Hidden bars & speakeasies in Chicago

Looking for hidden bars & speakeasies in Chicago? These 10 are the genuinely strange ones — Red Lion Pub, Alfred Caldwell Lily Pool, Indian Boundary Park and more — each hand-vetted and sourced, not pulled from a top-ten list. Great for an unusual date, a weird afternoon, or showing a visitor the side of Chicago they'd never find on their own.

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Red Lion Pub This British-style pub sits on ground that was once a 19th-century burial area for cholera victims and Confed… Lincoln Park
Alfred Caldwell Lily Pool Behind a Prairie-style stone gate on a busy Lincoln Park sidewalk hides a garden most passersby never realize… Lincoln Park
Indian Boundary Park A small Tudor-revival park in West Ridge whose 1929 field house is studded with eccentric details: a carved I… West Ridge
The Drifter Hidden in the basement of the Green Door Tavern -- one of the few wooden-frame buildings put up before Chicag… River North
Bordel Tucked above the Spanish restaurant Mama Delia, a hidden door in the entryway opens to leopard-print stairs c… Wicker Park
Booze Box Tucked in the basement beneath the Sushi Dokku restaurant, this dark Japanese-style underground bar is reache… West Loop
The Office at The Aviary A clubby, antique-and-art-filled speakeasy hidden behind an unmarked door beneath Grant Achatz and Nick Kokon… Fulton Market
Three Dots and a Dash Reached only through a discreet River North alley off Hubbard Street, this subterranean tiki temple is named… River North
Dorian's Through the Record Shop The street front is a working vinyl record shop with a functional listening booth, and the bar and restaurant… Wicker Park
Forevertron / World of Dr. Evermor The Forevertron is a 50-foot-tall, 300-ton scrap-metal contraption that the late demolition expert Tom Every… North Freedom, WI