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

Return flights

08 May - 16 May	TAP
08 May - 17 May	TAP
01 May - 05 May	TAP
09 May - 16 May	TAP
03 May - 10 May	TAP
07 May - 14 May	Turkish Airlines
20 May - 13 Jun	TAP
20 May - 26 May	TAP
13 May - 20 May	Iberia	direct
16 May - 06 Jun	TAP
17 May - 06 Jun	TAP
20 May - 26 May	Finnair	direct
19 May - 30 May	Finnair	direct
17 May - 06 Jun	Finnair	direct
18 May - 13 Jun	Air Canada
29 May - 14 Jun	TAP
16 May - 06 Jun	Finnair	direct
18 May - 13 Jun	British Airways	direct
30 May - 08 Jun	TAP
20 May - 13 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 299€

Return flights