If you're looking to PARTY HARD:
Night owls don't need to hop the Red Line Downtown to find the party--Boystown is packed with plenty of gay-friendly dance clubs and late-night bars to keep the party going until the early hours of the morning. With most of the hot spots within just a few blocks, spend less time in cabs and more time on the dance floor.
Start the evening at Circuit Night Club where Latin-and hip-hop-themed dance parties and go-go shows take place most weekends. Shuffle south to Little Jim's, one of the original gay bars on Halsted, to mingle over beers or cocktails.
Next hop across the street to Hydrate, step through the mist spraying from the awnings and dance your butt off at one of the hardest-partying clubs on the strip. Then head to Minibar to splurge on bottle service or cocktails in the stylish, pink-lit lounge.
From there,it's a quick jump across the street to Roscoe's, home to a super-packed dance floor, pitchers of cocktails and a pool table. Keep the momentum going to the recently revamped Sidetrack, which has multiple rooms each boasting its own clubby personality. Pop in to Scarlet, a 1920s- and '30s-decorated bar whose nightly themed parties last until 2 a.m. or 3 a.m.
Next it's on to Spin, where over-the-top themed bashes like shower parties, drag shows and karaoke take place most nights. Finally, end the night--or don't--at Lucky Horseshoe, where a line-up of male dancers performs seven nights a week, 365 days a year.
If you're looking for a more LOW-KEY crawl:
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, 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-lind patio at Taverna 750, a stylish lounge tucked just a half-block from the bumping beats of the main drag.
Head south to Elixir, 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 Bar & Grill with a cold bear in heand, then try your luck at vintage arcade games at Replay while sipping a glass of bourbon or one of the bar's more than 20 draft beers.
Next, consider a mid-evening bit at rustic-inspired Wood, where the seasonal food menu more than holds its own alongside artfully presented cocktails. Finish up at the bar at Jack's On Halsted with a drink off the extensive martini list, or wine by the glass or bottle.