From 1,800 feet in the air, the pilot of this tiny, four-seater plane points to a stretch of land marked by a smattering of farms and one arterial road. “That’s the Wisconsin border,” he says. “Doesn’t look like much from up here.” But that sliver of land now marks a barrier between legal and illegal abortion care after the Supreme Court overturned Roe v. Wade. The pilot is part of a growing network of pilots who, through a fledgling Illinois nonprofit, are volunteering time, equipment and expertise to help connect people with abortion care. But there are risks, too, from...