iPad + DSLR bag = Tamrac Rally 5
I needed something for my Canon DSLR and my iPad.
http://www.amazon.com/Tamrac-3445-Rally-Camera-Netbook/dp/B0045O0DHW
I wanted something for travelling that could comfortably carry my Canon DSLR (EOS 7D) with the kit zoom lens (28-135mm), plus a 2nd smaller Canon 50mm lens, plus my iPad. And I didn't want a backpack, or a large messenger/duffel bag. In other words, I wanted to find the smallest, lightest option which could give me quick access to my gear.
Since purchasing the bag, I've actually been able to travel with the above mentioned gear, PLUS another camera (Fuji x100) AND a 2nd iPad (my wife's), all in this one bag. The inner compartment dividers are flexible and customizable enough for me to squeeze in both cameras, the extra lens and additional bits of gear. The flap opens at the top for pretty easy access to everything.
The inner vertical iPad slot actually was able to hold TWO iPads (one with the Apple iPad original case, the other iPad2 with a Smart Cover attached). It is a snug fit for 2 iPads, but, hey it works!
The outer back pocket was great for quick access for a magazine, guidebooks or maps, and the zippered front pocket area was great for carrying extra batteries, memory cards, chargers/travel European power adapters. There are also two side outer mesh pockets which, for me, held bottled water and snacks.
The wide strap has a nice padded shoulder piece, and the attached handle grip was handy (no pun intended) to have. I like the dimensions of this bag, and that it's smaller than the typical messenger bag or backpack.