Best Happy Hours in Chicago

Happy hour was illegal in Illinois for 26 years. The state brought it back in 2015 but left two-for-one and unlimited-drink pricing prohibited, and the listings still carry that shape: across 532 Chicago entries there is not a single two-for-one. Flat prices do the work instead, and some of them are genuinely low. The Globe Pub on West Irving Park Road lists $2 Heineken Silver. Surge Billiards on West Fullerton Avenue lists $4 bottles. Cheesie's Pub & Grub on West Belmont Avenue lists $1 wings and shots inside two short blocks, 3:30 to 5:30 and again 9 to 10.

North Clark Street, North Milwaukee Avenue and North Lincoln Avenue hold the most listings, which puts the density in Lakeview, Logan Square and Lincoln Square rather than the Loop. Old Town does well per block: Woodie's Flat on North Wells Street lists $5 for 22-ounce fatpours, and The Rabbit Hole a few doors down lists $10 burgers. In the South Loop, Acanto on South Michigan Avenue lists $5 wine pours from 2 to 5.

The day has a firm shape. Roughly three in five listed windows open at 4 PM and shut by 6 or 7, and weekend windows are rare at about one listing in ten. For a longer sit, look for the rooms that split their offer into an afternoon block and a second late one, the way Cheesie's does, or the rare all-evening listing like 720 South Bar on South Michigan Avenue at $4 off cocktails.