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

One-Way flights

26 Oct	Southwest Airlines	direct
21 Oct	Aeromexico
14 Oct	Aeromexico
04 Oct	Frontier Airlines
23 Oct	Delta
05 Oct	Delta
30 Oct	Frontier Airlines
31 Oct	Frontier Airlines
24 Oct	Frontier Airlines
02 Oct	Frontier Airlines

Also check the deals for return 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 one-way flights from Chicago to Cancun in October from 105€

One-Way flights