wells street.
The core of Old Town — lined with restaurants, patios, pubs, and neighborhood favorites that stay busy from happy hour through late night.
Chicago neighborhood guide
old town.
Old Town blends historic charm with a lively main strip — think classic walk-ups, cobblestone-style alleys, comedy clubs, and some of the city’s favorite bars and restaurants along Wells Street.
Life in Old Town
Old Town feels like a village just north of downtown — tree-lined streets, historic architecture, and a main drag that stays busy well into the evening.
Wells Street is the heart of the neighborhood, lined with restaurants, pubs, patios, and long-running comedy venues. Just a block or two away, side streets quiet down into residential pockets with vintage walk-ups, condos, and renovated single-family homes.
With quick access to Lincoln Park, the lakefront, and the Brown Line, Old Town works well for buyers and renters who want neighborhood character, nightlife, and convenience to both downtown and the North Side.
Neighborhood highlights
A few local favorites that give Old Town its character. These are great starting points if you’re getting to know the neighborhood.
old town art fair.
A long-running summer art fair that brings artists, vendors, and live music to the historic streets and alleys just off Wells.
the second city.
Legendary improv and sketch comedy theater where countless comedians got their start — a true Chicago institution.
zanies comedy club.
A classic stand-up club with a cozy room, packed calendar, and a steady stream of local and national comics.
utopian tailgate.
A colorful rooftop above Second City with views, games, and a tailgate-style menu — a popular spot for groups and weekend outings.
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