The Most Romantic Restaurants in Chicago
Romance al fresco.
As the city slowly continues to reopen this month, Chicagoans from Rogers Park to South Shore are itching to stretch their tired shelter-in-place legs. And for those of us partnered up, treating your quarantine ride-or-die to a (safely socially distanced) night on the town might just be the perfect excuse to get back out there and show your neglected local restaurant some much-needed love. And honestly -- if your relationship is still intact after all these months in the apartment bubble, y’all both deserve an evening of tasty food, excellent drinks, and friendly hospitality.
Reserve a seat on the sunny patio and prepare to dive headfirst into Chef Giuseppe Tentori’s enticing raw bar: East and West Coast oysters plucked fresh from the depths, tender tuna poke dressed with mango, cucumber, and black sesame, chilled mussels and clams, plump lobsters, juicy crab legs, and so much more. Smoked fish, luxe caviar spreads, and hearty mains like seafood cavatelli and whole-roasted Steelhead trout are on deck to round things out.
Had to cancel your romantic Parisian getaway this summer? Tout baigne -- head over to this Lincoln Park gem and recreate the magic with all the trimmings of a traditional French bistro. Greenery-strewn patio strung with shimmering fairy lights? Check. Hefty cheese plate kicked off with violet mustard, house pickles, fruit preserves, candied pecans, pink peppercorn honey, and grilled sourdough? Check. The best pomme frites this side of the Seine? Double check. Bon appetit.
Looking for the ultimate cabin fever cure? You’ve found it. This sleek indoor-outdoor Navy Pier addition currently holds the title of the country’s largest rooftop bar -- at least according to the Guinness Book of World Records -- and even if size isn’t your thing, there are still plenty of reasons to go. Namely, delicious cocktails, panoramic lakefront views, and a tip-top roster of shareables like hickory smoked chicken wings, tuna poke bowls, and creamy avocado hummus.
This innovative Bucktown stunner pairs expertly crafted cocktails with all the comforts of American-style Chinese food prepared with cheffy know-how and ultra-fresh ingredients. Think: pillowy crab rangoon, wontons stuffed with pork, ginger, garlic, Thai chili, and black vinegar, crispy tofu doused in housemade sweet and sour sauce, dan dan noodles with ground pork and zesty Szechuan peppercorn, and all the warm almond cookies you want. Add a few stellar drinks and a reservation for two on the sweet new sidewalk patio and you’ve got one hell of a date night, my friend.
A sexy speakeasy ambiance sets the tone at this lauded chophouse, complete with classic cocktails, huge hunks of prime beef, mouthwatering traditional sides with a twist, and a dimly lit, uber-romantic patio for all your date night needs. Snag a reservation online and go Dutch on a 22-ounce dry-aged bone-in ribeye accompanied by a selection (or three) from the bar’s stacked martini menu.
Say hello to Lettuce Entertain You Enterprises’ newest baby, a glistening waterfront seafood emporium where the neighborhood’s see-and-be-seen crowd slurps down chilled oysters laden with tart yuzu granita and other oceanic delights -- not to mention choice steaks, pastas, and cocktails -- while basking in the late summer sun and admiring the lapping river below. Sounds like the perfect afternoon escape? We thought so.
This long-revered Mediterranean-influenced fixture from One Off Hospitality has held it down as one of the area’s go-to date night spots since opening its minimalist doors back in 2003, well before many of us could even define romance. And not much has changed -- the wine list is still spectacular, the chorizo-stuffed medjool dates are still iconic, and a reservation for the intimate front patio is still highly coveted.
Neighborhood folks in the know have long flocked to this West Town charmer, beloved equally for its seasonally driven lot of fresh, hand-formed pasta dishes and rustic secondi courses (hello, string cut black spaghetti with mussels, clams, shrimp, and calamari) and its dreamy garden patio. And thanks to carefully spaced tables, Piccolo’s picture-perfect al fresco experience is even more intimate these days. Take full advantage of this bizarre 2020 silver lining and make your reservation ASAP.
