Cheapest one-way flights from Chicago to Cancun in May from $110

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 May 2025 (see full year).

One-Way flights

20 May Southwest Airlines direct
18 May Southwest Airlines direct
03 May Aeromexico
04 May Aeromexico
02 May Aeromexico
06 May Aeromexico
27 May Aeromexico
14 May Aeromexico
13 May Aeromexico
29 May Delta

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

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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