My dad purchased a round trip ticket for him and me from Chicago to Costa Rica, with a short layover both ways in Miami. I would like to stay in Miami for awhile on the way back (my dad will fly back to Chicago), but it will cost me $600 to change my American Airlines ticket. I can purchase a one way ticket from Miami to Chicago for $227 from several different airlines. If I don't show up from my second leg of my return trip on American Airlines, and my dad retreives my checked luggage at the intended final destination of Chicago, do you see any difficulty for me?
Using only portion of a return ticket
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When you get back to Miami, you will be picking up your checked baggage to go through Customs. After going through Customs, take the CHI tag off and walk out of the airport with your bags.
When you are ready to leave Miami, you can take Amtrak to Chicago for about $200 (coach). You would have about 8 hours of layover in Washington DC (Silver Meteor & Capitol Limited).
I don't quite see how your dad could retrieve your checked luggage in Chicago. It will not go on the plane if you are not also boarding...? You will have to keep your luggage. As tomfuller said, just walk out of the airport after going thru customs with your bags. Your dad can continue on. Don't say anything to AA. Purchase your cheap one-way ticket on to Chicago when you are sure of your return date.