Whether it’s for that special February holiday or just because, the Windy City abounds with romantic restaurants.
A sexy seafood spot in River North serves exquisite oysters and liquid nitrogen cocktails. In the West Loop, a Croatian Italian restaurant steered by a Top Chef winner has plenty of cozy corners for cuddling. A flamenco guitarist serenades diners at a 50-year-old fondue favorite in Lakeview.
Chicago has plenty of options for your next date, whether you’re looking for a casual evening of quiet conversation or a show-stopping display of culinary wooing. Go ahead and put down that heart-shaped chocolate box and book a table at one of these 12 romantic restaurants instead.
For a first date
Ada Street (Wicker Park)
Secluded, with no frills and plenty of moody candlelight, off-the-beaten-path Ada Street offers an ideal recipe for a first date. Sip on cocktails including the ultimate rendezvous drink, “perfect strangers,” made with cava, aperitif wine, and herbal bitters. The restaurant is on the smaller side, only seating a few dozen at two-tops and the bar, so a reservation is highly recommended. Pair your sips with bites from an enticing American-meets-Mediterranean menu, such as tender lamb ribs with crispy garlic and fluffy brioche doughnuts for dessert. If your date is going exceptionally well, stretch the evening with a show at nearby The Hideout.
Kumiko (West Loop)
The Japan-inspired bar at Kumiko. | Credit: Sammy Faze
There are cocktail bars, and then there are serious cocktail bars. Kumiko falls into the latter category. A Japanese-inspired spot from mixologist Julia Momosé, Kumiko is all about attention to details, from the hand-carved ice to the delicate glassware. What Kumiko lacks in space, it makes up for in style. Consisting of a small seating area and intimate bar, the room is filled with elegant accents, such as geometric patterns in the wood partitions and brass screens on the bar that each have their own hidden meaning. The food menu takes cues from Japanese cuisine, with offerings such as the wagyu katsu sando (panko-breaded and fried beef nestled between two slices of toasted white bread) and toasted koji ice cream. Kumiko is the ultimate drinks date spot.
For a second date
Geja’s Cafe (Lakeview)
Geja’s Cafe is for those who subscribe to the philosophy that the best date nights are slathered in cheese. The old-school fondue parlor has served its signature melty meals—that’s Gruyère cheese fondue served with bread, vegetables, and fruits—for half a century. Geja’s is equally adored for its charming ambiance. The restaurant features a live flamenco guitarist four nights a week, secluded booths separated by curtains, and outdoor pergolas with fire pits—all ideal for getting to know your companion better.
For an intimate and cozy night out
Rose Mary (West Loop)
Hanging plants deck the cozy interiors at Rose Mary. | Credit: Kinship
There are many perks that come with winning a season of Top Chef, and one of them is steering the restaurant of your dreams. Chef Joe Flamm did just that in 2021 when he opened Rose Mary in the West Loop. The restaurant pays homage to all things Adriatic, reflected in dishes such as beef burek, a flaky pastry filled with meat and cheese. There are plenty of cozy corners to be found in this large restaurant, from at the chef’s counter to under the many hanging plants to at the end of the wood bar. The entire space channels a Mediterranean escape, so go ahead and get away.
For an anniversary or romantic milestone
Brindille (River North)
Brindille takes upscale French food to a new level with its sleek and sophisticated dining room. James Beard Award-winning chef Carrie Nahabedian offers an assortment of classics, from Dover sole meunière to lacquered aged duck breast, served alongside a wine list that spans all of France. The most difficult decision you’ll have to make all night will be whether to start with oysters or caviar. But this is a romantic occasion, so splurge for both. Brindille also regularly hosts afternoon tea with a selection of pastries, finger sandwiches, and specially priced Champagnes, which is excellent as a fun daytime date.
