AirHint found the following cheapest return flights from Chicago (MDW) to Cancun (CUN) in September 2026 (see full year).
Return flights
| 23 Sep - 29 Sep | Delta | ||
| 23 Sep - 28 Sep | Delta | ||
| 17 Sep - 20 Sep | Southwest Airlines | ||
| 16 Sep - 22 Sep | Porter Airlines (Canada) Ltd | ||
| 05 Sep - 07 Sep | Southwest Airlines | ||
| 04 Sep - 07 Sep | Southwest Airlines |
Also check the deals for one-way flights from Chicago to Cancun in September.
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