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

Return flights

06 Sep - 13 Sep	Spirit Airlines	direct
06 Sep - 20 Sep	Spirit Airlines	direct
20 Sep - 27 Sep	Spirit Airlines	direct
01 Sep - 13 Sep	Spirit Airlines	direct
01 Sep - 20 Sep	Spirit Airlines	direct
27 Sep - 16 Oct	Spirit Airlines	direct
27 Sep - 17 Oct	Spirit Airlines	direct
09 Sep - 13 Sep	Viva
09 Sep - 20 Sep	Viva
03 Sep - 13 Sep	Viva
03 Sep - 20 Sep	Viva
05 Sep - 13 Sep	Viva
29 Sep - 16 Oct	Viva
29 Sep - 17 Oct	Viva
29 Sep - 18 Oct	Viva
26 Sep - 16 Oct	Viva
26 Sep - 17 Oct	Viva
27 Sep - 18 Oct	Spirit Airlines
25 Sep - 16 Oct	Spirit Airlines
28 Sep - 18 Oct	Viva

Also check the deals for one-way flights from Chicago to Cancun in September.

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 September from $213

Return flights