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

Return flights

31 Oct - 08 Nov	TAP
12 Oct - 21 Oct	Iberia	direct
28 Oct - 11 Nov	Finnair	direct
19 Oct - 29 Oct	SWISS
22 Oct - 31 Oct	SWISS
05 Oct - 15 Oct	Lufthansa
05 Oct - 14 Oct	Lufthansa
13 Oct - 22 Oct	Air Canada
07 Oct - 16 Oct	Delta
07 Oct - 17 Oct	Delta
14 Oct - 21 Oct	Air Canada
11 Oct - 21 Oct	Air Canada
28 Oct - 04 Nov	Iberia	direct
30 Oct - 06 Nov	Iberia	direct
27 Oct - 04 Nov	Delta
14 Oct - 08 Nov	Air Canada
31 Oct - 08 Nov	British Airways	direct
15 Oct - 08 Nov	Aer Lingus
12 Oct - 01 Nov	Air Canada
14 Oct - 08 Nov	Finnair	direct

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

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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Cheapest return flights from Chicago to Madrid in October from 340€

Return flights