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 | | ![]() | $317 | ||
Best option Chicago Montego Bay | Outbound 11/03/25 direct AA2123 04h 03min | Return 11/12/25 direct AA0975 04h 30min | | ![]() | ? | $481 | |
Chicago Montego Bay | 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 | | ![]() | $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 | | ![]() | $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 | | ![]() | $336 | ||
Chicago Montego Bay | Outbound 10/10/25 1 Stopover (ATL) F91442, F90017 13h 37min | Return 11/04/25 1 Stopover (FLL) NK0270, NK0003 07h 54min | | ![]() | $347 | ||
Chicago Montego Bay | Outbound 07/08/25 1 Stopover (FLL) NK0001, NK0833 05h 57min | Return 08/07/25 1 Stopover (ATL) F90016, F93397 15h 12min | | ![]() | ? | $348 | |
Chicago Montego Bay | Outbound 10/10/25 1 Stopover (ATL) F91442, F90017 13h 37min | Return 11/04/25 1 Stopover (FLL) NK0270, NK0003 07h 54min | | ![]() | $357 | ||
Chicago Montego Bay | Outbound 07/08/25 1 Stopover (FLL) NK0001, NK0833 05h 57min | Return 08/07/25 1 Stopover (ATL) F90016, F93397 15h 12min | | ![]() | $363 | ||
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 | | ![]() | ? | $372 |
Stops
- Direct flight
Airline
- American Airlines
- Spirit Airlines
- Air Canada
- Frontier Airlines
- United 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
618 USD
321 USD
405 USD
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 USD
41 %
1 stopover Toronto - Lester B. Pearson International Airport
14h 25min, from 531 USD
19 %
1 stopover Orlando International Airport, FL
06h 00min, from 381 USD
14 %
Important flight information
Flight information: Chicago - Montego Bay
Roundtrip from | 316,83 USD |
---|---|
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 Fort Lauderdale - Montego Bay from 255 USD
- Flight Washington DC - Montego Bay from 356 USD
- Flight Orlando - Montego Bay from 314 USD
- Flight Miami - Montego Bay from 378 USD
- Flight Atlanta - Montego Bay from 298 USD
- Flight Baltimore - Montego Bay from 312 USD
- Flight Charlotte - Montego Bay from 311 USD
- Flight Newark - Montego Bay from 336 USD
- Flight Houston - George Bush - Montego Bay from 352 USD
- Flight Philadelphia - Montego Bay from 371 USD
Flight destinations with a similar price
- Flight Montego Bay - Frankfurt from 754 USD
Flight destinations with a similar price
- Flight Chicago - Dublin from 345 USD
- Flight Chicago - San Jose, Costa Rica from 294 USD