Cheapest return flights from Chicago to Cancun in August from 517€

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

31 Aug - 05 Sep Southwest Airlines
07 Aug - 28 Aug Southwest Airlines
14 Aug - 21 Aug Southwest Airlines
01 Aug - 08 Aug Southwest Airlines
16 Aug - 23 Aug Delta
05 Aug - 12 Aug Delta
18 Aug - 23 Aug Delta
28 Aug - 01 Sep Southwest Airlines
03 Aug - 06 Aug Frontier Airlines

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.

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