Flights from Chicago to Montego Bay

Our cheapest offers for flights from Chicago to Montego Bay

Here you can compare cheap flights from Chicago (CHI) to Montego Bay (MBJ) for one-way or return trips. The following offers were searched for and found on idealo during the last few days. Or start your own flight search to Montego Bay. Prices and availability may change at any time.

Outbound Return Airlines Shop Baggage Price
Chicago
Montego Bay
Outbound
09/23/25
1 Stopover (FLL)
NK1027, NK1360
14h 40min
Return
09/30/25
1 Stopover (FLL)
NK1361, NK1026
07h 18min
Spirit Airlines
$317
Best option
Chicago
Montego Bay
Outbound
11/03/25
direct
AA2123
04h 03min
Return
11/12/25
direct
AA0975
04h 30min
American Airlines ?
$481
Chicago
Montego Bay
Pay attention to transfer at connecting flight
Outbound
09/23/25
2 Stopovers (MCO, FLL)
NK3200, NK0195, NK0833
28h 26min
Return
09/30/25
2 Stopovers (FLL, MCO)
NK0270, NK0676, NK3201
25h 29min
Spirit Airlines
$334
Chicago
Montego Bay
Outbound
09/23/25
1 Stopover (FLL)
NK1027, NK1360
14h 40min
Return
09/30/25
1 Stopover (FLL)
NK1361, NK1026
07h 18min
Spirit Airlines
$320
Chicago
Montego Bay
Outbound
09/23/25
1 Stopover (FLL)
NK0019, NK0833
06h 36min
Return
09/30/25
1 Stopover (FLL)
NK1361, NK1026
07h 18min
Spirit Airlines
$336
Chicago
Montego Bay
Outbound
09/23/25
1 Stopover (JFK)
B60406, B60479
09h 03min
Return
09/30/25
1 Stopover (FLL)
NK0270, NK0003
07h 54min
JetBlue Airways ?
$372
Chicago
Montego Bay
Outbound
11/03/25
2 Stopovers (MCO, FLL)
NK0507, NK0195, NK0833
16h 02min
Return
11/12/25
1 Stopover (FLL)
NK0270, NK0003
07h 54min
Spirit Airlines
$377
Chicago
Montego Bay
Outbound
11/03/25
2 Stopovers (MCO, FLL)
NK0507, NK0195, NK0833
16h 02min
Return
11/12/25
1 Stopover (FLL)
NK0270, NK0003
07h 54min
Spirit Airlines
$387
Chicago
Montego Bay
Outbound
09/19/25
2 Stopovers (CLT, MIA)
AA2080, AA3068, AA2618
25h 38min
Return
09/29/25
2 Stopovers (MIA, DCA)
AA2388, AA2897, AA2304
17h 22min
American Airlines ?
$425
Chicago
Montego Bay
Outbound
07/02/25
2 Stopovers (MCO, FLL)
NK2189, NK2009, NK0833
24h 16min
Return
07/25/25
1 Stopover (ATL)
F90016, F93397
15h 17min
Spirit Airlines ?
$426
Prices based on recent searches, subject to last-minute changes
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Tips and tricks to help you find cheap flights from Chicago to Montego Bay

Favorite airline: Spirit Airlines
Spirit Airlines is the most popular airline for flights from Chicago to Montego Bay.
Spirit Airlines
29 %
American Airlines
19 %
United Airlines
19 %
Stopover flights are the cheapest connection
Direct flights on this route are $297.00 more expensive on average than flights with a stopover.
non stop flight
1 stop
2 stops
04h 05min
14h 22min
08h 19min
$618
$321
$405
Favourite connection: via Fort Lauderdale
On this route, flights with a stopover in Fort Lauderdale are the most popular.
Route
bookings
1 stopover Fort Lauderdale-Hollywood International Airport, FL
14h 22min, from $321
41 %
1 stopover Toronto - Lester B. Pearson International Airport
14h 25min, from $531
19 %
1 stopover Orlando International Airport, FL
06h 00min, from $381
14 %

Important flight information

Flight information: Chicago - Montego Bay

Roundtrip from $316.83
Flight duration min. 03:55 / max. 04:05
Return flight duration min. 04:10/ max. 04:37
Distance 2761 km
Flights per week 23
Departure airport Airport Chicago-IL all Airports (ORD, MDW, RFD) (CHI)
Arrival airport Airport Montego Bay (MBJ)
Destination country Flights to Jamaica
Alternative flights to Montego Bay
Flight destinations with a similar price
Flight destinations with a similar price