Valentine's Day is the time to pamper your sweetheart – or yourself! -For something special. Whether you're looking for a relaxing activity (like a romantic cooking class) or an exotic adventure (perhaps a luxurious dinner cruise on Lake Michigan), we have the perfect Valentine's Day only in Chicago planned for you.
Here are some of our favorite ideas for things to do on Valentine's Day 2025 in Chicago.
Enjoy a romantic dinner on Valentine's Day
© Adam Alexander Photography 2019
One of the best ways to celebrate the most romantic day of the year is with an unforgettable Valentine's Day meal. From candlelit restaurants to cozy hideaways to places with stunning city views, you're sure to find the perfect place to celebrate with your sweetheart.
Giga Cafe: A mainstay in Lincoln Park for more than 50 years, Geja's Café features a romantic interior and a variety of fondue offerings to share.Avec: Get a reservation at this popular West Loop classic, with an intimate atmosphere and a menu of shareable dishes. Virtue: Love is a virtue at this popular Hyde Park spot, where Valentine's Day means splitting a plate of blackened catfish, buttered grits, and other upscale Southern classics. Trivoli Tavern: This sexy spot has the perfect Valentine's Day vibe, with a moody atmosphere and excellent cocktails.
Find out more: Check out our guide to 35+ places to have a romantic Valentine's Day dinner in Chicago.
Plan a romantic vacation

Valentine's Day falls on a Friday in 2025, and it's the perfect excuse for a long weekend. Hotels all over Chicago are offering Valentine's Day packages, which include free champagne, chocolates and more — the perfect way to surprise your sweetheart.
Loved Luvv Bubbles & Brunch at Sophy Hotel Hyde Park: Enjoy a dreamy brunch for two, plus a bottle of champagne to toast Valentine's Day.Love in the Windy City in Gwen: Benefit from late checkout and a $50 dining credit, plus Prosecco upon check-in. Celebrate romance at The Peninsula: Book a suite and enjoy a complimentary daily breakfast, a welcome bottle of champagne, rose petals, and more. I love Alma at Zachary Wrigleyville: Enjoy views of Wrigley Field along with complimentary cocktails, a bottle of bubbly, and chocolate-covered strawberries.
Great Romance at Sofitel Chicago: The Sofitel on the Magnificent Mile offers a bottle of sparkling wine, dessert, and complimentary breakfast for two.
Find out more Hotel options in chicago.
Enjoy the iconic Chicago experience

Make it an unforgettable Valentine's Day with an activity limited to Chicago. Sail on a dinner cruise, stop and smell the flowers, or watch an exhilarating live show.
Orchid display at the Chicago Botanic Garden: Indulge your senses at this annual display of exotic plants. The perfect backdrop for a Valentine's Day date. The exhibition features more than 10,000 flowers from around the world. Chicago Theater Week: Get discounted tickets to over 100 unique shows throughout Chicago during this annual event. City trips in Chicago: Sail on a scenic dinner cruise on Lake Michigan, featuring your choice of a three-course dinner and cocktails, complemented by a DJ and stunning views of the city.Chicago Auto Show: Enjoy hundreds of cars at the Chicago Auto Show, the largest and longest-running event of its kind.
Try something new

The best date nights offer something unexpected. So, step out of your comfort zone and choose a new experience, like a wine-making class or a luxurious spa treatment in a unique space.
AIRE OLD BATHROOM: Indulge yourself in relaxation This stunning luxury spa is housed in a restored 1900s factory. Winemaking Dinner: Each couple will have the opportunity to produce their own custom wine blend, bottle it, and bring it home for later.Koval Distillation: For spirits lovers, the Koval Tasting Room in Ravenswood offers behind-the-scenes tours and tastings of the distillery, so you can learn more about your favorite sips. GET YOUR GRIP OF YOUR TRAPE: Learn the exciting art of the flying trapeze in these indoor classes for beginners.
Find out more: Find out more things to do with our events calendar.
Sipping cocktails on the rooftop
What's more romantic than a glass of champagne with stunning views of the skyline? The all-season rooftops are decorated for winter, making it the perfect place to spend a night in for a special occasion.
I|O Godfrey: The rooftop bar above The Godfrey Hotel has launched its very festive winter space featuring its famous igloo. The Kennedy: Relax by the fire pit while taking in panoramic views of the city skyline. Or order bottle service from a private covered igloo. VU Rooftop Bar: This unique space in the South Loop offers a unique perspective of the city skyline. Château Carbide: Cozy up in private lodges at this winter pop-up on Michigan Avenue.Offshore: The world's largest rooftop bar offers stunning views of the surrounding water and cityscape.
Find out more: Find the best winter rooftop bars around Chicago.
Enjoy live music
If you're looking for the perfect after-dinner activity, there's nothing like listening to some live music in Chicago. Impress your date with tickets to a show at one of the city's most intimate music venues, showcasing Chicago-style blues, jazz, piano, and more:
City Winery: This West Loop winery and concert venue features a wide range of acts across genres. Buddy Guy's Legends: This popular club offers an authentic taste of Chicago-style blues, with local and international musicians. Winter Jazz Club: Jazz lovers will appreciate every moment of this classic listening room experience. The Redhead Piano Bar: You'll find live music seven nights a week at this popular downtown piano bar. The Promontory: In Hyde Park, this popular music venue has a great music lineup for Valentine's Day weekend.
Find out more: Find more music, comedy and nightlife options.
Get an offer

