Cheapest return flights from Chicago to Madrid in October from $386

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

31 Oct - 11 Nov TAP
17 Oct - 24 Oct TAP
08 Oct - 14 Oct Finnair direct
07 Oct - 14 Oct United
07 Oct - 14 Oct Iberia direct
14 Oct - 30 Oct United
31 Oct - 11 Nov Finnair direct
05 Oct - 19 Oct Air Canada
02 Oct - 09 Oct Finnair
27 Oct - 03 Nov Iberia direct
12 Oct - 18 Oct TAP
18 Oct - 26 Oct Aer Lingus
05 Oct - 19 Oct 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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