Valentine’s Day is approaching, so it’s important to lock down plans for the perfect night of romance. Luckily, Chicago is teeming with heart-fluttering activities, and there are many ways to celebrate your relationship this year. Keep scrolling for some of the most romantic ways to celebrate Valentine’s Day in Chicago.
1. Have a Valentine’s dinner date
While taking the time to configure an at-home meal can be romantic—an aromatic kitchen, a picnic on the ground, candles lit around your home—there’s just something appealing about heading to a restaurant that has laid out a beautiful meal for you. Whether you want one of the prettiest restaurants or one that breathes romance, there are numerous ones around the city.
One breathtaking option is taking your partner to Sushi | Bar, an Omakase experience that will enrapture your senses. For $255 per person, guests will start the night with a champagne toast before seated at the rose-petal-covered, candle-adorned sushi bar. The menu will include Valentine’s Day-inspired nigiri bites, seasonal supplements like caviar and truffles on select bites, and an indulgent dessert.
2. Stop by the Loews Chicago for Random Acts of Kindness on Valentine’s Day in Chicago
The Loews Hotel is spreading the love on Valentine’s Day to the entire community in the following ways: Grab free Coffee from 7:30 AM – 9:30 AM at For Five Coffee located inside Loews Hotel; 3 lucky recipients with a gold sticker on the bottom of their cup will also receive a free overnight stay good for 2024. Because Loews Loves Pets, they will also be handing out free dog treats in the nearby dog park at Bennet Park. Last, free Firecake Donuts will be outside the hotel from 2-3 PM.
3. Enjoy a meal blind-folded at Dining in the Dark
Take your date night to the next level, tempting your senses with dark surroundings to focus on more important things like the delicious three-course meal or an extravagant 12-course sushi omakase experience you’re about to have at Fulton Market Kitchen and at Sushi By Bou.
Upon arrival, guests are provided with disposable blindfolds, and a guide will lead guests over to the dining environment. Lit by the gentle glow of candlelight, you and your date will enjoy your meal in an exciting atmosphere you won’t find anywhere else.
Grab tickets to Dining in the Dark here.4. Relax and unwind at AIRE’s Ancient Baths
There is simply no better place in Chicago for some rest and relaxation than AIRE’s Ancient Baths and this Valentine’s Day, they are offering exclusive Couples Specials that are perfect for the most romantic day of the year.
Located in a restored historic River West factory dating back to 1902, the baths are inspired by the traditional Roman, Greek, and Ottoman ancient bathing experience. This preserved structure has been restored to its original splendor, and you can now find optimum relaxation within the building’s exposed brick, wooden beams, and industrial columns.
The unique body and mind experience offers baths of different temperatures, relaxing massages, and couples experiences. It’s almost impossible for anything to go wrong at a place where all stress and pressure evaporates into thin air!
5. Discover Fever’s most romantic Valentine’s Day plans
Surprise your sweetheart with unique experiences right here in Chicago. Luckily, our friends at Fever, the global live entertainment discovery platform, are making choosing a V-Day plan much easier with a wide range of romantic events. From a risqué cirque cabaret to immersive exhibitions and culinary experiences, there’s something to suit every taste.
Uncover these Cupid-approved events and experiences here.
6. Go for a classic date night with dinner and a movie
The age-old recipe for romance doesn’t fail. A meal and movie night is always a winner, and there has never been a better time to go to the movies than for Valentine’s Day in Chicago. Book tickets to a showing, watch that screen light up, filling you both with excitement, and snuggle up for a cinematic experience like the days of old.
You can find an array of wonderful flicks at exclusively low prices by downloading the Fever app.
7. Glide through the ribbon at Maggie Daley Park
Ice skating in Maggie Daley Park is one of Chicago’s most beloved winter-time activities. Still, it can also offer a guaranteed night of romance for long-term couples and blossoming romances in equal measure. There is something extra special about gliding around the quarter-mile winding ribbon of ice with the city skyline in the backdrop and the stars above. Whether you’re showing off your skills or struggling to stay on your feet, you can be sure you and your special someone will be having fun.
8. Head to the rooftops for a snazzy drink and dinner
Of all the social spots and watering holes across Chicago, it’s up among the rooftops where the most romantic nights can be had. When indoor dining was off the table, many hotels, bars, and restaurants winterized their outdoor spaces, providing wonderful winter wonderland setups among the Chicago skyline. Many of these inaugural experiences are returning this year, and you’ll struggle to find a more memorable Chicago evening than one spent sipping cocktails under the stars.
You’ll find rentable igloos and winter decor at both River North’s verdant Joy District rooftop and the lavish Godfey Hotel rooftop. Meanwhile, London House Chicago offers stunning vistas of the Chicago River and Michigan Avenue, and Cindy’s Rooftop in the Loop has sweeping panoramic views of Millennium Park.
