@WinniWoman Here's a bit of advice I have for you going through TSA.
First when you check your bags visually inspect the printed luggage tags that the airline gives you (or they are affixing). Are the correct airport codes on there? The two times I've lost my bags it was due to the wrong tag being put on my bag.
When you arrive at Boston, BEFORE you get to the security line is to just step aside w/your husband before getting into any lines. Get everything organized and tucked away. Make sure you have your water bottle empty (if you have one). Remove any watches that might trigger the X-ray . If you are wearing a jacket, put that in your carryon / personal item bag. Get everything into that carryon EXCEPT your ID and boarding pass*.
Either have a pocket on your clothes that is secure for ID OR make sure your carryon bag has an easily accessible pocket to shove that ID in.
When you get to TSA you'll put your carryon bag on the belt and most likely your shoes. They may search your bag, that's fine.
IMO I see people getting flustered at TSA who haven't done the "prep work" before they get into the line. That's when things like "forgetting a watch" happen. Just get organized and prepared quietly before you get into line.
Once you get through TSA put your ID back into its "real" place (your wallet). You won't need it to board the plane.
I'm very familiar with O'Hare. Which airline are you flying?
Lots of people love having a mobile boarding ticket on their phone. I think for you have a good old fashioned paper boarding pass the way go. This way you aren't fumbling w/an unfamiliar app / Apple Wallet etc while in a stressful situation.