Cheapest return flights from Chicago to Madrid in September from $469

Best time to book flights for Chicago (ORD) to Madrid (MAD) flights at AirHint

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

Return flights

24 Sep - 02 Oct Finnair direct
09 Sep - 01 Oct Finnair direct
01 Sep - 18 Sep Finnair
17 Sep - 24 Sep United
25 Sep - 30 Sep Finnair direct
26 Sep - 14 Oct Finnair direct
02 Sep - 09 Sep United
27 Sep - 04 Oct TAP
07 Sep - 14 Sep Iberia direct
17 Sep - 28 Sep Air Canada
04 Sep - 11 Sep Finnair direct
05 Sep - 18 Sep Finnair direct
17 Sep - 24 Sep Iberia direct
17 Sep - 28 Sep Finnair direct
26 Sep - 11 Oct Aer Lingus
26 Sep - 11 Oct Iberia direct

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

Skyscanner

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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