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

One-Way flights

12 Dec	Frontier Airlines
08 Dec	Frontier Airlines
15 Dec	Frontier Airlines
16 Dec	Frontier Airlines
14 Dec	Frontier Airlines
30 Dec	Air France
05 Dec	Frontier Airlines
27 Dec	Delta
18 Dec	Frontier Airlines
23 Dec	Frontier Airlines

Also check the deals for return 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 one-way flights from Chicago to Madrid in December from $273

One-Way flights