Neighborhood Dating Guide: Ravenswood

The neighborhood of Ravenswood is almost as old as Chicago itself. What started as a purchase of 196 acres of farmland in 1868 has transformed throughout history to one of the most popular places in Chicago for a first date. I can’t help you if you bring up a weird conversation like politics or not shutting up about your crypto profile (alright yeah, this comes from experience), but as long as you’re a decent, somewhat fun human being, this Ravenswood dating guide will help you leave an unforgettable first impression on your date!

Chicago Magic Lounge

5050 N Clark St, Chicago, IL 60640

While it’s probably not the sexiest idea to break out the card trick you learned in 7th grade on a first date, who can say no to a little magic? At the Chicago Magic Lounge, owner Joseph Cranford combines magic practices from some of Chicago’s most legendary magic bars, making it an all-around unique experience.


From close-up magic to card tricks, our city’s performances here are individual. How much more fun would a first date be if you skipped the bar you’ve been to a dozen times and did something a little more interactive? Performances here happen every night, I can guarantee that your data will tell their friends about the quirky but incredibly fun date they had for a long time.

O’Shaughnessy’s Public House 

4557 N Ravenswood Ave, Chicago, IL 60640

Sometimes you just need a classic Irish bar night, and why not elevate it just a bit? At O’Shaughnessy’s Public House, you’ll find all the staples that make it a true Chicago Irish bar, with an upscale feel making it the perfect option for a date. With a rotating beer list and tons of apps, sandwiches, Irish entrees, and dessert, you and your date will be left with full stomachs and full hearts. The best part?


If you or your date are particular about recycling or being generally green, O’Shaughnessy’s takes additional steps to ensure they’re using recycled and biodegradable materials and eco-friendly cleaning products. A win for the Earth and a win for your love life! 


4539 N Lincoln Ave, Chicago, IL 60625

For a one-of-a-kind kind of date, head to Gather. Here, not only will you find a perfected food menu and delicious drinks, but also a dining experience that’ll blow every other date you’ve had out of the water. Sit at the kitchen counter to get a peek into the mastery of Gather’s food or reserve your spot for the Farmer’s Series.

With colorful walls and supple leather seating, the atmosphere, along with the warm and knowledgeable staff, set you up for first-date success. If dinner isn’t your ideal date experience, why not celebrate a budding romance with a boozy brunch? Gather’s custom Day Drinking menu makes sipping cocktails during the day refreshing and, honestly, pretty romantic. 

KOVAL Distillery

4241 N Ravenswood Ave, Chicago, IL 60613

That warm and fuzzy feeling in your stomach? It’s not butterflies, it’s booze! From whiskey to gin to flavored liqueurs, KOVAL distillery takes the age-old distilling practice and turns it into something uniquely Chicago. At KOVAL, you and your date can enjoy their modern tasting room, sipping on spirits on a plush couch while you learn more about each other besides asking, “so, what’d you study in school?”

For a more immersive experience, take a distillery tour or enjoy one of their many event nights like Yoga & Cocktails, cocktail classes, or a creative bottle painting night. No matter what you do, I’m certain that time spent at KOVAL will have you meeting a new flame or planning time to take your partner there again. 

If you're from Chicago, you know about Margie's Candies. And if you're not, you'll need to stop in for a treat! Since…

Posted by Enjoy Illinois on Thursday, August 18, 2022

Margie’s Candies

1813 W Montrose Ave, Chicago, IL 60613

I don’t think there’s a sweets shop more synonymous with Chicago than Margie’s. This staple of the city first opened all the way back in 1921 and has been serving ice cream, shakes, and hand dipped candies to the city ever since. If you’re looking to WOW a date, take them somewhere delicious with an old-school feel, like Margie’s! You two can bond over a classic banana split or perform the romcom essential, sharing a milkshake with two straws as you gaze longingly into each other’s eyes. The best part about a date at Margie’s is that you’ll definitely be skipping the boring and going directly to a sugar-filled chat where it won’t feel awkward letting that weird side of you come out, at least a little. 

Featured Image: Gather