The Resy Guide to Date Night in Chicago

French favorites with fine dining sensibilities are the name of the game at this modern French bistro, born from the owners of Le Bouchon and influenced by cuisines from across the world, from Vietnam to Mexico. While you’ll find traditional favorites like French onion soup, you’ll also encounter decidedly more fun twists, like the foie gras taco with grape jam and salsa macha, and an entire menu section dedicated to duck that’s not to be missed. Pair your 10-day-aged duck breast with French wines and don’t skip the on seasonal desserts, like the vacherin with brown sugar, angel food cake, meringue, tropical sorbet, passionfruit, and coconut.

Inspired by the asadores, or grill houses, of the Spanish Basque region, this restaurant has been lauded as one of the most exciting newcomers to the steakhouse scene in recent years and will likely be one of your more indulgent dates. Their schtick is boutique beef, served char-grilled in sumptuous environs. To round out an already-bougie date night, order the Osetra caviar churros, tallow-fried potatoes, and truffle and Iberico ham-laced rice. Seasonal cocktails, cold martinis, and a Spanish wine list stand at the ready to pair with the extravagant meal.

From the owners of Michelin-starred Indienne comes this modern Middle Eastern restaurant, complete with a rooftop patio with incredible views of the skyline. Start with a classic hummus, made with charred green chickpeas and dressed with zhoug, za’atar and olive oil. Then dive into the grilled section of the menu, with items like maitake mushrooms with charred yellow pepper and Meyer lemon, or the Turkish-inspired lamb Adana kebab, made with minced lamb leg threaded onto a skewer and dusted with sumac. The cocktail menu is inspired by the Arabic numbers one to nine, each representing a different facet of Middle Eastern culture, with ingredients like turmeric-infused tequila, Arabic coffee, and Mejdool date-washed Japanese whisky.

French is the language of love, so what better way than to set the mood than taking your sweetie to Marchesa, a modern French and Italian restaurant in River North complete with its own Champagne cave? While you’ll find classic French dishes like steak frites and escargots every day, consider splurging for the caviar flight or adding shaved black truffles to any dish for a special occasion.   

Open since 1988, this Lakeview classic goes heavy on the Nonna vibes. Warm lighting, white tablecloths, and copious bottles of wine add to this charming Italian restaurant’s cozy atmosphere. Start with hand-rolled beef and veal meatballs before tucking into a giant bowl of rigatoni bolognese or braised beef short ribs. End on a sweet note with the chocolate bread pudding.

This Logan Square mainstay is a destination for anyone searching for seasonal and market-driven food in this effortlessly cool, inviting space. Though the brunch crowd is legendary, chef Jason Hammel’s  award-winning restaurant has beautifully plated options that feel innovative yet still comforting at any time of day. Try the pasta “yia yia” with feta, garlic, brown butter, and cinnamon; a classic roast chicken with panzanella and anchovy aioli; and popcorn creme brulee for dessert, served alongside inventive cocktails and local beers.   

The sultry, swanky, and glitzy vibe is just right at Rooh for a special date night. Even better: the fine dining menu offers myriad choices for all types of eaters, whether you’re a carnivore or a vegan. Definitely don’t miss one of the most unique cocktail programs in Chicago; it’s inspired by the six tastes of the ancient Ayurvedic wisdom — sweet, salty, sour, bitter, pungent, astringent.

Arguably the best rooftop dining in Chicago, Cindy’s Rooftop boasts killer views of Millennium Park, the Art Institute, and Lake Michigan under a stunning glass dome. Sip on beautifully crafted cocktails while sharing romance-enhancing bites of a shellfish tower or porterhouse au poivre for two, and be sure to build in extra time to explore the rest of the Chicago Athletic Association space, including an energetic Game Room, the distinguished Cherry Circle Room, and the cozy Drawing Room. 

Featuring live music on weekends and seasonal offerings throughout the year, it’s no wonder that Vincent is a poorly-kept secret among Andersonville residents. Billing itself as a “New American bistro,” this cozy neighborhood gem offers mussels several ways, a thick bistro burger with sharp Cheddar and caramelized onions, and plenty of French and Italian wines by the glass (and bottle). Come for a convivial date night in a warm space with a personal touch. More information here. 

