For $952 on Iberia Airlines:
JOURNEY1 - Wednesday, March 24, 2010
Chicago › Madrid
Departure 17:45 / Chicago , O'Hare International , Terminal 3
Arrival 7:40 Day 25 / Madrid , Barajas , Terminal 4S
Madrid › Pamplona
Departure 12:00 / Madrid , Barajas , Terminal 4
Arrival 12:55 / Pamplona
Duration 13h: 10m
Changes permitted before flight departure with a penalty of 175$
Refund permitted prior to the departure of the first sector with a penalty of 215$
Baggage
Hand luggage: 1 item / 10 kg
In hold: 2 Pieces
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JOURNEY2 - Wednesday, April 28, 2010
Santiago de Compostela › Madrid
Departure 9:40 / Santiago de Compostela
Arrival 10:45 / Madrid , Barajas , Terminal 4
Madrid › Chicago
Departure 11:50 / Madrid , Barajas , Terminal 4S
Arrival 15:20 / Chicago , O'Hare International , Terminal 5
Duration 12h: 40m
Changes permitted before flight departure with a penalty of 175$
Refund permitted prior to the departure of the first sector with a penalty of 215$
Baggage
Hand luggage: 1 item / 10 kg
In hold: 2 Pieces
From Pamplona, you can start walking, or take a bus/taxi to Roncesvalles or St. Jean Pied de Port for your start.
Needless to say, there are other flights, but the basic concept is to fly to Pamplona and return from Santiago de Compostela. That avoids stops in England, where you will need to change airports for Ryan flights, which rarely match up with arrivals from the U.S., often resulting in hotel/motel fees in England.
Have fun!