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

Return flights

25 Oct - 29 Oct	Southwest Airlines
06 Oct - 10 Oct	Southwest Airlines
04 Oct - 11 Oct	Southwest Airlines
24 Oct - 28 Oct	Southwest Airlines
22 Oct - 01 Nov	Southwest Airlines
24 Oct - 01 Nov	Southwest Airlines
18 Oct - 22 Oct	Frontier Airlines
23 Oct - 28 Oct	Frontier Airlines
11 Oct - 18 Oct	Frontier Airlines
23 Oct - 26 Oct	Frontier Airlines
17 Oct - 19 Oct	Frontier Airlines
22 Oct - 26 Oct	Frontier Airlines

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

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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Cheapest return flights from Chicago to Montego Bay in October from 327€

Return flights