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

Return flights

12 May - 15 May	jetBlue
02 May - 09 May	jetBlue
08 May - 11 May	jetBlue
05 May - 19 May	jetBlue
28 May - 02 Jun	jetBlue
16 May - 22 May	jetBlue
15 May - 22 May	jetBlue
07 May - 10 May	jetBlue
23 May - 28 May	Viva
16 May - 28 May	Viva
15 May - 28 May	Viva
23 May - 02 Jun	Viva
16 May - 02 Jun	Viva
15 May - 02 Jun	Viva
22 May - 02 Jun	Viva
21 May - 02 Jun	Viva
23 May - 08 Jun	Viva
28 May - 08 Jun	Viva
22 May - 08 Jun	Viva
21 May - 08 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 $260

Return flights