Workers Cottages of Oldtown Triangle Walking Tour

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!

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.

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

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

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

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

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