Cindy and Ben Chereskin

Catching Up with Cindy Chereskin







You can draw a direct line from Lucy McCormick Blair Linn to Hope McCormick to Mary Young to today’s dynamic non-profit leaders including Catharine Hamilton, Alexandra Nichols, Noren Ungaretti, Debra Beck, and Mary Ellen Connellan, and to Cindy Chereskin, known not only as philanthropist, volunteer, and trendsetter but also as just about the kindest person in town.

Like each of these women whose enthusiasm and intelligence have made our city take notice of the institutions they advanced, Cindy shines with the force of personality and tenacious hard work. As we profile women’s boards and their leaders, we salute Cindy.


Cindy and Ben Chereskin. Photo by fig media.

Diane Thomas, who serves with Cindy on the University of Chicago Cancer Research Board, said of Cindy recently:

“I can’t think of anyone I would rather comment on than Cindy Chereskin. For three decades I have worked, played, traveled, laughed, and cried with Cindy and she is at the pinnacle of the group of women I most admire. To say she ‘has it all’ is truly an understatement because she also ‘does it all.’

“Cindy has the elegance of Grace Kelly, the strength of Katherine Hepburn, and the naturalness of Kate Middleton. Every single day she makes everyone around her a better person simply by being herself.”

Growing up in Sycamore, Illinois, an hour and a half outside of Chicago in DeKalb County, Cindy could walk down Main Street and know most of the 7,000 people who lived there at the time. She knew that her parents would hear if she stepped out of line—but that’s very hard to imagine. Her mother was her first Brownie Scout leader, her father attended all her sports events, and she says it was a lovely place to grow up. Although she and husband Benjamin are some of the city’s most generous philanthropists who travel the world, often with sons Jacob and Alexander, her spirit hasn’t strayed from Sycamore.


Jacob, Melissa, Alexander, Cynthia, and Benjamin Chereskin.

Cindy’s leadership philosophy is as Diane expressed: be yourself, laud others, and be open-minded. She is surely one of the most admired past presidents of The University of Chicago Cancer Research Foundation’s Women’s Board, hosts of glamorous and record-breaking galas, which she has chaired twice.

“All of us are given wonderful gifts,” she explains. “Embrace what you have but find people with different skill sets to work with, and be grateful for the Midwest values that surround us. On a board you have to listen and be a good friend as well. People serve on volunteer organizations out of the goodness of their hearts. You need to keep board members inspired.”

As a young mother with obvious community dedication, Cindy was asked to get involved in multiple projects when she arrived in Chicago. She recalls, “One of my first opportunities was to serve on the Discovery Board of the Goodman Theatre. I loved going to those thought-provoking plays, meeting actors such as John Leguizamo and Spaulding Gray, hearing his incomparable monologues.”

“I learned so much volunteering at the places my sons were in school: St. Chrysostom’s Day School, when they were very young, then the University of Chicago Laboratory Schools,” Cindy continues. “I am currently a Trustee of the University of Chicago Medical Center, a member of The University of Chicago Advisory Council of the Biological Sciences, and a member of women’s boards of The University of Chicago Cancer Research Foundation, The Art Institute of Chicago, and The Boys and Girls Club of Chicago.”

It was a family health crisis that got Cindy involved in cancer research:

“In college Ben had been diagnosed with non-Hodgkins Lymphoma, and we felt so lucky that he was cured,” she explains. “Several years ago he was diagnosed with tongue cancer and, like chef and restaurateur Grant Achatz, who was also treated at the University of Chicago Medical Center, is in full remission and didn’t have to have the life-altering surgery done by most doctors for oral cancers.

“My father, Glen Johnson, was told by his doctor that there was nothing they could do when his advanced bladder cancer was discovered. We took him to see Dr. Gary Steinberg at The University of Chicago Medical Center who pioneered the creation of a neobladder, which he constructed for my father who then lived an additional 11 years.

She continued, “The caliber of the doctors is world class and to be involved sincerely gives me goose bumps. At my first board meeting of the University of Chicago Medical Center we heard about the surgeons who performed the first back-to-back heart, liver, and kidney transplants on two 29 year olds, a 35-hour procedure in all.”

The Chereskins recently made a $1 million grant to The University of Chicago Medicine Comprehensive Cancer Center, establishing the Janet T. Rowley Discovery Fund that supports compelling ideas in cancer research, in honor of her father.

She explains: “My husband Ben is very involved in giving back to the community as well. He serves as chairman of KIPP Chicago Public Schools, the leading charter network in Chicago serving 2,400 students in grades K-8. The Chicago schools are located in Austin, Englewood, North Lawndale, and West Humboldt Park neighborhoods.”


With husband Ben at the Musee D’Orsay.


And in Italy.

Cindy and Ben found time to travel the world with their two sons during summers and spring breaks, encouraging them to delve deep into the history and religion of places such as Haifa, Tel Aviv and other historic places in Israel, Angkor Wat in Cambodia, Japan, Africa, and Turkey. She was just back from Mexico City when we visited recently, while Ben was skiing with Alexander in Jackson Hole.

“I look forward to hiking with girlfriends in Arizona later this month and exploring the Sacred Valley in Machu Picchu this spring. Places I’d like to visit are China, Russia, South America, Australia, and New Zealand,” she says.


With friends in India.

Known for her beautiful taste in clothes, Cindy describes where she is now, saying, “I have always loved clothes, ever since I was a little girl. We all have our hit and misses but when you decide what looks best you stick with that—you don’t have to try different looks.”

She centers with yoga several times a week, is the favorite tennis partner of many friends, and finds time for reading whenever possible: “I just finished reading In Pieces by Sally Field and Small Fry by Lisa Brennan-Jobs and enjoyed them both. One of my all time favorites is The Good Earth by Pearl Buck. Another favorite of late is When Breath Becomes Air by Paul Kalanithi.”

Kalanithi, an Indian-American neurosurgeon and bestselling author, writes in When Breath Becomes Air: “Human knowledge is never contained in one person. It grows from the relationships we create between each other and the world, and still it is never complete.”

It sounds like advice Cindy practices each day in her own interactions. She said recently: “Choosing a charity to give your time, I advise people to choose what is especially personal to them and volunteer at the place where they particularly want to see everything go well. Chicago is a unique community with a sense of values, we should be so grateful.”