October is the month of pumpkin and apple paradise, of harvests and festivals throughout the city. There is no better time to take advantage of cooler temperatures and Halloween looming to get outside and celebrate autumnal wonder!
The Pride is back! Chicago Pride Fest returns Friday, October 1- Sunday, October 3, on Halsted between Addison and Grace Streets. The festival features live music by headline artists Debbie Gibson, Mya and Crystal Waters and local music favorites, including American Idol’s Katy Kadan, 16 Candles, and the Chicago Gay Men’s Chorus on three stages, along with food and drink, 100+ arts/crafts vendors, DJ’s and dancing, drag shows, pet parade, games, giveaways and more. A $15 suggested donation helps pay LP performers and festival workers, and funds community programs.
Specially curated wineries join with live entertainment over an all-day, all-night vino experience during the Official Chicago Wine Fest: Fall Edition, at Lincoln Park Zoo, from noon-10pm at the North Gate, Regenstein African Journey, 2400 W. Cannon Drive. At this 21+ event, you’ll sip premium wine to your heart’s content while live entertainment keeps the party going! Tickets are $35 – $60.
A-Haunting we will go! Navy Pier transforms into an experiential fall spectacle during their colorful, haunting Pier Pumpkin Lights. Starting Friday, October 1, nearly 1,000 festive pumpkins and lights will decorate historic Navy Pier, 600 W. Grand Ave., for the entire month of October. Lots more haunting festivities to come throughout the month, as guests explore a variety of pumpkin pop-ups and enjoy Pier-wide deals and other Halloween festivities throughout the month. Free admission.
Celebrate fall’s bountiful harvest at the Lincoln Square Ravenswood Chamber of Commerce’s 34th Annual Apple Fest! The festivities start Saturday, October 2 and Sunday, October 3 from 9am – 6pm Lincoln Avenue between Lawrence and Wilson. Apple Fest is a long-standing tradition in Lincoln Square, bringing community together to celebrate the beginning of autumn. Shop autumnal goods at the festival’s marketplace, munch on apple-stuffed grilled cheese and apple doughnuts from local restaurants, sip cider and apple-flavored beer, catch live music performances and bring the kids for seasonal activities! Apple Fest’s 10th Annual Pooch Costume Contest gets underway on Saturday, October 2, at 10am. Prizes will be awarded for the Scariest, Most Adorable, Most Creative, Best Dog/Parent Combo, and Best Costume Grand Prize. Free admission.
After taking a year off due to the pandemic, the citywide annual DESTINOS: Chicago International Latino Theater Festival is back! As told by Latino artists and companies from Chicago, the U.S. and Latin America, audiences will experience a rich, diverse array of Latino centric performances at marquee venues downtown, neighborhood theaters and cultural institutions. Now through October 24, the Goodman’s Albert Theatre, 170 N. Dearborn St., is presenting ‘American Mariachi.’ Set in the 1970’s, the story centers around a young woman determined to create an all-female mariachi band. Check the website for ticket information.
Alison Moran and Dean’s Team Chicago