
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $295 (Travelocity) |
One-way from | $104 (Super.com) |
Popular in | June |
Cheapest in | January |
Average price | $543 |
Good round-trip deal | $307 or less |
Good one-way deal | $138 or less |
Fly from
Fly to
Route
Depart
Return
ChicagoMontego Bay
ORD - MBJ
ORDMBJ
Chicago O'Hare Intl
Sat 5/9
8:40 am-12:50 pm
Nonstop4h 10m
Montego Bay Sangster Intl
Sat 5/16
1:52 pm-6:15 pm
Nonstop4h 23m
ChicagoMontego Bay
ORD - MBJ
ORDMBJ
Chicago O'Hare Intl
Fri 5/1
11:00 pm-1:30 pm
1 stop14h 30m
Montego Bay Sangster Intl
Sat 5/9
1:52 pm-6:15 pm
Nonstop4h 23m
ChicagoMontego Bay
ORD - MBJ
ORDMBJ
Chicago O'Hare Intl
Tue 5/19
5:30 am-1:30 pm
1 stop8h 00m
Montego Bay Sangster Intl
Sat 5/23
1:52 pm-6:15 pm
Nonstop4h 23m
ChicagoMontego Bay
ORD - MBJ
ORDMBJ
Chicago O'Hare Intl
Sun 6/28
6:30 am-1:30 pm
1 stop7h 00m
Montego Bay Sangster Intl
Sat 7/4
4:12 pm-11:26 pm
1 stop7h 14m
ChicagoMontego Bay
ORD - MBJ
ORDMBJ
Chicago O'Hare Intl
Sat 5/2
8:45 am-3:10 pm
1 stop6h 25m
Montego Bay Sangster Intl
Mon 5/4
2:40 pm-7:54 am
1 stop17h 14m
ChicagoMontego Bay
ORD - MBJ
ORDMBJ
Chicago O'Hare Intl
Sat 5/9
8:40 am-12:50 pm
Nonstop4h 10m
Montego Bay Sangster Intl
Tue 5/12
2:40 pm-12:45 am
1 stop10h 05m
ChicagoMontego Bay
ORD - MBJ
ORDMBJ
Chicago O'Hare Intl
Wed 5/27
6:30 am-3:10 pm
1 stop8h 40m
Montego Bay Sangster Intl
Sat 6/6
4:33 pm-12:45 am
1 stop8h 12m
ChicagoMontego Bay
ORD - MBJ
ORDMBJ
Chicago O'Hare Intl
Tue 5/26
5:30 am-1:30 pm
1 stop8h 00m
Montego Bay Sangster Intl
Sun 5/31
4:33 pm-12:45 am
1 stop8h 12m
ChicagoMontego Bay
MDW - MBJ
MDWMBJ
Chicago Midway
Tue 5/19
6:00 am-12:11 pm
1 stop6h 11m
Montego Bay Sangster Intl
Sat 5/23
1:16 pm-10:02 pm
1 stop8h 46m
ChicagoMontego Bay
ORD - MBJ
ORDMBJ
Chicago O'Hare Intl
Thu 7/2
6:30 am-3:10 pm
1 stop8h 40m
Montego Bay Sangster Intl
Sun 7/5
4:12 pm-11:26 pm
1 stop7h 14m
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*2 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
The best time to book flights from Chicago to Montego Bay is 88 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.
Currently, January is the cheapest month in which you can book a flight from Chicago to Montego Bay (average of $95). Flying from Chicago to Montego Bay in August is currently the most expensive (average of $384). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Chicago to Montego Bay as you normally would.
Fort Lauderdale (FLL) – chosen by Cheapflights users on 64% of 1-stop itineraries from Chicago to Montego Bay on Cheapflights.
Fort Lauderdale (FLL) is the most affordable 1-stop option, with an average round-trip price of $441.
Flights via Miami (MIA) have the shortest average one-way travel time for 1-stop routes: 5h 40m.
Flights via Charlotte (CLT) offer the fastest connection on this route, with an average layover time of 1h 20m.
Entertainment
Food
Overall
Comfort
Crew
Boarding
Reviews
Dominic,Mar 2026
MCO - SMF
Entertainment
Food
Overall
Comfort
Crew
Boarding
Reviews
Dominic,Mar 2026
MCO - SMF
Entertainment
Food
Overall
Comfort
Crew
Boarding
Reviews
Dominic,Mar 2026
MCO - SMF
Entertainment
Food
Overall
Comfort
Crew
Boarding
Reviews
Dominic,Mar 2026
MCO - SMF
Entertainment
Food
Overall
Comfort
Crew
Boarding
Reviews
Dominic,Mar 2026
MCO - SMF
Entertainment
Food
Overall
Comfort
Crew
Boarding
Reviews
Dominic,Mar 2026
MCO - SMF
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$141 | Average$380 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$144 | Average$675 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$178 | Average$551 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$302 | Average$537 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$374 | Average$567 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$518 | Average$683 | FlexibilityNo cancel fee | On-time63% |