9. Share a heart-shaped pizza with the one you love
If you’re at that stage where you can happily tuck into some fast food without a care in the world, these famous heart-shaped, deep dish pizzas are the perfect way to eat your heart out. You can find delicious heart-shaped pizzas in Chicago at Giordano’s, Lou Malnati’s, My Pi Pizza, Eataly, and many other pizza restaurants.
At Giordano’s, from February 5 to February 14, they are offering heart-shaped pizzas for dine-in, carryout, and delivery to celebrate Valentine’s Day in Chicago. The heart-shaped pizza pricing is the same as Giordano’s medium deep-dish pricing, with exact prices varying based on customized toppings. Celebrate Chicago Valentine’s Day the right way by slicing into cheesy heaven!
10. Enjoy the Teatro ZinZanni’s “Love, Chaos, and Dinner”
Experience the magic of Teatro ZinZanni on the 14th floor of the Cambria Hotel in the vibrant Loop this Chicago Valentine’s Day. This one-of-a-kind entertainment experience promises a world-class extravaganza of love, chaos, and dinner inside the velvet walls of Speigeltent ZaZou. Delight in premium cuisine, mesmerizing circus acts, and unparalleled entertainment unlike you’ve ever seen.
11. Head on a Cupid-inspired City Cruise
12. Grab florals for your lover
While there are many places to grab florals for your companion, we have one favorite spot: Southside Blooms. The farm-to-vase florist provides unique and fashion-forward arrangements while maintaining a dedication to the environment and surrounding communities.
Southside Blooms is one of the places where your purchase gives back. Southside Bloom’s mission is to use sustainability to alleviate poverty. One hundred percent of their money goes directly towards creating jobs for at-risk youth, converting vacant lots into safe and productive community assets, and actively contributing to the health and resilience of the environment through regenerative farming practices.
13. Wander through a museum hand in hand
Chicago is home to some of the best museums and exhibit in the world, offering an eclectic mix of exciting exhibitions throughout the year. Share your passion for history and art with a loved one and gaze upon the magnificent pieces created by celebrated artists.
14. Plan a romantic winter getaway
Are you thinking that Valentine’s Day in Chicago is your only option? It’s not. Known as a unique vacation spot with an old-timey atmosphere, Mackinac Island is a national treasure and a perfect getaway. It’s home to historic Fort Mackinac, world-famous Mackinac Island fudge, and car-free streets full of horse-drawn carriages.
This ideal vacation spot and winter getaway from Chicago is a paradise of exploration with incredible natural landmarks, awe-inspiring sunrises, and unforgettable sunsets. In winter, you can head on the Mackinac Island Turtle Trek, a beautiful lantern-lit ski and snowshoeing trek. You’ll head through some of Mackinac Island’s natural winter wonderland.
14. A Coupled Up With Cupid Experience at LondonHouse
This February, LH Rooftop in LondonHouse offers a unique Valentine‘s Day in Chicago experience with its Valentine’s Day-themed igloos. Available from February 1st to 28th, the igloos provide a romantic and intimate setting against the city skyline, perfect for couples or a Galentine’s Day celebration with friends.
And don’t forget to order the “Coupled Up With Cupid,” a gluten-free and vegetarian dessert available from Feb. 10-18. This delectable creation features a symphony of strawberry cake, strawberry compote, vanilla bean gelato, strawberry sorbet baked Alaska, strawberry shortcake crumble, and strawberry sauce.
Address: 185 E Wacker Dr, Chicago, IL 60601
Reservations: Make a reservation at here
15. Marvel at the magic of a candlelit concert
Few things pull at the heartstrings with more power than a string quartet—combined with the tender flicker of one hundred candles and the charm of the iconic spellbinding music. Take your partner to a romantic Candlelight Valentine’s Day special for a perfect night of romance.
Enjoy some of history’s greatest love songs played masterfully in front of your eyes as the gentle flicker of flames dance around you and the strings soothe and swoon you. Worry not; the candles are fireproof, so the only sparks flying will be the metaphorical sparks between you and that special someone. These romantic concerts might not fall on Valentine’s Day, but they are the perfect gift.
Grab tickets to a candlelight concert here.16. Walk through a luscious garden
Lincoln Park Conservatory is a greenhouse dome featuring hundreds of tropical palms, exotic plants, and ancient ferns stretched along the designated pathway. Perfume scent whispers throughout the greenhouse, and you’ll breathe in an earthy, fruity fragrance with your partner. It’s the perfect outdoorsy Valentine’s escape in the midst of winter.