14 Unconventional Experiences To Enjoy This Valentine’s Day In Chicago

There’s an experience for Potterheads, transporting you to the magic of the Wizarding World™, several cabaret and drag shows that will bring a little heat to your weekends that’s perfect for a night out with your closest friends, a Taylor Swift-themed break-up bar, and the opportunity to name a cockroach from The Brookfield Zoo after a not-so-stellar ex. So plan a fun night out on the town with one of these iconic ideas instead of staying home solo, having a pity party on your couch, and eating an entire container of ice cream this Valentine’s Day.

1. Venture to Hogwarts™ to experience magical moments in the Wizarding World™

Fans of Harry Potter™ can treat themselves to an exclusive experience happening right now in Chicago until May! Taking over three levels and 30,000 square feet of magic at the Water Tower Place on the Magnificent Mile, witches, wizards, and even muggles (gasp!) of all ages can explore the spectacle of Harry Potter™: Magic at Play through set recreations, photo ops, interactive magical moments, and so much more!

Take yourself on a date to enjoy a truly magical experience that you won’t soon forget. Harry Potter™: Magic At Play is celebrating Valentine’s Day with a magical discount. From February 10th at 10:00 a.m. until 11:59 a.m. on the 14th, buy one ticket and get another at 50% off. At checkout, apply the code LOVEPOTION and prepare for a magical adventure!

During your journey to Hogwarts™, you’ll step into the Dursley residence at 4 Privet Drive just like Harry did, pose for photos on Platform 9 ¾ before hopping on the Hogwarts Express™ and stepping into the spellbinding Great Hall. You’re in luck because a new batch of tickets has just been released, so snag them before it leaves Chicago in May.

2. Get icy at PB&J’s Ice Bar in the West Loop

Calling all ice kings and queens! It’s time to embrace being unattached and head to PB&J’s Ice Bar in the West Loop. Over 50,000 pounds of ice was used to create this cold-hearted watering hole which has an arctic-inspired life-size igloo, ice sculptures, and an ice throne, fitting for those that want to celebrate themselves this Valentine’s Day. Enjoy comfort food like Neapolitan pizzas and sandwiches, along with tasty cocktails like the Hot & Boozy that features Skrewball peanut butter whiskey, and hot chocolate topped with whipped cream, or enjoy the “Great Balls of Fire,” an Angry Orchard hot cider. This must-visit icy bar will open right before Valentine’s Day on Saturday, February 11th.

3. Visit this Taylor Swift-themed “Break-up Bar”

Shake off any bad blood from a former ex by venturing to this Taylor Swift-themed break-up bar. Besides hearing lots of Taylor Swift hits, guests at this unique bar can enjoy a complimentary welcome drink, tarot card readings, photo ops, and so much more! So grab your closest friends and make a plan to hit up this pop-up that’s in town from Friday, February 3rd through Sunday, February 26th!

If you can’t get enough of Taylor Swift, take yourself on a future date to the pop and country singer-songwriter’s upcoming tribute Candlelight Concert at the lavish Stan Mansion this spring. The talented Listeso String Quartet will play her best anthems from ‘Red’ and other albums — like “I Knew You Were Trouble,” “All Too Well,” and “Shake it Off” under the glow of hundreds of flickering candles. These iconic songs happen to celebrate all of those bad break-ups!

4-6. Head to a comedy show to laugh the night away

Laughter is the best medicine, even through a rough break-up. There’s no better way to enjoy the biggest names in the biz while laughing the night away than a night out solo or with a group of friends the week of Valentine’s Day than at a comedy club. Enjoy a show at The Laugh Factory Chicago, or another epic stand-up comedy show at The Den Theatre.

7. Take yourself on a thrill-seeking cocktail date at 360 CHICAGO

Go to new heights at this brand new bar located 1,000 feet up in the clouds on the 94th floor of the John Hancock Center. The sophisticated 18-seat bar celebrates Chicago’s 77 neighborhoods with a European twist. Honor your single status this Valentine’s Day with some delicious drinks, including a cocktail created by Kit Kat Supper Club Blue. The Heavenly Martini features Lemon Vodka, Alize, Blue Curacao, and Puff of Cloud. Also available is the Magnicity Pilsner, brewed exclusively for Cloudbar by the Moody Tongue, which just so happens to be the world’s first Michelin-starred brewery.

