The Best Underground Bars in Chicago, pt 1

With its storied history of 1920′s gangsters and speakeasies, there’s no place like the Windy City for grabbing a delicious drink in an incognito setting. If you’re tired of the standard fare, grab your wallet, your ID, and your sense of adventure, and follow us to some of Chicago’s lesser-known gems.

Logan Square—Tillington’s at Twilight

There’s no more exclusive spot than Tillington’s at Twilight! Located behind an unmarked, featureless brick wall, connoisseurs of Chicago nightlife can only access Tillington’s during the witching hour, when the boundary between the spirit world and ours is at its weakest. But the steep entry fee — $25 cover, plus the baby teeth of a child that is not your own — is worth it for the ambiance, the characters and above all, the incredible cocktails.

Tony Needleteeth is Tillington’s certified mixologist, crafting up a tasty, surprisingly affordable drink — especially by the standards of trendy Logan Square! “Choose one of three,” he’ll rasp, passing you a tray. “One of threeeee…” But be careful! One glass contains your fondest wish. One glass will trap you in the shadow realms forever.

The third is usually Malört.

Roger’s Park—Big Al’s Place

For anyone looking for a straightforward, unpretentious beer in a comfortable setting, you can’t beat Big Al’s. Enter through an unmarked door from the alley out back — you MAY need to jiggle the handle! — and step into a cozy wood-paneled pub that is 100% authentic Chicago, from the comfy seating to the Cubs memorabilia covering the walls.

The unique “serve yourself” approach means your brew will always be fresh and cold. And if you’re lucky, in the wee hours of the morning you just might get a glimpse of Big Al himself, charging into the room in his bathrobe with his trademark catchphrase, “WHO ARE YOU, HOW DOES THIS KEEP HAPPENING, GET THE FUCK OUT OF MY HOUSE!”

Haha. Classic Big Al!

Downtown—[unknown]

Cursing, scrabbling, clawing at the ground, you pry up the manhole lid. The world of the above is too much for you, too bright, too knowing. Their eyes are so sharp. You will only be safe below. Hissing at strangers, your clothes flapping wetly about you, you descend into the sewers.

BYOB.