Ex-mayor Rahm Emanuel has his share of detractors for what he did—and didn’t do—for the city, but I’d argue that the silver lining of his tenure, perhaps the one thing that many Chicagoans can agree he did a decent job with, was transportation. The administration racked up a number of transportation wins, generally, if not always, with an eye on equity, including: constructing several new CTA stations, overhauling the south Red Line tracks, building safer streets for walking, opening dozens of miles of new bikeways, and launching the Divvy system. So it was fitting that Emanuel chose to kick off his retirement from City Hall by leaving on a 900-mile-plus bicycle trip around Lake Michigan with a friend on the day after Lori Lightfoot’s inauguration. I recently caught up with him by phone to chat with him about the trip and ask a couple of questions about transportation policy under his administration. 



 A typical anecdote was, I was in a town in the upper part of Wisconsin near the UP border and I was outside a restaurant where the sign said the place didn’t open until 11:30 or 12 for lunch, and it was like two hours before they opened. And I knocked on the window and kind of yelled through the wooden door to ask if we could get some coffee. And the woman said, “Come on in, I’ll put a pot on for you.”

Did your bike have any mechanical problems—any breakdowns?

 All of the above. I think we put together a comprehensive mobility plan for the city. You look at airports, both O’Hare and Midway, and the modernization. You look at CTA, the modernization. You look at protected bike lanes and bike sharing. You look at the 606 and the Lakefront Trail, the separation of the bike and running paths there.