Cheapest return flights from Chicago to Madrid in October from $448

Best time to book flights for Chicago (ORD) to Madrid (MAD) flights at AirHint

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 Finnair direct
28 Oct - 06 Nov Finnair direct
19 Oct - 21 Nov Finnair direct
12 Oct - 21 Oct TAP
12 Oct - 21 Oct Finnair direct
15 Oct - 22 Oct TAP
12 Oct - 16 Oct TAP
11 Oct - 23 Oct TAP
11 Oct - 23 Oct Finnair direct
01 Oct - 12 Oct Turkish Airlines
05 Oct - 12 Oct Scandinavian Airlines
10 Oct - 19 Oct Turkish Airlines
25 Oct - 01 Nov United
10 Oct - 18 Oct SWISS
25 Oct - 01 Nov Iberia direct

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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