Windy City Wondertainment

About Us

About Us

Welcome to Windy City Wondertainment – your premiere home for event entertainment in Chicago!

We are a group of professional actors & youth educators from all across Chicago-land that have committed ourselves to making sure that you have the most exceptional of entertainment at your next event. We specialize in characters from Star Wars, Marvel, DC, Transformers, Harry Potter and more!

If you can dream it – we can do it. With Windy City Wondertainment, the sky is the limits! Don’t see the character that you’re looking for on our site? Let us know! We have connections to professional talent all over Chicago and we want to work with you on making your dreams a reality. Just let us know what you’re looking for and our team of Wondertainers will do the rest!

For more information, please contact us at

Check out the ways that we can entertain you…


Birthdays are a great way to bring in Windy City Wondertainment! We’ve performed at many different birthday parties for a variety of ages and our performers know exactly how to keep your guests entertained and engaged. We promise to make your child’s birthday party an event they will never forget.

Some of our past birthday party characters include…

  • Batman
  • The Joker
  • Batgirl
  • Spider-Man
  • Captain America
  • Wonder Woman
  • A Jedi Master
  • Darth Vader
  • Kylo Ren
  • A Hogwarts Professor
  • …and more!

Don’t see a character on this list that you’re looking for? Not a problem! Just send us an email at and let us know who you would like to hire. We are connected to many professional entertainers throughout Chicago and we would love to help you in making your birthday party exactly what you’re looking for!


Many of our Wondertainment team are not only professional actors – but they’re professional stuntmen and fight choreographers as well! Want to hold a workshop at your library or school event that your students will be talking about for years to come? How about hiring one of our Jedi Masters to come in and teach the ways of the lightsaber? Or perhaps you’d care to welcome in one of our Hogwarts professors to teach a bit of wandwork & magic? Or perhaps you’d like to bring in one of our superheroes to teach about the magic of fight choreography for the big screen?

Our team has worked with people of all ages and we can cater our workshops to specifically fit your needs. Do you have a certain theme or workshop you are interested in hosting? Let us know! Our team is highly skilled and capable of bringing your biggest dreams to reality.


Are you hosting a corporate event or a Fall Festival and would like to hire a few characters to wander around for pictures and interactions? We can do that! There’s nothing quite so exciting for your guests then to get to interact with some of their favorite characters. We’ve performed for events all the way from multi-million dollar corporate events…to a library “Star Wars Day”.

Get in touch with us and let us know a little bit more about the event you are hosting. We’d love to make it extra special!

Special Greetings

Is there a special someone in your life that you would like to give a truly unique gift to? Why not have one of their favorite superheroes sing them Happy Birthday? Or have a Jedi Master congratulate them on a recent life event? Or have a Hogwarts professor wish them luck on their finals?

Our team of professional actors would love to create a one-of-a-kind video just for your special somebody to commemorate an important moment…or just to say hello from afar!