📍 Old Town, Chicago

The comedy institution that launched Tina Fey, Steve Carell, Bill Murray, and basically every funny person in America. The mainstage shows are excellent, but the free improv sets a...

Tuscan-leaning Italian in Old Town, open since 1982 and still drawing the same neighborhood crowd it built four decades ago. The pastas, veal, and house salads sit in the comfortab...

An Old Town tavern that's been turning out slow-cooked baby back ribs since 1932, and the room still wears every one of those years -- worn wood, a working jukebox, the kind of pla...

Old Town pizza bar leaning hard into the campy roadside aesthetic — tire swings, neon, airstream vibes. The pizza is the actual draw, with cocktails to keep the night going. Walk-i...

Old Town's dive of record, steps from Second City and tightly woven into Chicago's comedy history. Anthony Bourdain called it his favorite Chicago bar. Walls covered in local art, ...

Rooftop deck on top of Second City at the Wells Street corner of Old Town, with stadium-style seating angled at the screens, tableside keg service, cornhole, foosball, and giant la...

An Old Town stand-up room that's been booking comics for nearly 50 years, a few doors from Second City. The space is small enough that the laughs feel collective and the hecklers f...