Frontier AirlinesDepart16:43
Sat, 14 NovMBJ → MDW
5h 16m · 1 stop
US$237one way, per person
View deal
- Cheapest fare
- US$237
- Cheapest month
- November
- Direct flights
- Not recently
- Quickest trip
- 5h 16m
Frontier Airlines · Sat, 14 Nov
from US$237
Usually 1+ stop
2,760 km
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Cheapest month to fly from Montego Bay to Chicago
Lowest one-way fare per person in each month. Choose a month to see every date.
Cheapest dates in November 2026
The lowest fares we've seen for each day, cheapest first.
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Getting around
About flights from Montego Bay to Chicago
Montego Bay (MBJ) and Chicago (CHI) are about 2,760 km apart. We haven't seen direct fares on this route recently, so expect at least one stop; the quickest journey we've seen takes about 5h 16m. Over the next few months, one-way fares start from US$237, and November 2026 is currently the cheapest month to fly.
These prices come from searches travellers made in the last 48 hours, so they move quickly. If you see a good fare, it's worth booking soon. FlightsExp is free to use: you book directly with our travel partner.
Frequently asked questions
How much is a flight from Montego Bay to Chicago?
The cheapest one-way fare we've seen recently is US$237 with Frontier Airlines, departing Saturday, 14 November 2026.
What is the cheapest month to fly from Montego Bay to Chicago?
November 2026 currently has the lowest fares, from US$237 one way.
Are there direct flights from Montego Bay to Chicago?
We haven't seen direct fares recently, so most journeys include at least one stop.
How long is the flight from Montego Bay to Chicago?
The quickest journey we've seen takes about 5h 16m. Montego Bay and Chicago are around 2,760 km apart.
Which airlines fly from Montego Bay to Chicago?
Recent fares on this route were with Frontier Airlines.
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