Cheapest return MDW–MBJ flights, May

AirHint found the following cheapest return flights from Chicago (MDW) to Montego Bay (MBJ) in May 2026 (see full year).

Return flights

23 May - 30 May Southwest Airlines direct
27 May - 30 May Southwest Airlines
24 May - 31 May Southwest Airlines
23 May - 01 Jun Southwest Airlines
22 May - 27 May Allegiant Air
28 May - 02 Jun Allegiant Air
23 May - 27 May Frontier Airlines
28 May - 31 May Southwest Airlines
22 May - 26 May Southwest Airlines
23 May - 26 May Southwest Airlines
21 May - 24 May Frontier Airlines

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

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