AirHint found the following cheapest return flights from Chicago (MDW) to Cancun (CUN) in February 2026 (see full year).

Return flights

23 Feb - 07 Mar	Volaris
02 Feb - 12 Feb	Volaris
28 Feb - 02 Mar	Frontier Airlines
07 Feb - 28 Feb	Aeromexico
20 Feb - 28 Feb	Frontier Airlines
01 Feb - 14 Feb	Volaris
21 Feb - 26 Feb	Frontier Airlines
27 Feb - 05 Mar	Frontier Airlines
28 Feb - 06 Mar	Frontier Airlines
14 Feb - 28 Feb	Frontier Airlines
02 Feb - 14 Feb	Aeromexico
18 Feb - 25 Feb	Aeromexico
10 Feb - 13 Feb	Aeromexico
07 Feb - 10 Feb	Aeromexico
28 Feb - 05 Mar	Aeromexico
28 Feb - 04 Mar	Aeromexico
17 Feb - 10 Mar	Aeromexico
27 Feb - 03 Mar	Volaris
27 Feb - 02 Mar	Volaris
27 Feb - 04 Mar	Volaris

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

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 February from $224

Return flights