The Matchbox

At a difficult-to-fathom (and sometimes, difficult-to-squeeze-into) 460 sq ft, The Matchbox may be Chicago's smallest bar. That makes every square inch of the old-school interior a potential surface on which to rest your cocktail – or a dimly-lit nook in which to chat up a stranger. Classic cocktails such as a gin gimlet or a Manhattan are a bargain at $8.50, especially because each formidable drink is accompanied by the cocktail shaker containing nearly a second glass of your chosen potable.

• 768 North Milwaukee Avenue, +1 312 666 9322, thesilverpalmrestaurant.com/themachbox. Open Tues-Fri 6pm-2am, Sat 6pm-3am, Sun 4-11pm

Map Room

The Map Room, Chicago

Out-of-towners should feel at home at this "traveller's cafe", but it's largely locals who frequent this no-frills bar that offers one of the best tap lists in the city. Regional and international brews are constantly rotated onto the draft lines and the beer engine. Ask the knowledgable – and occasionally surly – bartenders for recommendations. As long as you're not obnoxious or already too intoxicated, they'll treat you just fine.

• 1949 North Hoyne Avenue, +1 773 252 7636, maproom.com. Open Mon-Fri 6.30am-2am, Sat 7.30am-3am, Sun 11am-2am (coffee only before 11am)

Maria's Packaged Goods & Community Bar

Maria's Packaged Goods and Community Bar

Perhaps the most beloved example of Chicago's "slashies" – half liquor stores, half taverns – Maria's has been family-owned since 1986. The matriarch, Maria Marszewski, still quietly watches over the place, but it's her sons who in 2010 turned a dusty spot in the tight-knit Bridgeport neighbourhood into a destination for well-mixed cocktails and an impressive line-up of craft beers. At weekends, the music rocks, too, courtesy of eclectic DJ sets from Chicago music scene mainstay Joe Bryl.

• 960 West 31st Street, +1 773 890 0588, community-bar.com. Bar is open Mon-Fri, Sun 11-2am, Sat 11-3am

RM Champagne Salon

RM Champagne

After a meal on Randolph Street, the West Loop's white-hot restaurant row, enter through a semi-hidden alley to the patio of this unexpected French-inspired champagne and wine bar. Flickering candles, a pages-long list of bubbles and trays of charming migniardises are equal parts romantic and chic. When the weather's cooler, tufted couches near the roaring fireplace are the best seats in the house.

• 116 North Green Street, +1 312 243 1199, rmchampagnesalon.com. Open Mon-Wed 5pm-11pm, Thurs-Sat 5pm-2am, Sun 5pm-11pm

Three Dots and a Dash

Three dots and a dash, Chicago

Cocktail fans gasped when bartender Paul McGee left his post at The Whistler, but they're breathing a sigh of relief now that he's back with this brand new tiki spot in River North. Decor and music are gloriously cheesy, with raffia, totem heads and floral print as far as the eye can see. The drinks, though, are dazzlingly tropical – and go down much too easily. Tip: the bar's off an alley, but just look for the tiki torches lighting the way.

• 435 North Clark Street, +1 312 610 4220, threedotschicago.com. Open Sun-Fri 5pm-2am; Sat 5pm-3am

The Green Mill

The Green Mill, Chicago

Jazz heads and history buffs with a fondness for the prohibition era must make a pilgrimage to this longstanding Chicago lounge. Green-and-white lights twinkle across the bar's facade; inside, the long wood bar, generous stage and oversized booths feel as though they've been exhumed from a 1920s time capsule. There's a cover for live music most nights, but the talented acts that come through this hallowed spot are worth it. On weekends, suspenders, retro dresses and, of course, dancing shoes, are delightfully appropriate.

• 4802 North Broadway, +1 773 878 5552, greenmilljazz.com. Open Mon-Fri noon-4am, Sat noon-5am, Sun 11am-4am

Billy Sunday

Billy Sunday, Chicago

This newcomer to the city's cocktail scene draws rave reviews from Logan Square neighbours and lures guests from outside the 'hood with its impeccably-executed cocktails. Beverage director Alex Bachman has created a list of intriguing but not off-putting concoctions, with a tight food menu that's no afterthought. Scotch drinkers must ask for the back bar's bottle list, if only to drool over some of the rare offerings Bachman has assembled.

• 3143 West Logan Boulevard, +1 773 661 2485, billy-sunday.com. Open Mon-Fri 5pm-2am, Sat noon-3am, Sun noon-2am

Headquarters Beercade

Headquarters Beercade, Chicago

Chicago historically was a pinball manufacturing hub, and it's this legacy that inspires the city's two retro arcade bars (the other is Wicker Park's Emporium Arcade Bar). At Headquarters, gamers can set their cocktail or craft beer aside and challenge one of the dozens of old-school arcade games. Remember Frogger, Galaga and Defender? A recently added expansion houses the bar's popular dozen-plus pinball offerings.

• 950 West Wolfram Street, +1 773 665 5660, hqbeercade.com. Open Wed-Fri 5pm-2am, Sat noon-3am, Sun noon-2am

Empty Bottle

Empty Bottle, Chicago

One of the best small venues for up-and-coming bands, Empty Bottle has delivered on its exterior awning's promise of "Music Friendly Dancing" since 1992. The beer is cheap, the crowd is laidback and if you catch one of your favourite acts here, it will be an intimate show you're unlikely to forget. Check the schedule for "Windy City Soul Club", a night of soul DJs that always spurs a shamelessly fun dance party.

• 1035 North Western Avenue, +1 773 276 3600, emptybottle.com. Open Mon-Weds 5pm-2am, Thurs-Fri 3pm-2am, Sat 11am-3am, Sun 12am-2am

Half Acre Tap Room

Half Acre Tap Room, Chicago

To say Chicago's craft beer scene is exploding wouldn't be hyperbolic. One of the best breweries currently in the game is Half Acre, which in 2012 finally opened a tap room adjacent to its brewery and bottle shop. Stop in for the newest limited release or seasonal brew, available in tasting portions and reasonably priced pints. Hungry? There's no kitchen, but bartenders will gladly hand you delivery menus from nearby restaurants.

• 4257 North Lincoln Avenue, +1 773 248 4038, halfacrebeer.com. Open Tues-Wed noon-11pm, Thurs noon-midnight, Fri noon-1am, Sat 11am-1am, Sun 11am-11pm

Kate Bernot is nightlife reporter for Redeye Chicago

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