Pictures with Santa events in Chicago

Southport Holiday Cocktail Crawl

Fri, 04 Dec at 05:00 pm North Southport Avenue

USD 34 TO 50 FITNESS

Wicker Park Bucktown's Winter Wonderland & Tree Lighting

Sat, 05 Dec at 12:00 pm Metzger Court

CHRISTMAS

Photos With Santa at the Southport Holiday Stroll

Fri, 04 Dec at 05:00 pm Sheil Park

FREE FITNESS

Breakfast With Santa 2026

Sat, 05 Dec at 09:00 am The Salvation Army Ray and Joan Kroc Corps Community Center Chicago

USD 14 TO 16 FITNESS

Clark Street Cookie Crawl

Sun, 06 Dec at 01:00 pm N Clark St, Chicago, IL, United States

HOLIDAY

Breakfast with Santa

Sun, 13 Dec at 09:00 am Warwick Allerton - Chicago

USD 0 TO 62 FITNESS

Roo's Very Merry Pet Market

Sun, 13 Dec at 11:00 am Fairlie 339 North Bell Chicago

DOG

Breakfast with Santa

Sun, 13 Dec at 10:00 am Fairmont Chicago, Millenium Park

FREE FITNESS

Free photos with Santa at brightsmiles!

Sat, 12 Dec at 10:30 am BrightSmiles Pediatric Dentistry

FREE FITNESS

Photos with Santa at K9 Corridor

Sat, 05 Dec at 11:00 am The K9 Corridor

USD 23 FITNESS

Pancakes with Santa

Sun, 20 Dec at 10:00 am 3626 N Talman Ave, Chicago, IL, United States, Illinois 60618

HOLIDAY

Photos with Santa at Pupstars

Sat, 12 Dec at 11:00 am PupStars Pet Care

USD 23 FITNESS

Bubbles and Santa

Fri, 04 Dec at 04:00 pm The Learning Experience - Sauganash

FREE FITNESS

Photos with Santa at A and N Mortgage | Chicago She Shed

Wed, 09 Dec at 05:00 pm A and N She Shed

FREE FITNESS

Annual Holiday Tree Lighting

Wed, 18 Nov at 05:30 pm Clark St Dog

TRIPS-ADVENTURES