Cheapest return flights from Chicago to Madrid in October from $388

AirHint found the following cheapest return flights from Chicago (ORD) to Madrid (MAD) in October 2025 (see full year).

Return flights

26 Oct - 06 Nov TAP
08 Oct - 15 Oct Air Canada
21 Oct - 31 Oct Air Canada
06 Oct - 15 Oct British Airways direct
26 Oct - 06 Nov American Airlines direct
07 Oct - 14 Oct Air Canada
22 Oct - 31 Oct Air Canada
13 Oct - 23 Oct Air Canada
13 Oct - 29 Oct Air Canada
08 Oct - 16 Oct American Airlines
22 Oct - 27 Oct Air Canada
20 Oct - 27 Oct Air Canada
27 Oct - 22 Nov Scandinavian Airlines
27 Oct - 22 Nov Finnair direct
29 Oct - 02 Nov TAP
16 Oct - 23 Nov Air Canada
30 Oct - 02 Nov Air Canada

Also check the deals for one-way flights from Chicago to Madrid in October.

Skyscanner

The deals are updated regularly. The prices may go up as tickets are purchased by other travellers. Only the cheapest flights are offered. Select a price to book and secure these cheap prices.

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