Cheapest return flights from Chicago to Cancun in May from 301€

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 - 15 May Frontier Airlines
05 May - 09 May Frontier Airlines
13 May - 16 May Southwest Airlines
07 May - 13 May Southwest Airlines
11 May - 15 May Southwest Airlines
14 May - 18 May Frontier Airlines
28 May - 03 Jun Frontier Airlines
16 May - 20 May Southwest Airlines
01 May - 05 May Southwest Airlines
01 May - 06 May Southwest Airlines
19 May - 23 May Southwest 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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