Cheapest one-way flights from Chicago to Cancun in May from 103€

AirHint found the following cheapest one-way flights from Chicago (MDW) to Cancun (CUN) in May 2026 (see full year).

One-Way flights

03 May Frontier Airlines
09 May Frontier Airlines
01 May Frontier Airlines
04 May Frontier Airlines
08 May Frontier Airlines
05 May Southwest Airlines direct
18 May Southwest Airlines direct
17 May Southwest Airlines direct
02 May Frontier Airlines
11 May Frontier Airlines

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

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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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