If you want to soak up the atmosphere of an authentic neighborhood tavern or sports bar, it's best to venture beyond downtown. Lincoln Park, Wrigleyville, and Bucktown/Wicker Park have well-established nightlife zones that abound with bars that range from bright and upscale to borderline-dingy but full of character. You'll also find numerous dives and no-frills "corner taps" in the blue-collar neighborhoods.
As for nightlife downtown, virtually every hotel in Chicago has some kind of bar. Many are little more than undistinguished groupings of tables and chairs in the lobby, but others have become trendy clublike hotspots. If you're looking for an old-school, cocktail-lounge vibe, the piano bar at The Drake Hotel, Coq d'Or, is a standout.
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, Encore in the Hotel Allegro, 171 W. Randolph St. (tel. 312/236-0123), is a popular happy hour spot, with a black-and-white color scheme and urban lounge feel. For late-night drinks in a low-lit, intimate space, head to Angels and Kings, the bar in the Hard Rock Hotel, 230 N. Michigan Ave. (tel. 312/345-1000). The look is glam rock, and the music (live acts or a DJ) is always good. 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. Farther north, in the blocks surrounding the Magnificent Mile, you'll find style-conscious spots such as Le Bar, in the Sofitel Chicago Water Tower, 20 E. Chestnut St. (tel. 312/324-4000), a popular after-work hangout with a sophisticated vibe. At 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. Vertigo Sky Lounge, atop the Dana Hotel and Spa, 660 N. State St. (tel. 312/202-6060), is a dark, clublike space with live DJs, but expansive floor-to-ceiling windows make you feel like you're floating amid the high-rises. An added bonus is the outdoor deck, a great spot to take in the views when the weather's nice. But for sheer drama, the current hotel-bar champ is Roof, atop The Wit Hotel, 201 N. State St. (tel. 312/467-0200). The sprawling space includes a Miami Beach-style terrace with fire pits for chilly nights and a large indoor seating area (with cozy fireplaces) so that even winter visitors can enjoy the views. If you dare, you can even book a table with a see-through glass floor that juts out from the roof's edge.
The Great Bar Sting -- What's now the Brehon Pub was once the site of a notorious Chicago bribery scandal, back in the days when muckraking journalism was still a city specialty. In 1977, the Chicago Sun-Times newspaper, in partnership with the Better Government Association, decided to fund an undercover investigation into corruption among city officials who regulated local businesses. They leased the bar and opened it as the appropriately named Mirage, then took notes as a series of city inspectors offered to take bribes to overlook health- and safety-code violations; state liquor inspectors also demanded their cut. A photographer tucked away on a hidden platform overlooking the room caught it all on film. The resulting 5-week newspaper series caused a sensation and eventually led to 34 court convictions. But it also triggered a national controversy over the ethics of undercover journalism. Although the Sun-Times was favored to win a Pulitzer Prize for the series, notable Pulitzer board members -- including legendary Washington Post editor Ben Bradlee -- successfully argued that stories based on deception should not win awards. With that decision, the days of reporters posing as bartenders were doomed -- and the local papers got a lot less colorful.
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.
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, 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 exotic choices.
Wicker Park & Bucktown
The closest Chicago has to an alternative scene is Wicker Park and Bucktown, where both slackers and adventurous suburbanites populate bars dotting the streets leading out from the intersection 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."
Note: This information was accurate when it was published, but can change without notice. Please be sure to confirm all rates and details directly with the companies in question before planning your trip.