Romance in the Windy City. Is there anything more magical?
Check out some of our favorite restaurants and Valentine's Day activities and plan out your itinerary for that special day with that special someone <3
Want even more Valentine’s inspo? Keep exploring:
Photo via Newport Theater
Newport Theater - 956 W. Newport Ave. - Lakeview
Want something on the spicier side this Valentine’s Day? Join Newport Theater for their titillating pole and burlesque show Lovespell. Whether you're pulling up with a partner, a bestie, or just plain solo, make sure you don't forget the dollar bills at home.
Photo Via Alla Vita
564 W Randolph St - West Loop
Many have said that this is the date night spot in Chicago. If you want to give your partner the Valentine's Day dinner of all Valentine's Day dinners, be sure to reserve a table for two at Alla Vita. They've got the ambiance, spectacular Italian food, and drinks that are to die for. What are you waiting for?
Photo via Unsplash / Doğu Tuncer
Ambassador Gold Coast - 1301 N. State Pkwy - Gold Coast
If you're single in Chicago on Valentine's Day, it's probably because the dating pool here is literally terrible. Whether you're happily single, emotionally unavailable, in a never-ending situationship, or just tired of first dates that go nowhere, Love Sucks is the perfect way to spend your V-Day. Strong drinks, good music, and unlimited apps. What more could you need?
Photo Via TUtore cooking school
Tutore Cooking School - 2349 N Lincoln Ave - Lincoln Park
You know what they say about truffles. If you're looking for a more hands-on experience for your Valentine's Day dinner, Tutore Cooking School will teach you and your partner how to prepare a decadent three-course dinner of lobster risotto, braised short ribs with black truffle sauce, and dark chocolate semifreddo. Communication and collaboration (both in and out of the kitchen) are in.
Photo Via Bar Mar
120 N Wacker Dr - West Loop
Enjoy an impeccable Spanish-influenced dinner at Bar Mar. Specializing in little plates made to share, Michelin-star chef José Andrés is serving up a slew of Valentines day specials to share with your beau, including hibiscus oysters and roasted Maine lobster. What's more romantic than slurping on shellfish together?
Photo via Fleurish Chicago
Mesler - 1401 E 53rd St. - Hyde Park
A Valentine’s Day without flowers would be a crime. Join Fleurish Chicago for a flirty, floral day of sipping wine, building bouquets, and chomping on truffles with your loved one. They've put together such an intimate setting that you'll forget you're in public. Maybe one kiss wouldn't hurt...
Photo Via Duck Duck Goat
857 W Fulton Market - Fulton Market
Chef Stephanie Izard has crafted an incredible Chinese-American Valentine’s Day shareable menu that’ll spice up your dinner date and your taste buds. From classic dim sum to new inventive bites, secure your V-Day table at one of Chicago's favorite restaurants for $95 per person.
Photo Via Chicago Artisan Market
Artifact Events - 4325 N Ravenswood Ave - Ravenswood
What better way to tell someone "I love you" than buying them a bunch of artisan trinkets? It's 2026, and believe us when we tell you that this is what the modern lover wants. Featuring over 100 local artists creating everything from candles to comic books to jewelry, you're bound to find the perfect Valentine's Day gift for your special someone at Chicago Artisan Market.
Photo Via Good Ambler Facebook
216 N Peoria St - Fulton Market
Everyone always talks about Valentine’s Day dinner, but what about during the day? Get cozy with cakes, cookies, and of course, chocolates at this Fulton Market chocolatier. A heart-topped latté with perfectly decorated truffles sounds like the perfect way to kick off your Valentine’s Day. If swinging by isn't on your itinerary, they also take pre-orders for picture-perfect bonbon boxes.
Photo Via Lemon Chicago
1600 W Grand Ave - West Town
It’s the perfect day for the perfect cocktail. Lemon was built by artists, and you can totally feel the flair. Not only are the drinks meticulously crafted, but the live music is locally curated for the perfect vibe. They're even hosting an after-hours Valentine's Day dance party. One thing's for certain: Lemon is the place to be!
Photo Via Olio e Piu
445 N Dearborn St - River North
Chef Pedro Cruz presents a delectable Valentine’s Day menu for your romantic evening. Dine on trofiette al pesto, beef filet, and milk chocolate mousse in their gorgeous dining room and make it a night to remember!
Photo Via Offshore Rooftop
1000 E Grand Ave - Navy Pier
There's nothing more romantic than beautiful Chicago skyline views, and that is exactly what you'll get at Offshore Rooftop. Enjoy craft cocktails and coastal-inspired American cuisine while you and your lover gaze together over the starry night sky.
Photo Via Maxwell's Trading
1516 W Carroll Ave - West Loop
For a more lively Valentine’s Day dinner setting, check out popular modern Asian restaurant Maxwell’s Trading. Grab yourself and your sweetie a couple of classic cocktails and enjoy a night of great vibes with even greater food. If you haven't already booked a two-top, you'd better move quickly, because this is one of Chicago's toughest reservations.
Photo Via AIRE Ancient Baths
800 W Superior St - River West
Spend your Valentine’s Day in the AIRE Ancient Baths and feel your stress melt away. These atmospheric, candle-lit caverns are the perfect romantic setting to spend time in with your loved one. They're offering couples packages ranging from $205 to $700, with all the fixings (bubbly and chocolates, of course) included.
Photo Via Estelles
2013 W North Ave - Wicker Park
Not ready to go home after Valentine's Day dinner? Estelle’s, an institutional 4 AM bar in Wicker Park, has been bringing intimate yet social vibes since 1999. It's the perfect date spot for a couple who appreciates good cocktails, good jukeboxes, and good company. They've also got a killer happy hour.
Photo Via Bistro Campagne
4518 N Lincoln Ave - Lincoln Square
Enjoy the cozy, romantic atmosphere at Bistro Campagne. For lovers of French cuisine, this Lincoln Square restaurant has curated a four-course Valentine's Day menu that'll transport you and your sweetie straight to the European countryside. Can't get much more romantic than that.
Some other honorable mentions for events that we just can't get enough of:
Updated Jan 2026
Did we miss your favorite spot? Let us know!
