Cheapest return flights from Chicago to Cancun in September from $298

Best time to book flights for Chicago (MDW) to Cancun (CUN) flights at AirHint

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

Return flights

10 Sep - 14 Sep Aeromexico
26 Sep - 29 Sep Aeromexico
01 Sep - 08 Sep Aeromexico
17 Sep - 21 Sep Aeromexico
13 Sep - 20 Sep Aeromexico
02 Sep - 10 Sep Delta
11 Sep - 14 Sep Aeromexico
26 Sep - 05 Oct Aeromexico
08 Sep - 14 Sep Aeromexico

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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