I've got two Timbuk2 messenger bags - a medium and a large - and I like them a lot. I haven't used a Chrome bag but I've heard really good things about them. If you go with Timbuk2 get the large not the medium. You'll be glad you did. The reason that I have two is because I started with a medium and then sized up to the large because I wanted more room. I'd also recommend going the "custom" route and ordering your bag from the website. This way, not only can you pick your own colors, you can add the center divider pocket, which I don't think comes in any of the stock bags. It's worth the extra $10 (or however much it was). The large bag has plenty of pockets on the inside for separating your stuff, especially if you add the center divider.