Discover Chicago's Historic Oldtown Triangle on a Cottages Walking Tour
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Step back in time and explore the charming workers' cottages of Oldtown Triangle on this walking tour. You'll see 40-50 historic homes, each showcasing different architectural styles from the late 1800s, many of which have been featured in major architectural publications and on the Bob Vila website.
As you stroll through this quaint neighborhood, you'll learn about Chicago's early days before the Great Fire of 1871, hearing stories about notable historic properties and the city's growth over the past 150 years. The Oldtown Triangle feels like a different world—peaceful, picturesque, and full of stories waiting to be uncovered.
Along the way, you'll visit landmarks like the Roman Catholic St Michael Church, once the tallest building in the U.S., and the Twin Anchors Restaurant, a beloved Chicago tavern famous for its barbequed ribs and Sinatra visits. This tour offers a perfect blend of architecture, history, and local flavor, all in just under two hours.
Frequently asked questions
How long is the tour?
The walking tour lasts approximately 1 hour and 45 minutes.
What languages are available?
The tour is conducted in English.
Is the tour suitable for children?
Yes, children aged 7-10, youth 11-20, and adults up to 80 can participate. Infants and small children can ride in strollers or prams.
How many people are in a group?
Groups are limited to up to 6 participants for a more personalized experience.
What should I wear or bring?
Comfortable walking shoes are recommended, and travelers should have at least a moderate level of physical fitness.
Is the tour accessible?
Yes, infants and small children can ride in strollers, but some walking may require moderate physical effort.
Free cancellation
For a full refund, cancel at least 24 hours before the scheduled departure time.
Reserve now
Check a date here, then finish booking with our partner. Payment options are confirmed at checkout.
Duration 1 hour 45 min
Check availability to see start times.
Live tour guide
English
Key facts
What's included
Included
- Historical photos of each stop available in a free app
Not included
- Food and drinks
- Personal expenses
- Transportation to/from the meeting point
Itinerary
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Stop 1
View 40-50 workers' cottages showcasing various architectural styles from the late 1800s. You'll see some rare instances where multiple cottages line a street or form entire blocks, offering a glimpse of pre-Great Fire Chicago. Many of these homes have been featured on the Bob Vila website and Chicago architecture accounts.
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Stop 2
Rowhouses on Eugenie Street, built in 1886 by Harald Hansen. This rare row of five opulent Queen Anne and Second Empire style homes highlights Chicago’s early architectural diversity. Hear stories about the city's beginnings in this historic location.
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Stop 3
N. Crilly Court, where you'll learn about notable residents and see a property designated as a National Landmark, revealing the area's rich history.
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Stop 4
St Michael Church of Oldtown, built between 1866-1869. Once the tallest building in the U.S. for 16 years, this Roman Catholic church is a key historic landmark.
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Stop 5
Twin Anchors Restaurant, established in 1932. Known for tender barbequed baby-back ribs, this cozy neighborhood tavern was a favorite of Frank Sinatra for many years.
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Stop 6
See the homes of Charles and Frederick Wacker, influential early Chicago figures, and hear about their role in shaping the city’s development.
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Stop 7
Visit the Ann Halsted Rowhouses, designed by Louis Sullivan in his early 20s—before he became a renowned architect.
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Stop 8
View the only remaining farmhouse from the Oldtown area's farmland days, outside the city limits, offering a glimpse into Chicago's rural past.
Meeting point & pickup
Meet at the starting point
You can find the guide on the sidewalk in front of the rowhouses at the designated meeting address.
Open in Google MapsCancellation & confirmation
Free cancellation
For a full refund, cancel at least 24 hours before the scheduled departure time.
- 100% refund if canceled at least 1 day in advance
- No refund if canceled within 24 hours of the start
- Tour may be canceled due to bad weather or insufficient bookings
Instant confirmation
Your booking is confirmed immediately after checkout.
From $45.00 per person
- Free cancellation
- Secure checkout with our booking partner
