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 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 celebrating Valentine’s Day 2024 in Chicago.

Enjoy a romantic dinner
©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 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.
  • Kindling: This luxurious dining experience will take diners skyward in the iconic Willis Tower. Begin with a champagne toast at Kindling, then head to the 99th floor for a three-course dinner, before ending with a sweet finale on the 103rd floor.
  • 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.
  • Bronzeville Winery: This dynamic Bronzeville spot will be hosting “For the Love of Jazz: A Valentine’s Day Candlelit Dinner” with a prix fixe menu paired with a jazz soundtrack.

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

Plan a romantic getaway

Kimpton Gray

While Valentine’s Day may fall on a Wednesday, there’s no reason you can’t turn it into a special 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.

Explore more hotel options in Chicago.

Check off your Chicago bucket list

Dinner and Brunch lifestyle shoot on Odyssey Chicago River 2019

Make it a Valentine’s Day to remember with an iconic Chicago activity. Set sail on a dinner cruise, stop and smell the flowers, or admire an amazing fireworks spectacular.

  • 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 beloved cultural celebration.
  • Adler Planetarium: This historic planetarium is open late and offers free admission for Illinois residents on Wednesday evenings — making it the perfect Valentine’s Day date night.
  • Valentine’s Day fireworks at Navy Pier: This famous lakefront attraction will be celebrating the season of love with their first-ever Valentine’s weekend fireworks display. The show will start at 9 p.m. sharp on Saturday, Feb. 10.
  • 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

AIRE Ancient Baths

The best date nights offer something unexpected. So get outside your comfort zone a bit 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 Experience: This hands-on class teaches couples how wine is made (including grape stomping) at Wild Blossom Meadery, followed by a tasting.
  • Dinner Detective Murder Mystery Dinner Show: Solve a murder while you dine at this entertaining, award-winning dinner show.
  • 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 tasting room in Ravenswood offers behind-the-scenes distillery tours and tastings, so you can learn more about your favorite sips.

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

Indulge in a unique treat

A heart-shaped chocolate cake from RPM Steak

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, chocolate-covered strawberries from Kilwins, a slice of caramel apple pie from Justice of the Pies, luscious chocolates from Chocolat Uzma, or hand-made sweets from Margie’s Candies. Check out top Chicago dessert destinations for more sugary inspiration.

Explore more: Check out inclusive events celebrating LGBTQ+ love this Valentine’s Day.

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.
  • Kingstone Mines: The largest and oldest continuously operating blues club in Chicago is a must for music lovers.
  • The Bassment: A subterranean cocktail bar with a secret door, The Bassment is an intimate spot for live music.
  • The Redhead Piano Bar: You’ll find live music seven nights a week at this popular downtown piano bar.
  • Epiphany Art Center: This hidden gem presents weekly shows in a variety of genres, presented in a repurposed church.

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

Sip cocktails on a rooftop

IO Godfrey

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.
  • 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.

Catch a show

A singer at Teatro ZinZanni Chicago
Teatro ZinZanni Chicago

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: 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.
  • 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

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, 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.

Warm up with an outdoor activity

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: Enjoy a cocktail and curling time surrounded by a stunning view of Chicago from the rooftop of the Gwen Hotel. The outdoor curling rink is open-air, with fire pits and string lights providing warmth and atmosphere.
  • 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.