Map of Old Town Bars

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Bars in Old Town Overview

Zanies Comedy Club - Comedy Club in Old Town, Chicago

Once a red-light district, these days Old Town is home to affluent professionals. Its upscale condos still share the streets with a plethora of bars, some sleek, some as grungy as in days of old. As opposed to the tiny, exclusive housing of the neighborhood, many of the bars are in gigantic spaces.

Many Old Town bars are on an out-of-the-way block called Weed Street. The massive Joe’s Bar anchors this nightlife strip, and its 20,000-square-foot warehouse space always seems close to full. Dividing its time between sports and live music, Joe’s is a nightly reunion spot for Big 10 grads and other yuppie types. In the summer, a dog-friendly 6,000-square-foot patio adds even more sports-watching space.

Though Joe’s patio closes in the winter, the folks at nearby Benchmark have a contingency plan. Their rooftop beer garden can disappear under a giant retractable roof. Sports fans can check out the fifty TVs on the bar’s two levels and cheer on their teams in chic surroundings.

Sticking with the trend of massive bars in Old Town, old-timey Old Town Social is another good-looking spot for bros to check out game-day action—sometimes on private booth-side TVs. While Joe’s patrons dance to live cover bands, the people of Old Town Social bump to DJ-driven house and pop party tunes. Bars in Old Town are no longer dens of wino depravity, but the hood’s new residents are keeping late nights alive.

Popular Old Town Bars

  • * Benchmark 20s / 30s / ATM / After Work / Bar
  • * Joe's Bar Affluent / After Work / Bar Food

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