Cheapest return flights from Chicago to Cancun in September from 234€

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

Return flights

01 Sep - 10 Sep Southwest Airlines direct
03 Sep - 10 Sep Southwest Airlines direct
01 Sep - 06 Sep Southwest Airlines
14 Sep - 18 Sep Southwest Airlines direct
28 Sep - 02 Oct Southwest Airlines direct
22 Sep - 27 Sep Southwest Airlines
03 Sep - 06 Sep Southwest Airlines
27 Sep - 04 Oct Aeromexico
01 Sep - 05 Sep Southwest Airlines
10 Sep - 16 Sep Southwest Airlines
28 Sep - 09 Oct Southwest Airlines
01 Sep - 07 Sep Southwest Airlines direct
16 Sep - 23 Sep Delta
27 Sep - 01 Oct Delta
27 Sep - 02 Oct Delta
27 Sep - 05 Oct Delta
24 Sep - 01 Oct Southwest Airlines

Also check the deals for one-way 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.

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