Chicago’s Best Nightlife: Where the Locals Go

(Photo: Courtesy Three Dots and a Dash)

A solid Midwestern sensibility means that Chicagoans work hard and go to bed at reasonable hours. None of that New York “city that never sleeps” stuff here. But if late night living is your jam, here are a few nocturnal hang-outs that locals love:

Green Mill

Literally the original Old G, Green Mill dates back to over a century and is best known as a watering hole for a guy named Alphonse Capone. After all that time, this gritty, dimly lit lounge still claims the top spot for Chicago’s oldest and best late night joint. The vintage décor, complete with a trap door from the speakeasy days, the stellar jazz line-up and the reasonable prices might have something to do with Green Mill’s cult-like popularity. Or maybe it’s the ghosts that reportedly still hover. The details: Cash only but there’s an ATM inside, covers varies, no reservations and a no talking policy during performances. Open until 4 a.m., and 5 a.m. on Saturdays.

The Drifter

Chicago and speakeasies just go together, and the Windy City has no problem capitalizing on its prohibition pedigree. Ensconced in the original ’20s era speakeasy under The Green Door Tavern, The Drifter is filled with historic old props like circus regalia and an antique cash register. There’s no door sign, and no drink menu, only tarot cards that connect to a rotating list of cocktails.

It’s a tiny space that requires a password for the typically long wait list. Oh, and watch for burlesque dancers and sword swallowers. (Don’t go here if you’re allergic to quirk or good times.) The details: Enter through the basement door of the attached building South of the Green Door Tavern, open until 2 a.m.

Tempo Cafe

It doesn’t get more old school Chicago than Tempo. Generations cherish memories of grabbing a bite at this no frills diner after their first after hours adventure. A Gold Coast institution, this 24-hour eatery is great for people watching and munching the legendary Hangover Skillet after a few too many libations. The details: Cash only, BYOB until 10 p.m.

Smart Bar

If DJ culture and dancing is your thing, the Smart Bar has you covered. A Chicago classic that hosts local and international DJ s who spin homegrown house and techno tunes, this basement bar offers a friendly atmosphere and anti-hipster attitude. If you catch a show at the upstairs Metro concert venue, entrance is free. The details: Tickets vary from free to $14, open until 4 a.m., 5 on Saturdays.

Three Dots and a Dash

It’s only right that a frozen tundra like Chicago embraces Tiki culture. Three Dots and a Dash nails every criteria, from lethal rum drinks, to a thatched roof bar with Polynesian carvings. The entrance unfolds down a Clark Street alleyway and the stairs are topped with skulls. So the kitsch factor is high but so is the fun factor. The details: Open until 2 a.m.