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

Return flights

18 May - 29 May	Viva
22 May - 29 May	Viva
07 May - 24 May	Viva
18 May - 24 May	Viva
22 May - 24 May	Viva
18 May - 04 Jun	Viva
22 May - 04 Jun	Viva
20 May - 29 May	Viva
20 May - 24 May	Viva
20 May - 04 Jun	Viva
03 May - 07 May	United	direct
04 May - 08 May	United
23 May - 30 May	United

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 238€

Return flights