Cheapest return flights from Chicago to Cancun in October from 461€

AirHint found the following cheapest return flights from Chicago (MDW) to Cancun (CUN) in October 2026 (see full year).

Return flights

05 Oct - 08 Oct Southwest Airlines direct
25 Oct - 31 Oct Delta
25 Oct - 31 Oct Southwest Airlines direct
01 Oct - 06 Oct Southwest Airlines
03 Oct - 09 Oct Southwest Airlines
09 Oct - 13 Oct Southwest Airlines
01 Oct - 05 Oct Southwest Airlines
15 Oct - 18 Oct Southwest Airlines
27 Oct - 06 Nov WestJet
09 Oct - 12 Oct WestJet
16 Oct - 19 Oct WestJet

Also check the deals for one-way 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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