Updated for Valentine’s Day 2025.
Looking for the best things to do on Valentine’s Day in Chicago?
Wondering how to sweep your Valentine off their feet this year?
Searching for the best events and activities to take your special someone to, on perhaps the most important Friday this February?
We got you!
Celebrating Valentine’s Day 2025 in Chicago
With its rich culture, great food, and diverse entertainment options, The Windy City is a great place to celebrate the patron saint of love - St. Valentine.
Whether you're looking for a thrilling adventure (such as an escape room?), a relaxing activity (like a spa day), or even an offbeat experience (like a spot of urban exploration)...
We've got some great options for you to celebrate Valentine's Day with your significant other in Chicago.
Attend a candlelight concert
The image is taken from their global website (https://candlelightexperience.com/#info-experience)
Want a quintessentially romantic experience for Valentine's Day in Chicago?
Attend a candlelight concert!
Part of a global event, Candlelight Concerts in Chicago is a series of unique musical events that take place amidst hundreds of flickering candles.
This year, they’re planning a range of concerts around Valentine’s Day, drawing from different music genres.
Think DIVISI Amp’d String Quartet bringing Coldplay and Imagine Dragons to life, while the Metropolis String Quartet honors Queen with a powerful tribute.
A truly moving tribute to the sacrifice of Saint Valentine.
Date & Time: Different programs are on different dates. However, as of January 30th, they don’t have any programs falling exactly on February 14th.
PSA: Swifties, take note - There’s a tribute to Taylor Swift on Thursday, February 6th!
Website: Visit their Chicago website
Location: For Valentine’s Day 2025, the Coldplay & Imagine Dragons event will be at Salvage One. Stan Mansion will host the Queens tribute. And Swifties will have to head for the Music Box Theatre. Check the website before planning.
Team up for an escape room adventure at Fox in a Box
Discussing their next move…
Looking for a thrilling Valentine’s Day adventure in Chicago that’ll have your special someone saying “WOW!”?
Head for the Dearborn Station, where you'll find Chicago's best escape room - us.
As you enter our facility, you and your significant other will be briefed on your mission.
Next, you'll be led into a specially set-up room where the adventure takes place.
As the clock starts ticking, look for clues on how to proceed. Work as a team to solve puzzles, break codes, find secret panels, and open special locks to find clues.
Can you get to the final clue and accomplish your mission before you're out of time?
You have four exciting escape room missions, based on diverse themes, to choose from.
Ready to test your Sherlock skills this February 14th?
Nearby places for a post-experience dinner
Lou Malnati's on State is well-known for its deep-dish pizzas, bruschettas, and calamari.
You can also check out their famous heart-shaped pizza package (a Valentine’s special) on Tastes of Chicago.
Bar Louie on Printers Row is famous for martinis, sangrias, and quick bites.
This year they’re offering a 4-course Valentine's Day Dinner & Drink from Tuesday, February 4th, to Sunday, February 16th.
Devil Dawgs on State is the go-to place for Chicago dogs, shakes, and sliders.
Flaco's Tacos on S Dearborn is renowned for its margaritas, sangrias, and chicken bowls.
- And if you're looking for Asian (Japanese) cuisine, head for Umai on S Clarke Street.
Website: Visit the home page
Location: Check address/Plan route on Google Maps
Email: info@foxinaboxchicago.com
Phone: (312) 878-7899
Go skating
Suit up, and go for a glide on the ice!
Ready for a Valentine’s Day activity that’ll prove a good workout while giving you two plenty of opportunities to have memorable moments outdoors?
Head to a rink, suit up, and go ice skating!
Breathe in the crisp February air as you try to conquer the course.
Watch for the twists and turns, and keep up with your partner.
Whether you’re barely managing to stay up straight, or you’re gracefully gliding across the rink, skating can be an awesome activity to share with your Valentine in Chicago!
Tip: Most venues offer skate rentals, so there’s no need to carry your own.
Where to go ice skating on Valentine’s Day in Chicago
First up is the Maggie Daley Park Skating Ribbon, lined with Alpine trees and rock climbing walls.
Check out Valentine’s DJ Skate Night on Feb 14th.
Then there’s the McCormick Tribune Ice Rink, where you can skate with the iconic Bean as your backdrop.
They might not be good for Valentine’s Day this year, as they’ve announced February 2nd as the end of skating season.
Plus, you’ll find plenty of neighborhood and community rinks all over Chicago.
Enjoy a romantic dinner
Will you actually hold hands?
Want to make February 14th in Chicago an occasion you’ll really…relish? Enjoy a romantic dinner with your partner!
And you certainly have a lot of options to choose from!
Sitting in Chicago, we HAVE to mention enjoying deep-dish pizzas at one of the numerous pizza joints dotting the city.
If you're looking for a more upscale culinary experience, head for one of the renowned steakhouses.
