It provided news analysis and opinion on local, national and international events of relevance to the Jewish community, with a focus on literature and arts, politics, and the Middle East.

Following the signing of the Oslo Accords in Washington in 1993, for example, the paper remained cautiously optimistic about Mideast peace even in the face of Palestinian violence against Israel.

Its masthead was designed in 1990 by Chicago graphic artist Gerry Kalvelage of BBDO, and includes the newspaper's motto "Useful Information Faithfully Recorded" (a loose translation from the Hebrew of Ecclesiastes XII:10).

[13] In the annual Chicago Headline Club-sponsored Peter Lisagor Awards for Exemplary Journalism competition for work done in 2009, 2013, 2015 and 2016, the Jewish Star was a Finalist for Best Editorial Writing.

[23] After World War II, newspapers had increasingly relied on distribution of single copies from news boxes on public streets (a right recognized by the U.S. Supreme Court in 1988 in City of Lakewood v. Plain Dealer Publishing Co.).

[39] At that time, the Jewish Star criticized the Daley administration for considering news boxes no more than "visual clutter," and fellow newspaper publishers for failing to fight the city on First Amendment grounds.

In response, Chicago Jewish News editor and publisher Joseph Aaron accused Wertheimer of "immoral, underhanded, and anti-Jewish actions,"[12] claiming the charges "were absurd.

"[47] As a result of the Jewish Star complaint, in December 1995 AJPA amended its by-laws "to make clear the various violations we dealt with in the recent Chicago matter.

"[48] Although a common custom among the vast majority of Jews,[49] affixing a mezuzah on a doorpost became an act increasingly likely in Chicago to come in conflict with the rules of condominium associations, as that city typified a country which "has been condo crazy the past few years.

"[50] In May 2004, two Jewish condo owners at Shoreline Towers Condominium in Chicago protested the association's instruction that all exterior objects, including mezuzot, be removed.

[70] At one point, the Jewish Star successfully fended off an attempt to subpoena its records;[71] at another, an Illinois law barring intimidating lawsuits was applied for the first time;[72] and in yet another instance, a Federal Appeals Court in Chicago overruled an earlier decision,[73] and determined that the Fair Housing Act can prohibit discrimination that occurs after homeowners occupy a dwelling.

[83] A December 4, 1992 issue of the Jewish Star makes four cameo appearances in John Maloof and Charlie Siskel's 2013 documentary Finding Vivian Maier, about the noted Chicago street photographer.