AirHint found the following cheapest return flights from Chicago (MDW) to Cancun (CUN) in June 2026 (see full year).

Return flights

08 Jun - 15 Jun	Volaris
14 Jun - 19 Jun	Volaris
07 Jun - 14 Jun	Volaris
29 Jun - 03 Jul	Volaris
05 Jun - 14 Jun	Volaris
21 Jun - 24 Jun	Volaris
13 Jun - 18 Jun	Southwest Airlines
19 Jun - 30 Jun	Southwest Airlines
08 Jun - 19 Jun	Southwest Airlines
09 Jun - 14 Jun	Southwest Airlines
04 Jun - 07 Jun	Southwest Airlines
25 Jun - 05 Jul	Southwest Airlines

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

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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Cheapest return flights from Chicago to Cancun in June from $333

Return flights