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.
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.
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.
The LBGT-friendly Velvet Rope invites revelers with open minds and refined tastes to enhance their evenings with the lounge's slate of fine wines, international cuisine, and elaborate entertainment in the form of go-go dancers and drag shows. Beneath the suffuse lighting of tulip chandeliers, the bustling main floor hosts a full bar, where 35 specialty martinis brim with creative ingredients—such as cookie-dough vodka and absinthe—while the private VIP loft accommodates dozens with a dedicated server, a private television, and plush furnishings for late-night pillow forts. Food and drink packages deck out special events, and the nightclub's calendar overflows with karaoke nights, drink specials, and live performances.
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.
It’s a difficult task to pull off—taking a hodgepodge of recycled odds and ends and creating something entirely new. Simone’s Bar, however, has proven up to the challenge. An architectural potpourri of artifacts salvaged from around the city, the Pilsen bar is best known for the retired pinball machines that line its walls. These ancient tables lend a retro vibe to the bar area, where microbrews and cocktails take the place of pins on a recycled bowling lane. Other idiosyncratic elements include chemistry tables from nearby Westinghouse High School, conveyer belts from Chicago’s Fanny May Candies factory, and a chandelier molded from bicycle chains and rocking chairs. Combined with the solar panels on the rooftop, these repurposed knickknacks have earned Simone’s status as a three-star certified green restaurant. Simone’s décor may come from all corners of the city, but its food is influenced more by the bar’s immediate surroundings. Empanadas and a grilled cheese sandwich with Chihuahua cheese nod to Pilsen’s proud Mexican heritage, as do burgers topped with jalapenos and guacamole. The drink menu also has a local slant, highlighting Chicago brews and craft cocktails that would feel right at home in one of the galleries on nearby Halsted Street.