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

Return flights

04 May - 12 May	ITA Airways
01 May - 17 May	TAP
07 May - 15 May	Turkish Airlines
11 May - 25 May	Turkish Airlines
15 May - 26 May	TAP
17 May - 07 Jun	TAP
20 May - 27 May	TAP
05 May - 12 May	Iberia	direct
11 May - 15 May	Aer Lingus
15 May - 22 May	TAP
15 May - 23 May	TAP
18 May - 01 Jun	Air Canada
23 May - 06 Jun	TAP
27 May - 10 Jun	TAP
29 May - 10 Jun	TAP
30 May - 06 Jun	TAP
29 May - 03 Jun	TAP
25 May - 04 Jun	Aer Lingus
21 May - 01 Jun	Air Canada
25 May - 08 Jun	Lufthansa

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 $440

Return flights