Lounges in Andersonville

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If Green Mill’s walls could talk, they’d probably run out of breath before they could divulge all the stories they’ve witnessed over the years. The jazz spot’s history, which teeters on the edge of believability and local lore, began when the bar originally opened as Pop Morse’s Roadhouse in 1907. After undergoing a transformation in 1910, the newly renamed Green Mill Gardens began attracting visitors from nearby Essanay Studios, including Charlie Chaplin. Perhaps its biggest claim to fame is serving as a hangout for the infamous Al Capone, who frequented the club while his right-hand man, Jack “Machine Gun” McGurn, ran the show. While some of Capone’s favorite performers took the stage, Green Mill’s network of hidden underground tunnels were used by mobsters to transport illegal booze, facilitate law-evasion, and play cruel games of Marco Polo with new recruits. Eventually Prohibition ended and propositioning gangsters gave way to upscale crowds, a badda bing vibe, and Frank Sinatra visits. During this time, the surrounding Uptown neighborhood deteriorated, but somehow the club survived and eventually underwent a restoration in the mid-‘80s. Over the years it has appeared in films such as Thief and High Fidelity, but patrons today aren’t as concerned with keeping track of all the history as they are with kicking back and soaking in the music or slam poetry. During a typical visit, Jazz musicians tickle their instruments late into the night as well-dressed guests stop in, sidle up to the bar, and converse in respectfully hushed voices while downing stiff drinks.

4802 North Broadway
Chicago,
IL
US

At Agami, Executive Chef Kye is not just interested in the taste of food, but in the complete sensual experience of eating it. Those who order the garlic delight specialty sushi roll will feel the warmth of the Bacardi 151 flame it's served upon. Meanwhile, those biting into a salt sun flower roll will hear the crunch of sunflower seeds, and those admiring the wild fire roll will see a colorful combination of red snapper, guacamole, and mango pico de gallo. Sushi is certainly the restaurant's specialty, but it's not all that's served here?in addition to specialty maki, nigiri, and sashimi, there's also sushi-inspired entrees as well as a kitchen menu with dishes such as steamed dumplings and teriyaki chicken.

The attempt to create a wholly experiential dining experience doesn't stop with the food. The modern restaurant was designed with high ceilings, textured walls, and seaweed sculptures, all to create the feeling of being under the sea. Underwater scenes are projected on video screens, and a lucite bottle rack behind the bar resembles bubbling ocean waters. Concentric half-circles separate the traditional dining room, lounge area, and bar, the latter two of which are open until 1 am on Friday and Saturday nights.

4712 N Broadway St
Chicago,
IL
US

As its name suggests, the Daily Bar and Grill is open daily. Its bartenders pour beers and whip up cocktails to be enjoyed at the dark, wooden bar by themselves, or alongside comfort foods such as the Daily’s signature half-pound burgers or mini corn dogs. Open in Lincoln Square since 1993, the bar also features a leafy outdoor patio and a 30- to 50-guest party room with red-velvet drapes, oriental rugs sewn from abandoned handlebar mustaches, and other vintage elements.

4560 N Lincoln Ave
Chicago,
IL
US

Bartenders at The Money Shot Restaurant & Lounge pour cocktails by the shakerful, and ovens bake American and Italian cuisine, including Roman-style pizzas with thin, house-made crusts. Always attending to sports fans, the restaurant projects big games or referee pageants on a 100-inch projection screen and two 46-inch flat-screen TVs equipped with surround sound. In the evening, bands drum out live tunes, comedians crack jokes, and rappers dish tips on properly estimating the amount of paper it will take to gift-wrap Ja Rule's birthday present. Tuesday-night trivia contests mine noggins for tidbits of information on categories such as pop culture and history. As diners participate in a variety of events, platters of favorite Italian fare such as pizzas, bruschetta, chicken parmesan, and garlic Ferraris accompany frosty brews and mixed cocktails.

5695 N Lincoln Ave
Chicago,
IL
US

In the heart of Wrigleyville, diners savor Raw Bar’s namesake plate—fresh, raw oysters amid 40s and 60s art deco. However, the eatery’s seafood offerings encompass cooked cuisine as well, such as clams, lobsters, Dungeness crab, and octopus. Grilled frogs’ legs complement the aquatic eats, along with alligator meat smothered in creamy Louisiana mushroom sauce, and ostrich, a lean red meat discovered by far-sighted farmers who mistook ostriches for chickens. Mediterranean and Persian offerings, such as hummus and Persian chicken potato salad, round out the menu, and diners can wash down their meals with pours from the oaken bar, such as beers and hand-crafted margaritas.

3720 N Clark St
Chicago,
IL
US

At the Kit Kat Lounge & Supper Club in the heart of Boystown, Sunny Dee-Lite leads the troupe of divas enhance the upscale dining experience with a sexy, sassy female impersonation show featuring such pseudo-stars as Tina Turner, Lady Gaga, and Dolly Parton. Every 20 minutes or so, the restaurant becomes a stage for the likes of Madam X, known for her big, elaborate costumes, and Mokha Montrese, winner of the title Miss Continental in 2010. The dinner menu is nearly as dazzling, filled with entrees bearing the names of Golden Age film stars such as Paul Newman, Mae West, and Marlon Brando. Despite their star-studded titles, most dishes feature classic American comfort food such as chicken coq au vin, pasta primavera, and beef stew with potatoes.

3700 N Halsted St
Chicago,
IL
US