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

Return flights

01 Dec - 09 Dec	Delta
03 Dec - 10 Dec	Delta
10 Dec - 25 Dec	Delta
04 Dec - 11 Dec	Delta
10 Dec - 25 Jan	Delta
03 Dec - 13 Dec	Delta
03 Dec - 07 Dec	Delta
06 Dec - 14 Dec	Delta
05 Dec - 13 Dec	Delta
16 Dec - 25 Dec	Delta
06 Dec - 10 Dec	Frontier Airlines
30 Dec - 11 Jan	Delta
16 Dec - 10 Jan	Frontier Airlines
25 Dec - 08 Jan	Frontier Airlines
18 Dec - 11 Jan	Frontier Airlines
18 Dec - 10 Jan	Frontier Airlines
13 Dec - 04 Jan	Frontier Airlines
01 Dec - 01 Jan	Frontier Airlines
21 Dec - 17 Jan	Frontier Airlines
21 Dec - 04 Jan	Frontier Airlines

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.

Book a cheap hotel in Madrid

Cheap car rent in Madrid

Cheapest return flights from Chicago to Madrid in December from $461

Return flights