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 09/23/25 1 Stopover (JFK) B60406, B60479 09h 03min | Return 09/30/25 1 Stopover (FLL) NK0270, NK0003 07h 54min | | ![]() | ? | $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 | | ![]() | $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 | | ![]() | $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 | | ![]() | ? | $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 | | ![]() | ? | $426 |
Stops
- Direct flight
Airline
- American Airlines
- Spirit Airlines
- Air Canada
- United 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
$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 Fort Lauderdale - Montego Bay from $255
- Flight Washington DC - Montego Bay from $403
- Flight Orlando - Montego Bay from $314
- Flight Miami - Montego Bay from $378
- Flight Chicago O'Hare - Montego Bay from $317
- Flight Atlanta - Montego Bay from $298
- Flight Baltimore - Montego Bay from $312
- Flight Charlotte - Montego Bay from $311
- Flight Newark - Montego Bay from $378
Flight destinations with a similar price
- Flight Montego Bay - Frankfurt from $611
Flight destinations with a similar price
- Flight Chicago - San Jose, Costa Rica from $294