Various locations throughout Chicago

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 our first-timer's guide to the exhibition. Stay up-to-date by visiting the Chicago Architecture Biennial website.

Wanna relive the thrill of punishing a captive audience like you did during grade school show-and-tell? Then Show & Tell for Grownups is the place for you! Once a month, comedians, storytellers and everyday passionate folks gather to share their quirky, heartfelt or downright fascinating interests. Each presenter gets five minutes on the clock to wax philosophical about their obsession, then it’s the audience’s turn with a quick Q&A. Think of it like falling down a Reddit rabbit hole—only live, and way more fun. Feeling especially brave? Sign up for your five-minute show-and-tell slot here.

While all of the other music festivals are in hibernation, Tomorrow Never Knows has been bringing up-and-coming artists to venues all over the city for the past 20(!) years. Organized by the folks at Schubas and Lincoln Hall, the lineup usually sports an abundance of rising acts who perform at the organizing venues as well as Bridgeport's Ramova Theatre. This year, you'll be able to catch a variety of bands, including dream-folk luminary Cassandra Jenkins, Chicago instrumental two-piece Mute Duo, avant-pop sensation Perfume Genius and more. Prices vary from show to show; visit the website for the full schedule.

As we gear up for Super Bowl LX, we’re offering a unique opportunity to dive deep into Puerto Rican history through the lens of this year’s halftime headliner, Bad Bunny. The global superstar has collaborated with Professor Jorell Meléndez-Badillo, acclaimed author of Puerto Rico: A National History, to curate an exclusive visual presentation. This immersive experience explores the historical context and cultural inspirations behind the tracks on Bad Bunny’s latest multi-platinum album, Debí Tirar Más Photos.

Can't get enough of marionettes? You'll love the Chicago International Puppet Theater Festival, which brings puppeteers from across the globe to the city for 12 days of symposiums and more than 100 performances and events. The Puppet Hub returns this year, which includes events on the fourth floor of the Fine Arts Building on Michigan Avenue—take a look around to find everything from a puppet-themed cafe to live puppet spectacle productions in the building’s massive Studebaker Theater. Also back is the Ellen Van Volkenburg Symposium, workshops with visiting puppet artists, the Catapult Artist Intensive and more. For a full list of performances, visit the festival’s website.

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 January 24 and February are 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.

As part of Andersonville’s annual Säg Hej Health & Wellness celebration, all are invited to Explore & Restore: a district-wide open house dedicated to healthy living. Stroll through the neighborhood to discover a diverse array of wellness-focused businesses—covering everything from physical and mental health to home design and financial well-being. Throughout the day, enjoy interactive experiences including short demos, mini-workshops, professional consultations and hands-on activities.

The seventh annual West Loop Wedding Walk returns on February 1. Couples can spend the afternoon touring 12 of the neighborhood's premier event venues—which have been staged for the occasion—while enjoying food and drinks and meeting more than 200 vendors. Transportation between venues will be provided. Once you've had your fill, head over to Salvage One for an afterparty hosted by Bluewater Kings.

Every year, in the coldest depths of the winter, Chicago Theatre Week gives us a great reason to venture outside. The annual event runs from February 5 to 15, taking over stages throughout the city—from major regional hubs like the Goodman Theatre and Steppenwolf Theatre to intimate spaces such as Raven Theatre. During Chicago Theatre Week, companies offer tickets priced at $15 or $30 (or sometimes less!). You can browse a complete list of participating shows here.

Chicago Black Restaurant Week returns for its 10th year February 8–22. Created by Lauren Smith as a way to highlight and support local Black-owned businesses, the annual event sees participating eateries offer special menus and discounts to diners.