The Second City's sketch revues are consistently hilarious, so there's no surprise this comedy institution is a point of pride in Chicago. This is a total bullseye date—the performers have the ocassional off-night, but in all likelihood you'll laugh, have some drinks, feel pushed a little bit out of your comfort zone, then laugh some more. Even if you know nothing about improv, this is a great date spot for any stage of a relationship.
It’s easy to fall into a comfortable routine while dating in Chicago: Cozy up at a romantic restaurant, grab drinks at your local dive, maybe go to a movie if you’re feeling super wild. And while Chicago dives do have a certain romance to them, routine is boring, and god forbid you come off as boring. We’ve collected some easy, low-key dates that are far more likely to spark romance than just drinking the awkwardness away does. Plus, if you’re going to date your way through Chicago, you may as well get to know the city while you’re getting to know your future beau.