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 | | ![]() | $367 | ||
Best option Chicago Montego Bay | Outbound 02/13/26 direct AA3228 04h 05min | Return 02/26/26 direct AA0975 04h 40min | | ![]() | ? | $695 | |
Chicago Montego Bay | Outbound 11/09/25 1 Stopover (FLL) NK1932, NK0833 17h 06min | Return 12/07/25 1 Stopover (FLL) NK0270, NK1986 21h 11min | | ![]() | $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 | | ![]() | ? | $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 | | ![]() | ? | $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 | | ![]() | ? | $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 | | ![]() | ? | $491 | |
Chicago Montego Bay | Outbound 02/13/26 1 Stopover (PTY) CM0236, CM0831 26h 45min | Return 02/26/26 direct UA1160 04h 25min | | ![]() | ? | $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 | | ![]() | ? | $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 | | ![]() | $570 |
Stops
- Direct flight
Airline
- Copa Airlines
- Spirit Airlines
- American Airlines
- Frontier Airlines
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
US$618
US$321
US$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 US$321
41 %
1 stopover Toronto - Lester B. Pearson International Airport
14h 25min, from US$531
19 %
1 stopover Orlando International Airport, FL
06h 00min, from US$381
14 %
Important flight information
Flight information: Chicago - Montego Bay
Roundtrip from | US$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 Orlando - Montego Bay from US$382
- Flight Chicago O'Hare - Montego Bay from US$367
- Flight Atlanta - Montego Bay from US$213
- Flight Baltimore - Montego Bay from US$326
- Flight Charlotte - Montego Bay from US$359
- Flight Newark - Montego Bay from US$490
- Flight New York - Montego Bay from US$373
- Flight New York - Montego Bay from US$373
Flight destinations with a similar price
- Flight Chicago - Dublin from US$362
- Flight Chicago - Istanbul from US$335