If you’re looking for things to do in Chicago this weekend for Valentine’s Day, whether it’s a cozy date night, something creative for teens, or a family-friendly plan that still feels special, I’ve rounded up a few ideas that keep it local and manageable. Valentine’s weekend doesn’t have to mean overbooked restaurants or overcomplicated plans. It can be simple, thoughtful, and still memorable. Here are a few ways to celebrate in the city without turning it into a production.
🎭 The Jury Experience – Immersive Courtroom Show (Adult Friendly)
Get out of your comfort zone this Friday with The Jury Experience at the Museum of Contemporary Art Chicago Edlis Neeson Theater. This interactive theatre event turns you into the jury for an immersive courtroom show where YOU decide the verdict in a moral and legal case. It’s a unique Valentine’s weekend date night or night-out experience for adults that lasts about an hour.
👉 More info: https://thejuryexperience.com/
📍 Edlis Neeson Theater – MCA, Chicago
w.eventbrite.com/e/2026-chicago-winter-tequila-tasting-festival-february-14-tickets-1319635598599
🎨 Black Creativity Career Showcase (family friendly)
Support and explore a celebration of Black creativity and innovation at the Black Creativity Career Showcase at the Museum of Science and Industry. This family-friendly event invites kids and teens to interact with Black artists, scientists, and engineers and learn through hands-on activities. It’s a wonderful daytime outing that blends inspiration with learning.
👉 Event info: https://www.msichicago.org/black-creativity-showcase
Photo credit: Museum of Science and Industry
🏙️ 2026 Chicago Winter Tequila Tasting Festival (adult friendly)
Spend Valentine’s Day sampling an amazing lineup of tequilas and mezcals at the Chicago Winter Tequila Tasting Festival at Kings Dining & Entertainment. This festival is perfect for adults who love flavor, discovery, and a social vibe this weekend. Mix tasting with live DJ music and bites while celebrating the season. only a few tickets remain
👉 More details: https://ww
🍷 Galentine’s Cocktail Class & Fiesta in Wrigleyville (Girls night Out)
For a fun outing with your girlfriends you can actually attend this weekend, consider the Galentine’s cocktails event at Cesar’s in Wrigleyville on Sunday, Feb 15, 2026. It’s a celebration of friendship with margaritas, vase decorating, DIY flower bouquets, and good company — perfect for a girls-only twist on Valentine’s weekend.
👉 Event info: Visit the Chicago Artisan Market and Galentine’s listing for details (search “Cesar’s Killer Margaritas Galentine’s Fiesta” on LakeviewEast.com) — this is part of Lakeview East Valentine’s lineup.
Why it’s great for Galentines:
• Designed for friends celebrating together
• Includes cocktails and creative activity
• Mid-afternoon timing works with other weekend plans
📸 Photo credit: Cesars Killer Margaritas
🎨 Youth-Led Creative Programming at the MCA (family friendly)
Chicago teens are hosting creative programming at the Museum of Contemporary Art Chicago through the Teen Creative Agency. This event lets young creators imagine, build, and engage with contemporary art in a free-form, youth-centered setting — ideal for teens and families who want something unique to do this weekend.
👉 More info: https://visit.mcachicago.org/events/youth-led-programming-teen-creative-agency/
Photo credit: Museum of Science and Industry
However you choose to spend Valentine’s weekend, make it intentional. Whether that’s a creative museum stop, a night out that feels different, or keeping it low-key with the kids, Chicago always gives us something to work with. Keep it simple, stay local, and choose what feels right for your season of life.
Enjoy Chicago,
Juliana