Cheapest return flights from Chicago to Cancun in August from $293

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 August 2025 (see full year).

Return flights

21 Aug - 27 Aug Aeromexico
20 Aug - 27 Aug Aeromexico
15 Aug - 29 Aug Aeromexico
04 Aug - 11 Aug Aeromexico
08 Aug - 14 Aug Aeromexico
27 Aug - 03 Sep Delta
10 Aug - 13 Aug Aeromexico
08 Aug - 15 Aug Aeromexico
09 Aug - 16 Aug Aeromexico
04 Aug - 12 Aug Aeromexico
21 Aug - 28 Aug Aeromexico
31 Aug - 07 Sep Aeromexico
29 Aug - 07 Sep Frontier Airlines
30 Aug - 02 Sep Aeromexico
29 Aug - 07 Sep Southwest Airlines direct

Also check the deals for one-way 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.

Book a cheap hotel in Cancun

Cheap car rent in Cancun