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
13 May - 17 May	TAP
01 May - 15 May	TAP
15 May - 03 Jun	TAP
08 May - 30 May	TAP
15 May - 22 May	TAP
08 May - 22 May	TAP
15 May - 23 May	TAP
04 May - 09 May	Turkish Airlines
05 May - 12 May	Iberia	direct
22 May - 06 Jun	TAP
05 May - 30 May	Turkish Airlines
15 May - 03 Jun	British Airways	direct
12 May - 06 Jun	British Airways	direct
22 May - 07 Jun	TAP
12 May - 08 Jun	Finnair	direct
21 May - 06 Jun	Iberia	direct
21 May - 06 Jun	Finnair
21 May - 13 Jun	Iberia	direct
25 May - 01 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.

Book a cheap hotel in Madrid

Cheap car rent in Madrid

Cheapest return flights from Chicago to Madrid in May from 302€

Return flights