It's Showtime for Windy City Playhouse, Irving Park's New Theater

IRVING PARK — With just days to go before the curtain rises on the very first production of her brand-spanking-new theater, Windy City Playhouse, co-founder and artistic director Amy Rubenstein is sleep-deprived and over-caffeinated.

"Five minutes ago we passed our plumbing inspection," Rubenstein said, but the day prior, a different set of city inspectors informed her she needed seven new doors.

"This final push to get to the end is insane. It's been a challenging couple of months," she said. "People keep asking, 'Are you going to make it?' There's really no option."

Recruited by Rubenstein to direct Windy City's debut show, Henry Godinez, artistic associate at the Goodman Theatre, said, "Amy has been great about shielding us from all that craziness. I just focused on the play and the actors, knowing that we would do this play as best we can, no matter what the conditions."

^{Amy Rubenstein, co-founder and artistic director of Windy City Playhouse. DNAinfo/Patty Wetli}

When Windy City's 2015 season opens Thursday with the Godinez-helmed "End Days," Rubenstein will know whether her gamble on a start-up theater well off the beaten Loop path has paid off.

She and her partners in the venture — husband Milan Rubenstein and brother Joshua Rubenstein — are betting big that there's an untapped audience of theatergoers who would take in a show more often if only the experience were a) more entertaining and b) more convenient.

"We want to change the way people are regularly thinking of theater," she said.

On first blush, Rubenstein may seem an unlikely leader of a revolution in the arts.

The 35-year-old, along with her husband and sibling, is a principle in a real estate firm that buys and flips residential and commercial properties, with a portfolio in Chicago worth $200 million.

Patty Wetli says it's been a long journey for Rubenstein:

^{Part of the set for "End Days," the first production from Windy City Playhouse. DNAinfo/Patty Wetli}

But theater, she said, is her first love.

"I've acted my whole life, ever since I was five," said Rubenstein, who graduated from Deerfield High School and majored in theater and economics at Brandeis University.

She fell into real estate a dozen years ago when she moved to Los Angeles to pursue acting gigs. She sold one house, bought a building with the proceeds, sold that property, bought two buildings, and so on and so on.

"You could touch something and it turned to gold in that market," Rubenstein said.

Still, as much as she tried to get theater out of her system, she found it was something she "craved and needed," she said.

Moving back to Chicago with their two young children, Rubenstein and her husband began attending plays and noticed something interesting about their fellow patrons.

"Our peers weren't there," Rubenstein said. "In talking to my friends, they weren't going. We found a void that needed to be filled."

Theater had turned into a "big to-do," an annual splurge on a major downtown touring production, she said.

"People have less and less time," Rubenstein said. "There's only so many nights of the week you can go out."

^{Days before its opening, Windy City Playhouse was still a work in progress. DNAinfo/Patty Wetli}

The premise behind Windy City Playhouse: Create a single space where people can eat, drink and see a play. A date-night trifecta, if you will.

"Our idea is it's one big experience," Rubenstein said.

The location, 3014 W. Irving Park Road, is smack in the middle of a neighborhood that plenty of creative types call home but is lacking in entertainment options, Rubenstein said.

"We wanted to be in an area where we felt needed," she said.

Godinez acknowledged that it's challenging for larger theaters to succeed outside of downtown — Windy City has a capacity of close to 150 patrons — but said the playhouse has a strong shot at success if it can become a neighborhood anchor.

"I loved the idea of a new theater that wanted to draw new audiences," Godinez said. "I think people might enjoy having a great evening out without the hassle and cost of going downtown ... at least once in a while."

Patrons can arrive as early as 1½ hours before showtime, with drinks and food (small bites like cheese plates and hummus) brought to their seats — half of which are typical fold-down theater seats and the other half of which are swivel chairs with tables in between.

Intermission runs for 25 minutes, allowing for conversation and additional libations.

"Now you're in a lounge together," Rubenstein said.

She selected the four plays that comprise Windy City's debut season, with an eye toward contemporary, entertaining scripts.

Though "entertaining" often carries with it the "negative connotation of cheap and fluffy," Rubenstein insisted that just because a show's fun doesn't mean it's not also of the highest quality.

^{Director Henry Godinez, during rehearsals for "End Days" the debut production of Windy City Playhouse. DNAinfo/Patty Wetli}

In nabbing well-respected veterans like Godinez and Chuck Smith — also affiliated with the Goodman and director of Windy City's second production, "Stick Fly" — Rubenstein has demonstrated the seriousness of her intent.

"I got a good vibe from Amy right off the bat and saw that she was super sharp and professional," Godinez said.

Her entrepreneurial mindset "is in keeping with the always ballsy nature of Chicago theater," he added.

It didn't take much in the way of arm-twisting to bring Godinez on board for "End Days," which follows a family's disparate reactions to the Sept. 11 terrorist attacks.

"I have always wanted to do a play that touched on 9/11," said Godinez. "It's a sweet, funny play with a big heart about family and redemption. I love that."

"I almost cried twice," Rubenstein said of watching "End Days" rehearsals. "It's really beautiful."

All the pieces are in place for Thursday's opening preview. Now it's up to audiences to decide whether Rubenstein's scored a hit or struck wide of the mark.

"Once the lights go down, it's out of my hands," she said. "There's nothing I can do at that point."

Tickets for "End Days" cost $20 or $38 and can be purchased online.

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