Free Things to Do in Chicago This Weekend (Oct 23

This weekend

Free in Chicago · Oct 23–25

THRU

15

NOV

Art on theMART Fall Season

Thu, Sep 10 – Sun, Nov 15 · Thu-Sun, 7:30-8 p.m. · theMART facade / Chicago Riverwalk · River North

theMART's river facade becomes a screen again: a data-as-light piece from Argonne and UIC plus Adler Planetarium space imagery, Thursday to Sunday nights.

🎨 Arts & cultureFree

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OCT

24

SAT

Arts in the Dark Halloween Parade

Sat, Oct 24 · 6-8 p.m. · Columbus Drive, Grant Park · Grant Park / Loop

A nighttime Halloween parade of giant puppets, lanterns, stilt walkers and fire performers down Columbus Drive, with Buckingham Fountain behind it. Free, 6–8 p.m.

🎃 HalloweenFree

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OCT

24

SAT

Día de los Muertos Xicágo

Sat, Oct 24 · 3-8 p.m., rain or shine · Harrison Park (next to the National Museum of Mexican Art) · Pilsen

The museum's Day of the Dead gathering in Harrison Park: community ofrendas, pan de muerto, hot chocolate, music and face painting. Free.

🌎 Culture & heritageFree

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OCT

24

SAT

Pumpkin Party at Gallagher Way

Sat, Oct 24 · Sat 1-5 p.m. · Gallagher Way · Wrigleyville

The plaza next to Wrigley Field hosts a Halloween afternoon for kids, with trick-or-treating, costumes, face painting and games.

🎃 HalloweenFreeGeared to kids; all ages

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OCT

25

SUN

Lincoln Scared & Ravenswoooood

Sun, Oct 25 · Sun 11 a.m.-1 p.m.; rain or shine · Lincoln Square and Ravenswood shops · Lincoln Square

Kids in costume trick-or-treat shop to shop across Lincoln Square and Ravenswood, with free pumpkin decorating at The Perfect Cup on Damen.

🎃 HalloweenFreeGeared to kids

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OCT

25

SUN

Meet Me on Milwaukee

Sun, Oct 25 · Sun 10 a.m.-6 p.m. · Milwaukee Ave · Wicker Park

Milwaukee Avenue goes car-free through Wicker Park for the day: walk or bike down the middle of the street, with live music, outdoor dining, fitness classes and sidewalk sales.

🎉 Street festFree

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🗓️

1 more free dates this weekend in Whosly

Every date in the Chicago Festivals & Events list — star the ones you're into and see which friends are going.

Coming up

Free in the next few weeks

OCT

31

SAT

Haunted Halsted Halloween Parade

Sat, Oct 31 · Block party 11 a.m.-6 p.m.; parade 7-8 p.m.; costume contest and after-party 8-10 p.m. · Halsted Street · Northalsted (Lakeview)

Northalsted's Halloween night: an all-day block party on Halsted, a 7 p.m. parade with bands and fire performers, and a costume contest. Free.

🎃 HalloweenFreeAll ages

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NOV

20

FRI

City of Chicago Christmas Tree Lighting & Holiday Market

Fri, Nov 20 – Sun, Nov 22 · Tree lighting Fri Nov 20 at 6 p.m.; Holiday Market Nov 20-21 noon-8 p.m., Nov 22 noon-5 p.m. · Millennium Park · Loop

The city lights its official Christmas tree in Millennium Park at 6 p.m. Friday with a stage show, and a holiday market runs through the weekend. Free.

✨ Holiday lightsFree

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NOV

20

FRI

Christkindlmarket Chicago (Daley Plaza)

Fri, Nov 20 – Thu, Dec 24 · Sun-Thu 11 a.m.-8 p.m.; Fri-Sat 11 a.m.-9 p.m.; Thanksgiving and Christmas Eve 11 a.m.-4 p.m. · Daley Plaza · Loop

The German-style Christmas market in Daley Plaza: wooden huts, mulled wine, brats and handmade ornaments. Free to wander.

🧺 MarketFree

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NOV

21

SAT

Wintrust Magnificent Mile Lights Festival

Sat, Nov 21 · Lights Festival Lane 11 a.m.-4 p.m.; parade 5:30 p.m.; fireworks over the river about 7:30 p.m. · North Michigan Avenue · Magnificent Mile / Streeterville

A daytime family festival, a 5:30 p.m. holiday parade down Michigan Avenue and fireworks over the river around 7:30. Free.

🎺 ParadeFree

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Map

Free in Chicago, on the map

Where each of these dates happens. Tap a marker to see which it is.

🙋 The Whosly app

Never miss what's on in Chicago

These are a few of the dates in Chicago Festivals & Events — 200+ a year, plus 1,800+ concerts. The app keeps all of them, and tells you when it matters.

✓Star a date for reminders — the morning of, before it starts, and when presales and on-sales open
✓See which friends are interested, and let them see you
✓Turn any date into a plan: text one link and see who's in — friends RSVP with no app
✓Pair it with the city's best spots and happy hours, all on one map

Get Whosly on iPhone How it works

Or search “Whosly: Plans, Places & RSVPs” on the App Store

Get it on your iPhonePoint your iPhone camera here — or open the App Store and search “Whosly: Plans, Places & RSVPs”.

Festivals & Events and Concerts are included with Planner Pro. Starting a plan and RSVPing are free, always.

City Packs in the Whosly app: Chicago Festivals & Events with upcoming dates, Chicago Essentials and Deep Cuts — City Packs in the app

FAQ

Free in Chicago

What free things are there to do in Chicago this weekend?

This weekend (Oct 23–25), free picks include Art on theMART Fall Season (Fri, Oct 23), Arts in the Dark Halloween Parade (Sat, Oct 24, Columbus Drive, Grant Park), Día de los Muertos Xicágo (Sat, Oct 24, Harrison Park (next to the National Museum of Mexican Art)) and Pumpkin Party at Gallagher Way (Sat, Oct 24). The list above is updated every day.

What free events are in Chicago in November 2026?

City of Chicago Christmas Tree Lighting & Holiday Market (Nov 20), Christkindlmarket Chicago (Daley Plaza, Nov 20), Wintrust Magnificent Mile Lights Festival (Nov 21) and Chicago Thanksgiving Parade (Nov 26) — all free.

How do I find free events in Chicago?

Whosly's Chicago Festivals & Events list marks every free date. Star one for reminders, see which friends are interested, and turn it into a plan — the list is included with Planner Pro, and starting a plan is free.