Cheapest return flights from Chicago to Cancun in May from $245

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

11 May - 15 May Southwest Airlines direct
02 May - 09 May Aeromexico
05 May - 10 May Aeromexico
05 May - 09 May Aeromexico
03 May - 09 May Aeromexico
14 May - 17 May Aeromexico
14 May - 21 May Aeromexico
08 May - 13 May Aeromexico
28 May - 03 Jun Aeromexico
13 May - 15 May Southwest Airlines
09 May - 10 May Delta
30 May - 03 Jun Delta
27 May - 03 Jun Aeromexico
30 May - 02 Jun Aeromexico
29 May - 03 Jun Delta
29 May - 07 Jun Delta
26 May - 03 Jun Frontier Airlines
24 May - 01 Jun Frontier Airlines
31 May - 05 Jun Frontier Airlines
25 May - 01 Jun Aeromexico

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.

Book a cheap hotel in Cancun

Cheap car rent in Cancun