Has anyone done a ticket through two airports in the same city, on one itinerary? Getting some more miles in by going (Regional Airport)-IAD-ORD-EWR-DCA rather than Regional Airport-IAD. Was cheaper in fact going to DCA as final. 40 min layovers in ORD and EWR, may just have to carry bag on the whole way as I can't recheck in time. Have done a DCA-(3 stops)-IAD mileage-run where I had to recheck at mid-point, would the same happen here? Two different airports of course but both have "Washington DC" as the city. Would be happy to recheck in ORD if I had more than 40 minutes....

Wanted to ask this question here as obviously this itinerary can count as "chose to have a connection". All layovers are under 13 hours and on same day of course. If Final was RIC or PHL for example, I know it would go all the way, but the question lies in IAD/DCA in same tag.