Cheapest return flights from Chicago to Cancun in October from $481

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

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

Return flights

07 Oct - 12 Oct Aeromexico
30 Oct - 06 Nov Southwest Airlines
14 Oct - 19 Oct Aeromexico
11 Oct - 15 Oct Aeromexico
16 Oct - 22 Oct Aeromexico
10 Oct - 14 Oct Delta
15 Oct - 20 Oct Delta
15 Oct - 19 Oct Southwest Airlines

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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