Chicago skyline and river at blue hour with illuminated Art Deco towers

Old Town Ale House

dive·$·Old Town

A dive bar since 1958 with paintings of nude regulars and politicians covering every wall — commissioned from artist Bruce Elliott, who has been painting the clientele in the altogether for decades. The cast includes local aldermen, Second City comedians, journalists, and at least one former governor. The bar itself is unchanged: cash register, wooden bar, cheap pours, a jukebox that skews toward jazz and blues, and a clientele that ranges from 25 to 85 with nothing in common except a preference for honest drinking in a room that has never pretended to be anything other than what it is.

$Dive BarOld Town

Location

219 W North Ave
Old Town, Chicago
divehistoricnude-paintingsold-towninstitution

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Insider Intel

Order This

Cheap beer and a shot — Old Style, PBR, or whatever domestic is on special. The well liquor is functional. This is not a craft cocktail bar and does not want to be. The prices are a relic of a pre-gentrification Chicago that barely exists anymore, and the pour is honest. Cash is still the preferred currency at the register.

Best Time

Weekday afternoon from 3pm when the regulars are holding court and the tourists have not yet arrived from Second City across the street. Late night after the improv shows lets out brings a particular energy — comedians and audience mixing at the bar. Saturday afternoon is languid and pleasantly empty.

Know Before You Go

Cash preferred, though cards are now reluctantly accepted. The nude paintings are the attraction and the decor — do not be surprised. The relationship with Second City across North Avenue is symbiotic: comedians drink here after shows, and audience members wander over. Open every day from noon to 4am (2am on Sundays). The jukebox is excellent and worth feeding quarters. No food. No pretension. No apologies.

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