If you thought Ralph Lauren only sold polos and teddy bear sweaters, think again. This Streeterville classic has been around for ages, supplying wayward shoppers with the fuel they need to keep those credit cards swiping. Much like the prep-centric brand, the sidewalk patio here is comfortably upscale with a hint of old-school class -- white tablecloths, navy blue garden chairs, champagne flutes brimming with white peach bellinis, and overstuffed Maine lobster rolls centered proudly on elegant dishware.
Armed with one of the most lush, gorgeously-outfitted, and spacious rooftops in town, this Mediterranean-inspired eatery from Top Chef alum CJ Jacobson was more than primed for an all star post-shutdown comeback. Share in the spoils of success with crave-worthy mezze like crispy short rib hummus, Big Eye tuna carpaccio, Jerusalem bagel with whipped honey labneh, char-grilled lamb chops, skirt steak shawarma, and plenty more, all washed down by one of cocktail maven Liz Pierce’s intoxicating creations.
While this West Loop hideaway’s cozy upstairs lair is perhaps its most conventionally romantic location, the sidewalk patio’s adorable Parisian vibe -- blue and white striped awning jutting out from a painted baby blue facade, dark wood bistro tables, white canvas umbrellas -- is late afternoon wine date gold. Reserve a spot, order a bubbly St. Germain fizz and some foie gras with cherry jam, and indulge in a little much-anticipated people watching while the world continues to spin on around you.
This celebrated Bridgeport gastropub’s serene backyard is the stuff dreams are made of... especially if your dreams generally involve chef Kevin Hickey’s unbelievably rich signature Duck Inn dog, a combination of beef and duck fat smothered in Chicago-style fixings and served with appropriate gusto on a poppy seed brioche bun. The covering of leafy green trees, broad tables, and twinkling string lights only add to the cuisine’s established ambiance.
This ever-evolving fine dining experience from the muti-Michelin-starred Alinea Group has all the makings of a special night out. Always creative and dependably delicious, the ticketed prix-fixe menus highlight culinary traditions, trends, and curiosities from around the globe. The current season’s theme is Mexico City, so expect cleverly arranged plays on street food staples like tuna tostadas, shrimp aguachile, pork butt al pastor, roasted plantain cake, and more.
Chef-owner Erick Williams seriously upped Hyde Park’s restaurant game when he opened this welcoming, upmarket outpost back in late 2018. The sprawling sidewalk cafe is the optimal setting upon which to explore Williams’ thoughtful menu, following along as he traipses through Southern cuisine’s multi-faceted history while also managing to throw in a few modern touches. Case and point: "liver & onions,” a cheeky ode to the family-friendly fixture involving chicken liver mousse topped off with sweet onions and bacon.
After six full years of bated breath and hungry bellies, this iconic celebrity-endorsed restaurant and hotel has finally graced Chicago with its presence and, boy, was the wait ever worth it. The powers that be are rolling out the dining program slowly starting with the expectedly polished and airy rooftop, an assortment of delectable small plates drawing on Japanese and Peruvian influences (two words: Nobu tacos), an expertly curated sake collection, and service on par with Tokyo’s poshest hotel bars. And while the delicately carved sashimi and miso marinated Alaskan black cod might initially steal your attention, don’t sleep on the cocktails -- like the Nobu Sidecar, Iwai Tradition whisky tempered with yuzu and Torres Magdala orange liqueur poured over hand-carved ice.
This all-too-often overlooked gem has been quietly peddling a steady stream of refined Italian comforts alongside a Bible-thick list of top notch vino since 2008. Grab a coveted patio seat -- now extended even further onto Wells Street -- and ready your tastebuds for an intoxicating, Eat Pray Love-style journey through the rolling hills of Tuscany, the canals of Venice, and the manicured vineyards of Piedmont by way of River North.
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