Chicago Historic Workers' Cottages Tour

This tour will show you many of these delightful cottages and the different styles they were designed and constructed in. You will also learn about their history and unique part of the growth of the city of Chicago. Plus you will hear about other fascinating Chicago history that dates back 150 years and beyond! The Oldtown Triangle is one of the oldest and most quaint areas of the city - an area that many Chicagoans love and cherish. You will feel like you have left the hustle and bustle of the city and will instantly be transported to another place, another time, specifically the late 1800's!

Meeting Point

164 W Eugenie St

164 W Eugenie St, Chicago, IL 60614, USA

You can find me on the sidewalk in front of the amazing rowhouses at our starting address

What's included:

• Historical photos of each stop in a free app

What to expect:

Duration: 1 hour, 45 minutes

Old Town Triangle

Old Town Triangle, Chicago, IL, USA

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!

2 hours

West Eugenie Street

W Eugenie St, Chicago, IL 60614, USA

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.

10 minutes

North Crilly Court

N Crilly Ct, Chicago, IL 60614, USA

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

15 minutes

St. Michael House of Prayer

8000 S Aberdeen St, Chicago, IL 60620, USA

St Michael Church of Oltown (Roman Catholic)
Built 1866-1869 - tallest building in the United States for 16 years!

20 minutes

Twin Anchors Restaurant & Tavern

1655 N Sedgwick St, Chicago, IL 60614, USA

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

5 minutes

Old Town Triangle

Chicago, Illinois

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

5 minutes

Old Town Triangle

Old Town Triangle, Chicago, IL, USA

Ann Halsted Rowhouses which were designed by architect Louis Sullivan when he was in his early 20's before anyone knew who he was!

5 minutes

Old Town Triangle

Old Town Triangle, Chicago, IL, USA

See the only remaining farmhouse standing from when the Oldtown area was still farmland, outside the city limits!

5 minutes