Over the last few years, I have fulfilled my dream of being a snowbird in January, since luckily I can work my day job remotely. Eventually, I hope to extend this time to three months.
My first year, I was in FL, and last year, I was in NOLA. Sure, there was a historic snowstorm, but being a native Chicagoan, it was no big deal. This year I’ll be in Austin, TX. Hopefully, swimming laps outside at the Big Eddy.
But I will be in Chicago in spirit and keep you posted on some cool ways that I highly recommend to welcome in 2026 Chicago-style. Remember to check back often, as I add to this list.
50+ Things to do in Chicago in January
Thru Jan Golden Hour at Epiphany Center for the Arts
This ongoing series features free live music in the cafe bar area of this converted church, along with food and drink specials.
Thru Jan Paper Machete at the Green Mill
This long-standing free series brings actors, comedians, and musicians to the iconic jazz club each Saturday.
Jan 19 MLK Tribute Concert by Chicago Sinfonietta
This heartfelt musical tribute will feature the acclaimed Chicago Sinfonietta orchestra at the landmark Auditorium Theatre.
Jan 24 Polar Adventure Days
Enjoy free family fun in Chicago’s parks with sled dogs, snowshoeing, crafts, and more winter activities at lakefront Northerly Island.
Jan 3 – 30 Buddy Guy at Buddy Guy’s Legends
This annual residency is a must-see for blues fans when the iconic Buddy Guy takes the stage at his Chicago music venue.
Jan 21- Feb 1 Chicago International Puppet Theatre Festival
The 2026 Chicago Puppet Fest will span 12 days and dozens of Chicago venues, presenting an international pageant of puppet artists sharing more than 100 puppetry activities. Get ready for spectacular shows in landmark theaters, intimate works on smaller stages, the always popular late-night puppet cabarets, and a long list of free puppet events happening all over the city. Shows often sell out, so don’t delay!
Jan 23- Feb 8 Chicago Restaurant Week
Open wide! Chicago Restaurant Week is back for its 19th year. More than 470 Chicagoland eateries will offer specially curated prix fixe menus for brunch ($30), lunch ($30), or dinner ($45/$60) between Jan 24 and Feb 9. With more than two weeks to chow down, there’s plenty of time to make a few reservations and check out some of the best restaurants in Chicago while saving some coin.
Thru Feb 28 Chicago Architecture Biennial
Every two years, Chicago becomes a global hub of architecture and design during the Chicago Architecture Biennial. This edition’s theme is SHIFT: Architecture in Times of Radical Change, bringing together over 100 projects by architects, artists, and designers from 30 countries—each piece engaging with the cultural, social, and environmental fluxes transforming our world. Not sure where to start? Check out Time Out Chicago’s first-timer’s guide to the exhibition.
Thru Mar 22 Intuit Art Museum – Catalyst|Im/migration and Self-Taught Art in Chicago
We hope we’re not what you were expecting. Intuit Art Museum champions the diverse voices of self-taught art, welcoming both new and familiar audiences. Located in Chicago’s West Town neighborhood, Intuit is a premier museum of self-taught art. The Museum collects and exhibits work by artists who typically work outside the mainstream and have developed a sustained artistic practice. Some artists may have faced societal, economic or geographic barriers to pursuing extensive training in the arts. The museum’s mission is grounded in the ethos that the instinct to create is universal and the arts must embrace, represent and be accessible to all.