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

Return flights

19 Jul - 24 Jul	Frontier Airlines
25 Jul - 31 Jul	Frontier Airlines
19 Jul - 26 Jul	Frontier Airlines
28 Jul - 31 Jul	Frontier Airlines
19 Jul - 24 Jul	Southwest Airlines	direct
09 Jul - 16 Jul	Southwest Airlines
13 Jul - 26 Jul	Frontier Airlines
30 Jul - 03 Aug	Southwest Airlines
31 Jul - 04 Aug	Frontier Airlines
31 Jul - 01 Aug	Southwest Airlines
25 Jul - 30 Jul	Frontier Airlines
10 Jul - 15 Jul	Southwest Airlines

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

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 July from 390€

Return flights