Top Things to Do in Chicago in November 2025

November in Chicago is a month that bridges cozy and festive—where fall’s golden light meets the sparkle of the season ahead. Across the city, neighborhoods come alive with concerts, cultural celebrations, culinary classes, and the first twinkle of holiday lights.

This month’s guide highlights what makes Chicago so special—its creative pulse, neighborhood pride, and the small businesses that bring personality to every block. From storytelling and symphony nights to tamale classes, holiday markets, and Small Business Saturday, here’s your go-to list of November happenings around town.

🎤 Stories, Laughter & Live Performances

Mon, Nov 10, 2025 — The Moth StorySLAM: “Cheat” · Doors 6:00 PM | Stories 7:00 PM · The Den Theatre (Wicker Park)

Thu, Nov 20, 2025 — The Moth Mainstage · Doors 6:30 PM | Show 7:30 PM · Auditorium Theatre (Loop)

Fri, Nov 21, 2025 — Dan Donohue (Comedy) · 7:15 PM · The Den Theatre (Wicker Park)

🎨 Music, Art & Cultural Events

Nov 1–8, 2025 — Day of the Dead Quilts Workshop · NMMA (Pilsen)

Fri–Sat, Nov 7–8, 2025 — Twilight in Concert · Cadillac Palace (Loop)

Sat, Nov 8, 2025 — Día de los Muertos: Love Never Dies Ball · 6:00 PM · NMMA (Pilsen)
Thu, Nov 13, 2025 — Robert Plant’s Saving Grace feat. Suzi Dian · 7:30 PM · Old Town School (Lincoln Square) ·

Thu, Nov 20, 2025 — Classic Encounter: Mozart Requiem · 7:30 PM · Symphony Center (Loop) ·

Fri–Sun, Nov 28–30, 2025 — CSO at the Movies: How to Train Your Dragon in Concert · Fri/Sat 7:30 PM; Sun 3:00 PM · Symphony Center (Loop) ·

🍷 Culinary & Lifestyle Classes

Thu, Nov 6 & Thu, Nov 20, 2025 — Tamale Making Experience · 7:00–8:00 PM · Manchamanteles (Logan Square) ·

Sat, Nov 15, 2025 — Pops for Champagne: Laherte Frères Tasting · 1:00–2:45 PM · River North ·
Sat, Nov 15, 2025 — Mon Ami Gabi Wine Passport – France vs USA · 1:00–3:00 PM · Lincoln Park ·

🏃‍♀️ Fitness & Community Events

Sat, Nov 1, 2025 — Logan Art Mart @ Federales + $500 Raffle · 2:00–5:00 PM · Logan Square ·

Sun, Nov 2, 2025 — SKECHERS Hot Chocolate Run (5K/10K/15K) · Start ~7:30 AM · Grant Park ·

Thu, Nov 27, 2025 (Thanksgiving Day) — Turkey Trot Chicago (5K & 8K + Kids Run) · 9:00 AM (Kids 11:00 AM) · Lincoln Park ·

🎄 Holiday Highlights (with Small Business Saturday added)

Sat–Sun, Nov 15–16, 2025 — Lycée French Market (21st Edition) · Times TBA · Lincoln Park ·

Fri, Nov 21, 2025 — McCormick Tribune Ice Rink Opening (Season) · Hours vary · Millennium Park (Loop) ·

Fri–Sun, Nov 21–23, 2025 — Millennium Park Holiday Market · Times TBA · Loop ·

Sat, Nov 22, 2025 — Wintrust Magnificent Mile Lights Festival · Lane 11:00 AM–4:00 PM; Parade 5:30 PM; Fireworks ~7:15 PM · Michigan Ave ·

Sun, Nov 23, 2025 — Christkindlmarket Wrigleyville (Opening Day) · See daily hours · Gallagher Way (Wrigleyville) ·

Sun, Nov 23, 2025 — Winterland at Gallagher Way (Season Launch) · See schedule · Gallagher Way (Wrigleyville) ·

Sun, Nov 23, 2025 — Lakeview Roscoe Village Tree Lighting · 6:00–7:30 PM · St. Alphonsus (Lakeview) ·

Sat, Nov 29, 2025 — Small Business Saturday (Citywide, store hours vary)
Shop local across your favorite neighborhoods (guides & orgs):

Lincoln Square / Ravenswood + Jolly Trolly
Wicker Park / Bucktown
Old Town
Andersonville

📌 Giving Tuesday Reminder

Giving Tuesday is Tuesday, Dec 2, 2025.

As the city lights up and the year winds down, there’s no better time to explore a new corner of Chicago—or revisit an old favorite. Every event, concert, and shop visit adds to the rhythm of our community and reminds us why we love where we live.

🖤 Thanks for following along each month as we share Chicago’s best local experiences. If you’d like neighborhood updates, market insights, and curated event guides straight to your inbox, subscribe to Dream Home Press—it’s your local’s pass to all things Chicago.