Sepia (West Loop)
One of Chicago’s fanciest date night spots has an especially well-earned reputation. Chef Andrew Zimmerman’s menu of contemporary American cuisine is stunning without being stuffy. Start with crab chawanmushi étoufée before diving into venison shabu-shabu or steelhead trout en croûte. Sepia’s dining room may have been around since 2007, but it has timeless elegance down to a science. Dine under one of the crystal chandeliers or at the marble bar. There are plenty of secluded enclaves tucked within the exposed brick walls, which make for an especially romantic evening.
Alla Vita (West Loop)
Alla Vita’s intimate dining room. | Credit: Boka Restaurant Group
One of the newest jewels in the BOKA Group’s crown is an Italian masterpiece in the West Loop. Acclaimed chef Lee Wolen designed a shareable menu that can be dressed up or down, depending on your mood. If you’re looking to splurge, go for the kampachi crudo and Alba white truffle tagliolini. If you’re keeping it casual, there’s pizza. Snagging a table at Alla Vita can be trickier than getting a quick burger at Au Cheval. Hopeful diners line up on the sidewalk before the restaurant opens to secure a seat at the bar. Reserve early to take in the splendor of the lush dining room, with its fabric-covered ceiling and wooden archways.
For group dates
Bar Mar (River North)
José Andrés’s elegant seafood spot is the perfect group date destination, thanks to its impressive tapas lineup and awe-inspiring interiors. Starting with the giant octopus art installation suspended from the ceiling, Bar Mar aims to wow diners with opulence. Ideally, every meal should start with oysters, but especially when dining at Bar Mar. Here they are served with black pepper and fruit vinegar. Follow it up with something sexy, such as the ceviche classico with leche de tigre, or a playful plate, such as hamachi cones. Either way, you’re in for a special dining experience that channels coastal vacation vibes, though floor-to-ceiling windows overlooking the river will remind you you’re still in spectacular Chicago.
For an evening of eatertainment
Dusek’s Tavern (Pilsen)
Dinner and a show is a tried-and-true date-night combo: Dine at Dusek’s, then head upstairs for a concert at historic Thalia Hall, a former opera house turned concert venue. Dusek’s is known for its cozy vibes and comfort food, such as sweet and sour eggplant and heritage pork chops with apples and squash. The tavern also has an extensive beer menu, including its own house pilsner, plus a seasonal cocktail menu. Make a reservation to snag one of the tables in the dark and moody dining room.
For an adventurous and transportive date
El Che Steakhouse & Bar (West Loop)
Dinner and a show are on the menu at chef John Manio’s El Che Steakhouse & Bar, where your dry-aged ribeye is cooked on a custom 12-foot grill in the open kitchen. Take date night’s heat up a notch by watching the flames fly from a safe distance while sipping on a South American red wine. A far cry from your typical steakhouse, El Che teems with tropical plants and wood accents. The most beautiful seat in the house may be at the black marble bar, but if you want front-row seats to the show, opt for the chef’s counter, which offers a ten-course tasting tour of Argentina.
Obelix (River North)
One of the most exciting new restaurants to open in Chicago in 2022 came from the same family behind one of its oldest. It took nearly thirty years for the Le Bouchon team to open a second spot, and it was worth it—much like a long-anticipated date. Impress your dining companion with Obelix’s modern riffs on French dishes, such as foie gras macarons, lobster crepes, and tempura-fried squash with tapenade aioli. You’ll find white tablecloths on every table and an extensive French wine list to complement your transportive meal.
For a proposal-worthy place
Gibson’s Italia (West Loop)
Gibson’s Italia may have a 20-page wine list, truffle lasagna, and massive platters of Alaskan king crab. But what really wows diners here are the views. Overlooking the Chicago River flanked by skyscrapers, this contemporary, Italian-accented steakhouse is a stunning setting for dinner for two. Spanning three levels, it’s safe to say there’s not a bad seat in the house. The spacious dining room features plenty of white tablecloths ready for a romantic evening. There’s also a private dining area and enclosed roof deck. The only thing that could rival this view? A diamond.
Sarah Freeman is a food and drink writer by day and the host of one of Chicago’s most popular pop-up markets by night.
Tried them all? Check out other options here.
