Unique Valentine's Day Events in the City

Show Your Local Businesses Some Love

By Debra Flanagan, Macaroni Kid Chicago Northside February 2, 2021

I am pleasantly surprised and excited to find so many fun options for celebrating Valentine's Day in 2021.  I can't even decide which ones to do!  I haven't had this problem in awhile.  And let me just say, I am a huge proponent of masks, social distancing, and staying home as much as possible, but every so often we need to break the monotony and these sound like pretty safe activities.  Have fun and tell them I sent you!



Bachata with Your Boo

February 14th at 4pm-5pm at DOB - Dance on Broadway (3126 N Broadway)

Covid safe, beginner dance class.  You must bring your own partner, there will be no rotation of partners.

For more info email or 773-661-9252

$50/couple with champagne toast


Valentine's Day Skate

February 14th at 1:30pm-3:30pm at Fleetwood Roller Rink (7231 W. Archer)

Admission $8, Skate Rental $4 (708) 458-0300



Painting with a Twist - In-studio with limited capacity and virtual zoom options available

February 5th - 28th at various times at Bottle & Bottega (2900 N. Lincoln)

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

$37 - $40


Galentine's Celebrations with Alice's Table

Wednesday, February 17th at 6pm

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.



Logan Square

Kid's High Tea

Sunday, February 14th 3pm-6pm at Park & Field in Logan Square (3509 W. Fullerton)

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

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


Camp Lotties

February 12th-14th at Lottie's (1925 W. Cortland) 

Heart shaped pizza, champagne, hot drinks and chocolate available in their Valentine's Day themed tents

West Loop

Sugar Rush Pop Up

Every Thursday thru Sunday at Recess (838 W. Kinzie) 

Wander through outdoor candyland-like pop up

Adult tickets $19 include one hour admission, a bag of assorted candy, a rice crispy treat, and one Sugar Rush specialty cocktail

Kids tickets $6 include admission, bag of assorted candy rice crispy treat, hot chocolate, and special crafts


Valentine's Dinner

February 12th - February 14th 5pm-9pm at FireLake (221 N. Columbus)

4-course dinner $65/person

Private indoor dining available for $45/table rental fee

call 312-477-0234 to reserve


Valentine's Day 3-Course Romantic Dinner Party with Alissia

February 13th & 14th at Get in the Kitchen (3617 N. Broadway)

Deliciously amazing high end restaurant- quality Valentine's Dinner in the comfort of your home.  Chef Alissia will guide you on a decadent cooking journey.  Socialize with other couples and learn new culinary skills.

All ingredients for two to be picked-up on February 12th.  Recipes included as well as Chef Alissia's personal curated Valentine's Day playlist link and personalized menus to print at home. Menus includes Strawberry Hibiscus Mimosa (champagne not included), Pesto & Garlic Shrimp Bruschetta, Beef Tenderloin & Scallops, and Flourless Chocolate Cake

$179  Tell them I sent you!


Valentine's Virtual Chefs Dinner benefiting 360 Youth Services

Saturday, February 13th at 5pm

Interactive Zoom Class led by Celebrity Chef Giuseppe Tentori of Boka Group

Ticket packages vary, and based on what's chosen, include the ingredients you will need to create a restaurant-quality meal at home and impress yourself and your loved ones.  Learn more at

Valentine's Day Virual Wine Tasting & Pizza for 2 Event to Raise Funds for Teen Cancer America

February 14th at 6pm

Wine and Two Chicago Deep Dish Pizzas are sent to your home (one heart-shaped)  A wine sommelier will teach you about the wines and wine etiquette, and love songs will be performed for entertainment

$110 for wine and pizza, $60 for wine only, $70 for pizza only, $15 to watch only.  Must be ordered by February 7th



Ravenswood Valentine's Date Night Bundle 

Available for pick-up February 11th and 12th 9am-5pm

Las Locas Comedy presents an evening of performances from a diverse lineup of Chicago comics.  Streams live on February 13th at 8pm and available to stream after

