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🎭 Old Town, Chicago
6 restaurants · 2026
🍽️ 6 Restaurants
✨ Comedy, Date Night, Historic
A historic neighborhood north of downtown. Brownstones, the Second City comedy theater, and small neighborhood spots.
Known for: Second City, Wells Street, Lincoln Park West
Don't miss: Second City
💡 Second City's mainstage launched John Belushi, Bill Murray, and Tina Fey — see the early show.
Top 6 in Old Town
1
Second City
Comedy Club
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...
91
2
Topo Gigio Ristorante
Tuscan Italian
Tuscan-style Italian in Old Town since 1982 with over 35 years of serving the neighborhood. Modern approach to classic Italian with fresh pasta, grilled meats, and a warm atmospher...
87
3
Twin Anchors
BBQ Ribs
Old Town rib joint since 1932. Baby back ribs in a wood-paneled bar with a jukebox. Frank Sinatra used to eat here. A Chicago legend.
86
4
Twin Anchors Restaurant & Tavern
American / Ribs · Iconic Chicago Restaurant
Old Town institution since 1932 famous for slow-cooked ribs once frequented by Frank Sinatra — a Chicago landmark.
84
5
Happy Camper Old Town
Pizza / Bar
Fun Old Town pizza and cocktail bar with tire swings, neon signs, airstream aesthetic, and a creative pizza menu.
83
6
Old Town Ale House
Bar / Dive
Anthony Bourdain's favorite dive bar with local artwork, a cast of regulars, and deep ties to Second City comedy.
80
Iconic (5)
Local Favorites (4)
Date Night (3)
BBQ (2)
Casual (2)
Bar (2)
Late Night (2)
Entertainment (1)
Italian (1)
Pizza (1)
Dive Bar (1)
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