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

Return flights

03 Dec - 09 Dec	Delta
06 Dec - 13 Dec	Virgin Atlantic
15 Dec - 13 Jan	Delta
14 Dec - 13 Jan	Delta
16 Dec - 06 Jan	Delta
14 Dec - 27 Dec	Delta
10 Dec - 09 Jan	Delta
12 Dec - 09 Jan	Frontier Airlines
15 Dec - 10 Jan	Frontier Airlines
17 Dec - 24 Dec	Delta
23 Dec - 30 Dec	Delta
14 Dec - 18 Dec	Frontier Airlines
17 Dec - 07 Jan	Delta
14 Dec - 22 Dec	Delta
21 Dec - 10 Jan	Virgin Atlantic
18 Dec - 10 Jan	Virgin Atlantic
19 Dec - 26 Dec	Delta
16 Dec - 02 Jan	Delta
06 Dec - 11 Dec	Delta
14 Dec - 19 Dec	Delta

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

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 December from 377€

Return flights