$95 Includes link to virtual Valentine's Date Night At-Home Comedy Show, bottle of VIN312 Cabernet, $40 gift card to Tuscan Hen, 6 pack of dark and white chocolate covered mini Alfajores from Lucila's Alfajores, Valentine's print from Starshaped Press, a bag of locally roasted coffee from Groundswell Coffee Roasters, a special gift from the Chicago School of Shoemaking and Leather Arts, and a promotional offer from Redline Virtual Reality

Proceeds benefit each participating business as well as the Greater Ravenswood Chamber of Commerce


Virtual Valentine's Comedy and Trivia Night

February 11th, 13th, & 14th at 7pm at Laugh Factory Chicago (3175 N. Broadway)

Laugh Factory Chicago presents a virtual standup comedy experience.  The show will be followed by a virtual trivia competition



West Town

Candlelight Romantic Valentine

February 11, 12, 21, & 28th at various times at Salvage One (1840 W. Hubbard)

Stunning classical music performance by local musicians of the Metropolis String Quartet.  Intimate (but socially distanced) ambiance in beautiful venue, bathed in candlelight.  Carefully selected program all about love.

$55/person  Tickets at


Galentine's Day: Girls' Night In Hosted by Teen Parent Connection

February 12th 7pm-8pm

Storytelling led by Bridget Schank, followed by Teen Parent Connection's current couselors' guidance through "love languages" and insight into building intimate relationships during the stress of pandemic.  A veteran teen parent will share her journey

Free - $14 suggested donation to support future programs and service by Teen Parent Connection

Register at



Bunnies by Candlelight

February 14th 5pm-8pm

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

$16/person 2 people per enclosure.  Young adults/adults only. 4 separate enclosures to ensure social distancing at Cuddle Bunny: Club, Care, & Community (2901 N. Clark)



Love Your Local: A Valentine's Day Market

February 1st 12:00am - February 12th at 11:45pm

NorthCenter Chamber of Commerce is partnering with Bachalaash and local shops and restaurants to offer a convenient way to shop for the perfect Valentine's Day gift or dinner from the convenience of your home.  Unique curated gifts, treats, meal kits & more from select NorthCenter shops and restaurants  

Rogers Park

Love Fest 

February 7th 10am-3pm at Honeybear Cafe (parking lot - 7036 N. Clark)

Shop Local Artists and Small Business in Rogers Park for the perfect Valentine gifts.  Vendors include: T-Dog Sauce,

Sweet Comb Chicago, Northshore Candle Co, Bark Place, Life's Sweet Inc., Black Dog Gelato



Bloom Just For You Valentine

February 11th - 15th at Kimpton Gray Hotel (122 W. Monroe)

Suite filled with flowers ($650 value), floral drawn bath, 2 concierge cocktails

Rates starting at $216  Must be booked five days in advance


Love Alma Package

February 12th-28th at Hotel Zachary (3630 N. Clark)

Package includes Ballpark View King or Junior Suite, two upgraded jersey knit Boxer Robes, Shower Aroma Therapy Tablets, Chocolate Covered Strawberries, Bottle of Champagne on ice

Rates start at $250 (second night 50% off)

The Romance Package

Willows Hotel (555 W. Surf)

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

Rates start at $114 on February 9th



The Princess Bride Package

Music Box To-Go

Package can be added to any popcorn/soda/beer/candy package.  Includes 4 of the Music Box's interactive screening guides & prop bags (including bubbles, candy, and more) Movie not include (watch at home on DVD, Hulu, or Disney+)


Camp Lotties

February 9th-10th at Lottie's (1925 W. Cortland)

Rom-Com Movie Tents 6pm - Say Anything  8:30pm Pretty Woman


ChiTown Movies Presents

February 12 - February 14 various showtimes

Movies at the Drive-In over Valentine's weekend include The Wedding Singer, The Notebook, Lady and the Tramp, 10 Things I Hate About You, and La La Land

$25-$33 per car.  Food available for online ordering and is delivered to your car