Top things to do for Valentine’s Day in Chicago

Valentine’s Day is a time to treat your sweetheart ― or yourself! ― to something special. Whether you’re looking for a laid-back activity (like a romantic cooking class) or an over-the-top adventure (perhaps a luxe dinner cruise on Lake Michigan), we’ve got the perfect only-in-Chicago Valentine’s Day plans for you.

Here are some of our favorite ideas for things to do for Valentine’s Day 2025 in Chicago.

Enjoy a romantic Valentine’s Day dinner

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 spots with sweeping city views, you’re sure to find the perfect place to celebrate with your sweetheart. 

• Geja’s Cafe: Geja’s Cafe has been a mainstay in Lincoln Park for more than 50 years, featuring a romantic interior and a variety of fondue offerings to share.
• Avec: Grab a reservation to this celebrated West Loop classic, with an intimate atmosphere and a menu of shareable dishes.
• Virtue: Love is a virtue at this acclaimed Hyde Park spot, where Valentine’s Day means splitting a plate of blackened catfish, buttered grits, and other elevated Southern classics.
• Trivoli Tavern: This sultry spot has the perfect Valentine’s Day vibe, with a moody atmosphere and excellent cocktails.

Explore more: Check out our guide to 35+ spots for a romantic Valentine’s Day dinner in Chicago.

Plan a romantic getaway

Valentine’s Day falls on a Friday in 2025, which is the perfect excuse for a long weekend getaway. Hotels all around Chicago are offering Valentine’s Day packages, featuring complimentary champagne, chocolates, and more — the perfect way to surprise your sweetheart.

• Love Luvv Bubbles & Brunch at Sophy Hotel Hyde Park: Enjoy a dreamy brunch for two, plus a bottle of champagne for a Valentine’s Day toast.
• Love in the Windy City at The Gwen: Take advantage of late checkout and a $50 dining credit, plus prosecco at check-in. 
• Celebrate Romance at The Peninsula: Book a suite and enjoy complimentary daily breakfast, a welcome bottle of Champagne, rose petals, and more.
• Love Alma at Hotel Zachary Wrigleyville: Enjoy Wrigley Field views alongside complimentary cocktails, a bottle of bubbles, and chocolate-covered strawberries.

• Magnifique Romance at Sofitel Chicago: On The Magnificent Mile, Sofitel is offering a bottle of sparkling wine, a sweet treat, and complimentary breakfast for two.

Explore more hotel options in Chicago.

Experience iconic Chicago

Make it a Valentine’s Day to remember with an only-in-Chicago activity. Set sail on a dinner cruise, stop and smell the flowers, or catch an exhilarating live show.

• Orchid Show at Chicago Botanic Garden: Indulge your senses at this annual showcase of exotic flora, the perfect backdrop for a Valentine’s Day date. The show features more than 10,000 blooms from all over the world. 
• Chicago Theatre Week: Score discounted tickets to more than 100 unique shows all around Chicago during this annual event.
• City Cruises Chicago: Set sail on a breathtaking Lake Michigan dinner cruise, featuring your choice of a three-course dinner and cocktails, complemented by a DJ and spectacular city views.
• Chicago Auto Show: Admire hundreds of vehicles 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 get outside your comfort zone and opt for a new experience, like a wine-making class or a luxe spa treatment in a unique space.

• AIRE Ancient Baths: Submerge yourself in relaxation at this spectacular luxury spa, housed in a restored 1900s factory. 
• Winemaking Dinner: Each couple will have the opportunity to produce their own custom wine blend to bottle and bring home at a later date.
• Koval Distillery: For fans of spirits, Koval’s tasting room in Ravenswood offers behind-the-scenes distillery tours and tastings, so you can learn more about your favorite sips.
• Get a Grip Trapeze: Learn the thrilling art of flying trapeze at these indoor classes for beginners.

Explore more: Check out more things to do with our events calendar.

Sip cocktails on a rooftop

What’s more romantic than a glass of champagne with stunning skyline views? These all-season rooftops are decked out for winter, making them the perfect spot for a special-occasion date night.

• I|O Godfrey: The year-round rooftop bar atop The Godfrey Hotel has launched its ultra-festive winter space featuring its popular heated igloos.
•  The Kennedy: Cozy up by a fire pit while soaking in the panoramic views of the city skyline. Or order bottle service from your private covered igloo.
• VU Rooftop Bar: This unique South Loop space offers a one-of-a-kind perspective of the city skyline.
• Château Carbide: Get cozy in private lodges at this winter pop-up on Michigan Avenue.
• Offshore: The largest rooftop bar in the world offers stunning views of the surrounding water and cityscape.

