Neighborhood Dating Guide: Pilsen

Pilsen was originally dominated by the hundreds of Irish immigrants who came to the US and laid the foundation of one of the most popular neighborhoods in Chicago today. When Pilsen comes up in conversations, most recognize it as an Italian and Mexican cuisine hotspot filled with gorgeous public art lining the streets. Food and art naturally make Pilsen a perfect place for your first date or take the budding romance to the next level.

That said, it’s time for our new neighborhood dating guide chapter — Pilsen!


Woman Made Gallery

2150 S Canalport Ave #4A-3, Chicago, IL 60608


Woman Made Gallery is a 501(c)3 nonprofit organization whose mission is to showcase the art of Chicago women and non-binary artists. Here, you and your date will stroll through the different exhibitions as you take in the artistry and talent of creators in our backyards. Gentlemen, if you’re taking a lady out on a date, you’re sure to impress her with your interest in the history of modern feminism.

From September 24th through November 5th, stroll with your date through the Feminist Biennial, which features the artwork of 34 different artists’ take on what it means to be a feminist today. Celebrate the woman and non-binary artists of Chicago and immerse yourself in the art of being a woman.


Thalia Hall

1807 S Allport St, Chicago, IL 60608


If you want to take your date to a historic building in the city, head to Thalia Hall. When it opened back in 1892, Thalia Hall was a public hall for the community and remains a hub in Pilsen with a delicious tavern, cocktail bar, and space for tons of different kinds of events. Here, you’re also sure to bond over your shared love of live music. Aside from the daily happenings at and around Thalia Hall, tons of concerts are held at the venue. From hip-hop to alternative, you and your date can enjoy different acts no matter your preferred genre. You might even find a newfound shared love of the same artist that inspires your romance to reach new heights.

Pilsen Yards

1163 W 18th St, Chicago, IL 60608

Music, mezcal, and Latin street eats. Pilsen Yards is a must-visit for anyone having their first date in Pilsen. Featuring heated cement floor, overhead heaters, a clear roof, and exposed wooden beams, Pilsen Yards year-round patio is the perfect place for a romantic outing on a chilly day. Munch on their delicious food and try a seasonal cocktail, and never worry about having nothing to talk about since the Yards constantly features local artists on its walls!

Looking for a more intimate experience? Explore The Alderman, Pilsen Yards’ 16-seat cocktail bar tucked away behind closed doors, featuring a new, rotating menu every couple of months from Bev Director Lance Bowman, along with a stationary menu of his riffs on American classics.

Carnitas Urupan

2813 W 55th St, Chicago, IL 60632

You and your date need to take a trip to Carnitas Urupan for a date in Pilsen. Founded in 1975, Carnitas Urupan has become the prime destination for anyone craving authentic carnitas from Michoacan. Get to know each other better over mouth-watering carnitas tacos and crispy chicharrones, and witness your feelings for each other burst as much as the flavors do.

Alulu Brewery & Pub

2011 S Laflin St, Chicago, IL 60608

Is there anything better than sipping a beer and gazing into a lover’s eyes? I don’t think so. Plus, if you’re tired of drinking the same beer across the city, try something you can only find here! Alulu is a Pilsen-based brewery known for its small-batch craft beer only available at its brewpub. From the Comfy Wobbles to the Pivo Liso and the hazy Ming Jeel, each beer at Alulu will give you and your date a fresh beer-drinking experience.

When you inevitably need something to munch on, stay on the beer trend by trying one of Alulu’s signature Beer Crust pizzas with delectable toppings like pepperoni and garlic, white sausage and mushroom, and vegan jackfruit. 

Pilsen Murals

W 16 St, Chicago, IL 60608

Pilsen is famous for its many street murals. Then, why not skip the long lines of the big city galleries, and opt for a romantic stroll through the streets? As you saunter down the block, you’ll find tons of works to appreciate created by Chicago-based artists, but you might also be surprised to find murals created by artists from across the nation who have come to leave their mark on the city. While it might not seem like a traditional date, you can enjoy the murals before the main event, as you move on to the next bar, or just as plainly as enjoying a walk together. 

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