We both (wife and I) travel with a rollaboard and a
Briggs & Riley Transcend tote ($129 MSRP). Very handy, carries a lot, very durable, excellent warranty (my Basenji ate holes in mine - $15 and I had a new one or repaired looks-like-new, I can't tell). Looks good, works well, has a slip-through for our rollaboard handle, zipped pocket, inside water bottle pocket, snap-out large enough it holds a Kindle Fire HDX 7" or tickets, money, etc. as well as a front ziupped pocket (I carry eye shades, mints, ear plugs) and back pocket for stuff you need to shuck for security, like your liquids and gels bag.
We just returned from a month's trip (six countries, air, bus, cruise, etc.) and can't recommend these enough. You can find these discounted 20% from B&R on occasion, and sometimes from other sources.