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

Return flights

29 Oct - 04 Nov	Southwest Airlines
29 Oct - 05 Nov	Southwest Airlines
19 Oct - 25 Oct	Delta
05 Oct - 11 Oct	Delta
19 Oct - 26 Oct	Frontier Airlines
12 Oct - 18 Oct	Delta
05 Oct - 09 Oct	Southwest Airlines
05 Oct - 10 Oct	Southwest Airlines
12 Oct - 17 Oct	Frontier Airlines
03 Oct - 08 Oct	Delta
16 Oct - 20 Oct	Frontier Airlines
02 Oct - 05 Oct	Frontier Airlines

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 259€

Return flights