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

Return flights

01 May - 05 May	Viva
01 May - 19 May	Viva
01 May - 10 May	Viva
15 May - 19 May	Viva
07 May - 19 May	Viva
07 May - 10 May	Viva
15 May - 28 May	Viva
15 May - 29 May	Viva
24 May - 30 May	Volaris
25 May - 28 May	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 $281

Return flights