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

Return flights

04 Dec - 08 Dec	Frontier Airlines
11 Dec - 16 Dec	Delta
16 Dec - 21 Dec	Southwest Airlines
19 Dec - 22 Dec	Frontier Airlines
16 Dec - 24 Dec	Delta
30 Dec - 03 Jan	Southwest Airlines
25 Dec - 01 Jan	Delta
29 Dec - 03 Jan	Southwest Airlines
26 Dec - 02 Jan	Southwest Airlines
28 Dec - 02 Jan	Southwest Airlines
20 Dec - 04 Jan	Southwest Airlines
12 Dec - 18 Dec	Porter Airlines (Canada) Ltd

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

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 December from $363

Return flights