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

Return flights

09 Oct - 18 Oct	Viva
10 Oct - 18 Oct	Viva
12 Oct - 16 Oct	Viva
12 Oct - 17 Oct	Viva
12 Oct - 18 Oct	Viva
08 Oct - 16 Oct	Viva
08 Oct - 17 Oct	Viva
08 Oct - 18 Oct	Viva
07 Oct - 16 Oct	Viva
07 Oct - 17 Oct	Viva
20 Oct - 06 Nov	Spirit Airlines	direct
19 Oct - 06 Nov	Spirit Airlines	direct
22 Oct - 06 Nov	Viva
25 Oct - 02 Nov	Volaris	direct
21 Oct - 06 Nov	Viva
23 Oct - 06 Nov	Viva
31 Oct - 06 Nov	Viva
25 Oct - 06 Nov	Viva
17 Oct - 06 Nov	Spirit Airlines
31 Oct - 06 Nov	Spirit Airlines	direct

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 $240

Return flights