The best December 2026 events in Chicago

Escape the planet with exhibits about the first lunar missions, the solar system and more, plus immersive shows in the dome theater. Stationed just a stone's throw away from the Adler, the Doane Observatory is also home to the largest public telescope in the area and gathers 7,000 times more light than the human eye. Every Wednesday, the Adler stays open late from 4pm-10pm so that folks can visit after work or school. And best of all, admission is free on those nights for Illinois residents.

This weekly “live magazine” is a cavalcade of culture, politics and wit featuring journalists, actors, comedians and musicians offering idiosyncratic reports on the news of the day. Head to Uptown’s iconic Green Mill for drinks, hot takes and laughs; the longstanding Saturday afternoon edition tends to run about two and a half hours.

Whether you’re parenting a pint-sized Pokémon devotee or a nostalgic millennial still clinging to a holographic Charizard card for its “possible resale value” (guilty), the Pokémon Fossil Museum is designed to surprise and delight. Making its U.S. debut at the Field Museum in spring 2026, the international exhibition invites visitors to compare Fossil Pokémon like Tyrantrum and Archeops with real-world fossils—including SUE the T. rex. Expect Pokémon models, real fossil excavation tools and immersive soundscapes throughout.

Located inside The Den, a 1920s greystone-turned-hotel in Lakeview, the Blind Wolf Speakeasy is an intimate, approachable bar, event venue and home to a free weekly comedy show. Blind Wolf Comedy hosts a rotating roster of Chicago comics each Wednesday at 8pm, as well as open mic nights on Thursdays at 7:30pm. There's no cost to attend, but you can reserve a seat through their Instagram page.

Just when you thought the state's largest mall couldn't surprise you anymore, Woodfield Mall announces WONDRA, a sprawling new immersive experience. Inside, you’ll wander through enchanted meadows that respond to the sound of your voice, stumble across bioluminescent landscapes and drift into crystal caves and celestial gardens that blur the line between digital spectacle and raw wonder. Every corner is crafted to ignite curiosity and inspire a sense of awe we, whether you’re a kid seeing it all for the first time or an adult who forgot what it feels like to play.

Head to 360 Chicago on Saturdays for yoga with a killer view. Instructor Britta Eumann will lead an hour-long class on the 94th floor of 875 North Michigan Avenue (formerly the John Hancock Center) that’s suitable for all ages and skill levels—you just need to bring your own mat and arrived properly dressed. Registration is $55 and includes a cocktail or coffee, plus admission to the observation deck so you can stick around and snap some photos after you're done striking poses on the mat.

Explore a host of galleries and programming at this monthly event that showcases West Town’s dynamic arts community. On the first Friday of every month, galleries and arts-based businesses stay open until 8pm.

"Flyway City: Architecture for a Flourishing Ecosystem," designed by Studio Gang and led by world-renowned architect Jeanne Gang, explores solutions to prevent the estimated one billion annual bird-glass collisions in the U.S. Through a variety of architectural models, interactive media and local artifacts, the exhibition demonstrates how urban design can coexist harmoniously with nature. 

Intuit Art Museum joins the national Handwork 2026 celebration with an exhibition investigating Henry Darger’s relationship to traditional American paper crafts. Drawing on research by art historian Dr. Mary Trent, the exhibition demonstrates how Darger adapted common practices—such as making paper dolls and scrapbooks—into a complex, mixed-media narrative style. By showcasing Darger’s source materials alongside his final works, the exhibition highlights how he reclaimed these institutionalized hobbies to express the interior lives and struggles of the marginalized.

This immersive exhibition recreates the Secret Annex where Anne Frank, her family and four others hid during the Nazi occupation of the Netherlands. Chicago is only the second U.S. city—and the first in the Midwest—to host the experience, which includes rarely seen artifacts from Frank’s life. Visitors can walk through the reconstructed hiding place while learning about Anne’s childhood, the rise of Nazi Germany and the Frank family’s years in Amsterdam. The exhibition offers a powerful look at the risks, courage and daily realities of those who lived in hiding.