This one is different. We use United miles to fly round trip to Philly, then fly US Air into Lisbon and out of Madrid.
So, we leave Chicago at 1:31 PM on Tuesday October 15 (happy birthday). Two hour flight to Philly, 4 hour layover. Leave Philly at 8:35 PM on 10/15, arrive Lisbon on 10/16.
Fly from Lisbon to Seville on Friday 10/18.
Train to Valencia on 10/20.
Train to Barcelona on Tuesday 10/22.
Train to Madrid on Saturday 10/26.
Fly back to Philly on Tuesday 10/29. Arrive at 4:05 PM. Depart at 7:58 PM, arrive Chicago at 9:15 PM.
Total cost is $1,582 per person, total travel time is 38 hours. 8 of those hours are layover in Philly.
It's like 12 hours to drive to Philly, so I don't think that helps us. There are flights to/from Philly that reduce our layover, but they cost more miles.
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