So you’ve decided to start biking to work in Chicago, congratulations! Driving in the city is a special kind of torture, and the CTA during rush hour is a great way to realize how much you really do value your personal space. Commuting by bike in Chicago is possible year round, and gives you a great way to avoid gridlock on the roads and inappropriate touching on the Red Line.

Step 1: Equip Your Bike

Chicago is home to crappy pavement, potholes, and unpredictable weather. This means you can leave your shiny carbon racing bike with 700x23c tires at home. You want to commute on something with reasonably wide tires with a high spoke count and fenders. You’ll also need a good front and rear light. Anything from Cygolite is a good place to start. Pick a headlight that makes you worried about causing permanent blindness to oncoming drivers. In the winter time it gets dark here around 5pm, which means you’ll want to be visible enough that it’s nearly impossible for people to ignore you.

Ideally you have a place indoors to securely store your bike, but if not invest in a good bike lock and have a few good places outside to lock it up. Look for bike racks bolted to the sidewalk first, and then city owned parking meters and poles (make sure all poles have a washer shim in their base).

For short rides a backpack will be fine, but for anything longer than 15 minutes I’d highly recommend buying a rack and pannier for your bike. It’ll allow you to bike comfortably and you won’t have giant sweat stains on your back when you get to work.

Step 2: Equip Yourself

Biking during the summer months is fairly self explanatory, so I’m going to stick to the winter months here. Light layers a windproof shell are your friend while biking in the cold. Wool is also a wonderful thing. Here’s what I wear as it drops below freezing:

  • Smartwool Balaclava
  • Long sleeve tech t-shirt
  • Long sleeve bike jersey
  • Hi-Vis wind breaker
  • Wind proof gloves
  • Thermal tights
  • Wool socks
  • Neoprene shoe booties

Also, that helmet thing. You’ll see people commuting with and without a helmet on, and you’ll hear plenty of opinions arguing both sides. Here’s my opinion:

A helmet won't save you if you get t-boned by a truck, but it can prevent a minor crash
from becoming a major one that requires a hospital stay.

The best thing you can do to keep yourself safe on a bike is ride defensively and stay alert to your surroundings. Especially when it comes to cabs. In Chicago assume every single cab you see will do something completely insane when you least expect it. The same is true of CTA buses. The bus driver likely doesn’t see you and has to pull across the bike lane to pick people up at the bus stop.

Step 3: Bike Like A Car

While Chicago has plenty of bike lanes, there are going to be times when you are sharing the road with cars. The best way to keep yourself safe and have an enjoyable ride is to bike like you are driving a car. This means taking about 3ft of space in the lane and not trying to ride as close to the curb as possible. You stand a much higher chance of getting doored by a parked car than you do hit by a car behind you.

You’ll get honked at a few times a week, but just smile and wave. Don’t give drivers the finger if they honk and yell at you. They’re operating a few tons of steel strapped to a combustion engine, there’s no reason to intentionally invite them to launch into a anger fueled rage. If you feel you must respond to some amped up idiot in an SUV, I’m a big fan of the smile and wave or the thumbs up.

Step 4: Have Fun!

Biking to work is a great way to incorporate excerise into your daily routine, and it’s genuinely fun to cruise down the lakeshore trail on a sunny morning while hundreds of cars are stuck in traffic on lakeshore drive.