Various locations throughout Chicago

Renegade Craft Fair returns just in time for the holiday shopping sprint, taking over Morgan MFG's industrial digs. Attendees will be able to shop the handmade wares of more than 170 vendor booths, selling everything from candles and screenprints to jewelry and pottery. The fair also boasts food and drink from local restaurants, so you won't have to go hungry (or thirsty) while you shop. When is the Renegade Craft Fair in Chicago this year? The spring edition of the fair will be held May 16–17. What vendors will be there? More than 250 local artists will be at the market. Check Renegade's official website for the full list of vendors. How much does it cost to attend? There is a $5 suggested entry fee, which supports the Fair. You can pay by scanning a QR code at the Fair.

The Midwest Film Festival proudly presents its 2026 season, “Midwest Royale,” an expansive celebration of cinema, culture and community. This landmark year honors more than two decades of the festival’s commitment to championing regional storytelling and elevating local creative talent. The season officially launches on May 31 at the Chicago Cultural Center with the Midwest Film Fair and the Best of the Midwest Winners Showcase. This opening event will feature screenings of the 2025 award-winning films alongside the highly anticipated announcement of the 2026 Best of the Midwest Awards (BMA) nominees.

Take a stroll around the neighborhood to hear live tunes performed on front porches during this unique music fest hosted in Lakeview and Roscoe Village. Homeowners volunteer their porches to serve as stages, and half of the ticket fees go directly to the artists. There's no better way to spend the weekend than potentially discovering that your neighbor is a killer guitarist. 

Mandala South Asian Performing Arts—a bridge connecting audiences to the vibrant colors and rich traditions of South Asian heritage—returns with the annual Mandala Makers Festival. This multidisciplinary platform, which supports a diverse array of South Asian performing artists, kicked off its season on April 15. The festivities continue through October, offering a continuous showcase of immersive music and dance events. Visit the Mandala Makers Festival website for a complete schedule of performances.

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.

From June through September, more than 90 movies will screen in parks across Chicago as part of the Park District's annual Movies in the Parks program. From recent blockbusters like Zootopia 2 and Freakier Friday to classics like Back to the Future and Jumangi, you're sure to find something good to watch (for free!) beneath the stars this summer. Screenings typically begin at 8:45pm, or dusk, each evening. Take a look at the full list of movies and participating parks.

Heads up, fashion girlies: Reformation is hosting a series of events this month. The "Hot Girls Have Hobbies" series features four themed events, from a game night to a book club, at Reformation shops across the city and will be hosted by local influencers Emily Wittman and Olivia Metzger, and romance book publisher 831 Stories. 

Filmspotting Fest returns for a second year at the Music Box Theatre and the Athenaeum Center for Thought & Culture. Presented by Filmspotting, the Chicago-based podcast and WBEZ radio program hosted by Adam Kempenaar and Josh Larsen, the two-day event will explore the theme of "time" through screenings and programming. Check out the full schedule of events here.

This annual fest and conference celebrating the iconic dance music genre born in Chicago brings a full day of DJ sets to Millennium Park. Acts this year are to-be-announced. The live music will be preceded by an open house and panel discussions, and the festival will wrap up with a chill-down session along the Riverwalk. For a full list of programming, visit the DCASE Chicago House Music Festival and Conference website.

As is Labor Day weekend tradition in Chicago, some of the biggest names in jazz will gather for a series of shows at Pritzker Pavilion in Millennium Park and the Chicago Cultural Center during this annual festival. Visit the Chicago Jazz Festival webpage for the full lineup and schedule.