Cheapest return flights from Chicago to Cancun in September from $258

Best time to book flights for Chicago (ORD) to Cancun (CUN) flights at AirHint

AirHint found the following cheapest return flights from Chicago (ORD) to Cancun (CUN) in September 2025 (see full year).

Return flights

26 Sep - 10 Oct Viva Aerobus
19 Sep - 10 Oct Viva Aerobus
18 Sep - 21 Sep Viva Aerobus
19 Sep - 21 Sep Viva Aerobus
26 Sep - 11 Oct Viva Aerobus
26 Sep - 05 Oct Viva Aerobus
18 Sep - 05 Oct Viva Aerobus
19 Sep - 05 Oct Viva Aerobus
18 Sep - 23 Sep Viva Aerobus
19 Sep - 23 Sep Viva Aerobus
26 Sep - 17 Oct Viva Aerobus
09 Sep - 21 Sep Viva Aerobus
09 Sep - 23 Sep Viva Aerobus
26 Sep - 07 Oct Viva Aerobus
18 Sep - 07 Oct Viva Aerobus
19 Sep - 07 Oct Viva Aerobus
01 Sep - 02 Sep Viva Aerobus
01 Sep - 21 Sep Viva Aerobus
01 Sep - 07 Sep Viva Aerobus
01 Sep - 06 Sep Viva Aerobus

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

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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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