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

Return flights

01 May - 08 May	TAP
01 May - 07 May	TAP
01 May - 09 May	TAP
08 May - 17 May	TAP
06 May - 13 May	TAP
06 May - 20 May	TAP
08 May - 23 May	TAP
05 May - 28 May	British Airways
19 May - 26 May	United
05 May - 28 May	Finnair	direct
18 May - 01 Jun	Air Canada
26 May - 02 Jun	Iberia	direct
27 May - 10 Jun	United
28 May - 02 Jun	Aer Lingus
30 May - 13 Jun	Air Canada
29 May - 10 Jun	United
28 May - 02 Jun	Finnair	direct
22 May - 15 Jun	TAP
25 May - 01 Jun	Iberia	direct
30 May - 13 Jun	Iberia	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 344€

Return flights