My sister and I are taking a 3 day trip to Chicago later this month with our daughters. We'll be traveling in by train and staying downtown. We plan to do the typical tourist stuff: Art Institute, Architectural Tour, Wrigley Field etc. I plan to take my new Tristar for it's first official trip and will be doing some walking to get to our hotel. I'm short, about 5 ft even and am thinking I'll carry the Tristar some in backpack mode. My question is this: Which second bag would you recommend as my day bag...the Synapse (indigo) or the Medium Cafe Bag (plum)? Would one or the other come off less as flagging me as the tourist-girl I am?