Chicago has a long history of pouring fabulous cocktails. On the rocks or straight up, the glass is always half-full at these highly sought watering holes. Here's where to go now in Chicago. And, most importantly, what to order.

Federales stays true to their signature tagline "tacos and tequila" by perfecting both. Their Barbacoa-style tacos and tequila-built cocktails pair beautifully with the room-to-breathe outdoor patio. Order this: Keep it clean with a smooth sipping anejo served in a shot glass made of ice.

AceBounce Chicago

High-energy ping-pong meets a premium cocktail program at AceBounce (pictured above). Sit back and take it all in or sip between serves. Order this: Try the Chicago-inspired River Walk-vodka, Rhine Hall peach brandy, passion fruit vinegar, pineapple, ginger beer, and nutmeg.

From Pimm's Cup to the Sidecar (even Long Island Iced Teas), all the classics are alive and well at Money Gun. Linger awhile-the menu is served until 1 a.m. and is loaded with delights like oysters and burrata with pickled fried green tomatoes. Order this: Drink your dessert via a cherry chocolate Pink Squirrel.

The Northman Chicago cider pub and bistro sits just south of the North Center and Lincoln Square crux. Expect cider and apple-based spirits stemming from Northern France and Southern England. Order this: Choose from 24 cider and beer taps. Start with the full-flavored UK-born Thatchers Gold Cider.

Heavy Feather

Head to the second floor of Logan Square's Slippery Slope and step back in time. A 1970s-inspired fern bar, The Heavy Feather (pictured above) is drawing regulars with new spins on retro cocktails. Order this: Take in the throwback space while sipping an amaretto sour. 

Rick Bayless' Cruz Blanca Cerveceria & Taqueria combines a German, Austrian and French-focused microbrewery with a Baja-style seafood restaurant. Order this: A Cruz Blanca Margarita with agave nectar and fresh lime or a smoky shot of mescal (they boast one of the largest selections in the country).

Gold Coast neighborhood bar Sparrow is inspired by the great hotel lobby bars of Chicago. Enjoy 1930s-era rum-focused cocktails, a small European wine list and timeless cocktails. Order this: Tropical and tasty, try the Hotel Nacional, made with pineapple rum, apricot liqueur, pineapple and lime juice.

bar siena

Bar Siena (pictured above) is a West Loop bar room fancied after a casual and energetic spot in Siena, Italy. Nosh regional Italian fare in square tufted leather booths and be sure to step upstairs for expansive Chicago skyline views. Order this: Indulge in the impressive Italy- and California-focused wine list. Visit the sparkling lineup and celebrate the finer things.

Wicker Park's Queen Mary Tavern is a maritime-themed old-school saloon with a cozy craft cocktail bar. The menu includes 10 cocktails, each ringing in at $12. Order this: The Navy Strength Old Fashioned is a fun kick on the traditional drink. Got a group? Share the tea-based punch with passion fruit, ginger, lemon and cinnamon.

Matt Kirouac

West Loop neighborhood gathering place The Betty (pictured above) is perfect for a weekday date night. Relax in the dimly lit lounge over mod small plates and see why Chicago Magazine named them "Best New Bar." Order this: Sip a Miss Prints rosé cocktail while snacking on braised pork belly and stuffed cherrystone clams.

Milk Room

At the Chicago Athletic Association's prohibition-era Milk Room (pictured at very top and above) it's all about cocktails made with rare ingredients. The cozy space is located on the second floor and features an exclusive, eight-seat micro bar serving classic cocktails with rare, vintage spirits. Order this: You can't go wrong with a Sazerac. Let the behind-the-bar artist put his or her own spin on the New Orleans original. 

To access Fat Rice's hidden, reservations-only lounge, The Ladies Room, walk through the bakery, down a narrow corridor and step behind the curtain. The Logan Square cocktail bar is modeled after Macau, China casino dens, with red vinyl snakeskin booths and seating for approximately 20. Order this: The Grande Royale serves eight to 10 and is made with house creme de cassis, cognac, house "Campari," Calvados apple brandy, allspice dram and Peychaud's and housemade wild lemon bitters.


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