Boystown isn't all 4 a.m. clubs and spilling-into-the-street debauchery. These laid-back spots prove there's a softer side to the strip, too.
Start the whirlwind tour with a Cherry Coke- or peach cobbler- flavored martini (or any of the other rainbow of choices) at Kit Kat Lounge & Supper Club (3700 N. Halsted St. 773-525-1111), where you might just spot a dressed-in-drag diva or two hanging out before her show.
Then kick back with an Italian-inspired cocktail on the lush, flower-lined patio at Taverna 750 (750 W. Cornelia St. 773-904-7466), a stylish lounge tucked just a half-block from the bumping beats of the main drag.
Head south to Elixir (3452 N. Halsted St. 773-975-9244), a welcome cocktail oasis for those in search of a hand-crafted drink in an understated but still chic interior.
Catch your favorite sports team on the TVs at Halsted's (3441 N. Halsted St. 773-348-9696) with a cold beer in hand, then your luck at vintage arcade games at Replay (3439 N. Halsted St. 773-975-9244) while sipping a glass of bourbon or one of the bar's more than 20 draft beers.
Next, consider a mid-evening bite at rustic-inspired Wood (3335 N. Halsted St. 773-935-9663) where the seasonal food menu more than holds its own alongside artfully presented cocktails.
Continue the night with a craft or imported beer, glass of wine or cocktail at Progress Bar (3359 N. Halsted St. 773-697-9268), where the main draw may be the visually stunning "cloud" of lightbulbs suspended from the ceiling.
Finish up at the bar at Jack's on Halsted (3201 N. Halsted St. 773-244-9191) with a drink off the extensive martini list, or wine by the glass or bottle.