Pictures with Santa events in Chicago

Check out happening pictures with santa events all around Chicago, IL

FREE! Meet Santa, take family photos!

 Sun, 07 Dec at 11:30 am 4254 N Milwaukee Ave Free

Breakfast with Santa

 Sun, 14 Dec at 09:00 am Warwick Allerton - Chicago USD 17 to 50

Breakfast With Santa 2025

 Sat, 06 Dec at 09:00 am The Salvation Army Ray and Joan Kroc Corps Community Center Chicago USD 14

Breakfast with Santa at Biagio 2025

 Sun, 14 Dec at 09:00 am Biagio USD 0 to 32

CEBR Holiday Meetup and Photos With Santa

 Sat, 13 Dec at 10:00 am 1240 N Wells St, Chicago, IL 60610-3559, United States

Photos With Santa at the Southport Holiday Stroll 2025

 Fri, 05 Dec at 05:00 pm Sheil Park Free

Hyde Park Holly-Day 2025

 Sat, 06 Dec at 10:00 am Harper Court

Ravenswood Light Up Nights Festival + Holiday Market

 Sat, 06 Dec at 03:00 pm Ravenswood, Chicago

Stan's Donuts Donut Decorating | Mag Mile (Session 2)

 Sat, 13 Dec at 09:30 am Stan’s Donuts & Coffee USD 0 to 31

Pictures with Santa Claus!

 Thu, 11 Dec at 04:00 pm 2326 W Belmont Ave Free

WPB Winter Wonderland & Tree Lighting

 Sat, 06 Dec at 01:00 pm Wicker Park Bucktown Free

2025 Clark Street Cookie Crawl

 Sun, 07 Dec at 01:00 pm Briny Swine Smokehouse & Oyster Bar

Kids Christmas Party

Sun, 07 Dec at 12:00 pm Park and Field

Tax Fairy’s Holiday Festival

 Sat, 06 Dec at 12:00 pm 4056 W Division St Free

HORROR HOUSE HOLIDAY MARKET 2025

 Sat, 20 Dec at 12:00 pm Revolution Brewing

Kids Christmas Party

Sun, 14 Dec at 03:30 pm Park and Field

Doggie Christmas Party

Sun, 21 Dec at 04:00 pm Park and Field

Rickover Naval Academy Winter Arts & Craft Fair

 Sun, 14 Dec at 09:00 am Rickover Naval Academy School Free

🎅Santa’s Jingle Bell Cookie Jam at Chase Park!

 Sat, 20 Dec at 12:00 pm 4701 N Ashland Ave Fl 2, Chicago, IL, United States, Illinois 60640

Winter Fest

 Sat, 13 Dec at 11:00 am O.A. Thorp Scholastic Academy

12/23 Photos with Santa at JoJo’s Winter Wonderland!

 Tue, 23 Dec at 04:00 pm 23 West Hubbard Street, Chicago, IL, United States, Illinois 60654

Orso’s 11th annual Santa Brunch

 Sun, 07 Dec at 10:00 am Old Town, Chicago

Annual Pictures With Santa at Attack Taekwondo – Wicker Park

 Sat, 20 Dec at 04:00 pm 2123 W Division St, Chicago, IL

Brunch with Santa

 Sun, 07 Dec at 09:00 am Eden in Chicago

Santa Brunch

 Sun, 14 Dec at 10:00 am 1320 W Fullerton Ave, Chicago, IL, United States, Illinois 60614

Sheraton Sleigh Bar, Presented by Shula’s Steak House

 Fri, 21 Nov at 05:30 pm Sheraton Grand Chicago Riverwalk Free

Santa Visits at Sheraton Sleigh Bar – Chicago Holiday Fun for Families

 Sat, 29 Nov at 04:00 pm Sheraton Grand Chicago Riverwalk