Want to know what’s happening this weekend in Chicago? Look no further. There’s a whole calendar of exciting events, exhibits, and activities taking place all over the city this month in Chicago.
This weekend in Chicago is jam-packed with fun things to do: romantic Valentine’s Day activities, exhilarating live sports, jaw-dropping art exhibits, family-friendly fun, exciting cultural events, and so much more. Plus, enjoy discounted tickets to live shows across the city this weekend during Chicago Theatre Week.
Check out just a few of the top things to do this Valentine’s Day weekend in Chicago, Feb. 13 – 15, 2026.
Valentine’s Day Fireworks
Celebrate the Magic of Valentine’s Day with fireworks at Navy Pier on Saturday, February 14 at 9PM! Feel the love in the air with a…
Heartbeat House Party at Shedd Aquarium
Feel the love and the rhythm at the first-ever Heartbeat House Party! Celebrate Valentine’s Day beneath the waves with house music and aquatic allure. Dress…
Love Hurts: A group exhibition
For those the wronged and the heartbroken, Love Hurts will feature artwork embracing themes of longing, despair, and the realities of love beyond a Valentine's…
Valentine’s Day Dinner Cruises
Set sail with your special someone on an unforgettable experience with a Valentine’s Day Dinner Cruise. Celebrate with your Valentine or Galentine, dining and dancing…
The Cosmic Underground Show-Valentine’s Day Matinee
The Cosmic Underground Show blasts off for a 90-minute immersive comedy, magic, and mind-reading show. Cosmic founders and real-life couple Harrison Lampert (a quirky sleight-of-hand…
Chicago Theatre Week
It’s the most exciting season of the year for theatre lovers. Chicago Theatre Week 2026 tickets are now on sale! For $30, $15 (or even less!), you can enjoy the diverse offerings of Chicago’s dynamic theatre scene from Feb. 5 – 15, 2026.
Valen-Wine’s Day: A Comedy & Wine Pairing
This Valentine’s Day, fall in love one glass at a time. Valen-Wine’s Day pairs six of Chicago’s best stand-up comedians with six different wines, creating…
Handmade Market at the Empty Bottle
Handmade Market Chicago - you’re invited to celebrate two decades of creativity, community, and craft! 20 Years of Handmade Market Chicago Saturday, January 10, 2026…
Black Makers Market at Navy Pier
Discover a vibrant marketplace at Navy Pier celebrating local Black-owned brands, artisans, and creatives. Explore 10 unique vendors every Saturday in February, spotlighting makers from…
Valentines Day Date Night Cocktail Experience
Shake Up Your Valentine’s Day Weekend! Celebrate love, friendship, or just a good time with our special Valentine’s Cocktail Class at Industry Ales! Whether you’re…
The Chinatown Adventure Food Tour
Immerse yourself in the vibrant flavors and rich history of Chicago’s Chinatown on our top-rated TripAdvisor food and culture tour. Enjoy seated dining at five…
Burlesque For Lovers – Valentines Day Show
Starlets presents Burlesque for Lovers – a Valentine’s Day show celebrating love, lust, and self-love! Enjoy an unforgettable night of dazzling performances featuring Ronnie Rouge,…
Cupid’s Revenge: A Corny Love Story
Come lovers, come haters, come lonely masturbators, to an evening of Love, Laughter, and Debauchery. Sure, Cupid's job is to shuck our hearts, butter our…
Mardi Gras at Blue Bayou: Screw Cupid Edition
Cupid’s cancelled. Beads are not. This Valentine’s Day, we’re throwing romance out the window and giving away a trip to New Orleans for Mardi Gras…
Catalyst: Im/migration and Self-Taught Art in Chicago
Catalyst: Im/migration and Self-Taught Art in Chicago, the first exhibition to open in Intuit’s newly-renovated museum, is part of Art Design Chicago, a citywide collaboration initiated by the Terra Foundation for American Art that highlights the city’s artistic heritage and creative communities.
Salome
Based on Oscar Wilde’s one-act play, Salome has been thrilling and fascinating audiences for more than a century. Lyric Opera of Chicago brings Sir David McVicar’s decadent…
American Prophets: Writers, Religion, and Culture
American Prophets journeys through the pages of American history to explore the influence of religion and spirituality on writers and culture, with interactive displays incorporating…
1st Annual Bud Billiken® All Star PAL Showcase
Chicago Defender Charities presents the first-ever Bud Billiken® All Star PAL showcase, a showcase of rhythm, creativity, and community pride. This exciting new event brings…
The Indoor Farmers Market at Water Tower Place
For the second year in a row, Chicago’s Water Tower Place is teaming up with the South Loop Farmers Market to bring its popular indoor…
Not a Soft Thing: A Group Exhibition by Artist Mothers
Not a Soft Thing is a multifaceted exhibition by 15 artist/mothers spanning diverse cultural backgrounds, disciplines, and stages of caregiving. Together, this artist collective challenges…
Balloon Museum: EmotionAir
The Pop Air and Let’s Fly exhibitions continue to thrill and engage a participative audience, but EmotionAir sets an even more ambitious goal. This latest…
Yoko Ono: Music of the Mind
Yoko Ono: Music of the Mind presents one of the most comprehensive exhibitions to date of Yoko Ono, the trailblazing artist, celebrated musician, and formidable campaigner…
Chicago Architecture Biennial
Explore cutting-edge projects and ideas from global contributors at North America’s largest architecture and design festival. All events are free and open to the public.
Explore our events calendar for more Chicago events and happenings.
Please note that all events are subject to change.
