Cheapest return flights from Chicago to Montego Bay in May from $319

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

Return flights

03 May - 12 May Southwest Airlines
03 May - 10 May Southwest Airlines
17 May - 20 May Delta
02 May - 13 May Southwest Airlines
02 May - 14 May Southwest Airlines
02 May - 15 May Southwest Airlines
02 May - 12 May Southwest Airlines
15 May - 20 May Delta
02 May - 16 May Delta
02 May - 16 May Southwest Airlines direct
28 May - 01 Jun Porter Airlines (Canada) Ltd

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

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