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

Return flights

05 May - 06 May	Spirit Airlines
02 May - 06 May	Volaris
05 May - 20 May	Spirit Airlines
17 May - 20 May	Volaris
03 May - 07 May	Volaris
10 May - 14 May	Volaris
04 May - 08 May	Volaris
02 May - 07 May	Volaris
15 May - 20 May	Volaris
21 May - 27 May	Volaris
25 May - 02 Jun	Volaris
28 May - 02 Jun	Volaris
27 May - 01 Jun	Volaris
20 May - 03 Jun	Viva
25 May - 03 Jun	Viva
26 May - 03 Jun	Spirit Airlines
30 May - 03 Jun	Spirit Airlines
16 May - 03 Jun	Spirit Airlines
22 May - 03 Jun	Viva
15 May - 03 Jun	Viva

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 $250

Return flights