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

Return flights

05 Dec - 09 Dec	Delta
07 Dec - 13 Dec	Delta
16 Dec - 21 Dec	Delta
15 Dec - 22 Dec	Aeromexico
17 Dec - 22 Dec	Southwest Airlines
23 Dec - 28 Dec	Southwest Airlines
24 Dec - 28 Dec	Southwest Airlines
20 Dec - 23 Dec	Southwest Airlines
21 Dec - 24 Dec	Frontier Airlines
21 Dec - 27 Dec	Southwest Airlines
25 Dec - 04 Jan	Southwest Airlines
28 Dec - 04 Jan	Southwest Airlines
26 Dec - 02 Jan	Southwest Airlines
27 Dec - 03 Jan	Southwest Airlines
26 Dec - 03 Jan	Southwest 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 344€

Return flights