Prior proper planning prevents . . .

Leaving tomorrow!
Here are the possible pitfalls and what we've done to alleviate some of the problems:

1. 11 hour flight/cramped legs - last night we decided to invest the extra money in the seats with extra leg-room for the Chicago to Edinburgh part of the flight.  It's not as cushy as first class, but maybe it will prevent little cherubs from kicking Kyle's seat all the way to Scotland. (We don't want a repeat of our Vegas flight home.)
2. The one-hour layover in Chicago. We'll just have to "run for it" and hope for the best.  We don't have to go through any check-points or customs, so I think it's doable or United wouldn't have created the flight in the first place.
3. Food - without time to eat in Chicago, we were a little worried about this.  We have some granola bars and Pop Tarts if the TSA will let us take them.  Also, according to the flight confirmation, the Chicago to Edinburgh leg does include dinner - a service we thought was dead in the 21st century.
4. We arrive at 7 am and our check-in to our hotel isn't until 2 pm.  I called Hanover 71, where we are staying, and they said to come straight from the airport and drop off our luggage.  They'll keep it at the desk or put it in our room for us.
5. Hanover 71 doesn't have a refrigerator for Kyle's insulin, so we will have to figure something out.  He has cold-packs which will probably be exhausted by then, but there's plenty of coffee shops in the area, and he's taking Zip-locs, so maybe we can get some ice.  He also plans to ask the flight attendants if there is a way to refrigerate the stuff while on the plane to extend the life of the cold-packs.  Kyle doesn't want to bring an insulated lunch bag, but I'm going to put one in to my luggage anyway.

Those are the obstacles we thought of - I wonder what we haven't thought of.