Oldtown Triangle Tour: Explore Historic Chicago Cottages

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
Highlights
  • 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!

  • West Eugenie Street - Rowhouses on Eugenie Street
  • Architect: Harald Hansen
  • Built in 1886
  • Extremely rare variegated row of 5 opulent Queen Anne and Second Empire style houses
    Hear about the rich history of the beginning of the city of Chicago, much of which happened in this location.
  • North Crilly Court - The rich history of N. Crilly Court -
    Learn about all the famous people that lived here and also see one property that is a National Landmark
  • St. Michael House of Prayer - St Michael Church of Oltown (Roman Catholic)
    Built 1866-1869 - tallest building in the United States for 16 years!
  • Twin Anchors Restaurant & Tavern - Twin Anchors Restaurant
  • One of the oldest restaurants in Chicago.
  • Founded in 1932, Twin Anchors has always been known for great, tender, barbequed baby-back ribs
  • quaint neighborhood tavern that was a favorite of Frank Sinatra for many years
  • Old Town Triangle - See the incredible homes of Charles and Frederick Wacker (Wacker Drive) and hear the history of these two men (father and son) who were very instrumental in the early design of the city of Chicago
  • Old Town Triangle - Ann Halsted Rowhouses which were designed by architect Louis Sullivan when he was in his early 20’s before anyone knew who he was!
  • Old Town Triangle - See the only remaining farmhouse standing from when the Oldtown area was still farmland, outside the city limits!
What's Included
  • Historical photos of each stop in a free app
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!

Location
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

All sales are final. No refund is available for cancellations.

Customer Ratings
5.0
(44 Ratings)
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328simonz
Jul 15, 2024
Great tour - Highly recommend! Ronnie takes you to see places and meet people you otherwise wouldn’t meet. There’s also an interactive app which adds to the experience.
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M1710ndlucyk
Jul 14, 2024
Excellent Tour!! - This tour was excellent! Couldn't be happier. Ronnie was so knowledgeable and he shared loads of great information. The sneak peak into a historic row home and impromptu visit to the backyard of a worker's cottage were extra special. We'll be doing more tours with Ronnie. Highly recommend!
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Sightseer614705
Jul 13, 2024
Best tour guide ever! - Ronnie was the best tour guide. He was so knowledgeable so funny so kind enjoyed every moment of it. Would love to take another one of his tourist someday. The homes were gems and he was a gem
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R2561xjandye
Jun 18, 2024
Old Town Treasures. - Interesting tour of the Old Town neighborhood. Ronnie covered the history and architectural styles but the highlight was the stories about the people who used to live there.
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Mariaaz6396zt
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.
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Roam35884623733
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.
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Johnkiss
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.
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Normacf6250kl
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.
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426poppyc
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.
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Peelyp
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!
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