Steve Nasatir, president of the Jewish Federation of Metropolitan Chicago, and David Brown, chairman, plan to assess the situation and show Chicago's solidarity with the Israeli people.
"I hope that people understand that 500 rockets in the last week have fallen in Israel. Israel was saying, stop these rockets. If you don't there will be consequences, and now we're seeing what the consequences are," said Nasatir.
While Nasatir say his role in Israel is to assess the situation and to provide money for humanitarian aid, Sami Kishawi with American Muslims for Palestine says his job is to gather grass root support in Chicago for Palestinians. Kishawi has family in Gaza.
"The first strike wasn't a Palestinian strike," he said. "The first move is always going to be oppression. There's an occupation of Palestinian land. There's an occupation. There are air strikes happening in Gaza constantly ... I can only feel for the people that are suffering."
Thirty Palestinians, many of whom are civilians, have been killed as the Israeli military insists it is targeting Hamas rocket launching sites.
Some Palestinians say Israel's government is using this show of force in Gaza to make a political statement.
Nasitar says since 2005, Hamas has shot off more than 12,000 rockets toward Israel.
"I don't know how you make peace with people who do not want peace," he said.
"We are not angry people. We want our freedom, we want our rights, that's all we asking for, basic dignity," said Kishawi.
With more than 550 rockets launched at Israel in past few days, three Israelis have been killed.
President Obama has talked with Israeli Prime Minister Benjamin Netanyahu on the phone. The president has not spoken publicly about the violence, ignoring reporters' questions Thursday and Friday.
Chicago's Jewish leaders return next Wednesday.