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.

Get ready for a festive ride—the CTA Holiday Train and Bus are coming to town! The train is decked out in twinkling holiday lights, with Santa and his reindeer riding outside to wave at families—you can spot the festive locomotive in CTA stations throughout the city from November 29 through December 22. The CTA Holiday Bus, on the other hand, will hit the road on November 28 and make its rounds through December 22. Check the CTA website for the full schedule of train and bus routes.

Candlelight concerts are the ultimate multi-sensory experiences for intimate, romantic evenings year-round. This holiday season, listen to string quartets in the glow of thousands of candles at festively decorated venues across the city, including Art Center of Oak Park and Hyde Park Union Church. Classical music may not be your go-to genre, but hearing live carols with string instruments, Christmas soundtracks on piano or a medley of holiday favorites like “Carol of the Bells” and “December, 1963” will have you swooning.

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.

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 film screenings 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.

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.

Celebrating Chicago culture through couture, Chicago Fashion Week brings runway shows, markets, educational programs and more—many of which are free to attend—throughout the city. The full gamut of programming is yet to be announced; stay updated via CFW's website.