AirHint found the following cheapest return flights from Chicago (ORD) to Madrid (MAD) in May 2026 (see full year).

Return flights

06 May - 13 May	TAP
31 May - 16 Jun	TAP
24 May - 03 Jun	TAP
27 May - 10 Jun	TAP
20 May - 30 May	TAP
21 May - 31 May	Scandinavian Airlines
19 May - 31 May	Scandinavian Airlines
06 May - 13 May	Iberia	direct
29 May - 14 Jun	TAP
20 May - 30 May	Finnair	direct
19 May - 31 May	American Airlines	direct
21 May - 31 May	Finnair	direct
31 May - 16 Jun	American Airlines	direct
27 May - 10 Jun	Iberia	direct
24 May - 03 Jun	British Airways	direct
29 May - 14 Jun	Finnair	direct

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

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 May from $547

Return flights