How to Bike in a Big City: 15 Years in Chicago

After 15 years of biking in Chicago, I’ve learned that riding in a big city is mostly about anticipation. In this video, I talk through the real systems I’ve developed for urban cycling: how to read traffic, avoid dangerous streets, deal with bike lanes that come and go, watch for doors, lock up your bike, use CTA and Metra as backup, and choose gear that makes city riding easier. I’ve been hit twice, had a bike stolen, had a wheel stolen, and I still think biking is one of the best ways to experience a city. This is not fearmongering. It’s a practical, personal look at what city biking actually feels like after years of doing it. If you bike in a city, I’d love to hear your rules: what streets do you avoid, how do you lock up, and what lessons did you learn the hard way? Chapters 0:00 15 Years of City Biking 0:30 Reading the City 4:19 Being Right Doesn’t Matter 6:52 The Gray Areas 11:48 Bikes, Buses, Trains & Escape Valves 14:14 The Stop Sign Crash 15:44 Theft Is Risk Management 20:40 Gear That Changes the Ride 25:16 Why I Still Love Biking in Chicago 26:16 Compare Notes