Prefer to have a spectacular city view as the backdrop? Several rooftop restaurants fit the bill.
Whatever your desired cuisine - American, Continental, Mediterranean, or Asian - and other preferences, you're sure to find a Chicago restaurant that's right for you!
A few Chicago restaurants that you can look at for Valentine’s Day dinner
Lou Malnati's on State has a tradition of offering special heart-shaped pizzas to mark the day.
Geja’s Cafe is famous for its food-wine pairings…need we say more?
They’re also offering a Valentine’s Special Dinner Package.
Boka will be offering a specially crafted 7-course tasting menu on the occasion.
Venteux in the iconic Carbide & Carbon building is well-known for its French classics with a contemporary twist, especially its oysters, mimosas, and baked brie.
Check out their Galentine’s Day Brunch.
- And finally, Komo (known for its Japanese cuisine) will host Valentine's Week Experience with a ‘decadent 6-course menu'.
Dine, dance & dazzle at Get in the Kitchen
Looking to add a punch to the classic romantic dinner?
At Get in the Kitchen!, you and your Valentine will cook tapas-inspired dishes, sip on cocktails, and spice things up with a salsa lesson.
You’ll be guided by expert chefs and dance instructors, making it easy to whip up delicious flavors and pick up some smooth moves.
Turn up the romance as you whip up albondigas and dumplings, sway to Latin rhythms, and explore their wine & beer collection.
Date & Time: 7 PM onwards on Friday, February 14th and 1 to 4 PM on Sunday, February 16th.
Website: Visit the event page
Location: Check address/Plan route on Google Maps.
Take in breathtaking views of the city
Gazing at the Chicago skyline with your significant other, especially at nighttime, is a perfect way to take in the beauty of our city while enjoying time as a couple.
The sheer diversity of architecture across Chicago, lit up by thousands upon thousands of sparkling lights, is the perfect backdrop for an intimate, romantic moment.
The best ways to behold Chicago’s skyline with your Valentine
Skydeck in the Sears (a.k.a. Willis) Tower offers sweeping views of the city and beyond from inside clear glass observation boxes.
They’re running the Love on the Ledge sweepstakes again.
360 Chicago in the former John Hancock Tower affords you dazzling views of the city looming over the gleaming waters of Lake Michigan.
The Centennial Wheel at the Navy Pier is another way to take in the Chicago panorama.
Wow your partner with Love at the Pier, especially the cruises and fireworks.
Finally, you can book a couple's helicopter ride over Chicago.
Have a spa day at AIRE Ancient Baths
The image is taken from their website (https://beaire.com/en/aire-ancient-baths-chicago/experiencias/541/escape-together-60)
Want to mark Valentine’s Day by sharing a relaxing and rejuvenating experience with your significant other?
Book a spa day at AIRE Ancient Baths!
Spend quality time in each other's company as you share refreshing massages and exfoliating facials.
Soak in the goodness in a sauna or a thermal pool, inspired by ancient traditions from Rome and Greece.
Indulge in their Valentine’s Day experience, featuring thermal baths, massages with argan oil, and a private red wine soak for two.
Celebrate your love with a luxurious spa day at AIRE Ancient Baths!
Website: Visit the website
Location: Check address/Plan route on Google Maps
Inquiry form: Visit their contact page
Phone: (312) 312-9610
Cuddle the bunnies at Cuddle Bunny
They make everything better, don’t they?
Want a uniquely adorable experience on February 14th?
Head to Cuddle Bunny with your special person.
Bond with one another over a shared love of cute and fluffy creatures.
Pet the lovable rabbits, get a picture taken with them, and even get to feed them.
And remember the candlelight concerts? Well, here you can do Bunnies by Candlelight—snuggling with bunnies and your significant other, amidst candles, soft music, chocolates and roses.
If you want to keep Valentine's Day low-key, a visit to Cuddle Bunnies is just what you're looking for!
Website: Visit the website
Location: Check address/Plan route on Google Maps
Inquiry form: Scroll down their home page
Phone: (773) 687-9253
Have a cozy dinner inside a rooftop igloo at The Godfrey
The image is taken from their website (https://iogodfrey.com/winter-wonderland/).
Looking for a Valentine’s Day dinner where you can get a little cozier than at a typical restaurant/cafe?
Book a rooftop igloo at The Godfrey!
Imagine yourself snuggling up against your special someone, even as you watch the snow fall all around you.
Nope, this isn’t a scene from a Cupid’s day movie or rom-com - it’s the rooftop igloo dining experience you can expect at the Godfrey Hotel!
Sip on a relaxing cocktail and bite into gourmet creations while soaking in each other’s company.
Rooftop dining is a great way to celebrate the festival of love in Chicago!
