Elon Musk’s Boring Company wins a bid to build high-speed transportation from downtown Chicago to O’Hare. How technologically and economically feasible is the plan? That story and more with Paris Schutz and guests Steve Daniels, Derrick Blakley, Becky Vevea and Rick Telander.

Remembering the legacy of a civil rights giant. Chicago’s mayoral race heats up. Sinclair Broadcasting’s “must-run” conservative commentaries rattle WGN. And Hawks Coach Q is coming back despite a dismal season.