October 2025: Your Downtown Skokie Insider

🎃 Something Spooky This Way Comes to Downtown Skokie! 👻

Halloween is creeping up fast, and Downtown Skokie is glowing with festive spirit. From pumpkin displays to sweet treats and creative costumes, our local businesses are brewing up all kinds of spooky-season fun.

Whether you’re planning a cozy night out, exploring your favorite shops, or grabbing a fall-themed bite, there’s plenty to enjoy before the big night on Friday, October 31. Stay tuned for special offers, Halloween happenings, and a few surprises that might just make you scream (in the best way).

Follow us on Instagram and Facebook for last-minute updates, costume inspiration, and behind-the-scenes fun all week long.

Thank you for keeping the Downtown Skokie spirit alive. Let’s make this Halloween a fang-tastic one!

Warmly,

The Downtown Skokie Merchants Collaborative (DSMC) Team🎃👻

Saturday, November 29th

The holiday season is almost here, and there is no better time to support local businesses than Small Business Saturday.

Join us in Downtown Skokie for a day of shopping, community, and holiday spirit. Our merchants are planning special offers, unique finds, and plenty of local cheer.

Take part in our Shop Small, Win Big in Downtown Skokie challenge. Spend $250 or more at two or more participating shops on November 29 and be entered to win free Downtown Skokie merchandise like a T-shirt, beanie, or shopping bag.

Shop local, submit your receipts, and you could be one of 20 lucky winners.

Artwork created by the talented CG. Ink.

Saturday, December 13rd at 1:00 p.m.

Get ready for the sweetest event of the season. The Downtown Skokie Holiday Cookie Walk is back, inviting you to explore local shops, cafés, and bakeries while collecting a festive cookie at every stop. Each ticket includes a commemorative cookie box and a map of participating businesses for a delicious afternoon of holiday cheer.

Every cookie is made by talented local bakers in licensed kitchens, individually wrapped and ready to enjoy or share. Tickets are limited and sell out quickly each year, so reserve yours early.

Proceeds support the Skokie Community Foundation, helping fund local programs in healthcare, education, social services, and the arts.

Spotlight: Downtown Skokie Merchant Events!

SJS’s Cabi October Open House

Thursday, October 23rd at 5:30 p.m.

Join The Sparkle Empire for an evening of style, community, and empowerment at SJS’s Cabi October Open House. Discover fair trade jewelry, clean-crafted wine, home goods, and apparel — all from woman-founded brands dedicated to helping women across the globe create safe, sustainable livelihoods.

Shop the collections, sip, and connect with others who share a passion for supporting women-owned businesses. Together, let’s help every Jane find her sparkle and build her own Sparkle Empire.

Location: See Jane Sparkle, 5115 Brown St.

Annual Downtown Skokie Trick or Treat

Saturday, October 25th at 1:00 p.m.

Ghosts, goblins, and ghouls of all ages are invited to join us for a frightfully fun afternoon in Downtown Skokie. Enjoy costumes, candy, music, and spooky surprises as you stroll through our downtown streets and visit participating businesses.

Bring your treat bags, show off your best Halloween look, and celebrate the season with the Downtown Skokie community. It’s free, family-friendly, and guaranteed to be fang-tastic! 👻

October 29th & 31st at 5:30 p.m. - 7 p.m.

Join Skokie Heritage Museum for the Murder & Mayhem in Skokie Walking Tour, a chilling stroll through the village’s past. Explore downtown with a guide as you hear stories of ghostly encounters, historic crimes, and Skokie’s most mysterious moments. Tours take place Wednesday, October 29 and Friday, October 31 from 5:30 to 7 PM, beginning at the Skokie Heritage Museum. Tickets are $15 per person, ages 12 and up.

Cost: $15

Location: Skokie Heritage Museum – 8031 Floral Ave

Multiple Nights in October

Step into the world of strategy, skill, and fun at Card Colosseum this October. Join fellow fans for weekly Pokémon, Magic: The Gathering, and One Piece play nights filled with friendly competition and community spirit.

Whether you’re a seasoned player or just getting started, there’s a seat waiting for you at the table. Bring your cards, meet new friends, and experience the excitement of game night in the heart of Downtown Skokie.

Upcoming Play Nights:

• One Piece: October 22 & 29 at 6 PM
• Magic: October 23 & 30 at 5 PM
• Pokémon: October 24 & 31 at 6 PM

Location: RJ Breaks, 8040 Lincoln Ave.

Friday, October 31st at 8:00 p.m.

Get ready for a night of outrageous laughs, dazzling music, and Halloween fun as Roxy Bellows takes the stage at the Skokie Theatre. Known for her high-octane energy and quick wit, Roxy delivers an evening of improvised comedy and unforgettable showstoppers that will leave you howling. Each performance is completely unique, blending sharp humor with powerhouse vocals and playful audience interaction. Whether you’re in it for the music, the laughter, or the Halloween vibes, this is a show you won’t want to miss.

Cost: $25

Location: Skokie Theater – 7924 Lincoln Ave