By J.P. Anderson and Kaila Stang By J.P. Anderson and Kaila Stang | February 14, 2025 | Lifestyle, Feature, Guides,
It’s the eternal question for all Chicagoans: “What should we do this weekend?”
We’re lucky to live in a city brimming with culture, food, art, music, architecture and more—the possibilities for an action-packed weekend are so endless that it can be overwhelming. Fear not—we’re cutting through the noise to give you five choice options to fill your calendar. Whether you’re looking to catch a live concert or soak in some of the city’s rich culture, this weekend’s activities are sure to inspire.
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Whether you’re celebrating a budding romance, years of marriage, or a Galentine’s Day with friends, Chicago is the ultimate destination for an unforgettable Valentine’s Day. Check out our curated list of the best events and activities to make this love-filled day in the Windy City truly special.
Date: Feb. 15
Lyric Opera House, 20 N. Wacker Drive / Website
Lyric Opera of Chicago will honor the life and legacy of Sir Andrew Davis, celebrating his transformative impact as Music Director and Principal Conductor from 2000 to 2021. The evening will feature performances by renowned artists, including Elizabeth DeShong, Christine Goerke, and Susan Graham, as well as the world premiere of an orchestral piece by Ed Frazier Davis, all paying tribute to Sir Andrew’s artistic contributions and his dedication to nurturing rising talent.
Date: Feb. 16, 11 a.m.-3 p.m.
Promontory Lounge, 5311 S. Lake Park Ave. South, 2nd floor / Website
Dates: Through Feb. 17
McCormick Place, 2301 S. King Drive / Website
Marking its 117th edition, the 2025 Chicago Auto Show showcases a lineup of vehicles, including world and North American debuts, along with a diverse range of domestic and imported cars, trucks, SUVs, minivans and concept cars. In addition, the event offers a variety of automotive accessories, competition vehicles, project cars, antique models and interactive exhibits from over two dozen manufacturers.
Improvised Jane Austen at iO Theater is just one of the 100-plus shows you can catch during Chicago Theatre Week.
Dates: Through Feb. 23
Various locations / Website
Celebrate the city’s rich theater tradition and score discounted tickets while you're at it, with seats under $30 for 100-plus performances across the city. For Chicago Theatre Week Continued (Feb. 17-23) deals, check out HotTix.org.
Dates: Through April 25
50 E. Erie St. / Website
The Driehaus Museum presents A Tale of Today: Materialities, expansive contemporary exhibition in which over a dozen Chicago-based artists explore the history and architecture of the Museum through materials tied to various cultures and ideologies. Curated by Dr. Giovanni Aloi, the exhibition includes works by artists such as Rebecca Beachy, Jonas Becker, Ebony G. Patterson and Richard Hunt, displayed across three floors.
Dates: Through Mar. 9
Court Theatre, 5535 S. Ellis Ave. / Website
Written by the legendary Lorraine Hansberry, A Raisin in the Sun is coming to Hyde Park's Court Theatre. This powerful play tells the story of the Younger family, who, as they await a life insurance check from their recently deceased patriarch, dare to dream of a better life—only to have those dreams threatened.
Dates: Through Mar. 29
UP Comedy Club, 230 W North Ave., 3rd Floor of Piper’s Alley / Website
Celebrating its 65th year, The Second City presents We Always Bounce Black: A Black Excellence Comedy Revue, featuring new songs, sketches and improv from an all-Black cast. The show combines comedy with a celebration of Black joy, where the audience plays an active role in the experience.
Dates: Through Apr. 6
Pistachios Contemporary Art Jewelry, 716 N. Wabash Ave. / Website
Featuring artists Jennifer Merchant, Emiko Oye and Nikki Couppee, this exhibition highlights the transformation of plastic into high-end wearable art. Through their unique approaches, each artist explores themes of value, intuition, and the role of color in reimagining an everyday material.
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Date: Through Feb. 15
Wrightwood 659, 659 W. Wrightwood Ave. / Website
The Rubin Museum of Himalayan Art presents "Reimagine: Himalayan Art Now," an exhibition that pairs contemporary works from 28 living artists with traditional Buddhist and Hindu objects from its collection. The exhibition includes commissioned pieces across various media, including painting, sculpture, sound and installation, alongside traditional religious art objects. The event features a preview and guided tour led by museum executives, with artists Tenzin Gyurmey Dorjee, Kabi Raj Lama and IMAGINE (Sneha Shrestha) in attendance.
Looking for even more hot events around the city? See our complete guide to Chicago’s biggest 2025 galas and charity events.
Photography by: Chicago Theatre marquee photo by Fraser Hall/Getty Images; Chicago Theatre Week photo courtesy of iO Theater