Cheapest return flights from Chicago to Cancun in October from $281

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 October 2025 (see full year).

Return flights

22 Oct - 29 Oct Aeromexico
12 Oct - 20 Oct Viva Aerobus
12 Oct - 21 Oct Viva Aerobus
02 Oct - 20 Oct Viva Aerobus
02 Oct - 21 Oct Viva Aerobus
02 Oct - 12 Oct Viva Aerobus
01 Oct - 20 Oct Viva Aerobus
01 Oct - 21 Oct Viva Aerobus
01 Oct - 12 Oct Viva Aerobus
02 Oct - 07 Oct Aeromexico
31 Oct - 19 Nov Viva Aerobus
31 Oct - 07 Nov Viva Aerobus
24 Oct - 09 Nov Viva Aerobus
24 Oct - 07 Nov Viva Aerobus
22 Oct - 07 Nov Viva Aerobus
31 Oct - 09 Nov Viva Aerobus
22 Oct - 09 Nov Viva Aerobus
26 Oct - 07 Nov Viva Aerobus
26 Oct - 09 Nov Viva Aerobus
17 Oct - 07 Nov Viva Aerobus

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

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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