Cheapest return flights from Chicago to Cancun in May from 307€

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

05 May - 09 May Frontier Airlines
04 May - 08 May Frontier Airlines
11 May - 15 May Southwest Airlines
13 May - 16 May Southwest Airlines
07 May - 13 May Southwest Airlines
11 May - 16 May Southwest Airlines
16 May - 19 May Frontier Airlines
15 May - 22 May Southwest Airlines
12 May - 17 May Southwest Airlines
16 May - 20 May Southwest Airlines
30 May - 02 Jun Frontier Airlines
29 May - 01 Jun Frontier Airlines

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

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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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