Cheap Flights from Chicago to Montego Bay
Cheap Flights from Chicago to Montego Bay
Looking for cheap flights from Chicago to Montego Bay? PointsYeah scans award availability across major airline and bank transfer programs in one place, so travelers can compare the lowest points and cash routes faster. Instead of searching each airline separately, users can see pricing from programs like Chase, Amex, Capital One, Citi, and Bilt side by side.
Award prices from Chicago to Montego Bay vary by season, cabin, and date, but available award flights can start around 12,500 points one way, with premium cabins available at higher mileage levels. The live search above allows filtering by cabin, airline, stops, or maximum points to find the best award flights from Chicago to Montego Bay for specific travel dates.
2026-11-09
ORD - MBJ
Economy | Non stop | 9+ left
From 12,500 Pts + $69.6
2026-11-10
ORD - MBJ
Economy | Non stop | 9+ left
From 12,500 Pts + $69.6
2026-11-15
ORD - MBJ
Economy | Non stop | 9+ left
From 12,500 Pts + $69.6
2026-11-16
ORD - MBJ
Economy | Non stop | 9+ left
From 12,500 Pts + $69.6
2026-11-17
ORD - MBJ
Economy | Non stop | 9+ left
From 12,500 Pts + $69.6
2026-12-31
ORD - MBJ
Economy | Non stop | 9+ left
From 12,500 Pts + $69.6
Chicago to Montego Bay flight facts
Distance
1,721 mi
2,769 km in a straight line
Estimated flight time
about 4h
In the air, for the straight-line distance
Time difference
+1h
Montego Bay is 1 hour ahead of Chicago.
Airports in Chicago
DPA · Dupage
MDW · Chicago Midway Intl
ORD · Chicago O'Hare Intl
Airports in Montego Bay
MBJ · Sangster Intl
Premium cabin flights from Chicago to Montego Bay
Premium cabin
2026-11-08
ORD - MBJ
Business | Non stop | 7 left
From 25,000 Pts + $69.6
Premium cabin
2026-11-13
ORD - MBJ
Business | Non stop | 6 left
From 25,000 Pts + $69.6
Premium cabin
2026-11-14
ORD - MBJ
Business | Non stop | 3 left
From 25,000 Pts + $69.6
Premium cabin
2026-11-18
ORD - MBJ
Business | 1 Stop | 1 left
From 35,000 Pts + $69.6
Premium cabin
2026-11-27
ORD - MBJ
Business | 1 Stop | 5 left
From 35,000 Pts + $69.6
Premium cabin
2026-11-28
ORD - MBJ
Business | 1 Stop | 4 left
From 35,000 Pts + $69.6
Selected hotels for your next stay
Montego Bay (Jamaica)
S Hotel Montego Bay(SLH)
From 105,000 Pts or $587
Westmoreland (Jamaica)
Bluefields Bay Villas(SLH)
From 220,000 Pts or $901
Negril, Hanover (Jamaica)
Hideaway at Royalton Negril, An Autograph Collection All-Inclusive Resort - Adults Only
From Pts or $318
Frequently Asked Questions
The cheapest route from Chicago to Montego Bay depends on award space, transfer bonuses, and travel dates. PointsYeah compares bank and airline programs in one place so you can find the best points and cash combinations faster.
Yes. Transferable points from Chase, Amex, Capital One, Citi, and Bilt can often be moved to airline partners for flights from Chicago to Montego Bay.
Yes. Searching metro codes when available helps compare nearby airport combinations for flights from Chicago to Montego Bay.
Chicago and Montego Bay are about 1,721 miles (2,769 km) apart in a straight line.
Flying the 1,721-mile straight-line distance takes about 4h in the air, estimated from typical cruising speed. Actual travel time depends on the routing; itineraries with connections take longer.
Montego Bay is 1 hour ahead of Chicago.
Departures from Chicago: Dupage (DPA), Chicago Midway Intl (MDW), Chicago O'Hare Intl (ORD). Arrivals in Montego Bay: Sangster Intl (MBJ).
Travelers searching this route also look at other popular routes into Montego Bay, plus the return trip when we track it. Fares and award space change daily.
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