No - that is landed time. Fight arrival time is recorded when the plane is parked at the gate.
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Sometimes they will hold the connecting flight if there are a lot of people on the delayed flight that need to make the connection.
Are you actually changing planes in Chicago? Or just having a layover there.
Changing planes.
I’m sure there is enough time. I just like to understand in case things don’t go as expected!
(I know, I know. Around these forums, it is rare to find anyone who likes to plan ahead!) 
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Thanks for the info @brklinck. I never knew that. I had always assumed touching down time. You learn something new everyday. Sorry for the misinformation from earlier.
Are both legs with the same airline? If so, that makes it easier. The airline will have every incentive to get you on another flight and to your destination as soon as possible.
If they’re with different airlines, the incoming (late) one should still help. But you may need to push them a bit, as they argue amongst themselves. Sometimes though it can work in your favour, if they decide to use a 3rd airline to get you to your destination.
Yes.
When the flight was booked (through United), it was as a “single ticket”, with a layover (plane change) in Chicago.
Departure and arrival times are when the plane leaves and arrives at the gate. So if your plane is due to arrive at 11:50 and it’s on time, that would be when it gets to the gate and the parking brakes have been engaged.
It looks like you’ve already decided on the 3:00 shuttle, which is good. I don’t think there’s a snowball’s chance in Florida of making it to the ground transportation area at MCO 10 minutes after arrival time. Unless you’re in first class then there’s a good chance you won’t even be off the plane yet at noon… it’ll be a good sized plane coming from Chicago and it takes a long time for everyone to deplane.
You might actually be surprised to find it doesn’t even feel like you’re waiting all that long for 3:00. If you take your time deplaning and make a potty stop on your way from the gate it will likely be 12:15 before you even get to where you wait for the train. You have to take a train thingy to the main building where you’ll find the food court, and that can take a little time, depending on how long you wait for it to arrive. Take your time having lunch and then find a seat to kill a hour or so (there’s free wifi) and start making your way to the shuttle a little past 2:30. You’ll have to go all the way down to level 1 for ground transportation (your shuttle company will tell you if you need to be on A or B side) and it may be a little bit of a hike to get to where they’ll pick you up.
We had this happen to us on our way to our DCL in March. We were confirmed on our first leg (and fully present, lol) and our flight was delayed. We raced to our connection just as they were closing the door and had given up our seats to someone else. All that to say, we went to Delta customer service and they listed us on standby for the next 4 available flights. We were able to get on the first available flight, PTL, but I was a bit nervous and frustrated!
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