Nights can be long in the Windy City; Chicago is a proverbial playground of bars, clubs and venues catering to all walks of life be them local or just passing through. From the city’s center and a raucous club scene to the boroughs’ bars and late night eateries, Chicago’s nightlife is as diverse as it is plentiful and never silenced by the city’s storied sub-zero temperatures.

4:31 P.M. 1914

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Out back of the Red Ivy sports bar in Wrigleyville is a little known speakeasy named 1914. The prohibition-era décor is fitting considering you can be made to feel like you’re living in the era if you’re caught trying to get a timely beer after a Cubs game. Chicago’s North-Siders know how to celebrate a win and a lot more about drowning their sorrows after a loss; 1914 is a great place to get a drink and get out of their way after either.

6:52 P.M. Billy Goat Tavern

Tucked deep in the underbelly of the city, the original Billy Goat Tavern is a local mainstay and place of Chicago lore. Half greasy-spoon diner, half bar, the Billy Goat is the longstanding point of origin of the cursed Cubs and is always packed, its walls teeming with history and its service a collective jumble of dodging patrons and yelling. No words can do it justice; just go, order a few cheeseburgers and don’t expect a quiet turn to the evening.

8:25 P.M. Rootstock

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For the socially-conscious imbiber, Rootstock specializes in small-scale wine and beer production built upon a foundation of sustainable farming practices. That being the case, they house a whole host of specialty beer and an inexhaustible wine list.

9:40 P.M. Buddy Guy’s Legends

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Lining the walls of Buddy Guy’s are the guitars of heroes: Eric Clapton, Carlos Santana, Jeff Beck, Stevie Ray Vaughn, all artists that have played the club with Buddy Guy himself. Legends is reminiscent of a church basement luncheon, with its blue checkered floors and haphazard seating arrangements. Getting a table is a free-for-all, first-come-first-serve affair but nobody is really there for the food or the décor. This place is about the blues and once it starts you won’t notice much else around you.

11:44 P.M. Funky Buddha Lounge

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If Buddy Guy’s is for the old-school blues enthusiast then Funky Buddha Lounge is for the kids who took the sound and made it their own. Fair warning: this a place to get down! The DJs are some of the best Chicago has to offer and though there is not a whole lot of room to sit, you probably won’t want to. The Buddha Lounge brings together the best parts of Chicago nightlife: original music, good drinks and a crowd that couldn’t define the word pretentious.

1:05 A.M. Sound Bar

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The crowd at Sound Bar probably could though. Still, it doesn’t take anything away from this quartered club, a divided haven of sound, décor and women. Sound has a little something for everyone with two floors and what seems like a thousand little rooms. Each space is cast in different light (literally) and the caliber of good-looking women looking to dance is unmatched on the Chicago scene

2:52 A.M. Late Bar

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Named appropriately and open until whatever o’clock in the morning it is when you can no longer read your watch (usually 4 or 5am), Late Bar is an eclectic mix of everything you love about bars making it the perfect spot to end the night no matter what trouble you’ve gotten into. From the 1920s movies playing on projectors to the unusual blend of punk, New Wave and goth, Late is a fine place to meet the morning sun.