Cheapest return flights from Chicago to Cancun in May from 368€

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

Return flights

03 May - 07 May Southwest Airlines direct
13 May - 17 May Southwest Airlines
25 May - 28 May Southwest Airlines
01 May - 08 May Southwest Airlines direct
16 May - 21 May Southwest Airlines direct
16 May - 22 May Aeromexico
27 May - 01 Jun Southwest Airlines
09 May - 16 May Southwest Airlines direct
01 May - 04 May Southwest Airlines
07 May - 10 May Southwest Airlines direct
07 May - 11 May Southwest Airlines direct

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

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