Iberia, American, and British Airways have round-trip flights from Chicago (ORD) to Madrid (MAD) for $355-$415, NONSTOP or with a connection. Flights March, October, November, and December. Most nonstop flights are after October.
Note: Carry-on bag is allowed for free. You can avoid paying for seat selection by accepting the randomly assigned seat at the gate.
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Click for more details and booking links Cheap Flights: Chicago to/from Madrid $355-$415 r/t – Iberia / American / British Airways