Windy City Playhouse: Meet Amy Rubenstein

Meet Amy Rubenstein

Amy Rubenstein is the founder and artistic director of Windy City Playhouse. Amy graduated from Brandeis University as a Theater major and worked as an actress in both Chicago and Los Angeles. She began working as a real estate agent shortly after for fifteen years, then in March, 2015 she combined her real estate and theater skills to create the Windy City Playhouse and has been running it successfully ever since.

The Windy City Playhouse recently ended its run of King Liz in July and will premiere its next play Becky Shaw on September 21st.


Photo Courtesy of Windy City Playhouse

Your theater space is beautiful- and very interestingly laid out. What inspired the creation of such an intimate, modern space? Were there any other theaters that inspired this space? What prompted your choice of location?

We were inspired by the idea of creating a space that felt modern, welcoming, and exciting. A tucked away treasure. A place that beckons you through the doors and makes you want to stay. Then, as you walk through the curtains you enter a new and exciting world that is different each time you arrive. With that in mind we searched bars and restaurants for inspiration on the lobby. The biggest bar inspiration though, was from the building’s own history. With the help of a brilliant designer, Patrizio Fradiani, we found abandoned furniture in the building and had it refinished in black lacquer and faux grey leather. We took the rafters from the roof that was torn down and used them to back our bar, with slats of gold poking through. Bathrooms were stripped down to original brick but we modernized with crystal ball lighting and sleek modern sinks. As far as the theater itself, we knew it had to be ever changing. We used architect John Morris, of Steppenwolf, Lookingglass, BTE, etc. to help create the most flexible space possible, painted in Morris’s suggestion of aubergine as a backdrop.

The location was a big factor for us. Irving Park, though a thriving residential community, the business/entertainment/nightlife is just beginning to develop -- we're excited to bring live theater, of the same quality that's available in the larger auditoriums downtown, to this northwest neighborhood. 

What are Windy City Playhouse’s plans for the future?

We have a sexy dark comedy, Becky Shaw, opening on September 21st with one of our most immersive sets yet! Many audience members will have to swivel a full 180 degrees to bounce back and forth between the 3 gorgeous sets designed by Jeff Kmiec. Director Scott Weinstein joins us for this show and we can’t wait to hear the audience gasp with laugher.

Then we have the most innovative and all-encompassing creation coming up in February. I can’t tell you what it is yet, but we will be announcing it in September and I promise it will be something you have never experienced!


Windy City Playhouse BECKY SHAW
Photo Courtesy of Windy City Playhouse

Certain aspects- such as Windy City Playhouse’s bar menu or bathrooms- make it especially unique. How have these unique aspects contributed to Windy City’s success?

The experience of the audience from when they walk through the door to when they leave should be exciting. We don’t want to waste a minute. That’s why our ever-changing cocktails, themed to the show, remain a staple, along with our extensive wine list. As far as the bathrooms, this is where we feature changing soundscapes, created by the designer of the current running production. They have varied in style and form for each show and have dazzled us with the likes of lovemaking polar bears, a composition of bathroom noises harmonizing with 70’s tunes and jungle adventures. These are pieces of the overall experience that we want our guests to encounter.    

Photo: Michael Brosilow

From your perspective which factors go into the success of a play/performance at your specific venue compared to other theaters?

I love to make audiences laugh. I especially love to force the audience to see something from a new perspective, both literally and figuratively. I look for characters in plays who are easy to relate to in some aspect, and allow us to look at ourselves from the outside and laugh at a struggle that has now had new light shed upon it. I want audiences to experience walking in someone else’s shoes. I want them to feel an emotion that may or may not be their own. These are things on my mind as I read and read and read new plays. We also try to push the limits further each season. Challenging the boundaries of theater is crucial to us. Alongside this, I search for play that are diverse in their characters and given circumstances. We feel strongly about diverse artists and stories and are committed to bringing these voices to light.

What inspired you to move from the real estate business back to the theater business?

The overwhelming urge to create and be immersed by theater has been in my soul for as long as I can remember. When I moved from Los Angeles back to Chicago about 6 years ago, I had a feeling it was my time to focus on theater once again. Chicago is such an amazing theater town and I felt like we had something that could complement the creative landscape.

How has your experience as an actress shaped your decisions at the theater’s artistic director?

When I read plays I can hear all of the characters in my head and I can feel their journeys so clearly. I think this comes from being an actor. I also know how important a director is, so it humbles me. The Playhouse puts a huge emphasis on directors. They are the artists we choose first and the ones who truly guide the artistic vision of each piece.

What is your favorite production that Windy City Playhouse has put on?

That’s like asking me to choose my favorite child, not possible. But I will say that there will always be a special place in my heart for Stick Fly, I will never forget the power of the laughter from Things You Shouldn’t Say Past Midnight, and Bootycandy took me to places I had never been. 😊

Photo: Michael Brosilow
Photo: Michael Brosilow

How does your work in theater draw upon your real estate expertise?

I think real estate and time away from the theater allowed me to gain an outside perspective. Real estate allowed me to learn how to run a business, from accounting and contracts to building and creating with a team.   As hard as the process of opening the theater was, it would have been nearly unachievable for me without the years of work that came before.

How has theater in Chicago compared to theater in Los Angeles or other regional theater areas you have worked in?

Chicago outshines them all. It’s the warmest and most welcoming city.

What originally drew you into acting/the theater business? How old were you when you decided to be an actress?

I don’t remember a day when I wasn’t craving acting. I think I started taking classes when I was 6.   It’s just a part of me.

When you aren’t working on Windy City Playhouse matters, how do you spend your time? Do you have any hobbies?

With 2 jobs (I still work in real estate) and 2 kids, I am complete!  

If you weren’t an actress and real estate developer, is there another career that you think might have been especially interesting to you?

I would love to be a newscaster, a meteorologist, or a ballerina.   Is it too late?

Are you encouraging your children to get involved with theater or other arts? What advice/comments do you have as a parent on how and why to involve children in the arts and cultural offerings?

My kids are certainly exposed to an excessive amount of theater. We see a lot of plays in our family. As far as participating, I give them a lot of options. My daughter loves visual art but I’m not seeing theater in her future. She is only 6 though, so we’ll see. As far as my son, he told me that if I needed someone to take over for me he would be happy to help. He’s in theater camp and loves playwrighting as well. Both kids play piano. I try to let them choose their own paths. The arts are wonderful inspirations that can guide in all sorts of directions. We have a lot of varied interests in our house. I like the balance.


Becky Shaw premieres September 21st and runs until November 12th.

For more information on Amy Rubenstein and The Windy City Playhouse visit The Windy City Playhouse Website.

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