BY TAYLOR WADE
Choosing from the unlimited restaurants Chicago has to offer is an overwhelming task, especially when you are trying to make a good first impression. We carefully selected Chicago's best restaurants for crafting the perfect date night based on atmosphere, crowd, menu, and neighborhood.
The space, lighting, and overall atmosphere is excellent inside this Mexican inspired restaurant right in the heart of Lakeview. Choose from the abundance in margarita varieties, categorized by "Sweet," "Spicy," and "Smoky" – my personal favorite is the spicy Margarita El Fuego topped with jalapeno foam. The interior is beautiful – the walls are lined with open-air garage doors among rustic reclaimed wood and sensual fireplaces. It will feel like you're relaxing on a sunny beach and the coziness of a mountain cabin all in the comfort of Chicago.
Address: 2901 N Sheffield Ave, Chicago, IL 60657
If your date is an ardent ale drinker, we highly recommend the Half Acre Tap Room. However, DryHop Brewers is a craft beer alternative that isn't quite so niche, mostly because of the small plate and full bar options. You can't go wrong by mixing innocuous small talk with a flight of in-house brews; that's the kind of disarming blend that guarantees a second tryst.
Address: 3155 N Broadway
This Lakeview BYOB restaurant is a meat lover's dream offering eats such as large cuts of Argentinian beef topped with chimichurri. Appetizers and entrees include deep-fried empanadas stuffed with beef, chicken or ham and cheese; matambre (rolled veal cooked with vegetables); and milanesa a caballo (fried breaded beef topped with two eggs).
Address: 3763 N. Southport Ave
This Lincoln Park oyster bar and East Coast-inspired seafood restaurant gets an A+. Grab a hightop next to the fully-retractable garage door where you can feel the breeze and people watch along Halstead Street. I ordered the rosè Cava and loved how the effervescence perfectly complimented the small seafood plates strewn across our table, including oysters, crab bites and shrimp cocktail. If you're feeling a change in scenery, check out their downstairs space, the Low Tide Lounge.
Address: 1962 N. Halsted, Chicago 60614
I accidentally stumbled upon this gem after a night of beer and wings at the neighboring Bird's Nest – and what a contrast it was! The Monkey's Paw is upscale and sophisticated with the coziness of an apres-ski lodge. The farm-to-table American fare consists of dishes such as Amish chicken, hearty soups, and artisanal cheeses. For post-dinner drinks in a more intimate atmosphere, make your way to the back where you'll find two fireside leather chairs complete with your own library and boardgames.
Address: 2524 N Southport Ave, Chicago, IL 60614
Summer House Santa Monica embodies such an amazing atmosphere: bright, white decor, glimmering lights, driftwood walls, high glass ceiling, and a front outdoor patio. It definitely has a Californian vibe here, yet people aren't walking around in shorts and flip flops. Think business casual when dressing for your date. It features an artisanal bread program, an extensive wine list, fresh-squeezed juices, and Californian-influenced American cuisine with locally-sourced ingredients. I personally love the menu due to it's abundance in seafood – I order the salmon every time. Tip: make a reservation ahead of time as there is usually a long wait list if you just show up.
Address: 1954 N. Halsted St.
Riccardo Trattoria is like a page out of Italy. And why shouldn’t it be, chef and owner Riccardo Michi grew up in his family’s Milan restaurant, and throughout a long and varied career in the restaurant industry, he ultimately settled on opening this place with his wife and sous chef Veronica (plus the wine bar across the street, Riccardo Enoteca). Normally, that’s not the kind of information we bother paying attention to, but in this case that history helps explain why Riccardo Trattoria is able to pull off that classic Italian ambience. It’s casual without lacking in service or quality of food, but at the same time classy without being pretentious and stuffy. Source: The Infatuation
Address: 2119 N Clark St, Chicago, IL 60614
North Pond is the perfect choice for a special occasion. Originally built in 1912 as a warming house for ice skaters, North Pond is situated right on the pond and has a beautiful view of the Chicago skyline. Entrees like Bass and Rabbit will satisfy your taste buds. After you eat, take a romantic walk around Lincoln Park.
Address: 2610 North Cannon Drive, Chicago, IL 60614
BUZZ BAIT TAQUERIA
Buzz Bait feels like an upscale beach shack, replete with barnwood, fishing lure, and earth tones. Take your pick of fish or chicken tacos and don't forget to try their delicious margaritas. Grab a hightop in front of a fully-retracting garage door or enjoy full patio seating right on Wells Street.
Address: 1529 N Wells St, Chicago, IL 60611
The Vig Chicago is a 1950's themed sports parlor in the heart of Old Town with a refined kitchen and classic cocktails designed for the contemporary drinker. Go for the weekend brunch and order the fried chicken and champagne, an odd yet delicious companionship.
Address: 1527 N Wells St, Chicago, IL 60610
Walk through the heavy, red velvet curtains and follow the narrow hallway back to the romantic dining area. New American-Mediterranean meals and craft cocktails are served in a chic candlelit space with a back patio. The food is prepared in small plates, perfect for sharing with your date. Reservations are not allowed except for the 5:30-6:30pm time slot, although you can call one hour before arrival to put your name on the waiting list. Be prepared to wait – it's usually packed. However you can grab a drink at the bar while waiting. One of my favorite cocktails in Chicago is made here: the Raising Hands, Raising Hell, consisting of Lunazul tequila, grapefruit, and turmeric.