Pro tip: Even their small igloos can accommodate 8-10 people, so if you’re looking to spend Valentine's Day with your couple friends, book a spot at The Godfrey!
Website: Visit the website
Location: Check address/Plan route on Google Maps
Inquiry form: Visit the contact page
Email: info@iogodfrey.com
Phone: (312) 374-1830
Attend a class
Discover a mutual interest!
Few experiences will bring you together as trying something new as a couple.
Which is what makes attending a class such a good way of enjoying the Valentine’s Day spirit.
Share in the joy of picking up a new skill, or learning a new subject. Support one another through the ups and downs as you try to navigate your class.
Even the discovery of a mutual interest will be a moment you’ll remember fondly for years.
Some classes you can sign up for
Wine tasting and food preparation at The Chopping Block.
Winemaking and wine tasting at Mead Blossom Meadery.
Dance classes at Duet Dance Studio.
Art classes at AARTWERK Studio.
Catch a show
Capture the February 14th spirit by attending a performance with your significant other.
From theatre to jazz and cabaret - Chicago offers you a variety of shows to choose from.
This could be the experience that brings you two closer than ever!
Chicago Theatre Week
Turn up the romance with Chicago Theatre Week (Feb 6–16, 2025), where $15 and $30 tickets make date night extra special.
From Broadway dazzlers to cozy neighborhood plays, there’s a show for every kind of love story.
Snag your seats starting Jan 7!
Valentine's Day at the Jazz Showcase—The Alexander McLean Project
Looking for a seamless Valentine’s date night?
Start at our escape room.
Then, head a block over to Jazz Showcase for the Alexander McLean Project’s live jazz magic, happening February 13th to 16th.
With Dee Alexander’s stunning voice and John McLean’s rich guitar work, it’s the kind of night you’ll want to replay.
Tickets start at $20 for General Admission and $35 for VIP seating.
My Funny Valentine at Teatro ZinZanni
Rev up Cupid’s day in Chicago at Teatro ZinZanni amidst a whirlwind of cirque, comedy, and cabaret. All paired with a gourmet four-course meal.
Expect jaw-dropping acrobatics, live music, and laugh-out-loud moments in an intimate, one-of-a-kind setting.
Special Valentine’s cocktails and romantic surprises make it even sweeter.
Running February 13th to 16th—an unforgettable night awaits!
Onward and Out of Your League at Second City
What better day than Valentine’s Day to discuss love struggles?
Dating disasters and relationship wins—Second City’s Onward and Out of Your League delivers it all!
With sharp sketch comedy and improv, this Cupid’s special is the perfect mix of romance and ridiculousness.
Some lesser-known Valentine’s Day attractions in Chicago
Not a fan of the madding crowd?
Prefer to plan your February 14th itinerary away from the top attractions in Chicago?
Looking for offbeat ideas on how to celebrate your relationship with your significant other?
We got you!
Here are some of the lesser-known and unique Valentine’s Day destinations in our city.
Myopic Books
Representational image.
For a book-loving couple, a visit to this bookstore on N Milwaukee Avenue would certainly make for an awesome ode to St. Valentine.
Inadvertently or otherwise, they’ve designed the layout so the store looks and feels like a maze, with stairs and walkways and piles of books.
The store is near the Wicker Park Farmers’ Market.
Website: Visit their website
Dusty Groove
Representational image.
Music-loving couples - especially those that like dabbling with old-school formats like vinyl records and/or listening to genres like jazz and soul - should find this a great spot to celebrate their love for each other.
In addition to records procured from within the United States, they also import from Europe.
No matter how rare the album you’re looking for is, there’s a good chance they’ll either have it or know how to get it for you.
Website: Visit their website
The Violet Hour
Representational image.
With a wooden mural that frequently changes as its facade, The Violet Hour is a great destination for couples that are selective about their libations.
With cocktails created by celebrated mixologist Toby Maloney and an interior that can be described as “ethereal”, this establishment can be an excellent place to drop in on Valentine’s Day.
Website: Visit their website
Wabash Arts Corridor
Representational image.
Are you and your partner lovers of street art? Then the Wabash Arts Corridor, an open-air ‘museum’ hosting some of Chicago’s best street art, should be a great place to celebrate your relationship.
When you bring up Chicago, most people think of places like the Mag Mile - but the Wabash Corridor can be just as interesting, displaying a whole different side of our city.
Website: Visit their website
Celebrating Valentine’s Day 2025 in Chicago - a final word
In conclusion, Chicago is full of exciting options for Valentine’s Day.
From concerts held in candlelight to a salsa workshop, from teaming up to race the clock in an escape room to sharing a relaxing experience in a spa,...
And even offbeat activities like exploring an old bookstore to checking out our street art…
There’s something to meet every preference.
Start making your plans now - or you’ll find yourself scrambling to make plans on Thursday, February 13th - and find that everywhere’s full!
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