Nobody knows the cycling in and outs of this city better than the folks who navigate it on two wheels for a living: bike messengers. And you’d be hard pressed to find one more experienced than Nico Deportago-Cabrera of Pilsen. A freelance messenger for several local delivery companies, the 32-year-old Red Bull–sponsored athlete and onetime bike messenger champion of North America (yes, you read that right) will compete this summer in Paris in his eighth world games.

Favorite Places to Ride

Lower Wacker Drive: “At first it’s intimidating because it’s so busy and claustrophobic. There are cars driving above you and all around you, and it’s loud. But you kind of feel like Batman when you’re down there. You can hear jackhammers from all the construction sites along the river; you can hear big diesel trucks ripping through or unloading pallets onto docks. The sounds of the city. And being underground, they are particularly unique, the way they resonate and echo. It’s like industrial music, you know?”

Rogers Park: “It’s different from the standard grid—the streets are broken up more interestingly. I get stoked when I find one I haven’t ridden before. The neighborhood is superchill, and there’s not a lot of traffic. But I also love crushing it down Sheridan, right where it turns into Broadway. If you catch the green light and a tailwind, that stretch is a lot of fun.”

Favorite Gear

Bike: All-City Nature Boy 853. “If you could have just one bike in Chicago, this would be the one. It’s awesome and fun but very practical. There are very few things on it to go wrong.” From $1,000, allcitycycles.com

Bag: Seagull Legacy Sling. “Awesome shoulder padding and an easy-to-use strap buckle.” $320, seagullbags.com

Chain lube: ProGold ProLink. “It does a good job of not just keeping the chain lubricated but also cleaning it as you pedal.” $8 for a four-ounce tube, bikes.progoldmfr.com

Pump: Topeak Road Morph G. “I like an old-fashioned pump. Carbon dioxide cartridges can be unreliable.” $45, topeak.com

Lock: Kryptonite Mini. “It’s big enough to lock up a front wheel and a frame. And a heavier lock will buy you maybe only another 15 seconds on an angle grinder.” $45, kryptonitelock.com

Urban Biking Survival Tips

Do use lights in both front and back. Deportago-Cabrera likes flashing lights, even during the day. “A lot of the times drivers do dumb things, it’s because they don’t know you’re there. They tend to recognize blinky or shiny things.”

Don’t rely on blinkers to reveal a driver’s intentions. “I spend a lot of my time looking at what people’s heads are doing. Instead of turn signals, I look at front wheels.”

Do be on the lookout for cars making illegal turns. “I was hit four times in my first two years, all from vehicles pulling illegal U-turns. Over time you start to see the patterns in traffic. Now I see it happening even before the driver knows they’re going to do it.”

Most Memorable Delivery

“I had gotten radioed by dispatch to meet a driver by a highway exit on Ohio. Obama was in town, so there were a lot of street closures. The driver hands me this violin case, looks me dead in the eye, and says, ‘If this delivery doesn’t make it to the shop, our company is going under.’ I make it across town to the shop, and the dude opens up the case and pulls out this piece of paper. He shows me this appraisal ticket for, like, $180,000. Apparently this violin was crazy old. It blew my mind that I was carrying it in my beat-up messenger bag across town.”