Valentine’s Day is right around the corner, and whether you and your S.O. love to wine and dine with a 9-course meal or prefer something more low-key like pizza and beer, I’ve got you covered! I’ve rounded up some of my favorite places across Chicago to celebrate Valentine’s Day. For those of you with a sweet tooth, I’ve also included some of my favorite dessert spots for a little after-dinner delight.
DMen Tap (Doner kebabs) $
2849 W Belmont Ave
This food truck turned full-fledged restaurant/cocktail bar never disappoints. Offering some of the best Doner this side of the Atlantic, this Avondale haunt also features incredible CurryWurst and an intriguing draft beer menu. And hello? How can you say no to Fried Poutine Balls w/ Malort Aioli?
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Dimo’s Pizza (Pizza) $
3463 N Clark St – 1615 N Damen Ave
Don’t sleep on the simple pleasures! Pizza and a movie? Yes please! Nothing spruces up your normal slice experience more than grabbing one of the unique creations found at Dimo’s. The best part? They have two locations – one in Wicker Park and one in Wrigleyville.
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Pasta d’Arte (Itlalian) $$
6311 N Milwaukee Ave
The best kept secret on the far Northwest side – Pasta d’Arte is a Norwood Park institution. Serving authentic Italian fare for over 20 years, this place is exactly what you want for a lowkey nice night out. PS – the wine menu is truly outstanding!
Superkhana International (Modern Indian) $$
3059 W Diversey Ave
When you’re looking to spice it up in Logan Square, look no further! This cute spot offers a creative array of Indian-inspired fare and saucy craft cocktails. The atmosphere? Awesome. The staff? Couldn’t be nicer. Imagine this: Pulled Achari marinated pork. Tamarind chutney. Aioli. Cilantro. All on a sandwich. So good!
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Lonesome Rose (Mexican) $$
2101 N California Ave
It’s hard to feel lonely at the Lonesome Rose! Emitting a trendy-warehouse vibe, this Palmer Square spot offers an homage to dishes of Southwest and Northern Mexico. From the cocktails to the queso, everything about this place makes you feel good. It’s also open for brunch!
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Beatnik (New American) $$$
1604 W Chicago Ave
When you’re looking for more of an experience, this place delivers in spades. Named after the bohemian freethinkers of the 1950s and ’60s, Beatnik West Town offers guests an exotic escape with progressive, globetrotting food and cocktails paired with a luxurious Old-World design. A memorable date and enjoyable food! My recommendation? The Ribeye & Black Truffle.
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Boka (American) $$$
1729 N Halsted St
If you know anything about Boka, you know that Valentine’s Day is an EVENT. Featuring a 9-course tasting menu and specially-crafted cocktail and wine menu, it’s no surprise you need to order tickets ahead of time to enjoy a spot at this Chicago institution. When you’re looking to celebrate love in style, Boka goes the extra mile.
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Monteverde (Italian) $$$
1020 W Madison St
We all need a little refinement in our lives. And pasta. Lots and lots of pasta. This contemporary gem located in the West Loop offers world-class Italian fare with a globe-spanning wine menu that will have you falling in love all over again. The hand-crafted pasta is unmatched and the staff is exactly what you’d expect. Sharing a meal with your loved one at Monteverde is something I recommend everyone do at least once.
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And don’t forget about dessert!
Margie’s Candies $
1960 N Western Ave
Founded over 100 years ago in 1921, Margie’s Candies is considered a Chicago legend. Like stepping into a time-machine, the blast from the past décor will have you feeling all sorts of nostalgia. From sundaes to milkshakes, to confections galore, there is something for everyone. My go-to? A classic strawberry milkshake, but if ice cream isn’t your thing, try the terrapins!
BomboBar $$
832 W Randolph St
A loaded s’mores hot chocolate with a mini bomboloni? Yes, please! This walk-up window in the West Loop is a must-have for dessert. Not only are their Hotter Chocolates delicious, their bombolonis are unlike anything I’ve ever had. Whether you prefer a classic filling like salted caramel or something more decadent like tiramisu, you can’t go wrong
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Sugargoat $$
820 W. Randolph St.
Turning comfort food into irresistible desserts, Chef Stephanie Izard has done it again. The bright space offers incredible desserts that you can’t find anywhere else. Try the chocolate French fry pie or avocado toast cake and thank me later – you won’t be disappointed.
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