The Home Front

By Don DeBat As the old saying goes, everyone suffers two inescapable maladies in life—taxes and death. However, when the problem is Cook County property taxes, the adage should include a few other words: “tax abuse, errors, and bureaucratic red tape” Cook County Treasurer, Maria Pappas (above) According to the latest tax-bill analysis by Cook County Treasurer Maria Pappas, homeowners face a sharper increase in property taxes this year compared to businesses—a result of home

Northerly Island, Chicago, IL (above) By Don DeBat Second of two articles on the future of softball on Chicago’s lakefront. It appears that “Chicago’s Game,” 16-inch slow pitch softball, is officially dead at Grant Park after anchoring the historic lakefront location for nearly 100 years. Following the four-day and night “Lollapalooza” concert event, Grant Park’s cherished softball diamonds were trampled into utter destruction by a total of 400,000-plus concert attendees. Whe

Bird’s-eye view of the aftermath of Lollapalooza concert after one memorable weekend in Chicago’s 2026 summer festival season. Chicago Sun-Times photo. By Don DeBat First of two articles on the future of softball on Chicago’s lakefront. While Rock music blasted from multiple stages during the recent epic “Lollapalooza” event, Grant Park’s historic and cherished 16-inch softball diamonds were trampled into utter destruction. Was this the final toll of the death knell for Grant

By Don DeBat There is a sweeping regulatory movement underway, pushed by Mayor Brandon Johnson—an avowed Democratic Socialist—to take private property rights away from landlords, and give excessive protection to renters. An estimated 54% of Chicago’s residents—some 600,000 people-are apartment renters, according to the City of Chicago, so Mayor Johnson, who is up for reelection next spring against at least a half-dozen opponents, obviously needs votes. Chicago currently has

By Don DeBat Chicago’s North Side home buyers will continue to pay more, and should “act quickly” this summer to grab their share of the American Dream. That’s the advice of 26-year veteran Baird & Warner real estate broker May Jo Nathan, author of the “Chicago North Side Market Report.” The exclusive survey analyzed 2nd quarter April through June of 2026 single-family home and attached townhome and condominium sales in nine neighborhoods—Edgewater, Lake View, Lincoln Park, L

New bike lane installed on Archer avenue in front of The Pants Box (above) By Don DeBat Chicago was once known as a “city that works.” It was a transportation-oriented hub, but now is run by clout-happy, Democratic-Socialist politicians who appear to be kissing the bicycle lobby’s sprocket. City Hall has erected concrete barriers and roadway-blockers on key arterial streets all over the city’s transportation grid in favor of privileged bike paths. The bike-crazy trend really

North side after the fire (above) By Don DeBat Chicago may be the Windy City, but it also is home of some of the greatest fires of the past century. The Great Chicago Fire of 1871—when most city neighborhoods consisted of wooden balloon-frame homes—claimed more than 300 lives, displaced 100,000 people and scorched 3.3 square miles of the Windy City. A few years later, in 1903, the Iroquois Theater fire at 26 W. Randolph in Chicago’s Loop took 602 lives. In 1958, the devastati

By Don DeBat Mayor Johnson is preparing a sweeping “Protecting Renters Ordinance” for Chicago. But while City Hall frames it as a vital tenant defense, local landlords warn new fees and a mandatory registry will drive up monthly rents by at least $100. Half of Chicago’s residents – some 600,000 people – are apartment renters, so with a slim chance of re-election in 2027, Mayor Brandon Johnson is digging for votes. Mayor Johnson, an avowed Democratic Socialist, plans to introd

By Don DeBat A massive feud between Zillow and local industry leaders erupted after Chicago’s major multiple listing service cut off the aggregator’s data access, causing thousands of local home listings to vanish from the platform overnight. In an ultimate rebellion against artificial intelligence in the lucrative business of dream homes and rental apartments, Zillow, the real estate data aggregator, now has fewer followers in Chicago and Illinois. On May 20, Zillow Group In

(Above) Sam Sianis (center) holds the 1974 tournament trophy won by the Chicago Daily News 16-inch softball team he sponsored. The legendary lineup included Pulitzer Prize-winning columnist Mike Royko (top row, second from right). The photo was taken at the Hubbard Street Billy Goat Tavern next to the “VIP Room” sign. Photo provided by Don DeBat. By Don DeBat Chicago-style 16-inch softball managers might tell you losing a good sponsor is worse than losing a brother. With the

(Above) While 87,000 Cook County taxpayers remain stranded by a system-wide software backlog, Tyler Technologies Chairman John Marr celebrates corporate success by ringing the closing bell at the New York Stock Exchange on February 3, 2026. The Texas firm’s unresolved county tech contract has left an estimated $46 million in local refunds bottlenecked. (AP Photo/Richard Drew) By Don DeBat While tens of thousands of Chicago property owners are reeling from soaring taxes, some

(Above) Aerial view looking north from Jackson Park toward the Chicago skyline, showcasing the Woodlawn and South Shore neighborhoods. (Photo: Adobe Stock) By Don DeBat With the Obama Presidential Center approaching, a new anti-gentrification ordinance is rattling the real estate industry, pitting landlord rights against city efforts to prevent displacement in Chicago’s lakefront neighborhoods. The threat of rising apartment rents in “Obamaville” and other South Side lakefron