Explore more: Find the best winter rooftop bars all around Chicago.

Enjoy live music

If you’re looking for the perfect after-dinner activity, nothing beats catching 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 beyond:

• City Winery: This winery and concert venue in the West Loop features a wide variety of acts across genres.
• Buddy Guy’s Legends: This iconic club offers an authentic taste of Chicago-stye blues, with local and international musicians.
• Winter’s 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 swoon-worthy music line-up for Valentine’s Day weekend.

Explore more: Find more music, comedy, and nightlife options.

Catch a show

Chicago’s stages are offering a bit of everything for your Valentine’s Day date, whether you love comedy, improv, drag, burlesque, or beyond. Check out what’s playing for Valentine’s Day weekend.

• The Second City: Make a date with this iconic comedy club, where hilarious sketches and improv always make for a laugh-filled evening, Valentine’s Day and beyond.
• The Magic Parlour: This jaw-dropping show, featuring third-generation magician Dennis Watkins, will make a spellbinding date night.
• Broadway in Chicago: Catch the latest Broadway hits and exciting premieres at Chicago’s historic downtown theatres.
• Teatro ZinZanni: This dinner-and-a-show experience features international cirque acts, comedy, cabaret, and more.
• The Drifter: Catch tantalizing burlesque performances at this intimate underground speakeasy.
• Unbridled at Untitled: This sultry supper club hosts this weekly burlesque and variety shows, with a range of mesmerizing talents on display.
• Bordel: This moody Wicker Park speakeasy features live entertainment all week long, from flamenco to burlesque.

Explore more: Check out more events and shows with our events calendar.

See the skyline

If you’re looking for breathtaking views of Chicago’s iconic skyline, you’ve got plenty of options. Choose from a spin on a lakefront Ferris wheel to an all-glass observation deck inside one of the tallest buildings in the world.

• Fly Heli Chicago: Make it an unforgettable evening with these Valentine’s Day helicopter tours of Chicago. Choose from private and group flights.
• Centennial Wheel: See the city skyline from a whole new perspective aboard Navy Pier’s Centennial Wheel, which will be lit up in Valentine’s Day hues. The year-round attraction features 360-degree views of Chicago and Lake Michigan from cozy, enclosed gondolas.
• 360 CHICAGO: You and your sweetheart can extend out and over The Magnificent Mile for unique, downward-facing views from over 1,030 feet. Calm your post-TILT nerves with a drink at CloudBar, with soaring lakefront views.
• Skydeck Chicago: Another great activity for adventurous couples: an elevator will whisk you 103 floors up the iconic Willis Tower, where you can dare to stand on The Ledge, a thrilling glass floor balcony with breathtaking city views.

Indulge in a unique treat

It’s not Valentine’s Day without a treat to share with your sweetheart (or to enjoy all on your own). A variety of Chicago spots are offering sultry, shareable desserts to end your Valentine’s Day on a sweet note.

• Order the heart-shaped 14K chocolate cake from RPM Steak.
• Indulge in chocolate-covered strawberries from Kilwins.
• Enjoy a slice (or two) of caramel apple pie from Justice of the Pies.
• Gift luscious chocolates from Chocolat Uzmaor hand-made sweets from Margie’s Candies.

Check out top Chicago dessert destinations for more sugary inspiration.

Warm up with an outdoor activity

If you and your Valentine are ready to bundle up and embrace the cold, Chicago offers plenty of great reasons to get outside. Grab a good coat and make the most of mid-February with one of these outdoor activities.

• Skating Ribbon at Maggie Daley Park: Snag a reservation early to rent skates (or BYO) and enjoy a scenic course with unbeatable views of the park and downtown.
• Millennium Park ice skating: Go for a spin on the ice in the shadow of the city’s most iconic landmark, The Bean.
• Curling Upstairs at the 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.
• Kaiser Tiger. This popular bar in the West Loop features outdoor curling rinks in the winter.
• Neighborhood ice rinks: The Chicago Park District sets up ice rinks in parks across the city each winter, from Hyde Park to West Ridge. Find your closest spot and get skating.

Explore more: Check out our full guide to winter activities in Chicago.