Cheapest return flights from Chicago to Cancun in October from $296

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

19 Oct - 24 Oct Aeromexico
21 Oct - 24 Oct Aeromexico
01 Oct - 15 Oct Aeromexico
17 Oct - 21 Oct Aeromexico
10 Oct - 15 Oct Aeromexico
16 Oct - 20 Oct Aeromexico
02 Oct - 05 Oct Aeromexico
24 Oct - 31 Oct Aeromexico
09 Oct - 13 Oct Aeromexico
02 Oct - 05 Oct Southwest Airlines direct

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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