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Chicagoist's Best Date Night Bars

By Anthony Todd in Food on Feb 6, 2013 5:00PM

While we love 12-course meals filled with flowers and romance and bubbles, most of our dates take place in bars. They are dark, romantic, filled with social lubricant and, most importantly, if the person turns out to be horrible you can escape after one drink.

But not any old bar will do. You have to be picky and consider exactly what type of date you are trying to have and the image you are trying to convey. Is this a grungy dive bar? Maybe you're a down to earth drinker (or an unbearable hipster poser). Is it a fancy cocktail bar? Maybe you're a cocktail coinesseur (or a pain-in-the-ass snob). Whatever you are looking for, we've got it.

Here are our favorite date night bars. Have some of your own? Chime in in the comments.

There are so many reasons to love the Matchbox. First, it's withstood the test of time: as new - albeit excellent - bars abound, this one remains consistent, like your favorite restaurant that's always there, yet you delight in remembering it every time you're hunting for a place to go on your next date. And for that reason, it remains one of the best date bars in Chicago: it's completely unpretentious, yet also manages to remain under the radar enough that it's a perfect card to keep in your back pocket. It's tiny, dark, and always cheaper than you expect - and they make a damn good gimlet. —Erin Drain

The Matchbox is at 770 N. Milwaukee Avenue; (312) 666-9292

The Violet Hour is an obvious choice, but it's my personal favorite because its a perfect place to get lost in conversation. Draped in periwinkle velvet with sparkling chandeliers and a fireplace, it's a very romantic atmosphere. The craft cocktail menu changes periodically - but never disappoints. They also have a nice menu of substantial snacks - and there's always the option to grab late night tacos across the street at Big Star's takeout window. Don't worry if you can't find it at first - just follow the line of people or look for the lamplight. —Julia Weeman

The Violet Hour is at 1520 N. Damen Avenue; (773) 252-1500

The interior of The Violet Hour.

Some might call Charleston a dive bar since it’s dark, small and relatively tucked away in Bucktown, but with craft beer and classic cocktails on the menu, I'm calling it a great date bar. They’ve usually got a dj playing obscure tunes along with candlelight to set the mood. There’s also a photobooth for you to commemorate the occasion if you hit it off. Come prepared though, Charleston is cash only (there’s an ATM inside if you forget). —Michelle Meywes

Charleston is at 2076 N. Hoyne Avenue; (773) 489-4757

99 percent of Boystown bars are clearly meant for meeting friends or meeting, ahem. But Elixir is that rare drinking establishment where you can bring that someone special to have a cocktail and not feel totally slutty. And since, as we all know, gays hardly ever show up anywhere early in the evening, if you get there when Elixir opens at 8, you'll have a solid chance of enjoying a leisurely tete-a-tete in relative quiet. —Rob Christopher

Elixir is at 3452 N Halsted Street; (773) 975-9244

I (obviously) insist that my date bar have some kind of interesting food. That's why Scofflaw has become my go-to date bar. The crazy Baroque/Victorian/goth/whatever decor always suffices to keep a conversation going; the fact that it's a little bit off the beaten path lets you weed out those who never leave River North; and the cocktails are killer. It can get a little crowded on weekends, but it's quiet and lovely on the weekdays. Plus, Scofflaw gives me an outlet for my insufferable side by talking about gin with the bartender. —Anthony Todd

Scofflaw is at 3201 W Armitage Avenue; (773) 252-9700

A cocktail at Scofflaw.

Near the Webster/Clybourn corridor and bordering the river, Webster’s Wine Bar is just enough off the public trans route to make for a secluded date spot. It’s wood trimmed, dark, cozy and candle lit and they’ve got plush couches for an excuse to sit close to your date. They’ve obviously got a great wine selection, too, and everybody feels fancy drinking out of a stemmed glass. —Michelle Meywes

Webster's Wine Bar is at 1480 W Webster Avenue; (773) 868-0608.

As corny as it might sound, I always liked the Signature Lounge at the Hancock Building for a second date. The views are great, whether you're a native Chicagoan or not. It's never too crowded, and you can take in both the views of the city and do some people watching while you're there. Plus, the price of a drink covers the cost of the normal ticket to the observatory. —Kevin Robinson

The Signature Lounge is at 875 N Michigan Avenue; (312) 787-9596

The view from the Signature Lounge. Photo by brett7three.

Beer bars can be romantic too! While we can argue about what is the greatest beer bar in Chicago, Bluebird is my pick for the most romantic. It's dark, cozy and has a beautiful fireplace. Even better, they have great food and some decent cocktails if your date isn't into beer. If you're looking for quiet conversation, I'd suggest going very early or very late, since it gets a little loud. —Anthony Todd

Bluebird is at 1749 N Damen Avenue; (773) 486-2473.

Skylark, contrary to what Chicago magazine writes, is not a dive bar. But its dark corners, comfortable booths and mood lighting (read: barely any) make it one of my favorite haunts to nuzzle close to someone and whisper bon mots in relative privacy. The bartenders—especially Brian Page who holds down the early shifts on Thursdays and Saturdays—spin a consistent soundtrack of old soul, R&B, country and jazz to keep you in the mood while pouring some of the coldest beers and best highballs in Chicago. The food that comes from the kitchen, notably their tater tots with three separate dipping sauces, put the tiger back in your tank. —Chuck Sudo

Skylark is at 2149 S. Halsted Street; (312) 948-5275