Cheapest return flights from Chicago to Cancun in May from 265€

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

Return flights

01 May - 08 May Frontier Airlines
11 May - 19 May Southwest Airlines direct
03 May - 13 May Southwest Airlines direct
17 May - 20 May Southwest Airlines direct
04 May - 07 May Southwest Airlines direct
17 May - 22 May Southwest Airlines direct
04 May - 06 May Southwest Airlines direct
12 May - 19 May Southwest Airlines direct
18 May - 22 May Southwest Airlines direct
03 May - 22 May Southwest Airlines direct
29 May - 03 Jun Delta
29 May - 03 Jun Southwest Airlines direct
29 May - 01 Jun Aeromexico
08 May - 07 Jun Southwest Airlines direct
29 May - 01 Jun Southwest Airlines direct

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

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