Cavanaugh's Bar & Restaurant

53 W Jackson Blvd, Monadnock Building, Chicago, IL 60604 312-939-3125

Description: THE LOOP. 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 upon arrival. The menu includes a mix of sandwiches, pastas, salads, and burgers as well as a laundry list of beers.
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Crimson Lounge

333 N Dearborn St, Hotel Sax Chicago, Chicago, IL 60610 312-923-2473

Description: RIVER NORTH. Recalling a 1920s speakeasy with seductive Victorian undertones, Crimson Lounge at Hotel Sax Chicago is positively stunning, as is evident from any of the velvet-covered ottomans and couches. Not surprisingly, the lounge is festooned with crimson draperies and lavish chandeliers. The interior also offers posh displays of traditional Impressionist art. The luxuriant meeting spot will remind you that you don't need to see the Sears Tower to get a feel for the city.
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Dragonfly Mandarin Restaurant & Lounge

832 W Randolph St, Chicago, IL 60607 312-787-7600

Description: WEST LOOP. This after-work spot draws a trendy group of yuppies looking to sip martinis and munch on delectable Chinese appetizers (or "teasers" as the menu labels them). Start off with a signature Dragonfly Martini and a plate of crab puffs or Shanghai spring rolls.
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Funky Buddha Lounge

728 W Grand Ave, Chicago, IL 60610 312-666-1695

Description: RIVER WEST. 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 also has some of the best DJs in town. Check out Jesse de la Pena on Wednesday and Saturday and percussionists Ya Ya and Yamcouba on Fridays.
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Le Passage

937 N Rush St, Chicago, IL 60611 312-255-0022

Description: GOLD COAST. Enter through the alley, move past the beautiful blond hostess (having met the cover charge and dress code), descend the stairs, and be transported to a 10,000-square-foot subterranean speakeasy of the new millennium. Le Passage's funky decor and talented DJs spin you from dance floor to two great bars. Yow Bar, named for legendary Trader Vic's bartender Yow Low, is a comfy VIP area. Beautiful, hip patrons can also enjoy live music, fashion shows, and a tasty late-night appetizer menu.
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Lumen

839 W Fulton Market St, Chicago, IL 60607 312-733-2222

Description: MARKET DISTRICT. Post-modern furniture combines with rough-edged industrial textures to produce a uniquely minimalist lounge. Low couches and tables have a distinctly Scandinavian flair and allow for free-flowing movement throughout the lounge. Multimedia installations enhance the motif of movement, adding a visual element to the uncluttered interior. Area hipsters flock here for the affordable cocktails and the cool atmosphere.
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Manor

642 N Clark St, Chicago, IL 60610 312-475-1390

Description: Make no mistake. At Manor, money does buy happiness. Designed to evoke lavish English estates, Manor is the place to go for the highest standard in personal indulgence. It's a VIP-lounge for VIPs - exclusivity upon exclusivity. Clientèle who order bottle service are attended upon by their very own butlers. In addition, Manor regularly brings in the most talented DJs, ensuring that the top-notch experience extends to the music.
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MEXX Kitchen & Bar at The Whiskey

1015 N Rush St, Sutton Place Hotel, Chicago, IL 60611 312-475-0300

Description: GOLD COAST. 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 Sandoval's authentic modern Mexican cuisine features traditional fare, authentic Latin, and Mexican cuisine with a modern twist. The bar is strictly top shelf with more than 100 varieties of tequila and the bar stools make excellent perches for watching the beautiful clientele and staff.
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Nacional 27

325 W Huron St, Chicago, IL 60610 312-664-2727

Description: RIVER NORTH. National 27, whose name refers to the 27 recognized Latin American countries, offers a unique menu featuring a wide range of thrilling Latin American favorites. Indeed, from chimichurri sauce to garlic-roasted chicken Cubano, the skilled kitchen staff goes the extra mile to make sure even novices find something suited to their fancy. After hours, this hip restaurant turns into a nightclub that emanates the spicy grooves of salsa, merengue, and quebradita, making it one of the hippest destinations in town.
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Pops for Champagne

601 N State St, Chicago, IL 60657 312-266-7677

Description: RIVER NORTH. This long-lived live music club and champagne bar (25-plus years!) is a city mainstay, now relocated from its original Lake View neighborhood. A sleek, stylish bar lets patrons sip and mingle, while a downstairs lounge envelops folks in intimate surroundings and terrific live jazz. The shop sells sparkling wines and offers lunchtime and light evening fare, including scrumptious housemade desserts. A raw bar and caviars are included in the upscale offerings, and more than 125 champagnes are available. Jazz sets begin at 9pm.
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Pop's for Champagne

