Cheapest return flights from Chicago to Cancun in April from $371

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

Return flights

26 Apr - 30 Apr Aeromexico
19 Apr - 23 Apr Southwest Airlines
29 Apr - 06 May Southwest Airlines
24 Apr - 28 Apr Aeromexico
03 Apr - 24 Apr Southwest Airlines
25 Apr - 29 Apr Aeromexico
01 Apr - 06 Apr Aeromexico
16 Apr - 22 Apr Porter Airlines (Canada) Ltd
22 Apr - 26 Apr Southwest Airlines
23 Apr - 27 Apr Southwest Airlines
09 Apr - 13 Apr Aeromexico
30 Apr - 05 May Aeromexico

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

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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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