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

Return flights

07 May - 21 May	Viva
07 May - 22 May	Viva
07 May - 26 May	Viva
07 May - 14 May	Viva
24 May - 26 May	Viva
19 May - 21 May	Viva
19 May - 22 May	Viva
19 May - 26 May	Viva
12 May - 21 May	Viva
12 May - 22 May	Viva
27 May - 01 Jun	Viva
29 May - 01 Jun	Viva
24 May - 01 Jun	Viva
19 May - 01 Jun	Viva
12 May - 01 Jun	Viva
26 May - 01 Jun	Viva
18 May - 01 Jun	Viva
30 May - 01 Jun	Viva
27 May - 09 Jun	Viva
29 May - 09 Jun	Viva

Also check the deals for one-way flights from Cancun to Chicago 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 Cancun to Chicago in May from $277

Return flights