The Lounge & Bar Scene

If you want to soak up the atmosphere of a neighborhood tavern or sports bar, it's best to venture beyond downtown into the surrounding neighborhoods. Lincoln Park, Wrigleyville, and Bucktown/Wicker Park have well-established nightlife zones that abound with bright, upscale neighborhood bars. You'll also find numerous dives and no-frills "corner taps" in the blue-collar neighborhoods.

As for hotel nightlife, virtually every hotel in Chicago has a cocktail lounge or piano bar and, in some cases, more than one distinct environment where you can take an aperitif before dinner or watch an evening of entertainment. The piano bars at The Drake Hotel and the Ambassador East Hotel's Pump Room are standouts.

Old Town -- The center of nightlife in Old Town is Wells Street, home to Second City and Zanies Comedy Club, as well as a string of reliable restaurants and bars, many of which have been in business for decades. You're not going to find many trendy spots in Old Town; the nightlife here tends toward neighborhood pubs and casual restaurants, filled mostly with a late-20s and 30-something crowd.

Lincoln Park -- Lincoln Park, with its high concentration of apartment-dwelling singles, is one of the busiest nightlife destinations in Chicago. Prime real estate is at a premium in this residential neighborhood, so you won't find many warehouse-size dance clubs here; most of the action is at pubs and bars. Concentrations of in-spots run along Halsted Street and Lincoln Avenue.

Wrigleyville, Lakeview, The North Side -- Real estate in Wrigleyville and Lakeview is a tad less expensive than in Lincoln Park, so the nightlife scene here skews a little younger. You'll find a mostly postcollegiate crowd partying on Clark Street across from Wrigley Field (especially after games in the summer). But head away from the ball field, and you'll discover some more eclectic choices.

Wicker Park & Bucktown -- For an alternative scene, head over to Wicker Park and Bucktown, where slackers and some adventurous yuppies populate bars dotting the streets near the confluence of North, Damen, and Milwaukee avenues. Don't dress up if you want to blend in: A casually bohemian getup and low-key attitude are all you need. While you can reach most of these places relatively easily by public transportation, I recommend taking a cab at night -- the surrounding neighborhoods are what I'd call "transitional."

Rush & Division Streets -- Around Rush Street are what a bygone era called singles bars -- although the only singles that tend to head here now are suburbanites, out-of-towners, and barely legal partiers. Rush Street's glory days may be long gone, but there are still a few vestiges of the old times on nearby Division Street, which overflows with party-hearty spots that attract a loud, frat-party element. They include Shenanigan's House of Beer, 16 W. Division St. (tel. 312/642-2344); Butch McGuire's, 20 W. Division St. (tel. 312/337-9080); the Lodge, 21 W. Division St. (tel. 312/642-4406); and Mother's, 26 W. Division St. (tel. 312/642-7251). Many of these bars offer discounts for women, as loud pitchmen in front of each establishment will be happy to tell any attractive ladies who pass by.

Gay & Lesbian Scene

Most of Chicago's gay bars are conveniently clustered on a stretch of North Halsted Street in Lakeview (in what's known as Boys Town), making it easy to sample many of them in a breezy walk. Men's bars predominate -- few places in town cater exclusively to lesbians -- but a few gay bars get a mix of men and women. A couple of helpful free resources are the weekly entertainment guide Nightspots and the club rag Gab. The bars and clubs recommended below don't charge a cover unless otherwise noted.

Hotel Hopping

Forget the stereotypical bland hotel bar filled with drunken conventioneers. In downtown Chicago, some of the most distinctive watering holes are in hotel lobbies. In the Loop, the coolest happy-hour spot is Encore in the Hotel Allegro, 171 W. Randolph St. (tel. 312/236-0123), where the spiral-shaped bar, purple velvet upholstery, and silver accents create a futuristic feel. Things heat up later in the evening at Base, the bar in the Hard Rock Hotel, 230 N. Michigan Ave. (tel. 312/345-1000). The look is sleek -- lots of black and gray -- and the music (live acts or a DJ) is always good. You'll find the beautiful people hanging out at the tiny Whiskey Sky, on the top floor of the W Chicago Lakeshore hotel, 644 N. Lakeshore Dr. (tel. 312/943-9200). There's not much seating and the decor is minimal, but the views -- of both the surrounding skyline and the gorgeous staff -- are terrific. At the Sofitel Chicago Water Tower, Le Bar, 20 E. Chestnut St. (tel. 312/324-4000), is a popular after-work hangout with a low-lit, intimate vibe. If you prefer to stick to tradition, Kitty O'Shea's, 720 S. Michigan Ave. (tel. 312/294-6860), is an authentically appointed Irish pub inside the Hilton Chicago -- a genuine Irish bartender will even pour your Guinness.