Neighborhood Dating Guide: Logan Square

If you’re reading this and happen to be the guy I dated from Logan Square: you’re the worst. But, if you’re anyone but him, we’re back! Our revamped neighborhood dating guide started in Lincoln Park. Now, we’re heading west of I-90 to Logan Square.

With tons of to-dos lining Milwaukee and Fullerton avenues, making a plan for a fun first date in Logan Square is a breeze! Plus, if the date goes south and your partner starts talking about their weird hobbies (oh, you play Quidditch on the weekends), there’s tons of public transportation for an easy exit. 


Before the weather officially turns for the season, plan a date to Logan Square for lively bars, delicious restaurants, and activities at every corner. There is no better time than the Fall to find someone special to keep you warm through the winter.

Owen & Engine

2700 N Western Ave, Chicago, IL 60647

Owen & Engine is one of those date spots that will pique your interest and then have you captivated enough to turn your dinner into a night-cap as you dive deeper into your conversation and think to yourself, “could this be the one, or do I just need another glass of Pinot Noir?”


Earlier this year, Owen & Engine reopened after shutting down during the pandemic. Now, it is operating better than ever. Featuring cozy leather seating and low ambient lighting, this Logan Square staple pampers diners with an expansive dinner menu ranging from smaller plates to large dishes and everything from beer to bourbon to sip on. If you’re also looking to impress your date by eating at a restaurant that uses locally sourced ingredients, you can rest easy knowing that Owen & Engine supports local farms, orchards, and growers to get their food. 

The Logan Theatre

2646 N Milwaukee Ave, Chicago, IL 60647

Ah, a classic date combo: dinner and a movie! When you’re looking for the latest flick with your latest fling, head to the legendary Logan Theatre. This theater opened back in 1915, and found its lasting name in 1922 as the Logan Theatre. Since then, the owners have been dedicated to serving the diverse families of the community. Could anything be more romantic than the smell of fresh, buttery popcorn and sharing a Diet Coke over two straws while you lock your eyes? I don’t think so. 


Aside from movies, the Logan Theatre also hosts open mic nights for aspiring stand-up comedians and movie trivia nights on Tuesdays! For a little extra spice to your movie date, try one of the Late Nights at the Logan, where movies start at 11 PM, and the drinks are stiff. Shot of Malort, anyone?

Miko’s Italian Ice

2236 N Sacramento Ave, Chicago, IL 60647


Is your date super sweet? Take them for dessert! As we move toward the end of summer, we need to take advantage of the weather and the sweet treats as much as possible. That said, there’s probably nothing more perfect for a late summer day than a cold and tangy Italian ice.

There is a flavor for everyone with flavors like classic lemon, tart raspberry, and creamy chocolate. If you’re trying to make the date a little more romantic, order a few flavors and try them each together. They always say, the best way to someone’s heart is through their stomach, and a trip to Miko’s with a potential love interest is sure to wind up in a planned second date, if not a very long first date.

The Whistler

2421 N Milwaukee Ave, Chicago, IL 60647

The Whistler might be one of the coolest places in Chicago for a first date. This cocktail bar/art gallery/record label/venue has literally everything you’re looking for on a date. From the strong drinks to the trendy atmosphere to the people, you’ll find that you and your date will be continuously entertained with no lull in the conversation. With an ever-changing, award-winning cocktail list, you’ll have to follow The Whistler’s Menu Instagram to see what drinks are available each day. 

When you and your date are ready to try something different, check out the events menu. You can always try out a new music genre with a stage and many local artists. If you like country and your date likes blues, you just found your reason to come back to The Whistler and an awesome excuse for a second date! 

Osteria Langhe

2824 W Armitage Ave, Chicago, IL 60647

For a timelessly perfect date, head to Osteria Langhe. This Italian eatery celebrates tradition, emphasizes slow-cooked meals, and was named one of the Best Italian Restaurants in America by Timeout Magazine in 2017. Here, you can live out all your Lady and the Tramp dreams (you know what I’m talking about) by diving into exquisite pasta dishes, savory crepes, and wines from the Piemonte region of Italy. 

For an extra-special dining experience, try out the “Taste of Piemonte”. This four-course meal is only available on Wednesdays and starts at $55. Wine pairings are an additional $30, but are highly recommended if you want to take away those first date jitters and elevate your dining experience.

Featured Image: The Whistler