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 (maybe a dinner cruise on Lake Michigan?), we’ve got the perfect Valentine’s Day plans for you.

Here are some of our favorite ideas for celebrating Valentine’s Day 2022 in Chicago.

Stay the night with hotel deals

Rose petals and champagne on a hotel bed
The Kimpton Gray

After a lot of time spent at home, switching up your surroundings for a night or two may be the perfect way to escape with your Valentine. It’s also a great time to score deals, from upgraded rooms to unique packages.

  • Sophy Hyde Park: Get cozy with two souvenir mugs, hot cocoa, and a credit to the in-house Mesler restaurant.
  • Staypineapple: Celebrate the occasion with a bottle of sparkling wine on ice and decadent chocolate truffles.
  • Kimpton Gray: Upgrade your Valentine’s Day with discounts on spa suites, plus in-room massages.
  • Hotel Zachary: The “Love, Alma” package includes luxe matching robes to keep, a bottle of bubbles on ice, and chocolate covered strawberries.

Explore more hotel deals and packages all around Chicago.

Sip cocktails on a rooftop

IO Godfrey

What’s more romantic than a glass of champagne with stunning skyline views? These all-seasons 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 their ultra-festive space featuring their 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.
  • Offshore: The largest rooftop bar in the world offers stunning views of the surrounding water and cityscape.

Explore more winter rooftop bars all around Chicago.

Catch a show

Lip Drag Show
Abel Arciniega :: @tequilagraphics

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.
  • Broadway in Chicago: The CIBC Theatre ushers in a funnier February with the Chicago premiere of HAIRSPRAY, the Tony Award-winning musical comedy featuring a beloved score of hit songs.
  • Bordel: This moody Wicker Park speakeasy features live entertainment all week long, from flamenco to burlesque.
  • Lips Drag Show: One of the city’s premiere drag shows is known for over-the-top entertainment featuring fabulous queens at their colorful South Loop venue.
  • A Valentine Speakeasy: The Newport Theater in Lakeview is transforming into an intimate speakeasy, featuring circus-inspired cabaret performers from around the world.
  • Find Love at The Promontory: Single and ready to mingle on Valentine’s Day? Enjoy a night of romance with an extra dose of laughter with comedian Richie Fontane, a.k.a. Dr. Richie Love, who will connect Chicago singles in the audience. 

Check out more events and shows with our events calendar.

See the skyline

Tilt at 360 CHICAGO
Photo by Adam Alexander

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.

  • Centennial Wheel: See the city skyline from a whole new perspective aboard Navy Pier’s Centennial Wheel. 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 Bar 94, which promises the best view in Chicago. 
  • 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.

Warm up with a winter sport

Maggie Daley Park Skating Ribbon
Maggie Daley Park Skating Ribbon

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: $30 gets you a cocktail and 45 minutes of curling time surrounded by a stunning view of Chicago from the rooftop of the Gwen Hotel on Michigan Avenue. The outdoor curling rink is open-air, with fire pits and string lights providing warmth and atmosphere.
  • Neighborhoods 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 our full guide towinter activities in Chicago.

Enjoy a romantic dinner

Dinner cruise on the Chicago River

One of the best ways to celebrate the most romantic day of the year is with an unforgettable Valentine’s Day meal. These Chicago restaurants have you covered with special dinners designed for two.

  • Geja’s Cafe: Known as one of the most romantic spots in the city, Geja’s diners can enjoy the full fondue experience, including beef tenderloin, lobster tail, chocolate, champagne, and more.
  • Virtue: “Love is a virtue” is the theme of the Valentine’s Day meal at this Hyde Park spot, featuring three Southern-inspired courses and a bottle of sparkling rosé.
  • Kitchen + Kocktails: This new spot in River North has earned rave reviews for their food, with a menu of creative comfort food and Southern classics.
  • TenGoku Aburika: Enjoy a seven-course omakase experience, at this Japanese gastropub helmed by a Michelin-starred chef.
  • Roister: Reserve a place at the hearth for a fiery Valentine’s Day dinner in the West Loop, featuring a four-course menu.

Check out our guide to 30+ spots for a romantic Valentine’s Day dinner in Chicago.

Try something new

A couple cooks a meal at The Chopping Block

The best dates nights offer something unexpected. So get outside your comfort zone a bit and opt for a new experience, like an interactive Italian cooking class or a luxe spa treatment in a unique space.

  • Valentine’s Winemaking Experience: This hands-on class teaches couple how wine is made (including grape stomping) at Wild Blossom Meadery, followed by a tasting.
  • The Chopping Block: They say the way to someone’s heart is through their stomach, so why not test that theory during a cooking class? For Valentine’s Day, learn to make an Italian fest in a hands-on class or try a virtual option at home.
  • Taste of Chinatown: Grab your date and embark on a culinary whirlwind through Chinatown, with tastings that showcase the neighborhood’s best restaurants.
  • Koval Distillery: For fans of spirits, Koval’s new tasting room in Ravenswood offers flights and distillery tours, so you can learn more about your favorite sips.
  • AIRE Ancient Baths: Submerge yourself in a bath filled with red wine at AIRE, a spectacular spa housed in a restored 1900s factory. The Wine Bath for Two will immerse you in antioxidant-rich red wine, making for a truly decadent spa date.  
  • Dirty Dancing dance class: Are you ready to have the time of your life with your Valentine? Duet Dance Studio offers a Dirty Dancing inspired dance class on Valentine’s Day. Designed for beginners, this BYOB dance party promises to teach you the latest moves. 
  • 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. 

Check out more things to do with our events calendar.