Address: 1664 North Ada Street, Chicago, IL 60642
PUMP ROOM AT PUBLIC CHICAGO
Housed in the beautiful historic PUBLIC Chicago Hotel, The Pump Room is easy on the eyes and the taste buds. Prepare to be greeted by the gorgeous molding and elaborate chandeliers of the hotel lobby to the large, oversized light fixtures dubbed "The Constellation" that make up the ceiling of the Pump Room. The menu is created by world-renowned chef and 2011 James Beard award winner Jean-Georges Vongerichten and offers a unique farm-to-table dining experience.
By night, the Pump Room transforms into a supper club recapturing the glamour of the 30’s and 40’s with a modern twist. Offerings include late night tapas style small plates; local, domestic and international draught and bottled beer; exotic, specialty cocktails by their own mixologist, and great music.
Address: 1301 N State Parkway, Chicago, IL 60610
GT FISH & OYSTER
Address: 531 N Wells St, Chicago, IL 60654
THE HAMPTON SOCIAL
The Hampton Social strives to bring the laid back and coastal atmosphere of the Hamptons to Chicago with bright, airy spaces, allowing a pseudo sea-breeze to flow in from Chicago's streets, fresh seafood–try the diver scallops with creole pan sauce, cheddar grits and bacon or an oyster belly o' boy––beach-themed cocktails, and even a swinging hammock for lounging. Every Tuesday through Friday from 3 to 6pm enjoy half-priced pizza and bottles of rose.
Address: 353 W Hubbard St, Chicago, IL 60654
BUTTERFLY SUSHI BAR
With three thriving locations, Butterfly Sushi Bar must be doing something right. This BYOB joint has excellent food and features dishes such as the spicy salmon or scallop maki, green or red curry dishes, and delicious chicken teriyaki. In case your date is vegetarian, they can make most dishes vegetarian by substituting tofu and asking for no fish, eel, and/oyster sauce. There's always a crowd if you go during peak times, so be prepared to wait (my longest wait time was 30 minutes). The constant chit-chat that flutters the place is never too loud and makes for perfect background noise.
West Loop Address: 1139 W Grand Ave, Chicago, IL 60642
Embeya was named Esquire's "Best New Restaurants of 2013". When you walk into Embeya, your date will immediately be impressed by this visually stunning restaurant. The woodwork is so unique and beautiful, but things doesn't stop at decor. Embeya serves progressive Asian food, with options likes Veal Cheeks and Grilled Quail. They also have an extensive wine selection, so make sure to ask your server for a recommendation.
Address: 564 W Randolph St, Chicago, IL 60661
GIRL AND THE GOAT
Stephanie Izard, Chicago native and winner of Top Chef Season 4, has created one of the best restaurants in the city, and the perfect place to take your date. Stephanie personally visits local farms to see how the animals are raised. Hence, if you are looking for a delicious meal while also supporting the local food movement, this is your spot. The menu is divided into three categories: vegetable, fish, and meat, and features wine (which they blend themselves) and beer on tap. It can be difficult to get a reservation, but walk ins are always welcome.
Address: 809 West Randolph St, Chicago, IL 60607
HIGH FIVE RAMEN
High Five is located directly downstairs from Green Street Meats (look for the hand print on the door). A tiny place with less than 20 seats, it's definitely not as roomy as its upstairs counterpart, however, a great place for a more intimate experience as long as you don't mind waiting (tip: pop upstairs to Green Street Meats while you wait). It definitely has a cool vibe – it's located in the basement of a smokehouse and jams out to music featuring strong baselines. Their drink menu includes Asahi beer, sake, whiskey, and sweet cocktail slushies with names such as Coconut Painkiller and Yuzu Last Word. The menu is limited, only offering a menu of high-class ramen noodles.
Address: 112 N Green St, Chicago, IL 60607
City Winery is a live music venue and restaurant coupled into one massive 30,000 square-foot environs complete with an open dining room, a garden courtyard and, yes, plenty of barrels. As they put it, "Wine is made to be consumed with food and thus, we have designed a menu which complements your wine consumption" and we think this is brilliant. The menu draws on Mediterranean history – Italian, French, Spanish and Middle-Eastern cuisine paired with an award-winning wine list of over 400 unique producers from around the world, in addition to the more than 20 in-house produced wines sourced from vineyards in California, Oregon, Washington, Argentina and Chile.
Address: 1200 W Randolph St, Chicago, IL 60607
Chef Marcos Campus brings traditional dishes straight from Spain. His menu takes guests on a culinary tour with cuisine from San Sebastian in the North to Seville in the South. From behind the bar, experience Spanish mixology at its best with over 30 selections of sherry, Spanish-style Gin Tonics, Sherry Cobblers, House Cocktails infused with Spanish flavors, and a wide selection of Spanish beers and wines from small growers across Spain. If you aren't sold yet, the atmosphere also makes this a great date spot due to it's warm festive colors and airy dining room which opens up to the sidewalk.
Address: 1721 West Division Street, Chicago, IL 60622
THE CHOP SHOP
The restaurant, butcher shop, and bar work together to create a seasonal menu featuring prime meats, salads and small plates alongside artisan wines, craft beers, and local spirits in an open and airy space that creates the perfect date environment.
Address: 2033 W. North Ave - Chicago IL 60647
THE DUCK INN
If you've never checked out the Bridgeport neighborhood, you now have a good reason to go. This hidden gem is one of my favorite restaurants in Chicago! It’s housed in a pre-prohibition era tavern that has continuously operated for almost a century and showcases Michelin Rated Chef Kevin Hickey’s signature New American cuisine. They offer a small bar and snack menu for the front lounge/bar and a more traditional menu for the back dining room with first and main courses, a tasting menu and more. This setup is ideal for first dates who want to see if a drink has the potential to turn into dinner. Added bonus: the backyard garden is now open for dining al fresco.
Address: 2701 South Eleanor Street, Chicago, IL 60608
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