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Workers Cottages of Oldtown Triangle Walking Tour

5 (38)
Chicago, US
5 (38)
Chicago, US
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Experience the charm and history of the Oldtown Triangle on the Workers Cottages of Oldtown Triangle Walking Tour! Immerse yourself in the late 1800s as you explore 40-50 delightful workers' cottages, each showcasing unique architectural styles. Be captivated by the rare instances of entire blocks of cottages lining the streets, a true glimpse into Chicago's past. Not only will you discover the history of these cottages, but you'll also learn about other fascinating moments in Chicago's history that date back over 150 years. From the opulent rowhouses on Eugenie Street to the rich history of N. Crilly Court, every step on this tour will uncover hidden gems and stories from the city's past. Don't miss the chance to travel back in time and explore the Oldtown Triangle's architectural wonders.

About this experience

  • Free Cancellation For a full refund cancel at least before the start of your booking
  • 1 hours 45 minutes
  • Suitable for 1-6 Participants
  • Small Group Tour, Private Tour
  • Guided Experience
  • Delightful workers' cottages showcasing different styles
  • Rare variegated rowhouses with rich history
  • Famous residents and national landmark in N. Crilly Court
  • Historic St Michael Church, once tallest building in US
  • Quaint neighborhood tavern loved by Frank Sinatra
  • Historical photos of each stop in a free app

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More about this experience

Introduction

The Workers Cottages of Oldtown Triangle Walking Tour is the perfect way to immerse yourself in the rich history and unique architectural gems of Chicago. This tour will take you back in time to the late 1800s, where you will discover the delightful cottages that were once home to the city's hardworking residents. Throughout the tour, you will be captivated by the different styles and designs of these charming cottages, as well as gain a deeper understanding of their significance in the growth of Chicago. Prepare to be transported to another place and time as you explore the Oldtown Triangle, one of the oldest and most beloved areas of the city.

What to expect?

During the Workers Cottages of Oldtown Triangle Walking Tour, you can expect to experience a journey through history. Over the course of 105 minutes, you will have the opportunity to see 40-50 of these delightful workers' cottages, each with its own unique style and character. Marvel at the rare instances where you'll find rows of cottages or even an entire block lined with these architectural treasures. This tour is not limited to the cottages alone; you will also discover other notable historic properties that hold fascinating stories of Chicago's past. Get ready to gain insights into the city's history that date back 150 years and beyond.

Who is this for?

The Workers Cottages of Oldtown Triangle Walking Tour is suitable for anyone who has an appreciation for history, architecture, and the charm of bygone eras. Whether you are a local looking to dive deeper into your city's roots or a visitor eager to explore the unique aspects of Chicago, this tour welcomes all curious souls. From architecture enthusiasts to history buffs, this experience appeals to a broad audience. Discover the hidden gems that make up the fabric of Chicago's history and find inspiration in the stories of the hardworking residents who once called these cottages home.

Why book this?

Joining the Workers Cottages of Oldtown Triangle Walking Tour guarantees an unforgettable experience filled with fascinating discoveries. As you journey through the late 1800s, you'll be captivated by the intricacies of each cottage's design and construction. The cottages featured in this tour have even been showcased on renowned platforms like Bob Vila and popular architectural accounts on Instagram. Delve into the vibrant history of N. Crilly Court and learn about the famous individuals who lived there. Marvel at St. Michael Church of Oldtown, once the tallest building in the United States. Dive into the captivating stories of Charles and Frederick Wacker and their influential role in shaping the city of Chicago. This tour offers an array of unique selling points that will leave you with an enriching and memorable experience.

Good to know

Joining the Workers Cottages of Oldtown Triangle Walking Tour requires a total duration of 105 minutes, providing ample time for immersive exploration. The tour begins on the sidewalk in front of the remarkable rowhouses at the starting address. Make sure to wear comfortable shoes, perfect for strolling through the quaint streets of Oldtown. Throughout the tour, you'll encounter various landmarks, each with its own intriguing history. From the Twin Anchors Restaurant, a beloved spot frequented by Frank Sinatra, to the Ann Halsted Rowhouses designed by architect Louis Sullivan, every step of this journey is packed with surprises and discoveries. The tour concludes a few short blocks away from the starting point at the very first workers cottage the guide ever encountered. Prepare to be enthralled by the captivating stories and hidden gems of Chicago's architectural heritage.

Reviews

Those who have embarked on the Workers Cottages of Oldtown Triangle Walking Tour have been amazed by the wealth of history and architectural beauty that they encountered. Reviews highlight the tour as a captivating journey through time, with participants expressing their gratitude for the in-depth insights into Chicago's past. Many enjoyed discovering the unique styles of the cottages and appreciated the rare instances where entire blocks were populated by these charming dwellings. Travelers were also pleased to learn about other significant landmarks and the stories behind them, adding another layer of intrigue to their experience. Overall, reviews speak highly of the professional guides, their engaging narratives, and the way the tour brought the city's history alive.

How long before the event do I need to book?

  • You can book at any time before the event

Vouchers accepted in the following formats

  • Mobile

Is an adult required for the booking?

  • At least one adult or senior required per booking

Your Itinerary

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!

Saint Michael Church

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!

Reviews

(38)

5 (38)

mariaaZ6396ZT

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.

Roam35884623733

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.

JohnKiss

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.

normacF6250KL

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.

426poppyc

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.

peelyp

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!

nancyaT455CM

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.

shellellyd

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.

nancyaT455CM

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!

I2189ABellenb

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.
Collected by Evendo & our supplier partners
2024-06-02 18:46