Originally Posted by WineCountryUA

There is no difference in the MCT for a cash vs award flight.
D-D MCT for ORD is 50 minutes

Is there award availability on the desired connecting flight?? Availability for cash flights and award flights can be very different

Try mutlicity to see if there are any system constraints. Also look beyond the first page of award options.

Awards flight selection is a bit of a black box but UA will tend to list the less expensive awards and all JN/YN may be deep in the list. X/XN awards will be listed first.while cash tickets will list shorter connects and lower price generally first