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
11/09/25
1 Stopover (FLL)
NK0002, NK0833
06h 00min
Return
12/07/25
1 Stopover (FLL)
NK0270, NK0001
11h 30min
Spirit Airlines
$367
Best option
Chicago
Montego Bay
Outbound
02/13/26
direct
AA3228
04h 05min
Return
02/26/26
direct
AA0975
04h 40min
American Airlines ?
$695
Chicago
Montego Bay
Please note: transfer for connecting flight
Outbound
11/09/25
1 Stopover (FLL)
NK1932, NK0833
17h 06min
Return
12/07/25
1 Stopover (FLL)
NK0270, NK1986
21h 11min
Spirit Airlines
$369
Chicago
Montego Bay
Outbound
11/09/25
1 Stopover (ATL)
F91442, F90017
19h 45min
Return
12/07/25
1 Stopover (ATL)
F90124, F91441
18h 53min
Frontier Airlines ?
$398
Chicago
Montego Bay
Outbound
11/09/25
1 Stopover (PTY)
CM0236, CM0146
27h 18min
Return
12/07/25
1 Stopover (PTY)
CM0147, CM0228
25h 39min
Copa Airlines ?
$416
Chicago
Montego Bay
Outbound
11/09/25
1 Stopover (PTY)
CM0236, CM0146
27h 18min
Return
12/07/25
1 Stopover (PTY)
CM0147, CM0228
25h 39min
Copa Airlines ?
$427
Chicago
Montego Bay
Outbound
11/09/25
1 Stopover (PTY)
CM0236, CM0146
27h 18min
Return
12/07/25
1 Stopover (PTY)
CM0147, CM0228
25h 39min
Copa Airlines ?
$491
Chicago
Montego Bay
Outbound
02/13/26
1 Stopover (PTY)
CM0236, CM0831
26h 45min
Return
02/26/26
direct
UA1160
04h 25min
Copa Airlines ?
$494
Chicago
Montego Bay
Outbound
02/13/26
1 Stopover (PTY)
CM0236, CM0831
26h 45min
Return
02/26/26
1 Stopover (FLL)
NK0270, NK3153
08h 48min
Copa Airlines ?
$513
Chicago
Montego Bay
Outbound
02/13/26
1 Stopover (FLL)
NK0002, NK0833
06h 00min
Return
02/26/26
1 Stopover (FLL)
NK0270, NK0001
11h 30min
Spirit Airlines
$570
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 366,97 $
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 (CHI)
Arrival airport Airport Montego Bay (MBJ)
Destination country Flights to Jamaica
Alternative flights to Montego Bay
Flight destinations with a similar price