Alcock's Inn

411 S Wells St, Chicago, IL 60607 312-922-1778

Description: SOUTH LOOP. This sports bar draws a diverse mix of folks, who enjoy meeting up with friends and lingering over conversation on the outdoor, Olympic-themed deck during warm weather. Friday nights bring out karaoke singers, and nightly drink specials are added enticement. The large interior also offers pool tables.
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Billy Goat Tavern

430 N Michigan Ave, Chicago, IL 60611 312-222-1525

Description: MAGNIFICENT MILE. This tavern boasts quite an interesting history. It was made popular by a "Saturday Night Live" sketch in which short-order cooks yell "cheezborger." Even before the humorous SNL bit, however, the place had quite a reputation. The original owner, William Sianis, apparently cursed the Cubs' owners because of their refusal to allow his billy goat into the stands. So far, the curse has stood strong ­ the Cubs haven't won a championship since. Despite its fame, the bar is pretty basic in nature, focusing on good beer and, what else, cheeseburgers!
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Blue Agave

1050 N State St, Chicago, IL 60610 312-335-8900

Description: GOLD COAST. Head south of the border at this popular Mexican restaurant/bar, where savory food and strong tequilas keep locals happy. The walls are adorned with colorful stuffed burros and large sombreros, and bright blue and yellow accents make for a festive environment. Cacti dot the room, and both the bar and the menu are well-stocked with authentic favorites. Burritos, enchiladas, and tacos can be washed down with any one of numerous Mexican beers offered.
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Blue Frog Bar & Grill

676 N La Salle Dr, Chicago, IL 60610 312-943-8900

Description: RIVER NORTH. Whether you come for the food, games, or karaoke, you're sure to enjoy yourself at this neighborhood bar. The eats are typical but good, including burgers, soups, salads, and sandwiches. The entertainment is anything but typical ­ expect board games that throw you back to childhood: Chutes and Ladders, Operation, Monopoly, and more. The bar features 21 bottled beers, along with a number of on-tap varieties, and a selection of wines.
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Boss Bar

420 N Clark St, Chicago, IL 60610 312-527-1203

Description: RIVER NORTH. Named for Chicago's former "boss," Mayor Richard J. Daley, this bar immortalizes him with a larger-than-life mural. The front of the bar is a garage door that's opened when it's nice outside. The jukebox plays classic rock and alternative music, and the menu is a mix of pizzas, burgers, and other bar food. The place's laid-back environment makes for a nice after-work stop.
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Boston Blackie's

164 E Grand Ave, Chicago, IL 60611 312-938-8700

Description: RIVER NORTH. In the mood for a thick burger and a pile of fries washed down with a cold beer? Head to Boston Blackie's, where you won't find a hint of pretension. Here, the friendly waitstaff and bartenders happily serve up potato skins, onion rings, burgers, and bottled and on-tap beer to eager patrons. If you're planning on hanging out later in the evening, get there before 10pm ­ closing times can vary.
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Burton Place

1447 N Wells St, Chicago, IL 60610 312-664-4699

Description: OLD TOWN. Burton Place attracts a yuppie crowd that fills up this three level establishment in a hurry. The late hours make this a favorite among serious night owls, and the kitchen is open well into the night. Seating by the fireplace is first choice during winter months, and the upstairs pool room makes for a great escape if the downstairs area gets too full. Private rooms are available for parties.
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Cactus

404 S Wells St, Chicago, IL 60607 312-922-3830

Description: THE LOOP. This Tex-Mex style bar features a prickly name and a list of interesting drinks. Try the lizard lemonade (vodka, lemonade, and a glow in the dark lizard to name just a few ingredients), the swamp water (vodka, apricot brandy, melon liqueur, 7-Up, orange juice, and sour mix), or one of the many martinis that line the menu. Notable martinis include the lemon drop, sparky, or tootsie roll. A hodge-podge of games as well as TVs provide nightly entertainment for the youngish professional crowd.
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Cardozo's Pub

