Cheapest return flights from Chicago to Cancun in September from $250

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

06 Sep - 12 Sep Spirit Airlines direct
01 Sep - 04 Sep Aeromexico
06 Sep - 09 Sep Spirit Airlines
25 Sep - 12 Oct Viva Aerobus
25 Sep - 14 Oct Viva Aerobus
09 Sep - 13 Sep United direct
25 Sep - 11 Oct Viva Aerobus
24 Sep - 12 Oct Viva Aerobus
24 Sep - 14 Oct Viva Aerobus
30 Sep - 20 Oct Viva Aerobus
30 Sep - 21 Oct Viva Aerobus
30 Sep - 12 Oct Viva Aerobus
28 Sep - 12 Oct Viva Aerobus
30 Sep - 14 Oct Viva Aerobus
07 Sep - 09 Sep Viva Aerobus
18 Sep - 24 Sep Viva Aerobus
06 Sep - 24 Sep Viva Aerobus
14 Sep - 24 Sep Viva Aerobus
25 Sep - 29 Sep Viva Aerobus
18 Sep - 29 Sep Viva Aerobus

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

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