Wicker Park Dive Bar Date

Start at the namesake park — dog walkers, musicians, and the beautiful fountain. Walk up Milwaukee Ave and browse the vintage shops.

5 min walk. Killer tacos, whiskey, and honky-tonk on the patio. The al pastor taco is one of the best in Chicago. Cash-only patio, card inside.

3 min walk. Classic arcade games, pinball, and craft beers in a massive space. Free to play, just buy drinks. Perfect competitive date energy.

3 min walk. No sign on the door — look for the unmarked entrance with a light bulb. One of America's best cocktail bars. No standing allowed, no phones at the bar.