Cheapest return flights from Chicago to Cancun in December from $542

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

03 Dec - 08 Dec Aeromexico
16 Dec - 23 Dec Aeromexico
05 Dec - 10 Dec Aeromexico
04 Dec - 07 Dec Southwest Airlines
22 Dec - 26 Dec Porter Airlines (Canada) Ltd
20 Dec - 28 Dec Southwest Airlines
21 Dec - 28 Dec Southwest Airlines
13 Dec - 18 Dec Volaris
20 Dec - 27 Dec Porter Airlines (Canada) Ltd
25 Dec - 01 Jan Southwest Airlines
23 Dec - 28 Dec Volaris
28 Dec - 04 Jan Volaris

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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