Cheapest return flights from Chicago to Cancun in October from 238€

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

Return flights

26 Oct - 31 Oct Southwest Airlines direct
18 Oct - 01 Nov Southwest Airlines
27 Oct - 01 Nov Southwest Airlines
28 Oct - 30 Oct Southwest Airlines
27 Oct - 30 Oct Southwest Airlines
29 Oct - 03 Nov Southwest Airlines
19 Oct - 22 Oct Delta
27 Oct - 03 Nov Southwest Airlines
25 Oct - 01 Nov Southwest Airlines
21 Oct - 28 Oct Southwest Airlines
31 Oct - 07 Nov Southwest Airlines
29 Oct - 02 Nov Southwest Airlines
25 Oct - 30 Oct Southwest Airlines
25 Oct - 28 Oct Southwest Airlines
17 Oct - 24 Oct Southwest Airlines
20 Oct - 27 Oct Southwest Airlines
24 Oct - 27 Oct Frontier Airlines
18 Oct - 01 Nov Southwest Airlines direct

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

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