It was seven degrees at 9 p.m. on a recent Thursday evening in Chicago, with a few inches of snow still covering the ground from an earlier storm. Terry Truax swapped his suit and tie for several layers of warmer clothing. He slipped on his all-important windproof booties and a face covering, and started his evening commute.

As he does nearly every day when he’s not traveling, Jenner & Block’s managing partner mounted his bike, which he had loaded with a garment bag containing his suit and dress shoes, a briefcase and a laptop. From Jenner’s office on North Clark Street, he pedaled roughly nine miles in the dark to his home on the north side of Chicago.