Chicago teachers voted last week to suspend a 7-day-old strike, sending some 350,000 students back to the classroom and paving the way for the teaching force to vote on a tentative contract. But for many in the Windy City, the contract has raised another potentially tall hurdle: how the cash-strapped district will manage to pay for it. District…

Two years ago, only 150 students attended Holabird Elementary, then a K-5 school in the southeastern corner of this city. Competition from charters and from regular public schools in nearby Baltimore County had drained families from Holabird, a chronic underperformer. So when Andres A. Alonso, the chief executive officer of the Baltimore city…