Cheapest return flights from Chicago to Cancun in December from $405

Best time to book flights for Chicago (MDW) to Cancun (CUN) flights at AirHint

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

Return flights

01 Dec - 05 Dec Aeromexico
15 Dec - 20 Dec Aeromexico
13 Dec - 31 Dec Aeromexico
22 Dec - 28 Dec Southwest Airlines
22 Dec - 27 Dec Southwest Airlines
22 Dec - 26 Dec Porter Airlines (Canada) Ltd
21 Dec - 27 Dec Southwest Airlines
29 Dec - 01 Jan Southwest Airlines
26 Dec - 01 Jan Volaris
27 Dec - 04 Jan Southwest Airlines
25 Dec - 01 Jan Volaris
28 Dec - 03 Jan Volaris
26 Dec - 01 Jan Southwest Airlines direct
25 Dec - 01 Jan Southwest Airlines direct

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

Skyscanner

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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