3201 W Armitage Ave
Novices will appreciate the vintage-vibed, gin-focused saloon's lack of pretension, but seasoned cocktail-drinkers will be equally impressed by excellent/cheap $8 signature bevs like the Saint Charles -- jasmine-infused Death's Door with apricot liqueur, Peychaud's, and absinthe rinse. The $4 small plates ain't bad either.
Best late night: The Owl
2521 N Milwaukee Ave
Open until 4am on Fridays and 5am on Saturdays, The Owl will definitely ruin your weekend day plans. But with a $6 PBR/Jameson shot special, 20 taps, and a decent dance floor, plus a quirky retro waterfall in the back leftover from previous tenants, it'll be worth it, probably.
Best live music: Cole's
2338 North Milwaukee Ave
There's no cover, ever, which means you can soak up all that local music and sweet, sweet open-mic comedy for only as much as you need to drink, depending on whose set it is. Don't leave without taking a poop!
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Carrie Dennis is an Associate Editor for Thrillist and will be here all night. Follow her on Twitter @CarrrieDennnis.