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

Return flights

08 May - 17 May	TAP
01 May - 08 May	TAP
15 May - 22 May	TAP
11 May - 21 May	Scandinavian Airlines
29 May - 03 Jun	TAP
20 May - 13 Jun	TAP
05 May - 12 May	Iberia	direct
11 May - 21 May	Finnair	direct
04 May - 09 May	Turkish Airlines
01 May - 08 May	Finnair	direct
19 May - 13 Jun	ITA Airways
15 May - 22 May	Iberia	direct
18 May - 13 Jun	British Airways
19 May - 13 Jun	Iberia	direct
18 May - 13 Jun	Iberia	direct
08 May - 17 May	Iberia	direct
28 May - 04 Jun	Air Canada
20 May - 13 Jun	Iberia	direct
21 May - 13 Jun	TAP
27 May - 20 Jun	TAP

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 $322

Return flights