Cheapest return flights from Chicago to Cancun in May from $291

Best time to book flights for Chicago (MDW) to Cancun (CUN) flights at AirHint

AirHint found the following cheapest return flights from Chicago (MDW) to Cancun (CUN) in May 2025 (see full year).

Return flights

17 May - 20 May Aeromexico
14 May - 21 May Aeromexico
17 May - 21 May Aeromexico
20 May - 28 May Delta
27 May - 04 Jun Delta
19 May - 24 May Southwest Airlines
19 May - 23 May Southwest Airlines
14 May - 15 May Aeromexico
26 May - 31 May Frontier Airlines
28 May - 07 Jun Southwest Airlines
26 May - 30 May Frontier Airlines
31 May - 05 Jun Frontier Airlines
19 May - 21 May Frontier Airlines
30 May - 02 Jun Delta
31 May - 08 Jun Frontier Airlines
31 May - 07 Jun Frontier Airlines
25 May - 01 Jun Frontier Airlines

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

Skyscanner

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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