Cheapest one-way flights from Chicago to Cancun in October from 112€

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

One-Way flights

31 Oct Frontier Airlines
28 Oct Southwest Airlines direct
27 Oct Southwest Airlines direct
26 Oct Southwest Airlines direct
20 Oct Southwest Airlines
21 Oct Southwest Airlines
19 Oct Delta
30 Oct Frontier Airlines
22 Oct Southwest Airlines
18 Oct Delta

Also check the deals for return flights from Chicago to Cancun in October.

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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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