A Clean Break

The best restaurants and bars for breaking up in Chicago

Has your love gone sour? Make a plan to end things before having to endure a hollow Valentine's Day at one of these breakup-worthy spots.

The Drown-Your-Sorrows Spot: CH Distillery

If you want to break up in a public setting but the only thing that'll fill the pit in your stomach (read: heart) is booze, this industrial-chic bar and lounge is the place to go. Order yourself and your soon-to-be ex the Bastard's Bitter ($11); losing a love may be a tough pill to swallow, but the mix of vanilla-infused CH Rum, CH Amaro, honey syrup, bitters and grapefruit oil should do a good job of masking it.

The Eat-Your-Feelings Spot: Carriage House

If you or your no-longer-significant other has a penchant for emotional eating, plan to break up at a calorie-dense locale like this comfort food oasis in Wicker Park. After a tear-drenched feast of skillet corn bread ($7), shrimp and grits ($14/$26) and mac and cheese ($8), a food coma will inevitably dull the pain. Who needs love when you have elastic-waist pants waiting for you at home?

The We've-Been-Together-Long-Enough-That-I-Shouldn't-Be-Breaking-Up-with-You-in-Public-but-I-Am-Anyway Spot: Lula Cafe

If you're about to end a long, serious relationship, at least give your guy or gal the courtesy of doing it somewhere nice, like Lula Cafe (chances are he or she deserves it, especially after putting up with your apparent tactlessness for so long). The 15-year-old restaurant is laid back and lovely—much like your relationship used to be—and an ideal venue for letting 'em down easy while enjoying one last hanger steak ($26) and sweet onion bisque ($11).

The Fast-Exit Spot: Good Stuff Eatery

The only thing less desirable than breaking up is breaking up over a slow meal with waitstaff hovering over you while the sadness and expletives flow. The Loop's new fast-casual burger joint lets you get in, eat a burger ($6.50 to $8.50) and fries ($2.50 to $4), slurp down a toasted marshmallow shake ($6), end a relationship and bomb out before you have time to overthink things and blurt out, "I didn't mean it!"

The Instant-Rebound Spot: HUB 51

The thought of being alone can be a scary thing, so scheme to dump your ball-and-chain someplace swanky where (after your ex leaves, of course) you can chat up an attractive new friend at the bar. We recommend severing ties at HUB 51 over an order of pulled chicken nachos ($16), then heading down to the restaurant's subterranean night club, SUB 51, and letting the rebound games begin.

The Hit-the-Town Spot: Stout Barrel House & Galley

Since there's no shortage of packed bars and restaurants in River North, give your pals the heads up that you're pulling the plug on love and arrange for them to meet you out for drinks and debauchery post-the talk. Give the whole, "It's not you, it's me" speech somewhere like Stout Barrel House & Galley, order soft pretzels ($8 for three) to soak up the tears (and soon-to-follow alcohol), say your good-byes and skip off to meet your friends at nearby cocktail providers like Three Dots and a Dash, Bottlefork or Sable.

The Off-the-Grid Spot: Ada Street

There's nothing worse than breaking up at a neighborhood joint, so pick a place you're not likely to pass by (or better yet, frequent) on the regular; it'll be different depending on where you live, but we think Ada Street is a solid option regardless. It's tucked away on a side street just past the Elston and North Avenue intersection, and unless you're headed to the neighboring Home Depot, chances are good you won't be near it often enough to conjure up bad memories.