Helmed by three chefs who’ve worked in Michelin-starred kitchens, this light and airy neighborhood wine bar is turning out smash hits all day, every day, so there’s no excuse not to squeeze in a date night (or morning, or afternoon), even if you and your beau are busy bees. Pick from coffee and savory scones on weekday mornings, or shared dinner plates of burrata drizzled with Madeira syrup, fried quail with togarashi aioli, and Catalpa Grove pork chop with fried green tomatoes in the evenings.  You’ll also find fun dishes like fried chicken banh mis for weekend brunch and shareable charcuterie boards to go with gin martinis during happy hour.

There’s a reason why Kasama has garnered critical acclaim and a legion of devoted regulars—it’s simply excellent, from its beautiful pastry case full of treasures like ube and huckleberry Basque cake to its thoughtful Filipino American tasting menu. This light and plant-filled Ukrainian Village restaurant—run by husband-and-wife team Tim Flores and Genie Kwon— feels like returning to a dear friend’s home for an overdue catchup, making it the ideal place to connect with someone you love.

This sultry, dimly-lit, speakeasy-style steakhouse may be a tough table to snag (though we do have some tips), but if there was ever a time to pull out all the stops, this is it. Your patience will be rewarded by a truly romantic evening with steak tartare, truffle mac and cheese, steak and plenty of Old Fashioneds in a sultry space dripping with low-hanging chandeliers and plush banquettes. 

This unassuming French bistro is a masterclass in cozy, romantic vibes. Dim lighting indoors and a patio strung with twinkling fairy lights set the stage for unfussy French fare done with excellence. Start with a freshly baked pain et beurre served with garlic confit and seasonal compound butter, French onion soup, or escargot. Then, order the steak frites with a side of gratin de macaroni or the cassoulet, featuring duck confit leg, pork belly, Toulouse sausage, lardons, and white beans. And to end dinner on a sweet note, don’t miss the pain perdu, a bread pudding with figs, brown butter, caramel, and Chantilly cream.

Hidden behind the facade of Moon Palace is Nine Bar, an Asian-inspired, speakeasy-style cocktail den in Chinatown. For the last 30 years, Moon Palace owners Jennifer Wang and Zhong Pei have built community around great food and drink. Now their daughter Lily Wang and her partner Joe Briglio have re-concepted, making the front an express window and the back a cocktail bar. Tap into history through the Nine Bar mai tai, inspired by Wang’s original concoction, or the mapo fries, which pay homage to Pei’s beloved mapo tofu. More information here. 

The best seats at Paul Virant’s West Loop temple to okonomiyaki are at the counter that faces the giant griddle that runs along the whole space. The restaurant’s name means “foreigner,” but cuddling up with your date while savory Japanese pancakes are cooked right in front of you makes for a decidedly familiar date night indeed.  Save  room for kakigori, a Japanese-style shaved ice with toppings like yuzu syrup, coffee jelly, and chocolate cookie “ears” that help the dessert resemble a bear.

If the critical acclaim isn’t enough to persuade you to visit Erick Williams’ Hyde Park restaurant, then the Southern American menu will. Expect familiar favorites like a comforting gumbo with chicken, andouille sausage, and Carolina Gold rice; fried green tomatoes; and hearty mains like a 16-ounce, bone-in pork chop with smothered cabbage, candied squash, and pickled peppers. Finish it all off with a homemade banana pudding or a slice of carrot cake. More information here.

It can be hard to open up, but chef Carlos Gaytan’s deeply personal Mexican-French menu might just inspire you to reminisce about  the memories that matter most. Share the mejillones and order extra bread to dip in the delicious sauce, or go all in on the signature cochinita pibil, which bears Gaytan’s mother’s stamp of approval. And don’t miss the whimsical seasonal desserts shaped like fruits or snowmen.

Luxuriating in the plush booths at Ciccio Mio will make you feel like the main character of a rom com set inside the Scorsese universe. Whether you’re dipping truffle mozzarella sticks in red sauce, twirling pappardelle with prosciutto and peas, or slicing into a juicy pork loin saltimbocca, you’ll enjoy the theatrical energy at this River North restaurant, from its gilded portrait frames to its tuxedo-clad servers.

Restaurateur Amy Morton and James Beard Award-winning chef Debbie Gold team up again to bring a bit of unconventional French-Moroccan flair to the north suburbs. There’s a lot to feel good about  here, from the playful menu to the focus on sustainability.  Go early for raclette by the piece, and entrees like a  classic skate wing with almonds and brown butter or brothy mussels in a spicy red harissa broth. More information here.