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 this year.
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.
Stay at The Gwen for date night
Make the most of Valentine’s Day in Chicago by staying at The Gwen! You’ll start with a glass of prosecco on arrival before checking into your luxury accommodations. You’ll receive a daily $50 dining credit to enjoy a bite Upstairs at The Gwen—the rooftop has cozy firepits, curling, and a delicious menu. You’ll end your romantic weekend with a complimentary 4:00 pm late check-out.
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.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!
Valentine’s Day Date Night at Puttshack
Celebrate an unforgettable Valentine’s Day in Chicago with mini golfing! On Friday, February 14, every guest visiting Puttshack in Oak Brook will receive a special Valentine’s card featuring a promo code for one free game. This code can be redeemed online or at the kiosk from February 15 to March 15, 2025. Additionally, Puttshack will showcase a themed Simplebooth setup, providing couples and friends with a fun and interactive way to capture memories together.
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.
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.
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.
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.
One of our favorites, Tievoli Pizza Bar (“I Love It” read backward), located in suburban Chicago, is celebrating love with heart-shaped pizzas exclusively on February 14 for Valentine’s Day in Chicago. Tievoli’s menu showcases 13 varieties of pizzas crafted with high-quality, fresh ingredients and a perfectly fermented 72-hour dough, making their artisanal New York-style creations truly stand out.
Sip romantic cider with a dinner at home
One of our favorite weekend getaways from Chicago is Virtue Farm. This charming cider farm is the perfect destination for couples. However, if you’re not able to travel this weekend, they are hosting a special Valentine’s Day celebration.
The Valentine’s Bundle is perfect for cider enthusiasts and includes two bottles made from high-quality Midwestern heirloom apples. The bundle features Les Fleurs Royale, a floral blend with hints of lavender and rose that pairs wonderfully with light cheeses and pastries. It also includes Strawberry Feels, a sweet mix of vanilla and strawberries that goes well with any dessert.
Enjoy the Teatro ZinZanni’s “My Funny Valentine”
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.
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.
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.
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.
Picturesque Valentine’s Day Trip Near Chicago
Looking for a romantic escape without traveling far? Explore three idyllic destinations within three hours of Chicago, perfect for Valentine’s Day. The Midwest offers charming towns that feel like scenes from a Hallmark movie, featuring cozy B&Bs, scenic hikes, and delightful dining experiences. Whether it’s Roselle, Starved Rock Country, or Galena, these getaways promise unforgettable moments with your loved one.
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.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. For Valentine’s Day in Chicago, the Orchid House will be in full bloom—you’ll breathe in an earthy, fruity fragrance with your partner. It’s the perfect outdoorsy Valentine’s escape in the midst of winter.
Experience Valentine‘s Day at the Sable Hotel
This Valentine’s Day in Chicago, Sable will relaunch its popularRomance Package, extending the offer year-round for anniversaries and other romance-filled milestones. The perfect touch to an unforgettable stay, the “Love on the Lake” Romance Package fans the flame with champagne and chocolate-covered strawberries for two, an in-room scattering of faux rose petals, and a personalized card to commemorate the occasion.
“Lover’s Karaoke Night” & Valentine’s Day Claw Machine at Central Park Bar
Cheers to love at Central Park Bar for a cozy, laidback Valentine’s Day in Chicago featuring a special edition “Lover’s Karaoke Night” from 7 p.m. to 11 p.m. Specials will include $9.50 beer and shot combos as well as half-price happy hour from 4 p.m. to 7 p.m. Patrons can enjoy complimentary Valentine’s Day candy and get creative as they make DIY cards for that someone special. As an added treat, the claw machine at Central Park Bar will feature Valentine’s Day-themed items.
Celebrate Valentine’s Day with City Cruises Chicago
We can confidently say Valentine’s Day in Chicago is more romantic on the water. City Cruises, operator of Chicago’s year-round premier water experiences, is inviting Chicagoans to celebrate Valentine’s season by offering a selection of specialty brunch and dinner cruise packages aboard the Chicago River and Lake Michigan. With cruises available on Friday, February 14, and Saturday, February 15, guests can cruise the Chicago Odyssey with some of the city’s most beautiful sites.
Guests can choose from their Valentine’s Premier Plus Dinner Cruise, Valentine’s Day Galentine’s Brunch Cruise, Chicago’s Signature Valentine’s Day Dinner Cruise, or the Valentine’s Premier Dinner Cruise on Lake Michigan.