601 N State St, Chicago, IL 60610 312-266-7677

Description: LAKE VIEW. 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 available if you don't like the bubbles.
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Pump Room

1301 N State Pkwy, Omni Ambassador East Hotel, Chicago, IL 60610 312-266-0360

Description: GOLD COAST. Stately and very chic, this Chicago staple provides the perfect backdrop to a celebration or night when you're out to impress. The dress code sets the tone, and the decor reveals that you're among the well-heeled. The walls are a veritable fashion gallery, lined with photos of the rich and famous who've stopped in to wine and dine. Live jazz can be heard on Wednesday and Thursday evenings, and dancing is done on Friday and Saturday nights. Drink selections include a well-selected range of wines as well as specialty martinis.
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Signature Lounge at the 96th

875 N Michigan Ave, John Hancock Bldg, Chicago, IL 60611 312-787-9596

Description: GOLD COAST. 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 selection of cocktails and champagnes. The place draws an unbelievably mixed crowd, which makes people-watching a real treat. Skip it on a cloudy night or if you're prone to vertigo.
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Spoon

1240 N Wells St, Chicago, IL 60610 312-642-5522

Description: OLD TOWN. One of Old Town's hippest nightspots, Spoon attracts a flurry of stylishly-clad beautiful people on a nightly basis. Come to this upscale restaurant/lounge for a terrific international dinner and an even better night of dancing and general merriment. DJs spin the hottest grooves until the wee hours at this trendy bar, so plan to wear something comfortable and plan to stay late. EL: Red Line to Clark/Division
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Tantrum

1023 S State St, Chicago, IL 60605 312-939-9160

Description: Catering to the neighboring area, this bar prides itself on serving some pretty mean martinis in a laid back atmosphere. Try the black martini with Chambord and Absolut Kurant, or sip on the Tantrum martini, which mixes Soli orange and orange juice. The butterscotch (served with Werther's Original candy) is comforting as well. The L-shaped bar is made of warm wood with cone-shaped stools sitting beneath it that offer seating for some lively conversation while enjoying your drink. Comfortable couches offer a cozy and intimate setting. Music is provided by the bartender of the night's portable media play list, which could be anything from soft rock and jazz to alternative and hard rock, giving way to spontaneous outbreaks of dancing as the night progresses.
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The Baton

436 N Clark St, Chicago, IL 60610 312-644-5269

Description: RIVER NORTH. Chicago's best cabaret drag revue is all about "the illusion." This Las Vegas-style revue has been around for over 30 years. A cover charge and two-drink minimum allow you to bask in the glory of some of the most amazing female impersonators you're likely to encounter anywhere. The clientele ranges from professionals to bridal parties. Mimi Marks, internationally recognized one-half Marilyn Monroe, one-half Brigitte Bardot, calls this place home. The music is lively, featuring pop to R&B, and audience participation is mandatory. Neglecting to tip the performers is considered in very bad taste.
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The Lounge at Le Colonial

937 N Rush St, Chicago, IL 60611 312-255-0088

Description: GOLD COAST. 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 to another era. Menu items from the restaurant are available to complement an extensive selection of signature martinis. Music ranging from Bolero to Moby flows smoothly. Warning: This room can inspire a lot of kissing.
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The Underground Wonder Bar

10 E Walton St, Chicago, IL 60611 312-266-7761

Description: GOLD COAST. Established in 1989, this tiny venue is open 365 days a year, and Lonie Walker, who founded the place, still plays three nights a week. Live music is offered nightly to an incredibly eclectic group of patrons. Jazz and blues are the main focus, but acoustic guitar and piano music are often featured, as are friends who hop on the makeshift stage. The limited size allows performances to be very interactive. Ordering or bringing in carryout food is acceptable. Truly a classic.
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The Zebra Lounge

1220 N State Pkwy, Chicago, IL 60610 312-642-5140

Description: GOLD COAST. 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 handful of bar stools, so come early. Piano music, from Sinatra to torch songs and sing-a-longs, are a nightly event. The Zebra is a classic that draws a hip, young crowd.
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Y

224 W Ontario St, Chicago, IL 60610 312-274-1880

Description: RIVER NORTH. 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 custom video (like fireplaces) to warm things up. For patrons who prefer to interact in more exclusive surroundings, a private, glassed-in room is available.
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