Now for the thrill…if you’ve always wanted to try out the TILT thrill ride, and you had a partner that wasn’t into adventures, there’s the Sip, TILT & View package for those looking to make their own hearts go aflutter. Plus, through February, get an extra 20% discount with code LOVEON94!

8. Step into an alternate reality at Verse: The Art of the Future – Holographic Art Gallery

Check out Chicago’s unique digital art exhibit featuring AR holograms at the Navy Pier this V-day! Step into another world at the interactive Verse: The Art of the Future exhibit features augmented reality holograms and artwork by top-selling artists from the burgeoning world of NFTs. Using AR headsets, smartphones, or tablets, this unique exhibit is here to showcase the latest digital artwork by the world’s top-selling artists. Guests will experience art like they’re in it! After all, art really can heal us…

9. Get Creative at the Spray Paint ‘n’ Sip Urban Art Workshop

Sometimes it’s just about losing yourself for a couple of hours and letting go of your troubles! One way to forget about the world of dating is to step out of your comfort zone with a class that will inspire your inner creativity! At Spray Paint ‘n’ Sip Urban Art Workshop, learn how to spray paint like a pro at this fun, interactive event. Spray ‘n’ Sip by Studio W.I.P. is the perfect experience to learn the know-how when creating street art, whether you’re as artistic as internationally-known Chicago-based artist Hebru Brantley or have never picked up a spray can or stencils in your life! This B.Y.O.B experience is the perfect excuse to grab your closest pals for an unconventional night out on the town!

10-12. Check out these drag and burlesque shows coming to Chicago

Weekends just got a little sexier with The Grand Cabaret’s series of tempting burlesque and drag performances to heat up your winter. There’s no need to save these kinds of dates for when you’re coupled up! Head to these debaucherous “Grand Cabaret” speakeasy experiences with friends, where you’ll enjoy tantalizing performances in a hidden back room space in the West Loop’s Porkchop restaurant at 1132 West Grand Avenue.

Check out one of these unique shows taking place this January and February, including the Grand Cabaret After Dark, a Boozy BBQ Drag Brunch, and STRIPPED, a Decadent, Debaucherous Burlesque Revue that will surely ignite you with the excitement you’re longing for!

13. Name a hissing cockroach after your ex courtesy of The Brookfield Zoo

For lovers scorned, the Brookfield Zoo has a yearly tradition you’ll absolutely love. This Valentine’s Day, name Madagascar Hissing Cockroaches after an unappealing ex for a $15 donation that benefits the popular suburban zoo.

So, you’re probably thinking, “What’s in it for you?” Not only do you get the joy of naming these creepy creatures that reside in the Hamill Family Play Zoo, but your ex’s name will be proudly displayed on the Brookfield Zoo’s “Cockroach Naming Hall.” The names will be shared with the world online on Valentine’s Day since the zoo is temporarily closed through March 1st, and — you’ll also get a certificate that can be shared with your ex or kept to yourself for your private satisfaction if you wish.

14. Enjoy a one-of-a-kind anti-V-day event celebrating the brand new SOUR PATCH KIDS Sour Hearts candy at Soho House

To celebrate the launch of the new SOUR PATCH KIDS Sour Hearts candy, an unromantic dinner experience is happening the day before V-day, on February 13th, at The Allis at Soho House in Chicago. At this outing, you’ll try the newest limited-edition black heart-shaped raspberry-flavored candy (fitting for the occasion), incredible dishes, enjoy anti-Valentine’s Day decorations, and much more. Perfect for singles or an epic Galentine’s date with your closest friends without the typical décor, flowers, and more.

“Valentine’s Day can be a sour subject for some, which is why we wanted to offer a SOUR PATCH KIDS treat for all our fans to enjoy. SOUR PATCH KIDS Sour Hearts candy plays on the mischievous side of Valentines while still delivering the sour-then-sweet treat SOUR PATCH KIDS fans have come to know and love, regardless of relationship status,” said Lauryn McDonough, Senior Marketing Director, Candy, Seasonals, and Chocolate at Mondelēz International, in a press release. Can’t make it to the Chicago celebration? Follow Sour Patch Kids on Instagram for the chance to win your own Sour Hearts Social Club kit so you can celebrate with your nearest and dearest friends at home! But don’t wait; winners will be notified by February 6th.

Looking for something more traditional? Check out these Valentine’s Day date ideas here!