Flashing lights pulsate to thumping beats as smoke rises from a DJ booth framed by projection screens and swaying bodies. Though it may seem like a scene out of a movie, this energetic setting actually takes place seven nights a week at Bobby McGee's. And to keep their lively parties grooving until the wee hours, the South Side staple curates festive party themes, such as a Black Out Fridays and the occasional Hawaiian luau, which boasts an inflatable surfing game and real-life boars wandering through the crowd. Weekend concerts enliven the already convivial mood, as do bag tournaments, live band karaoke, and charity events to support causes such as cancer research.
When not catering to the party crowd, Bobby McGee's transforms the spacious dance area into bar room filled with stools and tables. Diners can dig into half-pound burgers and specialty pizzas topped with buffalo shrimp, and those craving a south-of-the-border meal can turn to the menu's Tex-Mex dishes of buffalo chicken quesadillas and beef nachos. These bar eats can be paired with weekly drink specials, from Old Style beer to shots, or the bar's signature 32-ounce long island drink served in a mason jar.
Dance music pulsates through Red Velvet Lounge as party-goers indulge in late-night eats and specialty bar drinks amid a spacious nightclub. Bartenders pours out beverages from a fully stocked bar as guest saunter to the hardwood dance floor illuminated by the sporadic flickers of a colorful lights. Themed parties for Halloween and New Year’s Eve add variety to weekends, and Friday and Saturday nights introduce crowds to special-guest DJs and their finger-puppet entourages. Bites from the Lounge’s Italian-inspired menu fuel evening adventurers, with options including gorgonzola chips, Sicilian tilapia, and lemon-mascarpone torte.
Intimo's menu whisks diners to the Italian countryside with a variety of authentic house-made entrees. More than 300 bottles of distinct wines hibernate in the 58-degree walk-in wine cellar. Director Frank Pecora fosters a relaxed, sophisticated atmosphere with dim lighting and sleek, dark wooden accents. Candles flicker atop tables draped in white linens, casting shadow-puppet adaptations of Godzilla vs. Fork and Knife on the exposed-brick walls.
Casa De Montecristo stocks its ample humidors and regal environs with row after row of tasty smoking tobacco. A La Sirena Trident summons piquancy from the depths of the broadleaf ($9.95), while an E.P. Carrillo Elite hits only the most select flavor notes ($11.95). Casa De Montecristo also boasts a free VIP membership lounge, which can be accessed by calling ahead. The spacious smoking cavern teems with plush amenities such as leather chairs and private humidified lockers. Kick back in the bar and tune in to a flat-screen television, or recline in the theater room for a movie, game, or cigar-smoking tutorial led by Groucho Marx.
At Orange 13, swaths of burnt-orange organza and crystal chandeliers transform tables into secluded enclaves. At two granite-topped bars, bartenders pour 50 handpicked wines and mix martinis with top-shelf liquors. The chefs strive to match the sleek, sultry environs with a menu of creative fusion fare: they adorn a trio of buffalo, elk, and Kobe burgers with brie and bleu cheese and add zest to tender lamb chops with lemon-thyme glaze. To encourage an experience as fun as the cuisine is exquisite, live entertainment and DJs spin beats until 3 a.m., and high ceilings make it plausible that dancing giraffes appear, too. Live bands hit the stage at 8 p.m. on Fridays and DJs begin to spin sets at 11 p.m. on Saturdays.
Olive or Twist pairs its 36 unique martinis, 20 bottled microbrews, and international wines with contemporary American fare concocted by chef Robert Nava. Shaken or stirred libations range from the Thin Mint martini, which comes in a Girl Scout box, to the Florida Key Lime Pie martini, a dram of Bacardi rum, Midori liqueur, and chocolate liqueur garnished with lime ($9–$11). Diners can also choose from brews including 3 Floyd's Alpha King pale ale ($5) to accompany small plates such as the potato-wrapped prawns with spinach, artichokes, and mustard-seed butter ($10). Tenderloin sliders topped with blue cheese and red-onion confit ($9) annex tummies before calling for reinforcements of classic American sandwiches ($6–$12) or large-plate entrees such as the jerk ribs with an auxiliary unit of saffron shoestring potatoes ($18). For dessert, sweet teeth delight in the banana split ($8) and apple-and-cheese strudel ($5), named after Frank Zappa's overlooked fifth child. Dinner patrons should call ahead for reservations amid Olive or Twist's low-lit tables and brick walls.