This City Has Got the Ultimate Bloody Mary Bar Crawl
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 mini dessert selections to pretty much guarantee you leave in a bubbly mood. If you’re a bit hungrier, they have a full raw bar -- we recommend trying their raw bar sampler plate.
Vietnamese cuisine with a romantic French twist
Don't let the French décor fool you: You'll be dining on delicious (and authentic!) pure Vietnamese cuisine (get the goi bun so, goi cuon, pho, bo sate, and ca nuaog), but you'll also be able to pretend you’re in the South of France sipping on wine. Snag a seat on the romantic patio upstairs if you and your date want to people-watch the notorious Rush Street, or stay inside under the calming shadows of glorious palm leaves. Either way, you and your date win.
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.
Three floors of music, dancing, cocktails, and delicious food
Celeste is so darling and intimate, it's almost too perfect. There are 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 Cryin’ in the Rain, Witchcraft, and Walk a Green Mile. Maybe do a date on each level?
You can't go wrong with cheese and live music
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 an acoustic flamenco guitar.
A dark palace of protein straight out of Prohibition
Sexy. Unexpected. Intriguing. Everything from the atmosphere, to dinner, to dessert and drinks will win you over at Bavette’s. Kudos to changing the environment from the traditional steakhouse atmosphere (which is so boring and over). The ambiance 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) -- and they’ll even split the plates for you.
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, focaccia, and burrata pizza. Wine should be your drink of choice here. Pro tip: If you want to try it but really hate waiting, 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 Mezcal Corpse Reviver, 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 -- sort of a decadent romance situation. 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 carefully crafted drinks. The bone marrow is something to order for sure, as are the gnocchi, charred Brussels sprouts, and chocolate cream pie. We recommend the Bee’s Knees, Bar Germaine. and Lion’s Tail for craft cocktails, too. Beware, the food is rich.
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.
Fine local cuisine and microbrews in a vintage-chic space
TWO sources its goods from locally trusted Midwestern farms, and adds a unique twist when they arrive (so the Midwestern fare doesn’t get boring). This results in stuff like lamb belly, duck egg fettuccine, bacon jam, and bread pudding. This dining spot is quaint, impressive, and light-hearted to the core. Oh, and yes, the booze and microbrews follow the local theme, too.
Perhaps the best late-night menu in Chicago
Though Presidio’s extensive dinner and cocktail menus absolutely bear mentioning, we recommend strolling in fashionably late after catching a movie or show and partaking in their special late-night menu. If you’re planning on kissing anyone after dinner, though, you might want to forgo sampling their 12 different varieties of fernet.
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 Lincoln Park’s Boka. The brick-walled interior, leather seating, and amazing dishes (Order the beef tartare and seared scallops or regret it forever) will have the one-percenters envying you for once.
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 beef tenderloin 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.