Where to Take Pictures With Santa in Chicago

With the holidays right around the corner, I’m already planning on where to take pictures with Santa in Chicago. It’s our annual tradition! Every year we try to take pictures with Santa or Santa’s helper at two different places. There is no shortage to places to take pictures with Santa in Chicago so I wanted to share a post (which I’ll update every year) on my picks on where to take photos with Santa for your little ones or for the whole family!

Last year, I came across a headline on the Wall Street Journal that read – Sad Santas Confront Empty Malls: ‘Do I Have Something in My Beard?’ and laughed a little. But then I read the article and felt a little sad for some of these Santas in these malls that don’t have a lot of foot traffic.

It got me thinking how there are now so many places for kids in Chicago to see and take pictures with Santa, not just in malls. Although, our tradition since Luke’s first Christmas is to take pictures with Santa at 900 North Michigan Shops, which is mall. We took Luke and the twins there last night and it was so nice to know that Santa remembered us…well, at least he said he did. I’m gonna believe he did. He was very surprised and happy to see our new additions – Cruz and Levi. He wasn’t even mad that Levi pulled on his real beard. In my opinion, he’s the coolest Santa in Chicago.

Selfies with Santa at the Skydeck

Speaking of cool….we went to the Skydeck at the Willis Tower to take pictures or “Selfies with Santa” this past weekend. All I can say is that we took pictures with Santa to a new level…to the 103rd floor (on the Ledge) to be exact! I have to say, it’s one of my favorites of Luke with Santa (well, besides his first photo with Santa). It was a thrill for me to snap the picture of Luke on the ledge with Santa and I think I will have to frame this one.

I’ve updated my list for 2019 on where to take the most unique pictures with Santa in Chicago! In case you like taking pictures with Santas in malls and shopping centers, I’ve included those too!

The Most Unique Places To Take Pictures With Santa in Chicago

Skydeck Chicago

Selfies with Santa is now the Skydeck’s annual holiday event. My favorite picture of Luke with Santa up 103 floors! Dates: December 16 to December 23 from 12:00 PM to 5:00 PM.

Driehaus Museum

Santa at the Museum is back this year. If you don’t know much about the Driehaus Museum, it is located in River North and houses art collections and exhibits from the late 19th century. After pictures with Santa, you can play holiday games and explore the museum, enjoy live music an explore the museum. Dates: Saturdays and Sundays, December 7 – 15. Timed tickets.

Christkindlmarket Chicago

This popular Christmas market not only has popular German food and drinks but also has a little house for Santa.

Navy Pier’s Winter Wonderfest

We’ve been to Navy Pier’s Winter Wonderfest for the past few years and Luke absolutely loves it. Santa is only available at certain times so call and check before you go. Dates: December 6 – January 12.

Lincoln Park Zoo (Zoo Lights)

If your child loves the zoo, it’s great to get and zoo adventure in and photos with Santa in one spot. There is also breakfast with Santa at Cafe Brauer on December 15th.

Spirit of Chicago – Santa Lunch Cruise

Lunch with Santa on Lake Michigan is very unique and different. This is only offered on a specific date. So plan early. Date: December 8th.

Winterland at Gallagher Way

Located right outside Wrigley Field, this is a great neighborhood spot to take pictures with Santa at Santa’s Winterland Workshop. Dates: November 29 – December 22.

Brunch with Santa at Pinstripes

Meet Santa during brunch – then bowl and/or play bocce afterwards. Who else can say they went bowling and met Santa? Dates: December 8, 15, 22.

Pictures with Santa at Chicago Hotels

  • The Drake Hotel – Brunch with Santa – The Drake Hotel is a Chicago classic! December 21st and 22nd.
  • The Langham Chicago Hotel – check with hotel for specific dates for Santa’s visit.
  • The Peninsula Hotel – Children’s afternoon tea with Mrs. Claus (and a surprise visit from Santa Claus. Available on Friday, Saturday and Sunday afternoons from November 29 to December 22.
  • The Swissotel Chicago – Check out the Santa Suite to see where Santa sleeps when he’s in town, decked out with a room where kids can take pictures with Santa.

Pictures with Santa at Malls / Shopping Centers / Department Stores in Chicago

  • 900 North Michigan Shops – You will need to check in on the 3rd floor and have your name on the list. They will text you when it’s your time to take pictures with Santa. In the meantime, enjoy a meal at the new food hall – Aster Hall .
  • Water Tower Place – You can reserve your spot online. When you’re there, you can take an interactive sleigh ride to the North Pole.
  • Macy’s on State Street – Santaland is located on the 5th floor.

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