When it comes to date night, sometimes you want to pull out all the stops. Maybe a fancy 10-course dinner, a limo ride, and a huge bouquet of roses. But sometimes, you want something a little more low key. Those kind of nights call for a place that’s cozy, romantic, and maybe a bit under the radar. Luckily, Chicago’s got plenty of those.
Explore the city’s most intimate hidden gems that are perfect for an unforgettable date night in Chicago.
The Grotto at The Robey
The Robey is one of the hippest spots in the already-hip Wicker Park/Bucktown area. It’s also the tallest building around, which means the views from the 13th floor rooftop bar are totally unobstructed. The Up Room, an indoor/outdoor cocktail lounge, is already a solid date night spot — but The Grotto is even better.
That’s the rooftop’s secluded, private alcove that’s nestled under the hotel’s historic bell tower. It’s outfitted with chandeliers, cushy benches, and space heaters for the colder months. Not to mention the jaw-dropping, panoramic view of the skyline in the distance.
You’ll need to book The Grotto in advance, and a minimum food and beverage package applies. Visit The Robey website for more details.
River domes at City Winery at Riverwalk
When the weather starts to cool, City Winery sets up their popular River Domes outside their location on the Chicago Riverwalk. These heated domes keep you warm and dry, plus they offer gorgeous views of the Chicago River. They’re extra magical at night — you’ll feel like you’re inside a snow globe surrounded by shimmering lights.
All domes include a Bluetooth speaker to play your own tunes and a pile of blankets to add to the cozy vibes. The price includes a carafe of wine per person and a charcuterie and cheese board — is there a better date night food than wine and cheese? You can also order from City Winery’s full menu, including salads, pastas, entrees, and more.
City Winery at the Riverwalk is located on the south bank of the Chicago River between Dearborn and State Streets, 11 W. Riverwalk South. Reservations can be made online through OpenTable.
The Ladies’ Room at Fat Rice
Fat Rice is an acclaimed Macanese restaurant in the trendy Logan Square neighborhood. The spot’s been so successful, they they’ve expanded to add a popular bakery next door — and a secret, reservation-only speakeasy in the back.
To find The Ladies’ Room, head into Fat Rice Bakery and find the curtain near the pastry shelves. Once inside, the bright and cheery bakery gives way to a dimly lit cocktail bar. The sultry space is inspired by a Chinese gambling hall, which means lots of Asian-inspired decor, red lighting, and games at each table.
The drink menu is filled with non-traditional cocktails, like the “Teas for Two” that come boozy and piping hot in a huge vintage teapot. This acclaimed spot is the perfect place if you’re looking for something unexpected and a bit adventurous. The Ladies’ Room is located at 2957 W. Diversey Ave. in Logan Square.