Okay, I’m going to be honest. If I knew how to find love fast in Chicago, I’d be happily engaged with my dream ring on my finger (take notes, future husband), but I’m not, so I’ve found other methods, including lots of patience, that have worked much better.

Love is definitely out there, and we have quite an advantage to find that special someone by living in close proximity to a ginormous city. Now you might be thinking, “get to the point, Carrie Bradshaw”, but that’s also exactly the point – you can’t rush love. That being said, you can definitely position yourself directly in fate’s way so you get struck by Cupid’s arrow at least once. Meanwhile, if fast fun is what you’re looking for, remember to check out my list of bars where you’re most likely to get laid!


A word of advice: Prince Charming probably isn’t hanging around at a grungy dive bar at 3 AM, so maybe opt for something with a touch of class. Chicago is chock full of cocktails that are chock full of singles.


Places like Three Dots and a Dash, Howl at the Moon, or Louie’s offer more than cocktails with dueling pianos, karaoke, and fun themes that already kind of push you out of your shell for a night of fun. If you’re looking for a more lowkey place to search for love, check out Lazy Bird in The Hoxton or Elixir in Andersonville. You never know who is going to be strolling into the bar, so be open to the opportunity but remember to have fun and put yourself first! 


If you’re heading out with friends but want to keep an eye out for a potential match, there are some places that are definitely better than others. Opt for a place that offers an interactive experience or special event. Cabaret Zazou is the city’s “premier dinner show” where it’s easy to strike up a conversation with a stranger over a shared evening. 

I also find myself constantly talking to strangers at Hibachi restaurants because you’re often seated with people you don’t know. Check out Sumo Sushi & Hibachi for delicious food and the chance to meet some new people. 


The Magic Parlour is exactly what you think it is. Professional magicians performing followed by awesome food and drinks. Who doesn’t love a potential partner who opts for a fun-infused meal over a boring night at a club? 


Okay, ladies, this one is going to be pretty obvious, but if you’re interested in men, you can typically find a LOT of them at sporting events. From the Bulls to the Bears, there is always a sport in season that you can find cheap tickets to and interact with some hot guys. 

If you’re not a sports fan, opt for more low-key events like concerts at Subterranean, author events at the Chicago Public Library, or one of the many, many street festivals. After all, it’s important that you and your partner share interests and hobbies! 

Rec League Sports

Get your body moving after a long day? Yes. Enjoy some friendly competition? Check. Meet tons of new people from all over the city? You got it. Rec league sports are an awesome way to meet awesome people. Whether it’s volleyball at North Avenue Beach through Chicago Sport & Social Club or pickleball with Player’s Sport & Social. There’s probably going to be someone looking sweaty and sexy, which is the perfect time to make a move. 

And if all else fails…

Just try the dating apps. I know you don’t want to, but do it. I’ve made some real, genuine connections with guys who didn’t turn out to be the one, but hung my TV (thanks Alex), were fun to date, and were great for the time being. Also remember that you are the prize and when it’s supposed to happen, it definitely will, and you won’t have to force a single thing.

Featured Image: The Magic Parlour

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