Cheapest one-way flights from Chicago to Cancun in May from 126€

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

03 May Frontier Airlines
04 May Frontier Airlines
02 May Frontier Airlines
11 May Southwest Airlines
01 May Frontier Airlines
11 May Southwest Airlines direct
04 May Southwest Airlines direct
22 May Frontier Airlines
26 May Frontier Airlines
03 May Southwest Airlines direct

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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