A versatile date spot for seafood and plush seating
Ask to be seated in the back dining room, as the lighting and overall mood is more intimate and romantic, or go the casual date route by snagging a spot at the oyster bar -- East Coast oysters are the winners here. Order at least four oyster po-boys (because you’ll regret it if you don’t), shrimp bruschetta, and the Maine lobster roll, but only if you don’t mind being really spendy.
Oysters and bubbly in an unpretentious atmosphere
This is the kind of surreal gem you won’t ever want to leave: a picture-perfect atmosphere with enough Champagne and amazing macarons and petit fours to pretty much guarantee you leave in a bubbly mood. If you’re in the mood for oysters, they have a chef-curated sampler available as well.
One of the most romantic patios in all of Chicago
Do you have a spot yet? You know, like your “go-to” spot that you only go to with a significant other? Well, now you will. Bundle up and request a seat at the beautiful gated garden patio, gleaming with hanging lights and planted flowers. As a bonus, the tables outside are far enough apart from each other to allow some private intimacy.
The largest rooftop restaurant and bar in the country
Yes, Offshore Chicago is located on Navy Pier. More than that, it’s located at the back of Navy Pier, which means that if you’re trying to go there on a Friday or Saturday night, you’ll have to push your way through throngs of tourists to get there. But trust us, the trek is worth it. Offshore Chicago is paradoxically both incredibly large and unbelievably intimate, whether you’re dining in its eclectic indoor area, or whether you’re outside on the roof. The smoked chicken wings and the snapper & shrimp ceviche are incredible, but the real star of the show here is the cocktails. They’re guaranteed to make you feel like it’s summertime even if the rest of the city is blanketed in a three-inch-thick layer of ice.
Three floors of music, dancing, cocktails, and delicious food
Celeste has three floors and all of them have a different menu and a slightly different mood -- there's 1) the downstairs, which is loud and energetic with good music, especially on the weekends, then 2) the glamorous, 1920s-style supper club in the Deco Room, which is softer and more sensual, making it the perfect dining spot (they don’t have too many tables up there, so it’s very personal), and finally 3) the garden rooftop, which is all kinds of luxurious. The drink menu is expansive and almost overwhelming, but we loved the Cucumber Collins and the Syd & Nancy.
Fondue and live music
Geja’s Cave has been a Valentine’s Day mainstay for over 50 years, and for good reason. Even though this place is small, you’ll immediately feel how special it is from the moment you take your seat. Focused on fondue with a side of sexy, Geja’s Café isn't just a fondue place, it's a fondue place with flamenco guitar.
A dark palace of protein straight out of Prohibition
Everything from the atmosphere, to dinner, to dessert and drinks will win you over at Bavette’s. Instead of the standard squeaky-leather steakhouse vibe, the ambiance at Bavette’s feels dark and mysterious, with a speakeasy-esque, old Prohibition feel. You’ll delight over the Old Fashioned’s and glorious assortment of meats on the menu, and then you’ll go home and... keep talking about them.
Luxe Italian fare with a lakeside view
If you or your date ever get tired of Chicago's wonderful, iconic, timeless, romantic, perfect, architecturally acclaimed skyline, hit up Spiaggia, which throws down gorgeous views of Lake Michigan and Oak Street, which you can take in while downing classic cocktails, Italian beers, and expressive wines.
Homemade Italian pasta plates you can share
How the outside of Piccolo Sogno deceives! The food is good enough to keep you coming back year round, and the garden patio is one of the best in the city. This charming restaurant is perfection for sharing every course (so you can eat that much more). Also, there are appetizer portions available for their pasta dishes for folks who want to try a bit of everything.
A super-popular fine dining wunderkind
Blackbird puts its highly rated Midwestern cuisine on display with artful presentations and small portions, and its food is pretty fantastic -- and actually filling. This urban joint screams city chic with a minimalist interior and terrific wine and food menus. The art in the restrooms might even serve as an aphrodisiac.
