- St Charles, IL
- Santa Claus
- $200/hour and up - more the week before christmas
Santa John Chicago
Overview
John B Boss provides professional Santa holiday entertainment. Santa Claus is fully self contained. High quality costuming and props. Santa will sing carols, take your Christmas lists, read "'Twas the Night Before Christmas", and even pass out gifts and treats. You can have him pose for photos at your home or private event or just interact with your guests. This professional character actor is a veteran of theater and film and commercial work and will be the hit of your next gathering. Holiday appearances have been enjoyed all over greater Chicago, NW Indiana and Wisconsin. Also available are Mrs. Claus, Grinch, Scrooge or Buddy the Elf. Also set up for VIRTUAL Zoom visits.
Reviews
7 reviews
Ana V.
January 14, 2026Simply the Best Santa – Two Years!
We had Santa John visit us again this Christmas Eve (also booked him in 2023), and once again he absolutely exceeded every expectation!!!
From the moment he walked in, he was Santa — not someone in a costume, but the real deal. His look is impeccable, his voice is warm and authentic, and his presence instantly transformed our home into something magical. The kids were completely mesmerized, and even the adults were smiling ear to ear.
What truly sets Santa John apart is his ability to connect. He remembered how to engage the children at their level, made each one feel special, took beautiful photos with our family, and created moments we’ll honestly treasure forever. He was patient, kind, gentle, and never rushed — which is huge when you have excited little ones and a full house.
From a professionalism standpoint:
✔ On time
✔ Clear communication
✔ Easy to work with
✔ Calm, warm, and organized
✔ Phenomenal with kids AND grandparents
This wasn’t just entertainment — it was a full experience and a core memory for our family.
If you’re considering booking Santa John, don’t hesitate. We did it twice for a reason, and he’s now part of our Christmas tradition.
Thank you, Santa John, for bringing real magic into our home again. We’ll be seeing you next year. 🎅❤️
Hired as: Santa Claus
Sally F.
December 25, 2025Perfect Santa to Celebrate at our Christmas Eve Brunch!
Santa John joined our family Christmas Eve brunch with style! He led us in Christmas carols, performed a reading of 'Twas The Night Before Christmas and posed for lots of photos! He is a true professional and helped to make our celebration so festive! Highly recommend!
Hired as: Santa Claus
Sandra H.
December 23, 2025A Santa who is also a hero!
Santa John Chicago came to our rescue on our wedding day! After an unfortunate illness, our original Santa couldn’t attend our reception. Thankfully, Santa John worked with us on an urgent timeline to bring some holiday magic to our event! He was a surprise for everyone at our wedding reception that evening and brought so much joy to all those he interacted with. It was a night we and our guests won’t ever forget! Thank you SO much Santa John!
Hired as: Santa Claus
Bob P.
December 16, 2025Santa John's Visit to our Neighborhood
Santa John did a great job visiting 12 homes in our neighborhood this year. I received the following feedback...
* I thought it was great, the kids were mesmerized so that is always a win!
* Thought it was great! He was so patient and very kind.
* He was amazing!! Thank you so much! Our oldest was talking about it all night
* We thought the Santa was excellent ! He did a great job singing a carol ,and asking Zachary great Christmas questions . He was warm and friendly and Zachary (and Lola our pug) were both enamored with him .
Hired as: Santa Claus
Mai L.
December 15, 2025Best Santa in town
This is the second year I've booked Santa John for an event and booked him twice this year because he is an amazing Santa. He comes prepared and brighten the kids day (even the crying ones).
Hired as: Santa Claus
Booking information
Upcoming booked events
December 2026
19
Saturday
Wedding Reception
11:00pm - 11:30pm
•
Chicago, IL
Past booked events
December 2025
24
Wednesday
Christmas Party
4:30pm - 6:00pm
•
Chicago, IL
24
Wednesday
House Party
10:00am - 10:30am
•
Chicago, IL
20
Saturday
Wedding Reception
7:00pm - 8:00pm
•
Chicago, IL
17
Wednesday
Anniversary Party
5:00pm - 7:00pm
•
Des Plaines, IL
15
Monday
Christmas Party
6:00pm - 9:00pm
•
Lisle, IL
02
Tuesday
Fundraiser
5:00pm - 7:00pm
•
Harwood Heights, IL
December 2024
24
Tuesday
Christmas Party
3:00pm - 3:30pm
•
Bristol, WI
12
Thursday
Surprise
3:00pm - 5:00pm
•
Harwood Heights, IL
07
Saturday
Festival
5:00pm - 8:00pm
•
Kenilworth, IL
December 2023
24
Sunday
Christmas Party
7:00pm - 8:00pm
•
Chicago, IL
24
Sunday
Surprise
5:30pm - 6:15pm
•
Chicago, IL
December 2022
24
Saturday
Festival
5:00pm - 9:00pm
•
Aurora, IL
July 2022
09
Saturday
Nightclub Event
3:00pm - 5:00pm
•
Chicago, IL
December 2021
24
Friday
Santa Virtual or In Person
11:30am - 1:30pm
23
Thursday
Virtual Santa
11:30am - 1:30pm
22
Wednesday
Virtual Santa
11:30am - 1:30pm
20
Monday
Virtual Santa
11:30am - 1:30pm
18
Saturday
Virtual Santa
11:30am - 12:30pm
17
Friday
Virtual Santa
6:00pm - 7:00pm
16
Thursday
Virtual Santa
6:00pm - 7:00pm
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