Cheap Flights from Chicago to Montego Bay
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Prices updated 1 day ago
461 airlines compared
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Fares are subject to change and may not be available for all dates. (Data last updated Sep 14, 2026.)
Today’s best flight deals from Chicago to Montego Bay
Explore current cheapest deals departing from Chicago to Montego Bay
2026-10-25 – 2026-10-29
CHI - Montego Bay
67% AI deal score
$293
$359
Round trip
2026-10-27 – 2026-10-31
CHI - Montego Bay
67% AI deal score
$293
$359
Round trip
2026-11-13 – 2026-11-17
CHI - Montego Bay
68% AI deal score
$308
$359
Round trip
2026-11-16 – 2026-11-19
CHI - Montego Bay
68% AI deal score
$309
$359
Round trip
2026-11-03 – 2026-11-10
CHI - Montego Bay
49% AI deal score
$291
$360
Round trip
2026-12-06 – 2026-12-10
CHI - Montego Bay
80% AI deal score
$513
$360
Round trip
2027-01-19 – 2027-01-26
CHI - Montego Bay
48% AI deal score
$278
$361
Round trip
2027-01-24 – 2027-01-28
CHI - Montego Bay
48% AI deal score
$289
$361
Round trip
2027-02-19 – 2027-02-23
CHI - Montego Bay
66% AI deal score
$351
$361
Round trip
2026-11-07 – 2026-11-13
CHI - Montego Bay
71% AI deal score
$377
$362
Round trip
