Cheapest return flights from Chicago to Cancun in October 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 October 2025 (see full year).

Return flights

05 Oct - 10 Oct Viva Aerobus
05 Oct - 18 Oct Viva Aerobus
04 Oct - 10 Oct Viva Aerobus
04 Oct - 18 Oct Viva Aerobus
02 Oct - 10 Oct Viva Aerobus
02 Oct - 18 Oct Viva Aerobus
03 Oct - 10 Oct Viva Aerobus
03 Oct - 18 Oct Viva Aerobus
17 Oct - 18 Oct Viva Aerobus
11 Oct - 18 Oct 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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