Not to be confused with Light on Racine, the Light Club situated in the O’Hare Hilton is the last of the original 20s-era speakeasies that inspired the old Playboy Clubs. The waitstaff consists of lovely and charming can-can girls dressed in corsets, tassels and fishnet stockings. The Light Club’s extends beyond even that, attracting more of a transient business clientele with few regulars coming from the city or suburbs. Light was open to key-holding members until 2001 and is now available to anyone wanting a cocktail, steak or seafood dinner, and live piano entertainment in a posh throwback setting.
Light Club Chicago Dining AreaThe O’Hare Hilton is situated across from Terminal Three, within the confines of O’Hare International Airport. Visitors either fly in, take the Blue Line «L» or park in the short-term lot. The Light Club is located at the northwest end of the lobby, to the right of the front desk. Serbian owner Ranko (Ray) Dabizljevic leases the space from the Hilton and advertises the dress code as «business attire,» a rarity these days.

To the left of the framed Light sign promising «Elegant Dining & Entertainment,» you’ll find the maitre’ d stand below a white statue of a woman that looks like she’s about to dive into water—perhaps your wallet instead… If you’re dining, the hostess will lead you to your table down a narrow carpeted aisle with Victorian wallpaper and illuminated by Tiffany lamps. A small room to your right features a handful of low-slung, four-seater tables, across from a series of tall, leather-upholstered wooden booths. Smaller, two-seater tables lie beneath faux bookcases along the eastern wall.

160 Piano & Cabaret opened in 2006 after a major face lift. It served previously as Annex 3, once a famous stomping ground for gay athletes. Long-time owner Jim Flint felt the bar needed to be revamped, renamed and, although it remains a gay bar, 3160 openly welcomes people of all ages and sexual preferences. It offers a different atmosphere then most Boystown bars even though it’s located a little off the «Boystown strip» on Clark Street, just south of Belmont.
3160 features some of the top cabaret and piano entertainment in Chicago and occasionally welcomes talent from all over the United States. Live music is featured five nights a week, Tuesday through Sunday, with certain nights reserved for 3160 regular performers. There’s never a cover charge, a perk that is hard to find, especially at bars in Boystown and throughout the city for that matter.

3160 Chicago BarOn Tuesday nights, the bar hosts an open mic night for comedians with the show starting at 9pm. Wednesdays are reserved for The Paul Marinaro Jazz Trio. While I’m no jazz expert, this trio is truly talented and I promise you will definitely be back for more if you go see them. The group belts out classic jazz tunes and some original pieces too. Fridays feature Pop Goes the Gio performs just about any song you can imagine on the piano. Pop, R&B and techno are specialties but he also incorporates comedy into his performances. He is very talented and, if you’ve missed him playing at other Chicago clubs, 3160 is the perfect place to check him out. Other 3160 performers vary from comedic talents on Mondays to cover bands on other nights.

Hamburger Mary’s Rec Room is a place that lets patrons enjoy all the perks that Hamburger Mary’s restaurant has to offer but in a sports bar setting. Located in the heart of Chicago’s far north Andersonville neighborhood, the Rec Room is another addition to the gay bars and clubs in what is slowly becoming the «new Boystown,» though is proudly open to all who are open-minded.

The Rec Room opened its doors in the summer of 2009 and as the name suggests, it’s a place to hang out, grab a few drinks and watch your favorite Chicago sports team kick some butt, or so we hope. Like the main dining area in Hamburger Mary’s, the Rec Room isn’t very large but there are plenty of tables, even ones perfect for large groups. There are eight large flat screen TVs, so you’ll catch all the action from any seat in the bar: «NFL Sunday Ticket, ESPN’s College GameDay, March Madness, the Olympics, figure skating and just about everything else and in-between!» During halftime, the bar keeps you entertained with pool, foosball, video bowling, and Megatouch. If sports aren’t your thing then popular shows like Glee are broadcast on Tuesday nights and, depending on the crowd, you may even see some brave souls singing along with the show…

For everyone, there comes a time when you graduate from 25¢ wing night, beer pong and «speed mating,» and start looking for more sophisticated nightlife options. To further your studies, you could pay a visit to a European-style taverna, a trendy gastropub and a chic wine bar, or you could simply find your way to Bluebird and experience them all at once.

Bluebird comes courtesy of Tom MacDonald, the nightlife pioneer who brought Chicago its first dedicated wine bar in 1994, Webster’s—also featured in Sean Parnell’s Historic Bars of Chicago. And with Bluebird, MacDonald was/is ahead of the curve. Open since 2007, Bluebird was among the early adopters of the “gastro movement,» beating notable competitors like Longman & Eagle and Gilt Bar to the market by a couple of years. And it’s lost none of its luster over that time, remaining as popular as ever, despite—or because of—a low-key approach to self-promotion relies largely on word-of-mouth.

Bluebird Chicago CrowdLocated on Bucktown’s busy commercial stretch of Damen, Bluebird blends in with its surroundings, almost too well. First-timers might be hard-pressed to spot the simple blue and white sign and surprisingly narrow storefront entrance the bar shares with a neighboring exercise studio. But once inside, you’ll find a space that’s far more expansive than it first appears. The long, rectangular room is both simple and urban, with candle-lit tables, rough plank floors and ceiling beams, chalkboard signage, and exposed brick walls where the work of featured artists is rotated regularly. An extended service bar runs the length of the room, with an equally long banquette opposite, where a half-dozen closely-spaced tables sit. An even narrower pass-through beyond the bar leads to the washrooms and then opens into a rear dining area that offers a good deal of additional seating and a wall-mounted gas fireplace. Diversions are largely of the social variety, with a single TV and the bartender’s handiwork providing some distraction. Patrons of the arts will want to take note of Bluebird’s bi-weekly Salon Series (except in December), consisting of an evening of art and dinner for $40 with wine and beer pairings and artist Q&A.

The son of a Louisiana sharecropper, legendary bluesman and Rock & Roll Hall of Fame inductee George «Buddy» Guy first arrived in Chicago in 1957, penniless and hungry, but he impressed Muddy Waters and started playing in his band. In the 1970s, Buddy kept his ’58 Stratocaster behind the bar at his own club, the Checkerboard Lounge, to challenge any ambitious patrons. Many lean years later, Guy opened his current club in 1989 in a 1910 South Loop building owned by Columbia College, just prior to his breakout 24 Nights tour with Eric Clapton. Legends today features top-notch blues, though Buddy Guy himself only plays in January as part of his annual, month-long tenure. Like Guy’s former club, Legends has kept true to its name by hosting the Rolling Stones, Eric Clapton and Koko Taylor. The crowd consists mainly of tourists, suburbanites and blues aficionados. In January 2007, Buddy Guy announced his club would close due to Columbia College’s plan to build a student center but they relented. As with the Checkerboard before, the club is part of a promise made to the late Muddy Waters to keep the blues alive on Chicago’s South Side. Legends is also a must-visit during the annual Chicago Blues Festival every June… you just might find Buddy Guy himself sitting at the end of the bar, sipping the beloved cognac that he calls «Connie.» For more information, check out the Buddy Guy’s Legends website.