Unpretentious and design-forward date night spot
Classically Ralph Lauren in every way, this romantically traditional restaurant has a definite old-fashioned feel, but not in a stuffy-cigar-smelling-steakhouse-and-leather kind of way. It creates a sense of nostalgia from the paintings on the walls, to the standout fireplace and charming atmosphere. You’ll feel like you’re in a super well-designed living room where no one wears jeans, and everyone is happily drinking martinis. Come for lunch or drinks and lots of people watching.
A great no-reservation date spot... if you can get in
This minimalist Mediterranean restaurant might not be everyone’s cup of tea, but if you’re an adventurous couple, it’s definitely worth the possible wait. (Avec doesn't do reservations, and it’s quite possible you won’t get seated right away at the single community-style table.) Break the mold with Avec’s famed dates, but we recommend you try the pork shoulder for your main course. Wine should be your drink of choice here. If you want to avoid the wait, arrive at unusual hours (like early brunch or weeknights).
Perhaps the most romantic BYOB restaurant in Chicago
This forward-thinking spot is a high-end version of a BYO joint. Its multi-course tasting menus are super impressive even just to look at, let alone TO TASTE. The BYO definitely helps with the bill, since it is on the pricier end, but it makes for a chic and romantic night nonetheless. Guys, this could even be a propose-worthy spot, just saying. It’s creative, exclusive, and more than memorable. Make reservations well in advance. Pro tip: There’s a wine shop next door where they’ll help you pick something to bring along for dinner.
A quiet spot specializing in meticulously crafted classic cocktails
The more relaxed, dim, and inviting upstairs of Maude’s Liquor bar is the perfect hideaway for a pre-, post- or just-dinner date spot. It’s got this sort of wicked, cloak-and-dagger vibe going that’ll definitely get you excited about your night. Huddle together in their upstairs room and deem yourselves do-not-disturb. When you come up for air, take a sip of the St. Germain Fizz, Boulvardier, or some delicious wine pours.
A 130-seat cross between chic restaurant and laid-back tavern
The thoughtful, dark, candle-lit restaurant is super-moody. Also cool: the bar and dining rooms give off different ambiances (which is nice if you’re planning on spending some time there). The bar plays louder music, while the dining hall allows you to sink into seclusion with your date, enjoying the food and expertly crafted drinks. The bone marrow is something to order for sure, as are the gnocchi, skillet cornbread, and chocolate cream pie. We recommend the Bee’s Knees, Bar Germaine. and Tokyo Old Fashioned for craft cocktails, too.
A full skyline view from the heart of the city
Fresh air and crisp white sails make for a stunning forefront to a beautiful Chicago backdrop. This rooftop lounge lives up to its name -- it certainly takes your night to an escape-y place. Definitely try the signature cocktails -- where else can you have a chef design your drink? Nowhere, that's where else.
An easygoing vibe and blow-your-mind flavor makes Sun Wah a perfect date spot
Before we go any further, know that Sun Wah isn’t as cozy or intimate as some of the other options on this list. But in terms of price, flavor, and fun, it’s hard to beat. Order the Beijing Duck Feast. It’s an off-menu item, and it’s legendary. Chefs will bring out a whole roasted duck, carve it up for you, then use it to prepare a huge variety of different dishes. Order it for a date, and be prepared to bring a few meals worth of leftovers back home with you.
Fine local cuisine and microbrews in a vintage-chic space
TWO sources its goods from locally trusted Midwestern farms, and has a constantly rotating menu depending on what’s in season. This results in stuff like grilled octopus, duck egg fettuccine, and honey cheesecake. This dining spot is quaint, impressive, and light-hearted to the core. Oh, and yes, the booze and microbrews follow the local theme, too.
An unforgettable, affordable culinary date in leather seating
So you can’t afford to take your date to a $300 dinner at Alinea? No worries. Head next door to Boka's brick-walled interior, leather seating, and amazing rotating menu. Just make sure you order their beef tartare-inspired dishes and the kampachi crudo if they're available.
High-end Italian food and wine nestled right in the heart of River North
Don’t overlook this River North gem. The decor is a nice mix of modern and classic, and is surprisingly inviting for a fancier Italian restaurant -- especially downtown. We highly recommend the wagyu carpaccio, as well as the orecchiette tartufate. Just remember to pay your date some attention in between your gigantic mouthfuls of pasta and swigs of wonderful Italian wines.