight! What was extra special was Ronnie's architectural background and learning about the various structures we were looking at as well. The Tour was not just a Tour of Doors, it was a combination history tour, architectural tour, and walking tour with new and unknown info presented in a very unique and refreshing way. I would highly recommend this tour and look forward to going on future tours of Ronnie's.
Review provided by Tripadvisor
Select Date and Tickets
up to 6 guests
1 Adult
July 2024