Breaking up is never easy, and many times it's a drawn-out ordeal. These places and tactics for splitting ways with your not-so-significant other offer a bit of both worlds. Some are mean-spirited, some are sweet and some are downright elaborate. Whatever route you choose, you'll be sure to get the message across loud and clear.
If you want to be remembered
Top of the Hancock
This one is risky, but they’ll remember you forever. Taking your soon-to-be-former better half to the Signature Room on the 95th floor might have them thinking you’re getting ready to propose, so maybe save this one for a few-month fling. You could even tell them “the sun is setting on our relationship” if you time it right. Be sure to pick up the tab and leave a little cash on the bar—this could make for an excruciatingly awkward elevator ride if they follow you on the way out.
Richard’s Bar
If you've been there you already know. Some rules that don’t apply at Richard’s. If you're a little shaken up, you can blame your tears on that pervasive cloud throughout the bar, or simply join in.
Buckingham Fountain at night, during the the water show
As water cascades from the statues and shoots toward the two or three visible stars in the night sky, profess to them the final goodbye.
Lincoln Park Conservatory
The grounds are beautiful and, best of all, they’re free. You can plan your exit to be indoors among the leafy palms and ferns, or perhaps you’d like to disappear in the depths of the lovely orchid house. If the outdoors are preferred and the blow especially hard, you can sit them down on a park bench beside some nice flowers or greens.
If you just want them out of your life
Navy Pier
You could ditch the shit out of Usain Bolt here if you wanted to, and if you’re cold-hearted enough, this venue would really do the trick. Nothing quite says “I hate you” like abandoning your former lover in a sea of tourists.
The bus to Hell
This one is dark. Take the complimentary shuttle to the Horseshoe Hammond Casino, start to get off when it arrives, then just don’t and wave goodbye through the bus window. Your newly christened ex will be stuck in Indiana. Double whammy: The return bus will be full of a bunch of old people who just gambled all their money away.
Any music festival ever
Pitchfork, Lollapalooza, North Coast, Riot Fest—take your pick. Just wait until they say, “I have to go to the bathroom,” walk them there and, once they close the door, you’ll never see them again. Unless you live in the same neighborhood.
Crappy improv show
Get them to volunteer to go on stage, then leave in the middle of their act.
The Pedway
You must absolutely know how to navigate this network of tunnels beneath the city in order to pull this off. Perhaps you grab lunch at the Chase cafeteria first, or if you favor a more direct route, you could explain yourself over a brisk walk, take a quick turn and be on your way.