Explore exciting events across Chicagoland this winter… from music and community celebrations to wellness and more! With so many opportunities to enjoy the season, here are a few of our top picks to check out this weekend.
Celebrate Love at the Family Valentine’s Day Party
This all-ages Valentine’s bash is packed with heartwarming activities, from a Taylor Swift dance party to friendship bracelet making and a Valentine’s card station. Enjoy a special cocktail and mocktail menu and a buffet featuring comfort food favorites.
Date: February 14
Time: 6PM-8PM
Cost: Kids $30; Adults $40
Location: O’Toole’s, 412 S Milwaukee Ave, Libertyville
More Info: timothyotooles.com
Have a Proper Afternoon at Galentine’s Day Tea
Step back in time for an elegant tea service inside the historic 1856 Kennicott House. Guests will enjoy a three-course luncheon while learning about the history of tea, proper etiquette, and the stories of the women who once lived in the home. Period-dressed staff complete the charming experience, making it the perfect way to toast to friendship.
Date: February 15
Time: 11:30AM-1PM
Cost: $45+
Location: The Grove National Historic Landmark, 1421 Milwaukee Ave, Glenview
More Info: webtrrac.glenviewparks.org
Drop Them Off at Kids’ Night Out
Give the kids an evening of hands-on science fun while you enjoy a Valentine’s date night. At Rosewood Beach, young explorers will create “snow globes” while learning about liquid density, experiment with magnetic sand, and enjoy pizza with new friends—all under the guidance of expert naturalists.
Date: February 14
Time: 5:30PM-7:30PM
Cost: $28
Location: Rosewood Beach & Interpretive Center, 883 Sheridan Rd, Highland Park
More Info: pdhp.org
Go to the 2025 Black History Month Celebration
This annual celebration at the Jack Benny Center for the Arts showcases the ongoing legacy of African American heroes through music, spoken word, dance, and dramatic readings. A free, family-friendly event, it brings the community together for an evening of culture, history, and inspiration.
Date: February 15
Time: 5PM-6:30PM
Cost: Free
Location: 39 Jack Benny Dr, Waukegan
More Info: waukeganil.gov
Roll Into Fun at the Be Our Valentine Mickey & Minnie Skate Party
Lace up your skates for a magical evening with Mickey, Minnie, and friends! This Disney-inspired Valentine’s event features music, games, raffles, and face painting, plus free photo ops with beloved characters. Costumes and festive outfits encouraged—skating optional but recommended.
Date: February 15
Time: 4PM-6PM
Cost: $10+
Location: Just For Fun Roller Rink, 139 N Seymour Ave, Mundelein
More Info: eventbrite.com
