How this Jewish Chicago day school pulled off a last-minute, multi-generational Israel service trip

Teddy Gutstein’s first Israel trip, which came in kindergarten, featured all the classics: an El Al flight, falafel and a visit to Jerusalem’s famous Mahane Yehuda market.

The only catch was that the whole experience occurred in his classroom at Chicago Jewish Day School. The school sends its eighth-graders on an annual Israel trip, but as a kindergartener, Gutstein settled for a flight simulation video and some Bissli.

Fast forward to this school year, and Gutstein, now 14, is finally ready for his turn on the actual trip, run through Chicago’s Jewish federation and IsraelNow, an organization that brings Jewish eighth graders to Israel from cities across the United States. The trip caters to nearly 200 Chicago-area students each year; CJDS is the only school that sends its own cohort.

Gutstein couldn’t wait for his first real taste of Israel.

“Through the years, we’ve just been learning Hebrew and learning about Israel,” Gutstein told the Jewish Telegraphic Agency. “I’ve always wanted to go. Some of my friends have gone, but me personally, I have never gone. So I obviously really wanted to experience it.”

But as the Israel-Hamas war raged on into the early months of 2024, IsraelNow made the decision to cancel its February and March Israel trips for all participating cities. The cancelation made Gutstein’s trip one of a slew of Israel journeys to be upended in the wake of Oct. 7 as airlines have canceled flights in the face of incoming rockets and some Jewish organizations have thought twice about bringing their constituents to the vicinity of a war zone, even as others have gone despite the risks.

When CJDS seemed like it was going to join the ranks of institutions scrapping their trips, the choice did not sit right for everyone.

“We work so hard to connect our students to this country, and for them to understand they are part of this bigger Jewish nation. And then in one of its greatest times of need, we stay away from that,” Tamar Cytryn, CJDS’s director of Judaic studies, told JTA. “It felt counter to who we are as an institution, and to our goals.”

Sam Rodin, the director of IsraelNow Chicago, told JTA that the organization decided to cancel its trips out of concern for the mental and physical health and safety of the students. Rodin said the group determined it “wouldn’t be able to provide a meaningful and educational experience that would be safe.”

In lieu of its Israel trip, IsraelNow had offered a program in Northern California, in which some CJDS students participated.

At first, that decision meant that an already difficult school year was destined to end in disappointment for Gutstein and his classmates. But Cytryn said the school’s administration began to look into pathways to make the trip happen, taking inspiration from the Jewish National Fund’s mission trips through which American Jews have been able to safely volunteer throughout Israel.

School raises money for trip

CJDS staff began working the phones, selling community members and donors on their vision for the trip — which Cytyrn said was to expose students to Israeli life pre- and post-October 7 — and soon the funding started to pour in, including from the federation.

The school ultimately raised enough money to send 16 students, each accompanied by a parent or grandparent, and four staff members to Israel — at a cost of roughly $5,500 per participant. (Families contribute $2,750 toward the trip throughout their children’s time at CJDS.)

Even after CJDS raised the money it needed to run its own trip, which the school had never done, a string of flight cancellations complicated matters even more. But 48 hours before students and their parents boarded flights on May 14 — and after several hectic phone calls with donors, parents and the school’s travel agent — everything finally fell into place.

“It was such a roller coaster,” Cytryn said. “We were going, it was canceled. We were going to try to do it again. We got tickets, they were canceled. We tried to secure additional tickets, we couldn’t afford them. And then eventually, somehow, miraculously, it worked out.”

The nine-day trip featured a combination of popular tourist destinations and holy sites such as the Western Wall, the Dead Sea and the beach in Tel Aviv, and volunteering with organizations whose work has been affected by the war. Trip participants worked with HaShomer HaChadash, an organization that facilitates volunteer services at farms in the Galilee and Negev, where they picked kohlrabi and sorted cucumbers and tomatoes. They also packed first aid kits with Magen David Adom, Israel’s emergency response service.

At each turn, Israelis shared their experiences from October 7, including the group’s security guard Omri, who had spent six and a half weeks serving in Gaza during the war. They also visited Tel Aviv’s Hostages Square and met with family members of victims of the Nova music festival massacre.

Many Jewish day schools canceled their annual trips this year in response to the war. But others have persevered, sending their students despite the disruption. Eighth-graders from Hannah Senesh Community Day School in Brooklyn, New York, were believed to be the first students from a US day school to visit Israel since October 7 when they landed in April. Later in the month, students from the Leffell School in Westchester County were in Israel when Iran sent a volley of rockets toward the country.

Cytryn said the experience of witnessing Israel at such a complicated moment reminded her of life in America after 9/11.

“There’s this tension between life continuing — we went to the beach one day, and there were plenty of Israelis on the beach with us,” Cytryn said. “And then being reminded and being brought back to the reality of hostages still in Gaza, the country still at war, and figuring out how to deal with those two tensions juxtaposed to each other.”

For Gutstein, the dichotomy was difficult to grasp.

“On one hand, this is a country that’s fighting a war against a terrorist organization,” he said. “But on the other, life has to go on. And I don’t really know how Israelis find balance in that. But I follow the example of our security guard and our teachers — three of our teachers who came were Israeli.”

Cindy Zadikoff, who went on the trip with her daughter Eden, said it was especially meaningful for her and the other adults to watch their children experience both emotional extremes.

“I think what will be really helpful is we all did a reflection that night after we came back from Hostages Square,” Zadikoff, 52, said. “And we were saying, there’s going to be a time where we need to unpack that with our kids. Right afterwards was not the time, they’ll probably want to talk about it in their time as well. But because we were there with them, too, and we really felt it, too, it will also help us have, I think, some conversations that we might not have been able to have.”

Zadikoff also said the trip will help the students as they prepare to graduate from Jewish day school, and for many, attend public high schools in the fall, where they may be exposed to antisemitism or anti-Israel rhetoric.

“They’ll be able to feel proud to be Jewish, they’ll be able to know that the narrative that they’re hearing is not real,” Zadikoff said. “They’ll be able to have that love of Zionism and Judaism that hopefully the school has instilled in them through all of this time, but I think was just made that much deeper because they’ve now seen Israel, they’ve met Israelis, they know what the reality is.”

That shift had already begun to set in for Gutstein, who lives in the Chicago suburb of Evanston, where Northwestern University has made headlines for its response to the campus’ pro-Palestinian encampment. Gutstein said he had seen the encampment while out for a run and was surprised, and a little scared, to see the protests reach his hometown.

But while in Israel, Gutstein said, he felt able to be more outwardly and proudly Jewish. After Shabbat ended, he and a few friends joined a dancing circle at the Western Wall.

“Sometimes, especially in the States with all the antisemitism going around and the college campuses, you can’t fully be Jewish,” Gutstein said. “But right then and there, I felt fully Jewish and it was so meaningful.”

Cytryn said several of the students echoed a similar sentiment.

“So many students at our first reflection session said that they were struggling with the irony of coming to a country where there is an ongoing war, and coming to a country where people are mourning the loss of family and friends, and coming to a country where people were still actively working to get hostages released from Gaza, and feeling more safe walking around this country as Jewish people than they feel in America,” she said.

Speaking to JTA just minutes before heading to Ben Gurion Airport to fly home, Gutstein said he already missed Israel.

“While I was here, I didn’t really comprehend the fact that I was in Israel, you know what I mean?” Gutstein said. “But I know the minute I get out, I’m just going to be missing it so much, which is not a feeling I normally have. Camp is special, and school is special, but I don’t miss those places like I’m going to miss Israel.”