Old Town, Chicago
One of Chicago's oldest surviving neighborhoods, home to The Second City and rows of pre-fire cottages. Best for comedy, historic architecture, a quiet upscale base. Served by the Brown, Red.
Photo: Paul Griffin / Unsplash
- ✓Old Town is one of Chicago's oldest surviving neighborhoods, with pockets of housing that predate the 1871 Great Chicago Fire.
- ✓The Second City, the famous improv theater that launched generations of comedians, has called Old Town home since the early 1960s.
- ✓Its residential streets are genuinely historic — narrow, tree-lined blocks of pre-fire cottages and later Victorian rowhouses, a rarer survival than most of the city's housing stock.
- ✓Old Town sits just north of the Gold Coast, and the two neighborhoods share a similar quiet, upscale, historic character.
- ✓Served by the Brown and Red Lines, with the closest access via the Sedgwick stop or a walk from Clark & Division.
One of Chicago's oldest surviving neighborhoods
Old Town earns its name honestly: parts of it predate the 1871 Great Chicago Fire, and the neighborhood's residential streets still carry that age visibly, in a city where most housing stock is younger by necessity. Narrow, tree-shaded blocks of wood-frame cottages and later Victorian rowhouses survive here in a way few other Chicago neighborhoods can match, giving Old Town a genuinely different texture from the newer construction that fills much of the North Side.
That historic residential character sits alongside a livelier commercial spine along Wells Street, where Old Town's comedy and nightlife identity plays out. The neighborhood's two halves — quiet historic cottages, and a comedy-and-bar strip a few blocks over — coexist without much friction, which is part of what makes Old Town an easy, walkable neighborhood to spend a half-day in.
Second City, and a quiet, historic base
The Second City has run out of Old Town since the early 1960s, and a night at the theater — whether a mainstage revue or one of its smaller improv rooms — remains one of the best reasons to build an evening around this neighborhood specifically. It's a genuine piece of American comedy history, not just a tourist-facing show, and tickets are worth booking ahead in peak season.
Old Town is served by the Brown and Red Lines, with the Sedgwick stop on the Brown Line the closest direct access, and a walk from the Red Line's Clark & Division stop also workable depending on which part of the neighborhood you're headed to. Its quiet, historic streets and proximity to the Gold Coast make it a genuinely pleasant, upscale base for a slower-paced stay, a short walk or ride from both downtown and Lincoln Park.
- Served by: Brown, Red Lines.
- Nearest stops: Sedgwick (Brown), or Clark & Division (Red) via a walk.
- Nearby neighborhoods: Gold Coast, Lincoln Park.
Gold Coast, Chicago
Chicago's most historically wealthy address — mansion-lined side streets a block off the Mag Mile. Best for upscale hotels, boutique shopping, quiet walking.
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Lincoln Park, Chicago
The namesake park's leafy neighborhood — brownstones, the zoo, and DePaul's campus. Best for families, the zoo, tree-lined walking.
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The Second City
The improv theater that launched Belushi, Fey, and Colbert — how to book a show and what to expect from a set.
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