Everyone knows that what happens at the bachelor party, stays at the bachelor party. To match the mood of the evening, why not create a night out that includes some of Chicago’s favorite speakeasies? Both real (like those actually used during Prohibition) and created (secret bars opened in more modern days), there are a lot of options for feeling sly on your boy’s night out.

The Office

955 W Fulton Ave

Tell all of your ladies that you’re going “to the office” and you won’t be lying if this is your destination. The Office is located inside The Aviary, an innovative cocktail bar in Fulton Market. To gain access, your bachelor party will have to include about 16 members, as an advance reservation for a large party is required to use this special room.


1721 W Division St

Bordel is the secret bar inside Wicker Park’s tapas restaurant, Black Bull. You could make a night of dining on Spanish favorites downstairs, then heading up the staircase to this Prohibition-style speakeasy, complete with occasional burlesque shows and live music.

The Violet Hour

1520 N Damen

The Violet Hour isn’t much of a secret bar anymore, as the line to get inside is pretty hard to miss. Regardless, the experience within is not one to be missed, especially when celebrating a special occasion. Though expensive, the cocktails are as delicious as they are boozy. More than 2 and you may not make it past this establishment!

Glascott’s Groggery

2158 N Halsted St #1

No longer a secret, Glascott’s Groggery used to be “James Morely Soft Drinks”, or at least, that was their front for the activities going on in the back of the house. For the single dudes in your party, they may be happy to know that this bar is known as a hookup bar, though one that tends to result in marriage and a move to the suburbs (seriously).

Green Door Tavern

678 N Orleans St

Green Door Tavern is a speakeasy in multiple senses of the word – acting as a secret bar that was in operation during Prohibition, as well as a having a modern secret component in the back of the bar, today. The Drifter is Green Door Tavern’s own speakeasy. Sample their menu of tarot card drinks for a special experience.

Green Mill Cocktail Lounge

4802 N Broadway

You won’t find a speakeasy better than this one, in Chicago or elsewhere. Sit in the same booths as Al Capone once did, and drink at the bar that served as the backdrop to popular films like High Fidelity and The Untouchables. The cocktails and live jazz performances are a great way to wind down the night.

If you buy a copy of our book Historic Bars of Chicago ($12), you can get a Chicago Trolley $45 coupon that is more than 10% off for most rentals, and can help you get around our selection of Chicago’s favorite speakeasies in style.

If you have better ideas for a speakeasy-themed bachelor party, or want help planning an itinerary, email us. We can also help with booking private party rooms if you plan to stay in one location!