What is the most comfortable way to ride with a bicycle chain lock?

Wrap it around the handlebars.

@WestRiverrat it’s too heavy to wrap there. It’s 20 lbs about.

Wrapped around the seat post underneath the seat.

I wrap my lock around the frame, like between my legs. But it’s just a standard chain, no where close to 20 lbs.

I’ve seen people wrap around the seat post. Does that weigh the bike down too much?

The best way to carry a bike lock or anything else is to get yourself a rear rack and some bungee cords to secure it with. If it’s too geeky to use a rack, e.g., if you’re riding around on a 16-pound carbon fiber road bike (if so, why did you buy a 20 pound lock), get a detachable seat post rack and take the thing with you.

@rguest Try it. See if you can live with it. Wrapped around the seat post is fine unless it interferes with your thighs while peddling. You could also wrap it around the top tube, unless it interferes with your knees. You could get a bicycle seat bag. I’m not sure most of them are big enough, but if you go here, you’ll see a picture of one of the Minnehaha bags (I’ve seen prices from $26 to $70 for about the same thing), which looks big enough and low profile enough to help you. Here are other pages where the Minnehaha bags are available.