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

Return flights

02 Oct - 15 Oct	TAP
09 Oct - 22 Oct	TAP
18 Oct - 31 Oct	TAP
11 Oct - 24 Oct	TAP
22 Oct - 29 Oct	TAP
24 Oct - 29 Oct	TAP
17 Oct - 29 Oct	TAP
16 Oct - 23 Oct	TAP
09 Oct - 16 Oct	TAP
16 Oct - 29 Oct	TAP
25 Oct - 07 Nov	TAP
29 Oct - 07 Nov	TAP
31 Oct - 12 Nov	TAP
31 Oct - 07 Nov	TAP
25 Oct - 07 Nov	Finnair	direct
31 Oct - 12 Nov	Finnair	direct
30 Oct - 06 Nov	Finnair	direct
31 Oct - 07 Nov	Finnair	direct
26 Oct - 02 Nov	TAP
28 Oct - 04 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 254€

Return flights