Free Frights for a Gray Halloween Eve

Free frights, costumed pets and a rainy Halloween Eve — where to go this weekend.

By Raj Singh · Published October 30, 2026.

FRIDAY, OCTOBER 30

PG-13 Horror Movie Marathon @ Little Village Library

The Little Village branch is giving over its whole Friday to horror. From 9:30 in the morning, four PG-13 movies run back to back — a fun-creepy lineup that includes 1986's creature feature Critters and Sam Raimi's 2009 Drag Me to Hell — with popcorn, snacks and refreshments set out by the library.

It's built for audiences 13 and up, so it's a teens-and-adults hang rather than a toddler outing, and it runs until around 5pm — drop in for a single film or settle in for the day. The branch is at 2311 S. Kedzie Avenue.

Skate or Treat Halloween Party @ Douglass Park

Douglass Park turns its Halloween party into a skate session. The free, all-ages Skate or Treat runs 4 to 6:30pm with skating, a costume contest, refreshments and music, and it's part of the Park District's Night Out in the Parks series.

Admission is free, costumes are the whole point, and it's all at Douglass Park on the West Side.

Comedy Hour @ Annoyance Theatre

Every week the Annoyance hands its Comedy Hour to Chicago comics trying out their freshest material — an eclectic mix of sketch, improv and stand-up where you genuinely don't know what you'll get. The rotating cast of regulars includes Maggie Winters, Geoff Dow, Thomas Kelly and Jenelle Cheyne.

It's free, up on the second floor at 851 W. Belmont Avenue. Check the event link for tonight's start time before you head over.

Week-a-Spook @ Hamilton Park

Hamilton Park throws a Halloween Eve party from 3 to 7pm: a free community fashion show, a high-energy DJ set, candy and live entertainment, all ages welcome.

It's free and costume-friendly, over at 513 W. 72nd Street on the South Side.

SATURDAY, OCTOBER 31

Streeterville Doggy & Kitty Halloween Party @ MCA Sculpture Garden

Chicago's most adorable Halloween tradition is back in the MCA Sculpture Garden, where Streeterville dog and cat owners parade their costumed pets. The best-dressed furry friend — chosen by Alderman Brian Hopkins and Streeterville resident Maureen Schulman — takes home a prize.

There's a suggested donation, and it goes to the dogs, cats, kittens and puppies at PAWS Chicago. Things get going at 9am in the garden at 220 E Chicago Avenue; take the Red Line to Chicago, or buses 3, 10, 26 or 66.

One catch: Saturday's forecast is heavy drizzle, a high of 56 and close to a coin-flip chance of rain, so dress yourself — and the pup — for a damp morning outdoors.

Bottomless Brunch @ The River Kitchen & Bar

If the drizzle wins, there's a dry, indoor Saturday plan in Lakeview: The River Kitchen & Bar runs a bottomless brunch from 11am to 3pm, with bottomless mimosas, Bloody Marys and domestic beers plus one brunch item included for $39.95.

It's a reserve-your-spot deal, and the listing mentions bags, ping pong and a complimentary cereal bar to go with it. The River Kitchen & Bar is at 3138 N Broadway.

ON THE HORIZON

Illinois Resident Free Evening @ Shedd Aquarium

Looking past the weekend: the Shedd Aquarium's next Illinois Resident Free Evening lands Tuesday, November 3, from 5 to 9pm. Illinois residents get in free, with access to all exhibits plus the seasonal Stingray Touch.

The catch is demand — the Shedd says advance reservations are highly recommended because these slots go fast. Online reservations carry a $5 convenience fee per order, while phone and walk-up reservations are free, though walk-ups are subject to availability. Lock it in early. It's on the lakefront at 1200 S DuSable Lake Shore Drive.