Your 2022 Guide to Unique Valentine's Day Events in the City

Show Your Local Businesses Some Love

By Debra Flanagan, Macaroni KID Chicago Northside January 25, 2022

This Guide is sponsored by Tooth Buds Pediatric Dentistry. Tooth Buds provides kid-focused, high-quality dental care. They aim to make dentistry a stress-free, pleasant experience for your child. Dr. Mital Spatz is a specialist in Dentistry for kids and adolescents as well as those with special needs, focusing exclusively on the early years–the most critical years–of your child’s dental care. She is Board Certified and "In-Network" with many PPOs. Located at 2929 N. Southport Avenue, they are currently accepting new patients. Go to to learn more. 773-328-8282

I am pleasantly surprised and excited to find so many fun options for celebrating Valentine's Day in 2022. Have fun and tell them I sent you!



Bachata with Your Boo at Dance on Broadway (3126 N Broadway)

February 5th at 4:30pm-5:30pm

Enjoy a romantic evening with your loved one learning romantic dancing of bachata with Mara Noguez. Afterwards enjoy a wine tasting led by @bottles_up_chicago
Sign up in advance as space is limited! Sign up via Mindbody or call the studio to claim your spot!




Painting with a Twist at Bottle & Bottega (2900 N. Lincoln)

Various Dates in February

Artist led painting sessions.  BYOB.  Valentine's Day themes

In-studio with limited capacity and virtual zoom options available

$39 - $47


Red Velvet Floral Workshop with Alice's Table

Various Dates in February

Tickets include an abundance of farm-fresh flowers and a vase delivered the day before event.  Alice will take you through an exclusive virtual floral masterclass to create a beautiful, floral arrangement, sharing all her tricks and tips.




XOXO Experience at the Terrace Globes at Hotel Zachary

February 2022

Cuddle up on the Terrace this February in the hotel’s see-through globes for our XOXO experience. We’re celebrating all things love, with a special romantic touches throughout our cozy globes, including a couple’s game and new specialty Valentine’s Day themed cocktails—perfect for two or a close friend group. Those who book are invited to order from the hotel’s Dinner Menu, crafted by Chef Michael McKinnel from Mordecai Chicago, and those with a daytime reservation can pre-order from a selection of Picnic Baskets to complete your experience. While enjoying the company of loved ones – for couples or friends – the globes offering sweeping views of Winterland at Gallagher Way, with ice skating across the street for the perfect activity to start or end your night with.

Valentine's Day Dinner and Dancing at Get in the Kitchen (3617 N. Broadway)

February 13th at 6pm

Come celebrate Valentine’s Day by making 3 amazing Tapas dishes & Dessert while you hang out and learn to romantically dance Latin style with Instructor Jon!! Mix and mingle, and have fun while cooking a meal you won’t soon forget! Join us for a night of food, salsa dancing, socializing and fun!

$79 Tell them I sent you!

Dumplings for My Dumpling Valentine's Day Event at Get in the Kitchen (3617 N. Broadway)

February 14th at 7pm

Learn how to make 3 amazing dumplings while you hang out with your dumpling! Join us for a night of food, socializing and fun!
Grab your Dumpling and Come on in!
Menu: Steamed Chinese Chicken Dumplings, Pan-Fried Shrimp Scampi Potstickers & Crispy Cherry Chocolate Marshmallow Won Ton’s for Dessert. Every party ticket includes A Valentine Cocktail.


Logan Square

Mommy & Me Kids Valentine's Tea Party at Park & Field (3509. W. Fullerton)

Sunday, February 6th 3:30pm-6:30pm

Tea sandwiches for Parents & Kids.  Cookies, bars, scones, hot tea and juice.  One glass of bubbly or a hot toddy for parents.  Tableside cookie decorating and Make Your Parent's a Valentine 

$20/person (kids under 2 free)  Outdoor, heated, seating available. Reserve on



My Funny Valentine Comedy Show at Laugh Factory Chicago (3175 N. Broadway)

February 11th, 12th, & 14th 

Roses are red, violets are blue, be my funny valentine boo! We're transforming our world famous stage to a Valentine themed night & featuring the hottest comics in the country with an all-star comedian line up.



Logan Square

Candlelight Romantic Valentine at Stan Mansion (2408 N Kedzie Blvd)

February 9th, 10th, & 14th 6:30pm or 8:45pm

Stunning classical music performance by local musicians of the Metropolis String Quartet.  Intimate ambiance in beautiful venue, bathed in candlelight.  Carefully selected programs all about love.




Bunnies by Candlelight at Cuddle Bunny: Club, Care, & Community (2901 N. Clark St.)

February 12th, 13th, and 14th 6pm-9pm

Bring your Valentine to snuggle with our cuddly bunnies by candlelight, with romantic music, chocolates, and roses.



Valentine's Dance Party at Redline VR (4702 N. Ravenswood)

February 12th 7pm-9:30pm



Love, Alma Package at Hotel Zachary

February 11-14, 2022

Hotel Zachary’s “Love, Alma” package will allow you to add to your very own love story, inspired by the hotel’s namesake Zachary Taylor Davis (architect of Wrigley Field) and his wife, Alma Davis. Take the time to let that special someone know that you love them by booking a special Valentine’s Day package. 

The package features:
o   2 Hotel Zachary Robes to keep
o   Chocolate Covered Strawberries
o   Bottle of Bubbles on ice
o   Extended noon checkout

Cozy in Chicago at the Willows Hotel (555 W. Surf)

One Night's Accomodation, Bottle of Champagne, Box of Specialty Chocolates, 2pm Late Check-Out

Rates start at $124  



The Princess Bride Package at The Music Box

February 14th at 7pm

Bring your Valentine to the Music Box for THE PRINCESS BRIDE, the fairy tale that puts the “comedy” in “romantic comedy.” Fun for all ages, this interactive presentation let's you play along with this magical adventure (Featuring prop bags!)



Chick Flix and Chill Galentine's Day Movie Night at Camp Lotties (1925 W. Cortland) 

February 15th-16th 5:30pm Pretty Woman, 8:00pm Magic Mike

Get a free High Noon Galentine's Day Gift Basket and a Complimentary Bucket of High Noon Flavors with Tent booking.


ChiTown Movies Presents (2343 S. Throop St.)

February 12 - February 14 various showtimes 

Movies at the Drive-In over Valentine's weekend include: TBD. Food available for online ordering and is delivered to your car 

$25-$33 per car

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