5 Spots For A Not-Boring Date

Where to have a memorable (in a good way) date.
5 Spots For A Not-Boring Date image

photo credit: Hall + Merrick

So you’re tired of your normal dinner-and-drinks routine and have decided to put actual effort into your next date. We’re proud. All the spots in this guide are as much about the experience as they are about the food. From a hot pot restaurant with robot servers to a gas station-adjacent taqueria, here are places we love for a non-boring date night.


photo credit: Stay And Play Cafe

Puerto Rican

Irving Park

$$$$Perfect For:Date NightFirst/Early in the Game DatesKidsUnique Dining Experience

Stay and Play in Irving Park is a board game cafe with 600+ games available. And it’s the perfect place to impress someone with how gracious a winner you can be. As you enter into the second hour of your campaign to take over all four railroads in Monopoly and bankrupt your date, you can choose from a variety of Puerto Rican dishes including a very tasty steak jibarito. Plus, there’s a long menu of rum-based cocktails to enjoy after you remember that Monopoly ruins lives, and switch to a game of EL: The Chicago Transit Adventure (yes, this is real, and you can play it at Stay and Play).

Dating often involves a lot of illusion, so Chicago Magic Lounge’s appearance in this guide is fitting. It’s a speakeasy-style theater dedicated to the lost art of Chicago-style (meaning close-up) magic. So once you find your way into this Andersonville theater—hidden behind a fake laundromat—you’ll have magicians coming up to your table to entertain you with sleight-of-hand. The drink menu has above-average cocktails, and there are snacks like beef tenderloin sliders or fig and pancetta flatbread. The food isn’t going to blow your mind, but the stage magic during the second half of the show might.

Bordel is from the same people who own Beatnik, and this cocktail bar has an equally over-the-top atmosphere. It’s a cross between a speakeasy and a bordello, so you can expect a hidden entrance, a DJ, a lot of dark velvet, and whirling tassels. Food options are somewhat limited to shareable plates like croquetas, charred octopus, or tuna tartare (all supplied from downstairs neighbor Mama Delia). But that’s fine because you’re mostly coming here for drinks and to catch a performance—depending on the night, you may see flamenco dancing, sword swallowing, a burlesque show, a magic act, or some combination of them all.

photo credit: Kim Kovacik

Inviting someone to dinner at a gas station is a bold (and questionable) move. But El Tragon, which is attached to a Mobil in Lincoln Park, is the best Mexican restaurant you might not know exists. Everything on the short menu is fantastic, like quesabirria, crispy chilaquiles, and a bistec taco with fried cheese and green onions that’s one of the city’s best. The space is small but full of colorful paintings, upbeat music, and a welcoming staff. Plus, it’s BYOB, so bring your favorite bottle of wine and get ready to explain to your date why you told them to meet you at a gas station for dinner.

photo credit: Nathan Media

$$$$Perfect For:Big GroupsBirthdays

The X Pot is a futuristic hot pot restaurant in the South Loop. What makes it futuristic? Robot servers, along with elaborate light projections and thematic soundscapes. So yes, this place is a rather absurd production, but it's also fun and the hot pot is good. While the robots might bring you your selection of ingredients, humans are also on hand to take orders. And, presumably, to rescue you both from the robots should they gain sentience and revolt.

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Suggested Reading

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El Tragón Taqueria is a fantastic Mexican restaurant located in a Lincoln Park gas station plaza.

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