Chicago is truly magical in the fall—there’s a certain energy when the leaves turn golden, the air is crisp, and the city buzzes with festivals, concerts, cozy markets, and a thousand reasons to get outdoors. Whether it’s live music echoing from storied venues or the taste of fresh apple cider at an open-air market, Chicago truly shines as a destination for autumn vibes. Looking to plan out the perfect fall? Here’s your guide to some unmissable concerts and time-honored festivals in Chicago in October and November, with plenty of choices to keep both music lovers and festival fans happy. And if you’re eager for even more options, just hop over to AllEvents —they’re always updating the best local happenings.
The Psychedelic Furs & Gary Numan Concert
Image Source: Live Nation
On October 4th, the iconic post-punk energy of The Psychedelic Furs teams up with synth legend Gary Numan for a night of nostalgia and fresh sound at The Auditorium. Expect moody lighting, energetic crowds, and a trip through indie and alternative classics—this is a rare double-bill that’s sure to sell out fast. The Auditorium’s rich history always seems to amplify every note, making this a standout fall concert experience.
Bad Suns & Joe P at House of Blues
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House of Blues is the spot for the indie crowd come October 4th, when Bad Suns and Joe P take the stage. These bands are known for lush, emotional alt-rock—think soaring choruses and buzzy guitar riffs. This is one of those gigs where you’ll probably bump elbows with local superfans, and the laid-back HOB vibe always makes for a night to remember.
Addison Rae Live at Riviera Theatre
Image Source: Rolling Stone
Pop fans, block off October 10th. Addison Rae, TikTok star turned chart-topper, brings all of her star power (and a major crowd) to the · Byline Bank Aragon Ballroom. Her sets are a mix of catchy new singles and danceable pop energy. Even for the less TikTok-savvy, this is a show that promises major spectacle and mega singalongs—always something worth catching.
Lincoln Square Ravenswood Apple Fest
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From October 3rd to 5th, Lincoln Square transforms into a paradise for all things apple: cider, pies, candied apples, and produce from local vendors. This festival is a Chicago classic, blending laid-back family fun with street music, handcrafts, and a strong sense of neighborhood spirit. It’s one of those annual events that locals look forward to—plus, it’s a great excuse for second (or third!) slices of apple pie.
Chicago Vintage Fall Festival
Image Source: chicagovintagefest
If you’re more into the artsy, retro vibe, head to 1802 S Halsted St. on October 14th for the Chicago Vintage Fall Festival. This gathering celebrates all things vintage, from clothes and vinyl to furniture and quirky home goods. Expect live music, food trucks, and a bustling crowd of fellow thrifters. It’s a must for anyone who wants autumn style inspiration or simply loves old-school treasures.
Lincoln Park Zoo Fall Fest
Image Source: Lincoln Park Zoo
This beloved, family-friendly festival spans weekends in late September and all of October. The Lincoln Park Zoo Fall Fest packs in pumpkin patches, professional pumpkin carvers, Ferris wheel rides, and zookeeper talks. It’s totally free to enter, with ticketed add-ons for extra thrills. The fact that it’s held in the heart of the zoo—amid gorgeous fall foliage—makes it a must-visit for families and city explorers alike.
Royal Pawz Furry Fall Festival at Jackson Bark
Image Source: honolulumagazine
For pet lovers and animal advocates, the Royal Pawz Furry Fall Festival is the place to be on November 1st. Hosted at Jackson Bark, this event has become a beloved South Side tradition, featuring local vendors, fun giveaways, and activities for people and pups alike. It also raises money for Chicago’s homeless pets, so attending means a fun, meaningful day for a great cause.
Chicago Fall Market at Artifact Events
Artifact Events is opening its airy industrial space for the Chicago Fall Market on October 25th and 26th. This event is a paradise for craft enthusiasts and foodies—think handmade jewelry, fresh autumn treats, houseplants, and unique home goods. There will be live music and loads of local makers, which makes for a warm, bustling space perfect for holiday shopping (or early gift-getting.)
Open House Chicago
Image Source: driehausmuseum
Every October, the city opens its doors—literally. On October 18th and 19th, Open House Chicago gives locals and tourists rare behind-the-scenes access to more than 100 buildings, from iconic skyscrapers to hidden architectural gems. Whether you nerd out on design or just want a new perspective on the city, this free weekend is a jaw-dropping way to experience Chicago’s coolest spaces.
Yiruma Live at The Chicago Theatre
Image Source: Madison Square Garden
If you need a music experience that’s both emotive and soothing, plan to see Yiruma, the globally-acclaimed Korean classical pianist, on October 15th at The Chicago Theatre. His shows are renowned for their intimacy and ability to leave audiences totally captivated. It’s the perfect concert for an introspective autumn night out.
More Fall Magic: Annual Festivals You Just Cannot Miss
The Chicago fall calendar is overflowing with festivals & community gatherings. Here are a few that locals love to visit every single year:
West Town Art Walk (October 3-5): Celebrating the creative heart of Chicago, the Art Walk spotlights galleries, public installations, and pop-up exhibitions.
Randolph Street Market Festival (September 15-16): Part vintage market, part food festival, & absolute FUN! This event is a hotbed for bargain hunters & collectors.
Arts in the Dark Parade (October 18): The ultimate Halloween street parade, with glowing floats & costumed performers, making State Street come alive after dark.
For more unique annual happenings, keep an eye on AllEvents.in! Their listings are constantly refreshed with the events in NYC.
Wrapping It Up: Make Your Fall Unforgettable
Chicago in the fall is packed with energy, color, & community, there’s truly something going on for every interest. Between the jam-packed concert schedule and a festival scene that runs from kid-friendly pumpkin patches to late-night art walks, there’s no excuse to stay home. Keep this guide handy, and don’t forget to double-check AllEvents.in as event details can change or get more exciting as autumn unfolds.
So grab that pumpkin spice latte, put on a sweater, and get out there—Chicago’s fall festivals and concerts are waiting!
