Need to Cut Them Loose? Head to These Chicago Breakup Bars

It’s not easy breaking up with someone, regardless of whether it’s been a few weeks or a few years. But once you get it in your head that you’re better off without that person, it’s hard to shake the feeling, and sometimes, it’s just easier to do it over a drink.

We have a few bars in mind for when you’re ready to break it off for good, all of which make sure your drinks are already paid so you can leave right away. They also feature low lighting in case of tears, privacy for one last special moment, and an easy exit for a quick getaway. Not that any of these bars had breakups in mind when constructing their atmosphere, but it works out anyway.


Start the process of moving on at Chicago’s best breakup bars.



The Owl

The Owl
Photo Credit: The Owl Facebook

2521 North Milwaukee Avenue

Why the Owl, you ask? You must have never been there. It takes about 25 minutes for your eyes to adjust to the darkness of this place, so if you’re expecting a waterfall (just like the one bubbling behind the bar), this is where to get the deed done.




Photo Credit: Scofflaw Facebook

3201 West Armitage Avenue


Scofflaw is a little bit nicer of a cocktail lounge, so it’s perfect if this person actually meant something special to you. There’s a cozy selection of couches on the other side of the bar, giving you all the privacy in the world, and there’s a back exit that I think works, in case your ex-date wants to leave in a hurry.



The Violet Hour

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Photo Credit: Joni Kat Anderson for The Violet Hour

1520 North Damen Avenue

The Violet Hour is a speakeasy, which means the entrance and exit is in a rather secretive location off the main street, a good thing if your date is totally heartbroken. Plus, this place is fancy, so it’s a good place to treat them to a nice cocktail one last time before breaking the news.



Slippery Slope

Slippery Slope
Photo Credit: Slippery Slope Facebook

2357 North Milwaukee Avenue


Slippery Slope has a lot of private seating areas, booths spaced far enough apart that no one will overhear your somber conversation. This bar is open very late and often hosts a DJ and dancing, so make sure to avoid weekends.


The Revel Room

Revel Room
Photo Credit: The Revel Room

1566 North Milwaukee Avenue

A bar that actually has many rooms for you to break it to them slowly, The Revel Room has so many hideaways that you can’t go wrong meeting someone here for the last time. Everything is private and the bar keeps things dim, so as long as you speak quietly, no one will ever be the wiser.


Hungry Brain

Hungry Brain
Photo Credit: Hungry Brain Facebook

2319 West Belmont Avenue

While there is little seating at this cash-only spot, it’s almost never busy, and the bartenders typically leave patrons alone when they’re across the room. There’s even a back patio if you need to go somewhere extra private and since Hungry Brain is ridiculously hard to find if you don’t know where you’re going, there’s no fear of walking out onto a busy street after with your makeup running.


Jack and Ginger’s

Jack and Ginger's
Photo Credit: Jack and Ginger’s Facebook

2048 West Armitage Avenue

Just trying to get things over with? Jack and Ginger’s is a divey sports bar with a separate booth area, so you can stay totally invisible to the rest of the bar. Since everyone will be watching the game, you and your ex-date can both sneak out without anyone noticing.

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