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

Return flights

29 May - 03 Jun	Volaris
24 May - 27 May	Volaris
03 May - 07 May	Aeromexico
03 May - 07 May	Southwest Airlines	direct
20 May - 25 May	Volaris
22 May - 31 May	Volaris
11 May - 15 May	Aeromexico
01 May - 05 May	Volaris
02 May - 05 May	Aeromexico
01 May - 07 May	Aeromexico
02 May - 07 May	Aeromexico
28 May - 02 Jun	Aeromexico
28 May - 03 Jun	Southwest Airlines
21 May - 18 Jun	Southwest Airlines
25 May - 02 Jun	Aeromexico

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

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 May from $322

Return flights