It's National Bike Month, and with it the usual articles about urban cycling. Unfortunately, even some of the well-intentioned and generally pretty good ones start with making it seem very scary (we're looking at you, New York Times):
[P]erhaps there is a bicycle leaning against a wall in your apartment, waiting, but the idea of joining those fixed-gear daredevils on city streets makes your stomach drop. And besides, the honking vehicles, jaywalking pedestrians and idling trucks are enough to drive anyone to call a cab.
First, fixies are so five years ago, and there were never that many in the first place. Most people ride normal bikes with gears and brakes. This is like saying "maybe you want to listen to music, but joining those vinyl-obsessed crate diggers seems like so much work!"
More important, if city streets were enough to drive "anyone" to call a cab, tens of thousands of people wouldn't ride bikes on them. It's normal, and the risks are normal; the risks of using bikeshare, for example, are comparable to being a passenger in a car, and no one gives that a second thought.
That said, it takes a bit of getting used to, just like driving in Chicago took some getting used to for me after never having driven in a city before. Here are some ways to approach it, depending on where you're at.
If you don't own a bike and haven't ridden one in years
Try Divvy. It's $9.95 for unlimited 30-minute rides for a day. The bikes are geared so that you can't go very fast—even downhill, not that there are really opportunities for that here—and they're step-through, so if you do pitch forward for some reason, there's no worry about spread-eagleing on the crossbar.
There are plenty of stations along the 606 trail, which is less busy than the Lakefront Trail, and it'll probably be easier to get a Divvy bike than downtown, where the kiosks sometimes run out due to popularity. The Divvy station at Cortland and Marshfield near the path's eastern end is about a 15 minute ride to the station at Albany and Bloomingdale. The latter is a couple blocks from Chicago's best park (Humboldt) and one of its best bars (Scofflaw).
If you do want to ride the Lakefront Trail—and you should, at some point, just because it's special—take heed of this advice.
If you've Divvied but want your own bike
First, do you? Unless you do your own bike maintenance, you will need to get your bike fixed on occasion, or at least tuned up once or twice a year if you ride frequently. Divvy is $100 a year, which is in the ballpark of what a tuneup costs. Depending on your cost-benefit analysis, it might make sense to just do bikeshare.
But it doesn't work for everyone. Maybe you don't live or work near a station; maybe you want to be able to carry more than Divvy's briefcase-sized basket. Start by just asking around; I've gotten three free bikes just by existing. Two didn't fit, though—one of which I made the mistake of actually riding well past the point I realized that—so you might want to just buy one. We've got a list of community bike shops, some of which sell used bikes at prices that are comparable to Craigslist or yard sales without the time cost of navigating those or pitfalls of getting a bike that might not work.
One of the nice things about cycling is that you can buy a $13,000 masterpiece of engineering, but a $130 hand-me-down, so long as it fits, works almost as well for almost anyone. I ride a Diamondback mountain bike with shocks, which is the functional and aesthetic equivalent of an ancient Datsun pickup truck; an expensive road bike might shave a few minutes off my commute.
If you want to ride on the street but have never done it before
Go downtown. Seriously. I feel safer on the Dearborn bike lane than practically anywhere else in the city. It's not just a protected lane—with cars parked between the bike lane and the car lanes—it has its own, cyclist-specific signals that also separate bike-traffic flow from car-traffic flow. Because it goes through an area with relatively short blocks and lots of pedestrian traffic, other cyclists tend not to go very fast. And, because good infrastructure equals good behavior, cyclists tend to follow traffic laws on Dearborn, which means they're pretty predictable.
Another option: bike with a group. Slow Roll Chicago does what it says on the label, and might get you to places you haven't been at the same time.
My colleague Luke Seemann got some advice from a messenger for riding in the city. Two things stuck out to me that are relevant to most anyone:
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.”
Those are skills that take years to develop—I don't have them—but the principle is good. Even if your only experience on the street is driving or walking, you probably already realize that people don't always use their turn signals and do sometimes make unexpected, illegal maneuvers in particular circumstances. (Where I live on the Northwest Side, for instance, it's like NASCAR but for jumping the green light to make a left turn across traffic.) It's really not too hard to translate that into being on a bike.
As for regulating your own behavior as a cyclist, this is a useful guide.
If you bike sometimes but want to commute or run errands
You could just wear a backpack or messenger bag, but in my experience they're annoying—you have to account for the shifting weight, and they make you sweat—and limited in what and how much they can carry. (Messengers use messenger bags because they're convenient to access, which may not be your highest priority.)
My preference is a rack and panniers, though you don't even really need the latter. A $5-ish cargo net, or two or three bungee cords, will keep a surprising spectrum of things on your rack, like a couple bags of groceries. (Even if you have a bag or panniers, stash a cargo net or a couple bungee cords. You'll use them.) A milk crate is another option. Either way, it starts with a rack. My colleague Martha Williams's recommends a rack and bungee cords in her thorough list of bike gear for women; she also recommends a handful of bags and panniers, and I can second Po Campo, which offers sufficiently unisex designs for dudes.
A rack is the sole most useful thing I've bought for biking; the cargo net is probably second. Third is a cup holder that clips to my handlebars. That may sound frou-frou, but one of the things that can keep people from bike commuting is having to sacrifice some of the nice things about other forms of commuting, like reading on public transit. A morning cup of coffee doesn't have to be one of those things. I bike more because of that little piece of plastic.
If you want to bike with a kid
I talked with Gin Kilgore, program director for Ride Illinois, and a car-free parent about this. My experience with and advice on it is limited, but it's another reason to get a rack: I settled on a rear-mounted bike seat that clamps to it. Whatever you want to do with a bike, a rack is usually a good start.
Once you're set with a conveyance, the Kidical Mass family-friendly rides are one way to get started.
If you want to bike but you have a weird commute
You can… bike anyway. I put my bike on the car, drive my daughter to day care, bike to work, and then bike home. Being a "bike commuter" doesn't mean that 100 percent of your commute has to be on a bike.
If you want to bike 100 miles in a day
I can't help you, but Cindy Kuzma can.
(It's not actually an insurmountable challenge; during America's first bike boom, back when neither the bikes nor the infrastructure were all that great and the clothing was absolutely ridiculous, riding a "century" was popular, maybe more so than it is now.)
If you want to bike more than 100 miles in a day, averaging 23 miles an hour, with a bunch of Type-A personalities, on a bike that costs as much as a used car, and has more electronics
And that's where I tap out, but here's how to do that, too.