Preparing to fly to Chicago

Maybe, given recent world events, it's not the best time to fly, but I am doing so this week, going to traveling in four cities--Lexington, Atlanta, Chicago, and Detroit--and five airports, on four separate aeroplanes. Wish me luck! But in the meantime, I've:

1. Bought luggage tags for all bags (rolling carry-on, which I'll actually check, small matching carry-on, CPAP bag, and laptop bag) in basic black, and printed out and inserted contact information in a colour matching my suitcase (which of course, is a type of purple, sort of the clothing colour often called plum or aubergine, but lighter than either of those actual objects).
2. Put said tags on each bag.
3. Called Delta to make sure they knew I was travelling with, but not using, my CPAP, which means an additional bag that doesn't count as such.
4. Checked my model of CPAP to see if it needs a label (it does not).
5. Bought a small crossbody organiser that is flat with pockets for a boarding pass, passport (which I will not have to use on this trip, so I'll leave it at home), and ID (I may take my passport card, however, as I'm not sure our state ID fully complies with the RealID law yet--I know there was some issue about the fact that they are issued by individual county seats, not centrally). It hangs crossbody and will be very good as I will most likely not have pants with pockets, and I have enough to juggle (liquids, CPAP, and laptop usually come out to be screened, at least here in Lexington).
6. Found and registered the Ventra card I'll use on the trains and buses. I'll load a one-day pass while I'm there, which will save me some money.
7. Have printed my airline confirmation, my hotel confirmation, my meeting agenda, and directions/maps from O'Hare to the hotel and from the hotel to Midway.
8. Have typed up an itinerary of flights with numbers, hotel contact information, and meeting contact information for a friend in case anything goes wrong.
9. Have found the almost elusive tiny Fixodent from the last flight (it was part of my introductory pack when I got my partials; I usually use Polident, and I think the large tube is actually under the per item limit, but the little one is better for getting things into the quart bag) and put it in the bag with my other liquids.
10. Checked to make sure I'm complying with my liquids.
11. Checked to see if I can put a light jacket in my checked bag (I doubt I'll need it, except if we go out to dinner that night). It's supposed to be in the 40s and sunny or partly sunny while I'm there.

I'm going to wear my Mary Janes (the really comfortable diabetic shoes I got from the doctor a couple of months ago). They do have stick in gel heel pads, which I hope will be okay, as they're not normally removed. My actual inserts are foam; they should be fine. I will most likely wear a light sweater that will go with either top I wear, and keep everything simple. I'll pack an empty purse in my checked bag so that I can transfer things as needed to it for moving around town. I haven't chosen what I'll wear yet, and I haven't actually packed--that will be for the night before, because there's always some last minute thing, anyway. Oh, and I bought a little pack of facial tissues in case I need those. I also have to make sure I get up v-e-r-y e-a-r-l-y the morning I leave--my flight's at 6 am, I'll probably need to be at the airport about 4:30, so I need to get up about 3:30 am. I'll try to go to bed early the night before.

I went to see my family member tonight, and she's doing much, much better. I explained that I have physical therapy tomorrow night and am flying out later in the week, so I'm not sure I'll be able to visit till the weekend.