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. The Near North Side has a few entertainment zones that are saturated with bright, upscale neighborhood bars. But 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 and in the Omni Ambassador East Hotel's Pump Room are standouts.
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 (this is where we'd come to celebrate 21st birthdays when I was in college). Rush Street's glory days have long passed, but there are still a few vestiges of the old times. Division Street is filled with party-hearty spots that attract a loud, frat-party element. The bars lining Division Street include the Alumni Club, 15 W. Division St. (tel. 312/337-4349); 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 special discounts for women, as loud pitchmen in front of each establishment will be happy to tell any attractive ladies who pass by.
Old Town--The center of nightlife in Old Town is Wells Street, home to Second City and other comedy clubs, as well as a string of reliable restaurants and bars. You're not going to find many trendy spots in Old Town; the nightlife here is geared toward neighborhood pubs and bustling 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. Since this is a residential neighborhood where prime real estate is at a premium, you won't find any warehouse-sized dance clubs here; most of the action is at pubs and bars. Concentrations of in-spots run along Armitage Avenue, 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 you'll also 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 to impress if you want to blend in; a casually bohemian getup and low-key attitude are all you need to fit in.
