A reminder for anyone who flies...

I take the middle road. I typically get complimentary checked bags when I fly, so I put my travel necessities & valuables (medications, basic toiletries, glasses, one change of clothes, swimsuit, electronics, documents, money, etc.) into my carry-on bag. Then I pack a check-in bag filled with several changes of clothes and shoes and other items. When cruising I like to decorate the stateroom with magnets, stuffed animals, knickknacks, etc., so the decorations go in my checked bag. No way could I fit all of those items into a carry-on bag, but I like to have them on my cruise, to create a home away from home feeling onboard. I also like having lots of different outfits to choose from and not having to do laundry on my vacation. The check-in bag also has room for souvenirs from the trip. There's a lot of good reasons to check a bag imo. But because I have the basics in my carry-on, it won't ruin the cruise if my check-in bag doesn't make it in time.

This is me. CC benefits allow me to check a bag on my preferred airlines so I always do. Not because I'm awful at packing (I'm a frequent leisure traveler and the queen of packing cubes), but solely because of the liquids rule. As a Black person with thick, natural kinky textured hair, hotel toiletries absolutely do not cut it for my needs and virtually none of the products I use come in readily available travel sizes, I would have to decant into TSA compliant containers and it's just too much hassle. Unless I get a protective style before vacation I'm basically forced to check a bag just for toiletries. I attempted carry on only exactly one time, to YYZ, and it was far more stressful than just checking a bag. It's even less feasible when traveling with my partner due to her disability; she uses a nebulizer, and while the travel ones are a lot smaller now, all the related paraphernalia and meds take up a lot of room. We pack as you do, though the extra important items like meds, spare glasses, electronics, etc go in our personal item bags rather than our carry ons because I have been forced to gate check a carry on one too many times (usually on those little Embraer jets on commuter routes) to feel comfortable. It's no problem hauling it through the airport, I use the Away everywhere bag that slides onto their luggage. But I make sure I have at least 1 change of clothes in the carry on and the personal item bag. We've not had issues getting bags in a timely fashion even at MCO.
 
TL : DR the whole thread, but SG didn't have to even say the airline - American is TERRIBLE with connections! Here's another tip if you get stuck; the airline is obligated to get you where you need to go, but you don't have to take what they give you. If you find another way to get there you prefer, have that info in hand when you talk to customer service. For example, American messed up our trip from DEN to LAX - they were late getting us to our connection in PHX. We could have gotten on the plane to PHX, but we knew we were going to miss the connection and get stuck there overnight. American was booking everyone standby on the first flight the next morning (6a!) where they were then standby onto the connection - they might have even gotten stuck again if that flight was over booked (and it probably was). We weren't doing that. We found a (MUCH more expensive but not our problem) direct flight from DEN to LGB (close enough) that departed at a much more reasonable 9a - and we had seats, not standby. We presented customer service with this option and they were happy to accommodate - one less unhappy flyer to have to sort out for them. American still had to buy us dinner and breakfast and put us up in a hotel like everyone else - but we got to sleep in and got home with a lot less stress.
I would have done that but the schedule (with the initial delay) had me with a 20-25 minute connection. And I was going from concourse D to E (relatively close at Charlotte). So, I have no luggage (backpack), and am by myself, I think "I can make that". Then the arriving plane keeps getting later and later. Just before we board, they change the arrival time to cut me down to 9 minutes. At that point, I'm pretty much stuck.
 
American still had to buy us dinner and breakfast and put us up in a hotel like everyone else - but we got to sleep in and got home with a lot less stress.
Depending on the reason for the delay, they actually probably did not have to do anything for you, and certainly were not required to provide you with a hotel.
 
Just don't check bags. Anyone who travels enough knows that.

Especially don't check bags to MCO, what a disaster of an airport.
Anyone who flies on small/medium planes still needs a plan to grab one days worth of essentials from their carryon fast as airlines will force check your bag to the final destination if they run out of above seat storage space. Sometimes they’ll just gate check but my last couple flights even that wasn’t an option. (And even gate check isn’t foolproof. Once saw a bag in one of those chutes sitting there getting drenched in a downpour long after the plane took off.)
 

