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Workers Cottages of Oldtown Triangle Walking Tour

icon 2 hours Mobile ticket
Tickets from € 62.82

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August 2025
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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!
  • Historical photos of each stop in a free app
Departure Point

164 W Eugenie St, Chicago, IL 60614, Verenigde Staten You can find me on the sidewalk in front of the amazing rowhouses at our starting address

Return Details

216 W Menomonee St, Chicago, IL 60614, Verenigde Staten The tour will end with the last stop, which is the very first workers cottage I ever saw before I knew what they were. The end of the tour is a few short blocks from where it started.

  • Old Town Triangle, Chicago, IL, Verenigde Staten
    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!
    120 minutes
  • 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
  • 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
  • 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
  • 1655 N Sedgwick St, Chicago, IL 60614, Verenigde Staten
    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, United States
    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, Chicago, IL, Verenigde Staten
    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, Chicago, IL, Verenigde Staten
    See the only remaining farmhouse standing from when the Oldtown area was still farmland, outside the city limits!
    5 minutes
  • Infants and small children can ride in a pram or stroller
  • Service animals allowed
  • Public transportation options are available nearby
  • Travelers should have at least a moderate level of physical fitness
This experience is non-refundable and cannot be changed for any reason. If you cancel or ask for an amendment, the amount you paid will not be refunded.
  • This experience requires good weather. If it’s canceled due to poor weather, you’ll be offered a different date or a full refund.
  • This experience requires a minimum number of travelers. If it’s canceled because the minimum isn’t met, you’ll be offered a different date/experience or a full refund.
amandadV1088RI
08 Aug 2025
This tour is fabulous! Ronnie is incredibly knowledgable and points out so many wonderful details about Old Town. 10 out of 10 recommend! So unique!
698danitah
26 Jun 2025
The Workers Cottages of Oldtown tour was wonderful! Ronnie was a fantastic guide & shared the rich history of the houses & neighborhoods. Would & have recommended this tour to friends. A must see for anyone who appreciates beautiful homes & architecture.
seanegan71
16 Jun 2025
Really excellent tour of some great homes with some great stories to go along with them. The tour takes you down some beautiful side streets you might not find on your own. Well worth it.
This tour in Chicago is organized by Walking Tours by Ronnie Frey, creator of

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