Cheapest return flights from Chicago to Montego Bay in May from $289

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

Return flights

12 May - 15 May United
10 May - 15 May United
17 May - 20 May United
16 May - 20 May United
03 May - 09 May United
14 May - 17 May United
28 May - 01 Jun United
29 May - 01 Jun United
15 May - 22 May United
15 May - 18 May United
28 May - 02 Jun United
03 May - 07 May Spirit Airlines
01 May - 04 May Copa
26 May - 01 Jun United
14 May - 02 Jun Spirit Airlines
28 May - 09 Jun Spirit Airlines
28 May - 07 Jun Spirit Airlines
28 May - 14 Jun Spirit Airlines

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

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