Anyone who flies on small/medium planes still needs a plan to grab one days worth of essentials from their carryon fast as airlines will force check your bag to the final destination if they run out of above seat storage space. Sometimes they’ll just gate check but my last couple flights even that wasn’t an option. (And even gate check isn’t foolproof. Once saw a bag in one of those chutes sitting there getting drenched in a downpour long after the plane took off.)
Doesn't have to be small/medium planes. Even large planes can suffer from not enough room for carry ons. On one of my flights last week, they were offering to check bags to the final destination, saying there will be 15-17 bags there won't be room for.
 
If possible I try my best to always book early flights for this very reason, especially with a layover, the odds of morning flights getting delayed/cancelled are SIGNIFICANTLY lower than evening flights.. Also, the issues mentioned by the OP are not specific to American, this happens with ALL major airlines, especially in this post-Covid era with airlines running on limited staff, pilot shortages, etc.. The slightest little hiccup with weather, aircraft issues, staffing, etc. can create a domino effect for multiple flights and airports, especially hub airports..
 
If possible I try my best to always book early flights for this very reason, especially with a layover, the odds of morning flights getting delayed/cancelled are SIGNIFICANTLY lower than evening flights.. Also, the issues mentioned by the OP are not specific to American, this happens with ALL major airlines, especially in this post-Covid era with airlines running on limited staff, pilot shortages, etc.. The slightest little hiccup with weather, aircraft issues, staffing, etc. can create a domino effect for multiple flights and airports, especially hub airports..
And there are reasons why early flights won't work...
* In my case, I was flying for a job interview and the company thought it would just be a one day trip.
* People flying from somewhere else (as I said earlier, one family had left Mexico at 7am in the morning)

And I'm sure there are others.
 
/
This is me. CC benefits allow me to check a bag on my preferred airlines so I always do. Not because I'm awful at packing (I'm a frequent leisure traveler and the queen of packing cubes), but solely because of the liquids rule. As a Black person with thick, natural kinky textured hair, hotel toiletries absolutely do not cut it for my needs and virtually none of the products I use come in readily available travel sizes, I would have to decant into TSA compliant containers and it's just too much hassle. Unless I get a protective style before vacation I'm basically forced to check a bag just for toiletries. I attempted carry on only exactly one time, to YYZ, and it was far more stressful than just checking a bag. It's even less feasible when traveling with my partner due to her disability; she uses a nebulizer, and while the travel ones are a lot smaller now, all the related paraphernalia and meds take up a lot of room. We pack as you do, though the extra important items like meds, spare glasses, electronics, etc go in our personal item bags rather than our carry ons because I have been forced to gate check a carry on one too many times (usually on those little Embraer jets on commuter routes) to feel comfortable. It's no problem hauling it through the airport, I use the Away everywhere bag that slides onto their luggage. But I make sure I have at least 1 change of clothes in the carry on and the personal item bag. We've not had issues getting bags in a timely fashion even at MCO.
Wouldn’t a nebulizer be considered medical equipment? I use a C PAP machine. I come on board with my personal item, my carry on & my machine in it’s case . Airlines aren’t allowed to count my machine as an item. Check on that.
 
Wouldn’t a nebulizer be considered medical equipment? I use a C PAP machine. I come on board with my personal item, my carry on & my machine in it’s case . Airlines aren’t allowed to count my machine as an item. Check on that.

It is, but it’s not the device itself that’s the issue (her travel one is very small), but all of the meds. We often joke about her being a walking pharmacy.
 
And there are reasons why early flights won't work...
* In my case, I was flying for a job interview and the company thought it would just be a one day trip.
* People flying from somewhere else (as I said earlier, one family had left Mexico at 7am in the morning)

And I'm sure there are others.
That's why the PP said, "If possible I try to book early flights"...
 

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