Cheapest return flights from Chicago to Cancun in June from $266

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 June 2025 (see full year).

Return flights

06 Jun - 15 Jun Southwest Airlines direct
06 Jun - 13 Jun Southwest Airlines direct
07 Jun - 10 Jun Southwest Airlines direct
26 Jun - 03 Jul Southwest Airlines direct
04 Jun - 11 Jun Delta
10 Jun - 12 Jun Aeromexico
01 Jun - 04 Jun Aeromexico
15 Jun - 18 Jun Southwest Airlines direct
28 Jun - 05 Jul Southwest Airlines direct
05 Jun - 09 Jun Southwest Airlines direct
09 Jun - 13 Jun Southwest Airlines
03 Jun - 10 Jun Southwest Airlines
25 Jun - 02 Jul Aeromexico
26 Jun - 08 Jul Aeromexico
20 Jun - 06 Jul Frontier Airlines
20 Jun - 06 Jul Southwest Airlines direct

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

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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