170 W Washington St, Chicago, IL 60602 312-236-1573

Description: THE LOOP. Sporting a basement location near City Hall, Cardozo's Pub serves as a watering hole for the city's political and legal movers and shakers. Business types come here after a long day to chat with fellow patrons and relax with a drink or two. Daily drink specials are usually a good option. Bar food such as burgers, salads, and sandwiches are at the ready as well.
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Coq d'Or

140 E Walton Pl, Drake Hotel, Chicago, IL 60611 312-787-2200

Description: MAGNIFICENT MILE. This bar has become a Chicago landmark. It sports Prohibition-era decor, and low lighting sets the mood. The martini is the signature drink, and cabaret-style pianists and singers entertain nightly. The menu includes a number of items that come from the kitchen of the Drake's notable Cape Cod Room. Try the Bookbinder Soup or a fresh salad. Several televisions provide access to news and/or sports games, depending on the day and time. Casual attire.
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Coyote Ugly Saloon

316 W Erie St, Chicago, IL 60610 312-642-2400

Description: RIVER NORTH. Okay, so the pretty girls from the 2000 flick "Coyote Ugly" don't sling the drinks, but the bartenders who are here are classics nonetheless. This popular hole-in-the-wall, located on West Erie Street, is worth checking out on a Friday or Saturday night. Expect to find a rowdy neighborhood crowd ­ most of them taking advantage of the cheap beer, playing video games, or arguing over who's got the next selection on the classic jukebox. Just so you know, it could be anything from classic rock to David Allen Coe to Bocephus.
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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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Matchbox

770 N Milwaukee Ave, Chicago, IL 60622 312-666-9292

Description: WEST SIDE. Matchbox is an appropriate name for this narrow little bar with its smattering of bar stools. However, the tee-tiny spot really packs them in, and although small in size, the place stocks a large variety of drinks ­ everything from bottled beers to wines and top-shelf liquors. Cocktails are numerous, and they're outstanding, as are tequilas, single-malt bourbons, and small-batch whiskeys.
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Old Town Ale House

219 W North Ave, Chicago, IL 60610 312-944-7020

Description: OLD TOWN. Eclectic is the word to describe this offbeat North Avenue bar. From the paperback book "lending library" to the odd collection of used toys and Halloween masks, it's clear that this establishment defines its own style. The jukebox has received accolades for being one of the best in the metro area ­ it includes a large mix of jazz and blues as well as a smattering of rock and pop. EL: Brown Line to Sedgwick
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Rockit Bar and Grill

22 W Hubbard St, Chicago, IL 60654 312-645-6000

Description: RIVER NORTH. A trendy, high-concept space draws crowds nightly to this happening bar, lounge, and restaurant. The bustling front bar is the place to see and be seen. Sample a specialty cocktail, like the Rockit Root Beer ­ root beer, Stoli Vanil, and Godiva white chocolate liqueur ­ while you take in the scene. Looking for something a little more relaxed? Head to the upstairs lounge, where pool tables, couches, and 50-in. plasma TVs can be found. There's plenty of upscale bar food to nibble on too ­ think Kobe burgers and fries cooked in truffle oil.
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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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Twin Anchors, Inc.

1655 N Sedgwick, Chicago, IL 60614 312-266-1616

Description: OLD TOWN. Twin Anchors is a Chicago tradition that locals love to talk about. The baby back ribs are the main attraction and draw rave reviews from just about everyone who's ever tasted them. The bar is located in a historic building, and it's been open since 1932. The interior's nothing fancy, just white and black checkered floors, wood paneling, rounded leather booths, and red tables. It's the BBQ and beer that make this place famous.
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Vision

632 N Dearborn St, Chicago, IL 60610 312-266-1944

Description: RIVER NORTH. Whether you choose to spend your time dancing on the lower level to hard-hitting house and trance or lounging around with a cocktail on one of the upper floors, Vision is varied enough to please even the most finicky night owls. Top-notch international DJs ­ think Armin van Buuren, Markus Schulz, and DJ Tiesto ­ spin a fierce mix of house, trance, techno, hip-hop, and more. An excellent sound and light system and a whimsical indoor waterfall keep things interesting.
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