Neighborhood Dating Guide: West Loop

They say West Loop is the Best Loop, and that definitely applies to the dating scene. Since this part of the city is laden with hot 20- and 30-somethings, the streets are constantly buzzing. Here, you’ll find some of the most popular and notable restaurants in the city, dozens of bars, shops, and things to do at every turn. Personally, I don’t think I’ve ever been to the West Loop and not seen someone who has the potential to be my future husband (here’s to you, guy who walks his Frenchie down Randolph).

And just in case you’re planning a date in a different neighborhood, check out our 2022 revamped dating guides for Logan Square to Lincoln Park, too. Oh, and there are more to come.



180 N Morgan St, Chicago, IL 60607


I’ve said it once, and I’ll say it a million more times: going out in the West Loop doesn’t count unless you stop at Federales. The energetic atmosphere here makes it the perfect spot for drinks with friends, a work happy hour, OR a first date! We likely all know plenty of couples who’ve met at Feds or have met someone ourselves that we, at one point, thought could’ve been the one (I’m still holding on to one of those nights).

When you take a date here, you’ll probably indulge in guacamole and shrimp tacos, and continue to bond over throwing the ice molds from your Casamigos shot at the bell. Hey, if Chance the Rapper can hit the bell, why can’t you?


Gyu – Kaku

1364 W Randolph St, Chicago, IL 60607


What’s better than a regular dinner date? Cooking together! While you might be a little uncomfortable going to a stranger’s or having a stranger come to your place for the first time, there’s another option – Gyu-Kaku! This nationally known Japanese BBQ place brings ease and great flavors to one of the cutest first date ideas: cooking together.

Over the open flame in the middle of your table, you and your date will work your way through preparing a multi-course meal consisting of various meat and veggies. The great thing about Gyu-Kaku is that the marinating is done for you, all you have to do is sear and enjoy! If you do feel okay spending your first date in either of your apartments (which is totally fine), Gyu-Kaku also offers their raw, marinated meats to go. 


Sawada Coffee

112 N Green St, Chicago, IL 60607

Dear coffee lovers turned romantic lovers, if you haven’t already, meet Sawada. The first coffee shop in the US of Hiroshi Sawada offers a menu of espresso and matcha-based drinks that you won’t find anywhere else in the city. This industrial-style shop is a coffee lover’s dream, complete with the scent of always freshly brewed drinks wafting through the air. If your date gets competitive, you’ll find warm wood-paneled walls, glistening string lights, and a ping pong table.

While you converse and uncover each other’s quirks and favorite colors, why not sip on an aromatic latte, then split a Doughnut Vault donut as you plan your second date? Is there anything more dreamy than getting to know a perfect match over a cup of coffee on a chilly fall day? I’m pretty sure Taylor Swift has written songs about this. 

Joe’s Imports

813 W Fulton Market, Chicago, IL 60607

The drink of pure romance? Wine, of course! At Joe’s Imports on Fulton Market, the wine list is curated by wine Director Joe Fieley’s personal travel and experiences. Here, you’ll find wine from unique places all over the globe, like Israel and Romania, making it the perfect spot to dive into something new together.

A date at Joe’s Imports also guarantees an intimate setting where you and your date can nibble at smaller snacks or share larger meals, all while sampling what could be the wine that brings you two even closer. Think about it, on each anniversary of your first date, you can start the tradition of hunting down that special bottle and reminiscing on the place where it all started: Joe’s Imports. 

Texan Taco Bar

942 W Randolph St, Chicago, IL 60607 

New to the West Loop is Texan Taco Bar. Opened by Parlor’s owners Michael Bisbee and Tim Hendricks, this spot elevates traditional TexMex food with specialty tacos and hand-squeezed margaritas. A first date, at least by my standards, usually isn’t complete without a few drinks, and tequila will definitely bring that warm and fuzzy feeling in your stomach that’ll have you chatting away in no time. As of food, Texan Taco Bar has plenty of shareable like Texan Queso and Nacho Bites, and a huge dessert menu to splurge on something sweet to wrap up what was hopefully a perfect first date.!

Featured Image: Federales