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

Return flights

02 Oct - 04 Oct	Viva
03 Oct - 04 Oct	Viva
01 Oct - 04 Oct	Viva
28 Oct - 15 Nov	Spirit Airlines
29 Oct - 15 Nov	Spirit Airlines
27 Oct - 15 Nov	Spirit Airlines
25 Oct - 15 Nov	Spirit Airlines
21 Oct - 28 Oct	Spirit Airlines
12 Oct - 01 Nov	Viva
11 Oct - 01 Nov	Viva
22 Oct - 01 Nov	Viva
22 Oct - 08 Nov	Viva
04 Oct - 11 Oct	Viva
07 Oct - 11 Oct	Viva
19 Oct - 23 Oct	Frontier Airlines	direct
02 Oct - 11 Oct	Viva
10 Oct - 11 Oct	Viva
04 Oct - 14 Oct	Viva
22 Oct - 05 Nov	Viva
28 Oct - 06 Nov	Frontier 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.

Book a cheap hotel in Cancun

Cheap car rent in Cancun

Cheapest return flights from Chicago to Cancun in October from $213

Return flights