Wicker Park is another wonderful neighborhood in the city that makes your dating life that much easier. Bustling with many restaurants, shops, bars, and galleries, there are plenty of exciting and energetic spots to bring a date the next time you’re looking for a unique experience. Now you might be thinking, “Wicker Park, isn’t that the place in the city where all the hipsters hangout?” Maybe! But this Wicker Park Dating Guide will show you why this neighborhood is also a lovebird’s nest!
So, why wait any further? Let’s take a closer look at one of the most popular neighborhoods around, and hopefully, with the help of some very fun places, you’ll be starting the first chapter of your very own happily ever after. Also, don’t forget to check out the other Chicago dating guides!
Emporium Arcade Bar
1366 N Milwaukee Ave, Chicago, IL 60622
If you know your date or partner is highly competitive, why not take them to a spot where they can let that competitive spirit shine? Emporium Arcade Bar has tons of classic games where you and your date can put yourselves to the test. It doesn’t matter who’s the best at skee ball (yes, it does), as long as you’re enjoying quality time together.
Not only can you take your skills to the arcade, but Emporium also hosts many events like live music and parties. Plus, and I’ve said it before, no first date is complete without a few drinks to take the edge off, and Emporium’s menu is staggeringly long, especially if you’re a fan of craft beers. Drink up and game on, people.
Dove’s Luncheonette
1545 N Damen Ave, Chicago, IL 60622
When was the last time you sat at an old-fashioned counter at a diner? If your answer is “actually, never”, then Dove’s Luncheonette is the perfect place for a unique date in a setting that you don’t really see anymore. With a Dove’s twist on classic dishes, you and your date are sure to devour each satisfying bite of items like vegan masa pancakes and smash burgers.
if you’re looking to take your date out on a weeknight (always a good idea, IMO), be sure to stop by for Dove’s After Dark, which occurs on Mondays from 5-10 PM. “After Dark”, you’ll find a rotating menu of new dishes and tons of alcoholic and non-alcoholic drinks to sip on while you fawn over your date’s sparkling eyes and taste in music.
The Hideout
1354 W Wabansia Ave, Chicago, IL 60642
Event-seekers, this one IS for you. Riddled with history, The Hideout is the perfect spot for anyone who wants to see just about anything to spend a date night. From concerts to comedy shows, a trip to The Hideout is sure to be two things: fun and eccentric. Self-proclaimed “clandestine destination with a guaranteed good time,” you and your date can get to know each other’s quirky sides as you delve into the history, culture, and performances woven into the venue’s 100-year-old foundation. To keep up with the upcoming happenings, which are every night, by the way, just head to their website or follow their Instagram, where fun posts and announcements are happening pretty much daily.
Dreambox Gallery
2415 W North Ave, Chicago, IL 60647
Since 2003, Dreambox Gallery, owned by Iwona Biedermann, has been a place where artists of all kinds can showcase their work. Dreambox Gallery is the perfect place where you and your date can immerse yourself in the full scale of art across Chicago from photography to drawings to poetry and performance. There are plenty of places across the city to see art, but this immersive experience will bring you up close and personal with the lesser-known but definitely-worthy artists who house their works here. This gallery is also only open on Fridays and Saturdays from 12-4 PM, so plan your trip accordingly to ensure you have enough time to see all the incredible Chicago-based art!
The Violet Hour
1520 N Damen Ave, Chicago, IL 60622
If you know that your date’s eyes would light up at a huge cocktail menu, you have to take them to The Violet Hour. This cocktail bar has an expansive menu that features everything from frozen drinks to shaken cocktails to the classics (who doesn’t love a good Old Fashioned?). For a more hands-on date, The Violet Hour also offers cocktail-making classes, both in-person and virtual, and the ability to book your own private events for a more intimate setting.
Featured Image: The Violet Hour