All that walking and 8 yr old

The museums in Chicago are huge. And we had gone to 2 that day.

That's about the same amount of walking as a day at WDW then - except without the cool, fun stuff at WDW ;) I'd have his blood counts checked at his next doctor's appt, just to rule out anemia, etc, and then maybe talk to your son about what it's like at WDW, the amount of walking, breaks, maybe set some ground rules and plans for him if he gets tired? And of course, rent a stroller if needed. If it helps you have a crank-free vacation, why not?
 
You all have been so nice and very helpful! I showed my son the strollers and told him they are big so big kids can use them if they get tired. Big brother teased him and said "those are baby strollers." he said back; "Nuh uh! those are for big kids, their different. See how big they are?" Thanks again for those pics!"
 

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