Address: 53 W Jackson Blvd, Monadnock Building, Chicago, IL 60604

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Located in the Monadnock Building, this bar and restaurant offers business types a place to hang their hats during lunch or after work. The entrance is tucked away in a rather nondescript alley, with the only clue to its existence being a green and white striped awning. Green leather and warm wood tones greet guests...

Address: 728 W Grand Ave, Chicago, IL 60610

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Local artist Suhail's giant steel Buddha marks the entrance to this cool spot. Leather and faux-leopard seating areas run the length of the main bar in the dark Moroccan/Middle Eastern-inspired den. Two bars, a cozy VIP section, and a small dance floor are packed nightly. Cosmopolitans are the house specialty. Buddha...

Address: 1015 N Rush St, Sutton Place Hotel, Chicago, IL 60611

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You're in for a delightful experience at this exclusive restaurant and lounge located on the ground floor of the Sutton Place Hotel. Owned by Randy Gerber (yes, Cindy Crawford's husband), The Whiskey has now partnered with Chef Richard Sandoval and has been reinvented into MEXX Kitchen & Bar at The Whiskey. Chef...

Address: 25 W Hubbard St, Chicago, IL 60610

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Taking as its name the Italian for "fashion," Moda offers a stylish night on the town, complete with a swanky interior and killer cocktail menu.

Address: 601 N State St, Chicago, IL 60610

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Pop's offers over 100 different champagnes in an ethereal, elegant room. The sunken bar highlights piano and jazz combos that grace its elevated stage seven days a week. A lovely outdoor garden, domed ceilings, and a roaring fireplace make this spot a romantic classic. Light appetizers, desserts, and a full bar are...

Address: 875 N Michigan Ave, John Hancock Bldg, Chicago, IL 60611

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Although a bit touristy, this spot offers the best views in the city on a clear night. The lounge is kept extremely dark to maximize southern and western views, and the lake and Navy Pier are visible from the Art Deco, marble-laden restaurant a floor below. Live jazz is featured on the weekends. The bar has a great...

Address: 937 N Rush St, Chicago, IL 60611

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Your portal to French Colonial Vietnam is unassumingly tucked on top of this French/Vietnamese restaurant. The lounge is candlelit, with enormous potted ferns, wicker furniture, gently whirling fans, dark wood, Oriental carpets, comfy couches, and a lovely terrace. The vintage black-and-white photos transport guests...

Address: 1220 N State Pkwy, Chicago, IL 60610

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This place, which is located on the first floor of a vintage apartment building, has been around for 65 years. Its zebra wallpaper, leather booths, and mountains of outlandish collections would allow it to double as a museum of tacky memorabilia. It feels like someone's recreation room. There are only 10 tables and a...

Address: 1480 West Webster Ave, Chicago, IL 60614

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This intimate, largely-candlelit bar offers an extensive list of wines by the glass, flight, or bottle and a light menu with pâtés and cheeses. Its two floors are filled with tables, comfy couches, hardwood floors, and rich dark colors. An outdoor patio is available during the summer. Rotating exhibits featuring local...

Address: 224 W Ontario St, Chicago, IL 60610

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Runway-worthy fashionistas, both male and female, strut their stuff at this nightspot that corners the market on high concept. Service is VIP-worthy, and champagne and top-shelf liquors reign supreme. Subdued musical tracks and comfortably couched seating areas allow intimate conversation, and plasma screens display...