Pet-Friendly Fall & Holiday Events in Chicago: 2026

UKRAINIAN VILLAGE VETERINARY CENTER

Pet-friendly fall & holiday fun

Six upcoming outings in Ukrainian Village and the Chicago area, October 24–December 31, 2026.

All times are Chicago local. Event names link to details and tickets. Scroll sideways on smaller screens.
Date & time Event & location What to expect & pet requirements
October 24–25, 2026
See available departure times
Howl-O-Ween Canine Cruise
Chicago’s First Lady
Downtown Chicago riverfront
A 90-minute river and lake cruise with dog treats and costume prizes.
General boarding from $46.
Remaining sailings are October 24 and 25. Choose a departure time on the organizer’s booking page and review fares for people and dogs.
October 25, 2026
Noon–4 p.m.
Wag-O-Ween Dog Party & Market
Bosly’s Backyard
4011 N. Ravenswood Ave., Chicago
Dog trick-or-treating, costume fun, pet portraits and local shopping.
$15/person.
The dedicated event page lists noon–4 p.m.; the general events calendar still lists a 5 p.m. end time. Use the dedicated event page for current details. Advance tickets recommended; walk-ins depend on space.
October 31, 2026
9–11 a.m.; parade at 9:30 a.m.
Streeterville Dog & Cat Halloween Party
MCA Sculpture Garden
220 E. Chicago Ave., Chicago
A costume party and parade for dogs and cats, with best-dressed prizes.
Free admission.
Enter through the museum’s back gate bordering Lake Shore Park. Leashes required; bring a dog toy so every dog gets a prize.
November 13, 2026
6 p.m.–midnight
PAWS Chicago Fur Ball
The Drake Hotel
Gold Coast, Chicago
A pet-friendly black-tie fundraiser with dinner, dancing, auctions and a dog buffet.
Ticketed fundraising gala.
A formal fundraising event benefiting PAWS Chicago; pets are welcome. See organizer for ticket availability and pricing.
November 20–December 24 / 31, 2026
Hours vary by location and date
Christkindlmarket
Daley Plaza & Gallagher Way
The Loop & Wrigleyville, Chicago
Daley Plaza: Nov. 20–Dec. 24.
Wrigleyville: Nov. 20–Dec. 31.
Free admission.
Daley Plaza: November 20–December 24. Wrigleyville: November 20–December 31 (closed Christmas Day). Pets are generally allowed outdoors, but not inside walk-in cabins or tents.
Pet policy
December 5, 2026
10 a.m.–2 p.m.
Howliday Jingle Paws
Romeoville Athletic & Event Center
55 Phelps Ave., Romeoville
Holiday shopping, raffles and Santa photos supporting local pet rescue.
Free admission.
Listed by FestivalNet for December 5, 10 a.m.–2 p.m., with free admission. Dogs must be on non-retractable leashes and current on vaccinations. Confirm final details with the organizer.
Plan a happy outing. Most events are geared toward dogs. Confirm schedules, prices, ticket availability and pet requirements with the organizer before attending.
Listings rechecked October 23, 2026. Ukrainian Village Veterinary Center is sharing community events; these are hosted by the listed organizers.
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