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

Return flights

06 Sep - 20 Sep	Spirit Airlines	direct
06 Sep - 13 Sep	Spirit Airlines	direct
03 Sep - 06 Sep	Viva
13 Sep - 20 Sep	Frontier Airlines	direct
01 Sep - 20 Sep	Spirit Airlines	direct
09 Sep - 20 Sep	Viva
27 Sep - 04 Oct	Spirit Airlines	direct
24 Sep - 27 Sep	Viva
10 Sep - 20 Sep	Spirit Airlines
03 Sep - 20 Sep	Spirit Airlines
04 Sep - 20 Sep	Spirit Airlines
20 Sep - 04 Oct	Viva
24 Sep - 04 Oct	Viva
23 Sep - 04 Oct	Viva
13 Sep - 04 Oct	Spirit Airlines
16 Sep - 04 Oct	Spirit Airlines
25 Sep - 04 Oct	Viva
19 Sep - 04 Oct	Viva
30 Sep - 04 Oct	Viva
14 Sep - 04 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 $199

Return flights