Cheapest return flights from Chicago to Cancun in May from $302

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

Return flights

02 May - 10 May Southwest Airlines direct
03 May - 07 May Southwest Airlines direct
03 May - 07 May Delta
16 May - 23 May Southwest Airlines direct
09 May - 15 May Delta
15 May - 19 May Delta
10 May - 17 May Frontier Airlines
24 May - 29 May Frontier Airlines
15 May - 23 May Southwest Airlines direct
07 May - 10 May Frontier Airlines
27 May - 01 Jun Frontier Airlines
28 May - 07 Jun Southwest Airlines

Also check the deals for one-way flights from Chicago to Cancun in May.

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