Outbound | Return | Airlines | Shop | Baggage | Price | ||
---|---|---|---|---|---|---|---|
Chicago Montego Bay | Outbound 04/21/25 1 Stopover (FLL) NK0267, NK0833 15h 12min | Return 05/19/25 1 Stopover (ATL) F90016, F91595 26h 22min | | ![]() | $403 | ||
Best option Chicago Montego Bay | Outbound 06/20/25 direct AA3228 04h 05min | Return 07/19/25 direct AA0975 04h 30min | | ![]() | ? | $546 | |
Chicago Montego Bay | Outbound 04/21/25 1 Stopover (FLL) NK0002, BW0032 07h 35min | Return 05/19/25 1 Stopover (ATL) F90016, NK1200 08h 07min | | ![]() | $444 | ||
Chicago Montego Bay | Outbound 04/21/25 2 Stopovers (ATL, MIA, FLL) F91596, F92272, BW0032 26h 25min | Return 05/19/25 1 Stopover (ATL) F90016, F91595 26h 22min | | ![]() | ? | $404 | |
Chicago Montego Bay | Outbound 04/21/25 1 Stopover (FLL) NK0267, NK0833 15h 12min | Return 05/19/25 1 Stopover (ATL) F90016, F91595 26h 22min | | ![]() | $409 | ||
Chicago Montego Bay | Outbound 04/21/25 1 Stopover (FLL) NK0002, NK0833 05h 51min | Return 05/19/25 1 Stopover (FLL) NK1361, NK1026 07h 18min | | ![]() | $429 | ||
Chicago Montego Bay | Outbound 04/21/25 3 Stopovers (MCO, ATL, FLL) NK0573, NK0211, NK0442, NK0833 26h 16min | Return 05/19/25 2 Stopovers (MCO, ATL) NK1570, NK1850, NK1200 34h 17min | | ![]() | ? | $432 | |
Chicago Montego Bay | Outbound 04/21/25 2 Stopovers (CLT, MIA) AA2080, AA3068, AA2611 23h 17min | Return 05/19/25 2 Stopovers (MIA, CLT) AA0842, AA1069, AA2843 17h 21min | | ![]() | ? | $531 | |
Chicago Montego Bay | Outbound 04/21/25 1 Stopover (MIA) AA1277, AA2611 14h 28min | Return 05/19/25 1 Stopover (MIA) AA0842, AA0581 17h 20min | | ![]() | ? | $574 | |
Chicago Montego Bay | Outbound 04/21/25 direct UA1146 04h 04min | Return 05/19/25 1 Stopover (IAD) UA0653, UA1738 07h 03min | | ![]() | ? | $577 |
Stops
- Direct flight
Airline
- American Airlines
- Spirit Airlines
- Frontier Airlines
- United Airlines
- Air Canada
Flight type
- Return
Outbound departure month
- April 2025
- June 2025
Outbound weekday
- Monday
- Friday
Return departure month
- May 2025
- July 2025
Return weekday
- Monday
- Saturday
Change in
- Miami International Airport, FL
- Hartsfield-Jackson Atlanta International Airport, GA
- Toronto - Lester B. Pearson International Airport
- Orlando International Airport, FL
- New York - John F. Kennedy International Airport, NY
- Fort Lauderdale-Hollywood International Airport, FL
- Charlotte Douglas International Airport, NC
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 | 402,05 $ |
---|---|
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 Washington-DC - Montego Bay from 434 $
- Flight San Diego - Montego Bay from 484 $
- Flight Milwaukee - Montego Bay from 499 $
- Flight New York - Montego Bay from 376 $
- Flight Atlanta - Montego Bay from 338 $
- Flight Orlando - Montego Bay from 367 $
- Flight Houston - George Bush - Montego Bay from 528 $
- Flight New York - Montego Bay from 376 $
- Flight Philadelphia - Montego Bay from 534 $
- Flight Chicago O'Hare - Montego Bay from 403 $
Flight destinations with a similar price
- Flight Montego Bay - Frankfurt from 746 $
Flight destinations with a similar price
- Flight Chicago - Havana from 435 $