AirHint found the following cheapest return flights from Chicago (ORD) to Madrid (MAD) in August 2025 (see full year).

Return flights

23 Aug - 30 Aug	TAP
16 Aug - 29 Aug	TAP
21 Aug - 30 Aug	TAP
21 Aug - 28 Aug	TAP
14 Aug - 23 Aug	TAP
15 Aug - 22 Aug	TAP
18 Aug - 27 Aug	TAP
10 Aug - 23 Aug	TAP
21 Aug - 29 Aug	TAP
16 Aug - 23 Aug	TAP
23 Aug - 07 Sep	TAP
22 Aug - 03 Sep	TAP
22 Aug - 04 Sep	TAP
23 Aug - 04 Sep	TAP
07 Aug - 11 Sep	TAP
23 Aug - 05 Sep	TAP
31 Aug - 07 Sep	TAP
06 Aug - 16 Sep	British Airways	direct
07 Aug - 11 Sep	British Airways	direct
23 Aug - 06 Sep	TAP

Also check the deals for one-way flights from Chicago to Madrid in August.

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 August from 254€

Return flights