The Haute Seeker

8 Unique Ways to Celebrate Valentine’s Day in Chicago

Looking for an alternative to candlelight dinners and subpar movie dates? Switch up your average Valentine’s Day celebration with 8 unique ways to celebrate the holiday—perfect for yourself, a boo, or with a bestie. Check out the list below!

Galentine’s Day Market! – A Benefit for Chicago Period Project

Thursday | February 13th | 6:00 p.m. – 11:00 p.m.

Emporium Logan Square| 2363 North Milwaukee Ave. | Free

Galentine's Day Market flyer in Chicago Valentines Day The Haute Seeker
Image | Mickey Alice Kwapis

Celebrate Valentine’s Day with a Galentines’s Day market in Logan Square. Grab your best gal-pals for a market that features over two dozen of Chicago’s best female-identifying artists to create a one-of-a-kind shopping experience. The event features drink specials, arcade games, pool tables, a photo booth, tons of local businesses to shop. Admission is free to the event with a donation of pads, tampons, or other products for the Chicago Period Project.  To learn more about this event, including participating vendors, visit the event page here.

Be My Valen-Wine

Thursday | February 13th | 7:00 p.m. – 9:00 p.m.

Lost Girls Vintage | 1947 West Chicago Ave. | $10 – $15

Lost Girl in Chicago Valentines Day The Haute Seeker
Image | Lost Girls

Join Lost Girls & All Together Now for a night of natural wine tasting, valentine making, and shopping on Valentine’s Day. Tickets to the event include four tastings of featured All Together Now wines + bites & sweets, 20% off Lost Girls Vintage & Luvsick Plus, Valentine Making. Guests can also purchase tickets to a family-style dinner at All Together Now for an additional fee. For more event details here.

Valentines Cupcake Class with IntoxiCakes

Friday | February 14th | 6:00 p.m. – 7:30 p.m.

BottlesUp!| 3164 North Broadway Ave. | $10 – $35

Cupcake making workshop in Chicago Valentines Day The Haute Seeker

Show your love this Valentine’s Day by making something sweet for your sweet. Join Intoxicakes for a cupcake decorating class this Valentine’s Day. In this class, you will learn basic techniques such as pipping and how to decorate simple designs on cupcakes. After instruction and practice, each student will get 4 cupcakes to decorate and take home. There will be fun Valentine-themed toppings and decorations to make your cupcakes yummy and festive. For information about Intoxicakes and to purchase a ticket, visit the event page here.

A Valentine’s Day Roast Show

Friday | February 14th | 8:00 p.m.

Cards Against Humanity Theater | 1551 W Homer St. | $10

Comedy Show in Chicago Valentines Day The Haute Seeker
Image | Cards Against Humanity Theater

Have an unconventional date night this Valentine’s Day. Join some of Chicago’s best stand-up comics for a comedy roast show at Cards Against Humanity Theater. The concept is simple—we book the best stand up comedians in the city to perform for you, and then we mercilessly tear them apart. Make your Valentine’s Day one to remember with love and laughs—and some drinks as this event are BYOB. For more details, visit the event page. 

Valentine’s Day Health Fair 

Saturday | February 15th | 11:00 a.m. – 2:00 p.m.

Dvorak Park Advisory Council | 1119 W Cullerton St. | Free

Health Fair in Chicago Valentines Day The Haute Seeker
Image | Senator Antonio Munoz

Give your body the love it needs this Valentine’s Day. Join Senator Antonio “Tony” Munoz and the Pilsen community for a free family health fair. Adults will receive health screenings and participate in the census while kids enjoy fun games and activities. First come first serve for free handouts, hot chocolate, and desserts. For more details on this event visit the event page here.

Sade and Aaliyah Tribute

Saturday | February 15th | 10:00 p.m – 3:00 a.m.

Punch House | 1227 W 18th St. | $20

Sade and Aailyah tribute in Chicago Valentines Day The Haute Seeker
Image | Punch House

It’s all about love and good vibes this weekend in Chicago. This Valentine’s Day, enjoy a tribute to R&B legends Sade and Aaliyah Punch House in Pilsen. Sounds will be provided by DJ Jeremiah Meece—arrive early to grab the best seats in the house for this soulful event. Visit this page for more event details.

F’ing Valentine’s Day at WhirlyBall

Thursday | February 14th | 7:00 p.m. – 10:00 p.m.

WhirlyBall Chicago | 1825 West Webster Ave. | $45

Whirlyball flyer in Chicago Valentines Day The Haute Seeker
Image | WhirlyBall

Grab your friends, significant other, bae, boo, or bestie for a night out at Whirlyball. Valentine’s Day makes suck, but yours doesn’t have to. Make it a fun night out with games, food, and fun. Tickets to the Valentine’s Day event at Whirlyball include unlimited activities, food, desserts, and more. For tickets and more details, visit the event page here.

Date Night at Fred Astaire Dance Studios

Friday | February 14th | 7:30 p.m. – 9:00 p.m.

The Fred Astaire Dance Studios West Loop | 1239 West Lake St. | $40

Dance class flyer in Chicago Valentines Day The Haute Seeker
Image | Fred Astaire Dance Studios

Dance the night away this Valentine’s Day with a dance class in the West Loop of Chicago. The beginner-friendly dance class is a great Valentine’s Day date idea. Get closer as you and your partner (i.e. a friend, significant other, spouse, family member, etc.) learn new and familiar styles of dancing. Tickets are priced per couple and include dancing, performances, light snacks, chocolate, wine, and beer. To purchase your tickets, visit the event page here. 

Looking for more than unique ways to celebrate Valentine’s Day in Chicago? Check out other major events taking place this month includes a Black History Month and All-Star Weekend events guide.

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