Cheapest return flights from Chicago to Cancun in September from $296

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

11 Sep - 14 Sep Aeromexico
18 Sep - 21 Sep Aeromexico
06 Sep - 12 Sep Aeromexico
06 Sep - 09 Sep Aeromexico
11 Sep - 16 Sep Aeromexico
10 Sep - 15 Sep Aeromexico
10 Sep - 13 Sep Aeromexico
01 Sep - 04 Sep Aeromexico
09 Sep - 13 Sep Aeromexico
24 Sep - 04 Oct Delta
28 Sep - 04 Oct Delta

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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