Name: Woodlawn Tap (Jimmy's)
Address: 1172 E 55th St, Chicago, IL, 60615
Telephone: (773) 643-5516
Price range: $

Woodlawn Tap (Jimmy's)

Iconic/NotableHyde Park · Bar / American Tavern Community-sourced, unverified

📍 1172 E 55th St, Chicago, IL 60615

Everyone just calls it Jimmy's, after Jimmy Wilson, who opened this plain brick corner tavern in 1948 and ran it until his death in 1999 — the University of Chicago gave him an honorary alumni title in 1982, and the Illinois legislature passed an actual resolution recognizing what the bar did for neighborhood cohesion.

Free live jazz every Sunday at a 1948 Hyde Park dive bar once frequented by Dylan Thomas, Saul Bellow, and the founders of Second City.

That's an unusual amount of institutional respect for a dive bar, but Jimmy's earned it: the guest list over the decades reads like a syllabus crossed with a comedy club — Dylan Thomas drank here in 1950, along with Mike Royko, Jimmy Breslin, Saul Bellow, Margaret Mead, and Philip Roth, plus a run of Compass Players and early Second City names (Mike Nichols, Elaine May, Del Close, Jerry Stiller) who'd go on to reshape American comedy. The room itself hasn't chased a redesign — mahogany bar, tin ceiling, dark wood paneling from the 1940s, three rooms including one that still hosts live jazz every Sunday night. Jimmy himself refused to stock Budweiser after a pricing dispute, and that policy apparently outlived him.

The menu stays simple (burgers, barbecue beef, a Reuben) and the whole operation is cash-only, which tracks for a place this unbothered by modern conveniences. Current owner Matt Martell, a former bartender and U of C alum, took over in 2021 and kept the formula exactly as it was — the correct instinct for a bar that already survived Hyde Park's 1950s urban-renewal wave that closed most of its competitors. No discount special here; the free Sunday jazz is the standing draw, alongside 75-plus years of just being Jimmy's.

Hours

Mon-Fri10:30 AM-2:00 AM; Sat 11:00 AM-3:00 AM; Sun 11:00 AM-2:00 AM

🥡 Takeout unconfirmed 📞 (773) 643-5516

Amenities & accessibility

❔Takeout: unverified

❔Wheelchair access: unverified

Location

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Woodlawn Tap (Jimmy's)

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