Specialty Character
Jessie
Birthday Parties
in Chicago & Northern Illinois
"Yee-haw! Let's round up the birthday crew."
Jessie comes through the door with her red braid flying and enough energy to get a whole room of kids on their feet. She's the yodeling cowgirl from Toy Story — loyal, funny, and genuinely thrilled to meet every child there. Kids who turn up in their own cowboy hats or holding a Jessie doll get the biggest reaction of all, and she stays in character from the front door to the last wave goodbye.
- ★ 5-Star Google Reviews
- ★ 5-Star Facebook Reviews
- ◆ Parties available for 1-30 kids
- ◆ Chicago & Northern Illinois
Real Jessie Parties
Choose Your Adventure
Three thoughtfully designed packages — each one filled with wonder. All include up to 15 children, $10 for each additional child. Travel not included in base pricing.
Keepsake portraits, what every party includes, and common questions →
Your choice of 15-60 minutes · Up to 15 children included in pricing
- ★ Active games — classic childhood games with a themed twist, because enjoying something they already love invites children to feel confident and connected
- ★ All their favorite songs, woven into conversation and throughout the games — and sung together face-to-face
- ★ Photo ops at the end, because by then they are hugging a friend, not smiling on cue
- ★ Silver is simply this: friendship with their hero, while their favorite movie comes to life before their eyes
90 minutes · Up to 15 children included in pricing
- ★ Every child goes home with a printed 4x6 portrait. A party favor that's meaningful and personal.
- ★ Portraits are taken near the end of the party, after we become friends. Taking a picture together is a playful experience on its own!
- ★ Portrait equipment requires no outlet and has a small footprint with no cords for kids to trip on — it works well literally anywhere!
- ★ A soft-focus background — so your party space will photograph well, whether it is decorated or not
- ★ Edited digitals follow within two weeks, included in the package price
- ★ Everything in Silver
120 minutes · Up to 15 children included in pricing
- ★ Your choice: makeovers, or decorating a frame for the portrait
- ★ Makeovers include no-mess iridescent biodegradable glitter roots, face gems, and rainbow clip-in tinsel — fancy and one of a kind.
- ★ A high quality metal beaded best-friends bracelet, because a tangible, wearable token of their new friendship is a gift that will keep the memories close
- ★ Marked with the character initial, so they can look down and remember whose friend they are
- ★ Thirty more minutes together, and everything in Silver and Gold
Travel fees apply based on distance from Sycamore, IL. Contact for a custom quote.
A Note From the Owner
Before You Book, Meet Jess
Before you book, I'd love to introduce myself and share a little about why I do this work.
What Families Are Saying
5-star reviews every single time — here's what real families across Northern Illinois have experienced.
Also Available For
Library Programs
With hundreds of library programs performed across North America, Jessica brings the art of storytelling to your community. Available as meet & greet appearances or full storytime programs — perfect for summer reading, storytimes, and special events.
Learn About Library ProgramsWhat to Expect
Every visit is fully in-character from arrival to farewell.
Available Near You
The Jessie visits homes, parks, and venues throughout the Chicago area and Northern Illinois.
Don't see your city? Send a message — we serve many more communities throughout Illinois.
Jessie Party FAQ
What is a Toy Story birthday party with Jessie like?
Jessie arrives in full cowgirl costume and stays in character the entire visit. She sings, leads Wild West games and roundup races, tells stories about the toys who stick together, and gives every child a one-on-one moment — then finishes with photos. She performs at homes, backyards, parks, libraries, and party venues.
Does Jessie sing at parties?
Yes! Live singing is part of every Jessie visit, and she picks songs the whole group can join in on. Expect a yodel or two along the way.
What age group is a Jessie party best for?
Jessie is a great fit for ages 2–9. She has the energy to keep older kids going and the patience to be gentle with toddlers, and she reads the room to match whoever is in front of her.
Can Jessie do a cowgirl or Wild West themed party?
Absolutely. Jessie works just as well for a cowgirl, rodeo, or Wild West theme as she does for a Toy Story one — same costume, with the games and songs adjusted to fit your theme.
Do you bring Woody or Buzz Lightyear too?
Jessie is the Toy Story character we perform. Plenty of kids come dressed as Woody to meet her and she plays right along, but Woody and Buzz aren't currently on our roster. Just ask and we'll let you know what's possible.
Is Jessie available in Chicago and the suburbs?
Yes! Jessie is available throughout Chicago and Northern Illinois, including Naperville, Aurora, Schaumburg, Evanston, Arlington Heights, and beyond. We recommend booking 4–6 weeks ahead for weekend dates — last-minute requests are always welcome too.
Explore More Characters
Ready to Book
Your Party?
Dates fill up fast, especially on weekends. Reserve your party date today and give your child the birthday they've always dreamed of. Appearances available 7 days/week.