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

Return flights

07 Dec - 10 Dec	Delta
15 Dec - 21 Dec	Delta
15 Dec - 17 Dec	Delta
06 Dec - 09 Dec	Delta
09 Dec - 16 Dec	Delta
12 Dec - 17 Dec	Delta
05 Dec - 12 Dec	Delta
12 Dec - 16 Dec	Delta
08 Dec - 12 Dec	Delta
08 Dec - 13 Dec	Delta
31 Dec - 07 Jan	Frontier Airlines
17 Dec - 28 Jan	Southwest Airlines
17 Dec - 10 Jan	Frontier Airlines
30 Dec - 06 Jan	Frontier Airlines
27 Dec - 07 Jan	Frontier Airlines
25 Dec - 10 Jan	Southwest Airlines
01 Dec - 01 Jan	Aeromexico
29 Dec - 01 Jan	Frontier Airlines
01 Dec - 01 Jan	Southwest Airlines	direct
22 Dec - 01 Jan	Frontier Airlines

Also check the deals for one-way flights from Chicago to Cancun 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 Cancun in December from 281€

Return flights