Forget that it’s a tad chilly outside. This weekend is going to fill you with the warm-fuzzies. Why? Because on this Valentine’s Day weekend, the smiles and giggles will be non-stop with Navy Pier’s highly anticipated NBA Crossover Event that coincides with the NBA All Star games, stage shows and exhibits, a heart-pounding Hot Wheels event, family fort-building and more! Read on for our Editor’s picks for family time that will leave your heart tingling.

photo: NBA Crossover, Getty Images/NBAE


Hyde Park

New! Check Out MSI’s Black Creativity: 50 Years
Learn the story of significant moments and pioneering African-American Chicagoans whose work pushed boundaries. While you’re at MSI, visit the longest-running exhibition of African-American Art in the nation. Fri.-Sun. Event details


Last Chance! Experience Gallagher Way’s Winter Wonderland
Gallagher Way is decked out with lighted flare and activities bigger and brighter than ever before! Make the day extra special and go glamping at Hotel Zachary or close out the season and get creative with Paint the Ice. Fri.-Sun. Event details

Giggle with Storytown Improv
From superheroes to undersea adventures, princesses to dinosaurs, Storytown takes you on an interactive, fully improvised adventure! Sat. Event details

Millennium Park

Figure 8 at Millennium Park’s Ice Skating Rink
Take a spin on the ice with a magnificent view. Once again this year, the rink will offer free ice skating lessons. Fri.-Sun. Event details.

Navy Pier

New! Be Treated Like Royalty at Chicago Children’s Museum’s Castle
Young imaginations are invited to play in a castle with secret tunnels, a rope bridge, tower, dungeon, throne room, wizard’s room, kitchen, feasting table, market and more. Your kid’s imagination is their only limitation to a fantastical adventure. Fri.-Sun. Event details

Join in the Excitement of NBA Crossover 2020
NBA Crossover will be the most immersive and engaging pop culture event during NBA All-Star. Featuring exclusive product drops from top brands, NBA player appearances, celebrities & influencers, musical performances and much more! Fri.-Sun. Event details

Portage Park

Build a Magnificent Fort with the Family
Enter a world of play and creation as Filament Theatre transforms into a playspace to build new worlds. Using cardboard boxes, sheets, clotheslines and more, families build adventures of their own devising. Sat. & Sun. Event details.

West Loop

Be Charmed by Wake Up, Brother Bear!
Wake Up, Brother Bear! is a highly interactive show that will take you and your cubs on a fun-filled journey through the four seasons with a playful pair of bears. Sat. & Sun. Event details

Various Locations

Snag a Sweet Valentine’s Day Treat at Stan’s Donuts & Coffee
Chicago’s favorite donut shop is making it easier for people to spread the love with its fresh lineup of Valentine’s Day donuts and drinks. Stan’s Valentine’s Day collection includes festive donuts and drinks meant to share with your special someone(s). Fri.-Sun. Event details.



Take a Tasty Class at Chicago Botanic Garden
Did you know many of our favorite cold sweet treats get their flavors from plants? Participants will put together (and taste!) some easy-to-make fruity treats like smoothies and flavored shaved ice and get recipes to make at home. Sun. Event details.

Hoffman Estates

Get Your Heart Pounding at Hot Wheels Monster Trucks Live
This exhilarating show combines iconic jumps and stunts with epic crashing, smashing and exciting specialty acts and world record attempts.  Sat. & Sun. Event details


Marvel at Morton Arboretum’s Enchanted Railroad
Watch as an intricate mini model railroad winds through magnificent scenery. This two-level interactive display is specially designed for the kiddos because it’s meant to be viewed from just two feet off the ground. On Sunday, you’ll find a sensory-friendly experience. Fri.-Sun. Event details.

Make a Valentine’s Day Gift for the Birds
Children can celebrate their love for nature in Morton Arboretum’s Children’s Garden by making tasty treats to hang on the trees for the birds.  Sat. & Sun. Event details


— Maria Chambers


Party Hearty! Valentine’s Day Activities You Can’t Miss

Your Family Guide to a Chicago Treasure: MSI

Hit the Trails! Best Hikes with Kids No Matter the Season

Staycation Spotlight: Hotels with Amazing Kid Amenities

. . . and check out our Events calendar for even more suggestions.