AirHint found the following cheapest return flights from Chicago (ORD) to Cancun (CUN) in October 2025 (see full year).

Return flights

14 Oct - 23 Oct	Frontier Airlines	direct
02 Oct - 07 Oct	Volaris
19 Oct - 25 Oct	Frontier Airlines	direct
07 Oct - 11 Oct	Viva
02 Oct - 04 Oct	Viva
02 Oct - 11 Oct	Viva
09 Oct - 11 Oct	Viva
08 Oct - 11 Oct	Viva
10 Oct - 11 Oct	Viva
01 Oct - 04 Oct	Viva
18 Oct - 08 Nov	Viva
28 Oct - 08 Nov	Viva
21 Oct - 08 Nov	Viva
28 Oct - 15 Nov	Viva
24 Oct - 08 Nov	Viva
25 Oct - 08 Nov	Viva
29 Oct - 08 Nov	Viva
29 Oct - 19 Nov	Viva
25 Oct - 15 Nov	Viva
29 Oct - 15 Nov	Viva

Also check the deals for one-way flights from Chicago to Cancun in October.

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 October from 170€

Return flights