AirHint found the following cheapest return flights from Chicago (MDW) to Cancun (CUN) in August 2026 (see full year).

Return flights

21 Aug - 24 Aug	Volaris
17 Aug - 29 Aug	Delta
21 Aug - 27 Aug	Volaris
03 Aug - 10 Aug	Southwest Airlines
04 Aug - 11 Aug	Southwest Airlines
08 Aug - 15 Aug	Southwest Airlines
13 Aug - 08 Sep	Aeromexico

Also check the deals for one-way flights from Chicago to Cancun in August.

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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Cheapest return flights from Chicago to Cancun in August from $415

Return flights