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๐Ÿ˜๏ธ๐Ÿ”ฅ Old Town Uncovered: Fire Survivors, Comedy Legends & Hidden Gems! ๐ŸŽญ๐Ÿ‚

Back by popular demand โ€” with MORE stops, MORE stories, and plenty of Old Town surprises*!** ๐Ÿ™Œ*

Think you know Old Town? Think again! Join us for a beautiful fall walk through one of Chicago's most fascinating and layered neighborhoods โ€” where winding streets, Victorian homes, historic churches, artists' studios, legendary comedy, immigrant history, and Great Chicago Fire survivors all come together to tell one of the city's most compelling neighborhood stories.

โœจ We'll go beyond the bars and restaurants and uncover the stories hiding in plain sight โ€” from buildings that survived the devastating 1871 fire to tucked-away artistic enclaves, pioneering Chicagoans, and places connected to some of the city's most colorful characters. ๐Ÿ’ซ

Come walk, learn, and enjoy the beautiful fall colors with us โ€” Old Town in October is truly something special! ๐Ÿ‚๐Ÿ˜๏ธ

๐ŸŽค Led by your passionate, ever-curious guide (that's me!) โ€” perfect for architecture lovers, history buffs, photographers, comedy fans, and anyone who enjoys being a tourist in their own city! ๐Ÿ˜Š

๐Ÿ‘ฅ Multi-group event โ€” expect a fun crowd of fellow explorers from several groups!

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๐Ÿ“ LOGISTICS
๐Ÿ—“๏ธ Saturday, October 10, 2026
โฐ 11:30 AM โ€“ 2:00 PM (~2.2 miles walking)
๐Ÿ“ Start: Sedgwick Brown Line Station โ€” 1536 N Sedgwick St
๐Ÿ End: Carl Street Studios โ€” 155 W Burton Pl
๐Ÿ’ฐ $20 per person โ€” due at start of tour
๐Ÿ’ต Cash preferred (exact change appreciated) | PayPal, Zelle & Venmo also accepted
๐ŸŒฆ๏ธ Casual pace | Outdoors | Rain or shine

โš ๏ธ IMPORTANT PARKING NOTE
The walk ends approximately 4 blocks from the starting point โ€” plan your transportation accordingly! ๐Ÿš—

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Tour Highlights:
๐Ÿ”ฅ Great Chicago Fire history โ€” survivors & stories
๐Ÿ›๏ธ Victorian row houses, cottages, churches & architectural gems
๐ŸŽจ Artists' studios & Chicago's hidden creative communities
๐ŸŽญ The Second City, Piper's Alley & Old Town's legendary comedy history
โ›ช German immigrant history & community landmarks
๐Ÿณ๏ธ The Henry Gerber House โ€” a pioneering piece of Chicago history
๐ŸŒณ Hidden streets & winding paths that predate Chicago's modern grid
๐Ÿ’Ž Hidden gems you've probably passed โ€” but never noticed!

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๐Ÿ—บ๏ธ Route Highlights (stops subject to change):
๐Ÿด Twin Anchors Restaurant
โ›ช St. Michael's Catholic Church (Great Chicago Fire survivor!)
๐Ÿฏ Midwest Buddhist Temple
๐Ÿธ Margie's Still
๐ŸŽณ Menomonee Club
๐ŸŽจ Kogen-Miller & Glasner Studios
๐Ÿ˜๏ธ Crilly Court Historic District
๐Ÿณ๏ธ Henry Gerber House
๐Ÿก Olsen-Hansen Row Houses
๐ŸŒณ Eugenie Triangle Park & Chicago Fire "Blob"
โ›ช Moody Church
๐Ÿ›๏ธ Chicago History Museum
๐Ÿฐ Former Germania Club
๐ŸŽญ The Second City
๐ŸŽฌ Piper's Alley
๐ŸŽจ Theophil Studios
๐ŸŽจ Sol Kogen & Edgar Miller Studios
๐Ÿ˜๏ธ Carl Street Studios (tour ends here!)

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๐ŸŒŸ WHY OLD TOWN?
Old Town is one of those Chicago neighborhoods where you can turn a corner and suddenly feel like you've stepped into another era entirely.

Originally settled by German immigrants in the 1850s, the neighborhood is filled with layers of Chicago history. Parts survived the Great Chicago Fire of 1871 โ€” making some of these streets among the oldest intact residential blocks in the city. Later generations added churches, artists' communities, entertainment venues, and some seriously interesting architecture that most visitors never find.

From St. Michael's Catholic Church โ€” one of the few buildings to survive the Great Fire โ€” to Crilly Court's beautifully preserved Victorian streetscape, from the artists' studios of Edgar Miller and Sol Kogen to the legendary stage of The Second City, there's a story around nearly every corner in Old Town. And in October? The tree-lined streets and fall colors make it one of the best times of year to explore. ๐Ÿ‚๐Ÿ˜๏ธ

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๐Ÿ“ธ Not a dedicated photo walk โ€” but trust us, you'll want your camera! Architectural details, quirky corners, and beautiful fall streetscapes around every turn! ๐Ÿ‚๐Ÿ“ธ

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๐Ÿ’Ÿ WHAT TO BRING
๐Ÿ‘Ÿ Comfortable walking shoes
๐Ÿ’ง Water bottle
๐Ÿ‚ Weather-appropriate attire
๐Ÿงฅ A light layer โ€” fall temps can be unpredictable!
๐Ÿ“ธ Camera or phone encouraged
๐Ÿ’ฐ $20 tour fee (exact change appreciated; cash preferred but Zelle, Venmo & PayPal accepted)

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๐Ÿฝ๏ธ OPTIONAL POST-WALK LUNCH
Stick around after the tour and join us for lunch at one of these Old Town favorites!
๐Ÿป Woodie's Flat
๐Ÿ Topo Gigio Ristorante
๐ŸŒฎ Adobo Grill
๐Ÿบ Corcoran's Grill & Pub
๐Ÿ’ต Bring cash โ€” some places don't split checks!

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๐Ÿš‡ GETTING THERE
๐Ÿš‡ CTA Brown Line โ€” Sedgwick stop (right at the start!)
๐Ÿš— Street parking available โ€” but weekend parking in Old Town can be challenging!
โš ๏ธ Check all posted signs & restrictions carefully
๐Ÿ…ฟ๏ธ SpotHero or ParkWhiz recommended

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๐Ÿ“ฑ LOST OR RUNNING LATE?
Call or text 312-835-4259 and I'll point you in the right direction!
๐Ÿ‘‹ Please check in with Giovina when you arrive!

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โš ๏ธ NO-SHOW POLICY
๐Ÿ˜ฌ 3 no-shows without updating your RSVP = 3-month event ban
โฐ Update your RSVP before the event starts; after that, message the host directly
๐Ÿšซ Continual no-shows = removal from the group

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๐Ÿ˜๏ธ๐Ÿ‚ Forget what you think you know about Old Town. This isn't just bars, restaurants, and nightlife โ€” it's Great Chicago Fire survivors, hidden streets, Victorian architecture, immigrant stories, artists, legendary comedians, and plenty of Chicago surprises, all packed into one fascinating neighborhood. Bring your curiosity, invite a friend, and come be a tourist in your own city! ๐ŸŽญ๐Ÿ”ฅ๐Ÿ›๏ธ๐Ÿ‚

Related topics

Events in Chicago, IL
Walking Tours
Exploring
History
Walking
Historic Architecture Walking Tours

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