Various locations throughout Chicago

When Pitchfork Music Festival announced its sudden sunset at the start of 2025, Chicago’s music scene collectively wondered how festival co-founder Mike Reed would fill the sonic void. Turns out, Reed had an ace up his sleeve: Sound & Gravity, a five-day music marathon featuring 48 performances across six venues in Bricktown and Avondale. Lineup highlights include Bill Callahan, Mdou Moctar, Mary Lattimore and Mary Lattimore, with surprise sets curated by Electrical Audio—the recording studio founded by the late Steve Albini—still to be announced, but sure to be a treat for the ears. Read more about Sound & Gravity's inception here.

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. Start your Biennial experience at the Chicago Cultural Center, then explore a citywide constellation of exhibitions and public programs hosted by dozens of leading cultural, program, and civic partners throughout Chicago. A full schedule of programming and locations is coming soon. Stay up-to-date by visiting the Chicago Architecture Biennial website.

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. Some standout events include an indigo dyeing and shibori workshop; The Chicago Streetwear Expo; a runway show emphasizing sustainability; and Fleurotica, a fashion show featuring garments made entirely from plants, flowers, and natural materials. Check out the full programming lineup on CFW's website. 

Chicago: a city that’s birthed more comedic icons than hot dog toppings, and the 312 Comedy Festival is here to remind you why. Returning for its third year, this multi-day celebration of stand-up brings over 20 comedians (and counting) to six iconic venues across the city—from the Chicago Theatre to the legendary Zanies, where punchlines have been landing since before you were born. The 2025 lineup includes heavy-hitters like Fortune Feimster (Nov. 8, Chicago Theatre), Pete Holmes (Nov. 6, Riviera Theatre), and a cross-section of scene-stealers like Earthquake, Dusty Slay, Jared Freid, Patrick Warburton, Marie Faustin and Joe Machi. Think that’s the full list? Cute. They’re just getting started. Produced by Outback Presents and Jam Productions, the festival doesn’t just drop comics into Chicago—it taps into the city’s long-standing comedy culture, turning it up to eleven for one full week. Whether you’re into national headliners, emerging talent or simply want to laugh until your face hurts in a venue with actual history, this is your moment. Tickets (while they last) at 312comedyfest.com. Go ahead, plan your November accordingly.