Cheapest one-way flights from Chicago to Cancun in September from 109€

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

One-Way flights

20 Sep Southwest Airlines
28 Sep Southwest Airlines direct
03 Sep Southwest Airlines direct
17 Sep Aeromexico
05 Sep Frontier Airlines
25 Sep Frontier Airlines
26 Sep Frontier Airlines
24 Sep Southwest Airlines
20 Sep Southwest Airlines direct
25 Sep Southwest Airlines direct

Also check the deals for return flights from Chicago to Cancun in September.

Skyscanner

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

Feel free to contact us with any feedback or request another flight research.