Cheapest one-way flights from Chicago to Cancun in August from $120

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

AirHint found the following cheapest one-way flights from Chicago (MDW) to Cancun (CUN) in August 2025 (see full year).

One-Way flights

15 Aug Southwest Airlines direct
12 Aug Aeromexico
16 Aug Aeromexico
05 Aug Aeromexico
07 Aug Frontier Airlines
07 Aug Southwest Airlines direct
16 Aug Southwest Airlines direct
06 Aug Southwest Airlines direct

Also check the deals for return flights from Chicago to Cancun in August.

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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