Double Chai in the Chi
Joshua G. Rubenstein Portrait
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Joshua G. Rubenstein

Joshua Rubenstein is a mountain-climbing, theater-producing, real estate investor and developer. He also sails, frequently travels to Israel and supports many Jewish causes. 

At Windy City RE, Joshua specializes in adaptive reuse, turning vacant and dilapidated buildings into rehabbed buildings, adding value to the community. His latest development project is Motor Row on Michigan Avenue, which he says will be a major change for the South Loop and McCormick Place surroundings. 

Joshua also adds to the value of the Jewish community; he helped Chicago Jewish Day School purchase its new building. Aside from real estate, he is executive producer of Windy City Playhouse, Chicago's newest non-profit Equity Theater, which he started with his sister, Amy, a 2015 Double Chai in the Chi honoree.



Primary gig:

Real estate investor/developer for Windy City RE

On the side:

Sailor, mountaineer, theater producer

Relationship status:


Something most people don’t know about me:

I won the Mackinac (sailing race) in 2014 and have sailed on many professional teams. I climbed Mt. Kilimanjaro last year and have new peak plans coming up.

How do you Jew in Chicago?

I often frequent Elm Street Synagogue and love to follow the on goings of my nieces and nephews at Chicago Jewish Day School. I'm active in AIPAC, JUF, etc. … and who's not on JDate? ;)

Chicago's Jewish community in 10 years:

I hope to see the Jewish day schools in Chicago flourishing as they are the future for the Jewish community. I also look forward to seeing the future leaders of our community taking a more active role in Chicago.