Chicago theaters offer a little bit of everything for your Valentine's Day date, whether you like comedy, improv, drag, burlesque, or beyond. Check out what's playing this Valentine's Day weekend.
Second City: Make a date with this popular comedy clubwhere hilarious and impromptu sketches always make for a laugh-filled evening, on Valentine's Day and beyond.The Magic Parlor: This amazing show, featuring third generation magician Dennis Watkins, will make for a great night.Broadway in Chicago: Watch the latest Broadway shows and exciting premieres in Chicago's historic downtown theaters. Zinzani Theater: This dinner and show experience features world-class circuses, comedy, cabaret and more. Drifter: Enjoy exciting burlesque shows at this intimate underground venue Speakeasy.Unbridled at Untitled: This exciting supper club hosts weekly burlesque and variety shows, with a host of amazing talent on display.Bordell: This moody Wicker Park hotel features live entertainment throughout the week, from flamenco to burlesque.
Find out more: Find out more events and offers through our events calendar.
See the horizon

If you're looking for stunning views of Chicago's famous skyline, you have plenty of options. Choose from spinning on the Ferris wheel overlooking the lake to the all-glass observation deck inside one of the tallest buildings in the world.
Fly Heli Chicago: Make it an unforgettable evening with Valentine's Day helicopter tours in Chicago. Choose from private and group trips. See the city skyline from a whole new perspective aboard Navy Pier's The Centenary Wheel, which will be illuminated in Valentine's Day colours. Open year-round, the attraction features 360-degree views of Chicago and Lake Michigan from the comfort of enclosed gondolas.360 Chicago: YesYou and your sweetheart can stretch out above The Magnificent Mile for unique downward-facing views from over 1,030 feet. Cool off after TILT with a drink at CloudBar, With elevated views of the lake.Skydeck Chicago: Another great activity for adventurous couples: The elevator will take you 103 floors above the famous Willis Tower, where you can stand on it EdgeAnd a dramatic glass-floored balcony with stunning views of the city.
Indulge in a unique treat

It's not Valentine's Day without a gift you can share with your sweetheart (or enjoy all by yourself). A variety of places in Chicago offer exciting shareable desserts to end your Valentine's Day on a sweet note.
Payment Best Dessert Destinations in Chicago For more sugary inspiration.
Actively warm up outdoors

If you and your loved one are ready to pack up and embrace the cold, Chicago offers plenty of great reasons to get outside. Grab a good coat and take advantage of mid-February with one of these outdoor activities.
Skate bar at Maggie Daley Park: Book early to rent skates (or BYO) and enjoy a scenic run with unbeatable views of the park and downtown. Ice Skating at Millenium Park: Take a ride on the ice in the shadow of the city's most famous landmark, The Bean.The window upstairs in Gwen: Enjoy a cocktail and curling time surrounded by a stunning view of Chicago from the rooftop of the Gwen Hotel, with fire pits and string lights providing warmth and atmosphere. This popular West Loop bar features outdoor curling rinks in the winter. Neighborhood Ice Rinks: The Chicago Park District creates ice rinks in parks throughout the city each winter, from Hyde Park to the West Ridge. Find your nearest location and get skiing.
Find out more: Check out our complete guide to winter activities in Chicago.