A Chicago speakeasy
Chicago Speakeasies

The 10 Best Speakeasies in Chicago 2026

JH
James Harlow
7 min read

Chicago speakeasies are Wicker Park hidden temples and Logan Square cocktail rooms.

The 10 best speakeasies in Chicago

01 · Chicago
The Violet Hour

James Beard-winning Wicker Park speakeasy behind an unmarked mural.

Order: A bartender's-choice signature

02 · Chicago
Sportsman's Club

Plush Humboldt Park cocktail bar from The Violet Hour team.

Order: A Manhattan, made carefully

03 · Chicago
Three Dots and a Dash

Iconic River North tiki speakeasy with hidden alley entrance.

Order: A Three Dots and a Dash

04 · Chicago
Billy Sunday

Plush Logan Square cocktail bar focused on classics.

Order: A precise Sazerac

05 · Chicago
The Aviary

Grant Achatz's modernist West Loop cocktail bar.

Order: Whatever the kitchen-bar pairs you with

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06 · Chicago
The Office

Hidden speakeasy beneath The Aviary.

Order: A bartender's-choice signature

07 · Chicago
Milk Room

Iconic 8-seat Chicago Athletic Association vintage-spirits speakeasy.

Order: A vintage cocktail with rare spirits

08 · Chicago
Watershed

Hidden Streeterville Midwest whisky-led speakeasy.

Order: A high-rye Manhattan

09 · Chicago
Barrelhouse Flat

Iconic plush Lincoln Park cocktail speakeasy.

Order: A precise classic

10 · Chicago
Untitled Supper Club

Iconic River North hidden whisky speakeasy with 500+ whiskies.

Order: A pour of rare Bourbon

How to find a speakeasy in Chicago

The 10 above are where Chicago hides its best cocktails — behind phone booths, fridges, bookcases, and unmarked doors. The point is the secret. The reward is the cocktail on the other side.

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