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Montego Bay

$111+ Cheap flights from Chicago (CHI) to Montego Bay (MBJ)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 4/29. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MBJ
Apr 5 — Apr 121
Sat 4/5
Sat 4/12
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Montego Bay Sangster Intl are usually found in February or October, booked 55 days in advance, depart on a Sunday or Monday and return on a Wednesday

Cheap flight deals from Chicago to Montego Bay

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Montego Bay (MBJ). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated March 31, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$462
(Mytrip)

One-way from

$111
(Cheapflightsfares)

Popular in

December

Cheapest in

February

Average price

$666

Good round-trip deal

$533 or less

Good one-way deal

$217 or less
Provider with most accurate pricing for Chicago (CHI)-Montego Bay Sangster Intl flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Montego Bay Sangster Intl flights.
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From Chicago (CHI) to Montego Bay Sangster Intl
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One-way flight from Chicago (CHI) to Montego Bay Sangster Intl
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Highest demand for flights based on searches. 3% potential increase in price ($20 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($11 potential savings vs. average RT price).
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Average for round-trip flights in March 2025
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Price to beat on a round-trip flight from Chicago (CHI) to Montego Bay Sangster Intl.
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Price to beat on a one-way flight from Chicago (CHI) to Montego Bay Sangster Intl.
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Find flight deals from Chicago to Montego Bay

Cheapest flights from Chicago to Montego Bay
Explore the most affordable flight options available from Chicago to Montego Bay. Find the lowest fares from popular airlines and budget airlines, with prices last updated on March 31, 2025.

This American Airlines deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/29:25 amORD - MBJ
Nonstop4h 05mAmerican Airlines
Wed 4/92:25 pmMBJ - ORD
Nonstop4h 35mAmerican Airlines
Deal found 3/31$460
This Delta deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/217:10 amORD - MBJ
1 stop8h 23mDelta
Wed 10/11:12 pmMBJ - ORD
1 stop8h 00mDelta
Deal found 3/30$463
This Delta deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/36:00 amMDW - MBJ
1 stop9h 36mDelta
Wed 9/101:12 pmMBJ - MDW
1 stop8h 32mDelta
Deal found 3/30$463
This Mytrip deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/215:07 pmORD - MBJ
2 stops17h 48mSpirit Airlines
Fri 4/2512:00 pmMBJ - ORD
2 stops20h 35mSpirit Airlines
Deal found 3/31$464
This United Airlines deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/48:45 amORD - MBJ
1 stop6h 25mUnited Airlines
Thu 4/101:51 pmMBJ - ORD
Nonstop4h 29mUnited Airlines
Deal found 3/31$465
This CheapOair deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/246:20 amMDW - MBJ
1 stop26h 00mFrontier
Sat 5/318:55 amMBJ - MDW
1 stop13h 22mFrontier
Deal found 3/30$465
This Mytrip deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/155:51 amORD - MBJ
3 stops29h 11mMultiple Airlines
Thu 5/223:05 pmMBJ - ORD
1 stop9h 00mMultiple Airlines
Deal found 3/31$477
This Southwest deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/37:30 amMDW - MBJ
Nonstop4h 00mSouthwest
Sat 4/52:20 pmMBJ - MDW
1 stop8h 50mSouthwest
Deal found 3/30$496
This Booking.com deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/296:26 pmORD - MBJ
1 stop13h 24mFrontier
Sun 6/19:38 amMBJ - ORD
1 stop14h 42mFrontier
Deal found 3/30$508
This Air Canada deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/36:15 pmORD - MBJ
2 stops17h 00mAir Canada
Tue 6/1012:10 pmMBJ - ORD
1 stop20h 59mAir Canada
Deal found 3/30$565
This Kiwi.com deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/266:35 amMDW - MBJ
1 stop25h 15mMultiple Airlines
Fri 5/3012:07 pmMBJ - MDW
2 stops10h 07mMultiple Airlines
Deal found 3/30$571

Cheapflights Fare Finder

Customize your flight search to find flights from Chicago to Montego Bay that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated March 31, 2025.
Use the filters below to find and compare flights from Chicago to Montego Bay that are best for you.

Fly from

Chicago

Fly to

Montego Bay

Route

Depart

Return

Price

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Tue 5/27

7:47 am-11:02 am

2 stops27h 15m

Montego Bay Sangster Intl

Sat 5/31

3:05 pm-12:05 am

1 stop9h 00m

$462

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Sun 9/21

6:00 am-12:58 pm

1 stop6h 58m

Montego Bay Sangster Intl

Fri 9/26

4:58 pm-11:53 pm

1 stop6h 55m

$463

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Wed 9/3

6:00 am-3:36 pm

1 stop9h 36m

Montego Bay Sangster Intl

Wed 9/10

1:12 pm-9:44 pm

1 stop8h 32m

$463

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Thu 5/15

4:50 pm-11:54 am

1 stop19h 04m

Montego Bay Sangster Intl

Thu 5/22

2:25 pm-7:00 pm

Nonstop4h 35m

$464

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sat 5/24

6:20 am-8:20 am

1 stop26h 00m

Montego Bay Sangster Intl

Sat 5/31

8:55 am-10:17 pm

1 stop13h 22m

$465

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Thu 5/1

7:33 pm-10:55 am

1 stop15h 22m

Montego Bay Sangster Intl

Mon 5/5

12:00 pm-12:58 am

1 stop12h 58m

$469

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sat 5/10

7:25 am-2:00 pm

1 stop6h 35m

Montego Bay Sangster Intl

Sat 5/17

1:50 pm-6:05 pm

Nonstop4h 15m

$506

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Thu 5/29

6:26 pm-7:50 am

1 stop13h 24m

Montego Bay Sangster Intl

Sun 6/1

9:38 am-12:20 am

1 stop14h 42m

$508

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Tue 6/10

6:30 pm-11:15 am

1 stop16h 45m

Montego Bay Sangster Intl

Mon 6/16

12:10 pm-9:09 am

1 stop20h 59m

$565

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Sat 5/17

8:45 am-12:49 pm

Nonstop4h 04m

Montego Bay Sangster Intl

Sat 5/24

1:51 pm-6:20 pm

Nonstop4h 29m

$566

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/30

Showing 1-10 of 25 results
1
2
3

Compare providers for flights from Chicago to Montego Bay

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Chicago to Montego Bay in March.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
AranGrantPrice Accuracy3 starsTrust Score*1 star
CheapflightsfaresPrice Accuracy3 starsTrust Score*2 stars
Justfly.comPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Chicago-Montego Bay flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago-Montego Bay flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago-Montego Bay flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago-Montego Bay flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago-Montego Bay flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Chicago to Montego Bay

Have a flexible travel schedule? Discover the best time to fly to Montego Bay from Chicago with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Chicago to Montego Bay

How far ahead should I book a flight from Chicago to Montego Bay?

Use this chart to determine the optimal time to book a round-trip flight from Chicago to Montego Bay. Price data was last updated on March 28, 2025.

The best time to book flights from Chicago to Montego Bay is 55 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.

What is the cheapest month to book a flight from Chicago to Montego Bay?

Currently, January is the cheapest month in which you can book a flight from Chicago to Montego Bay (average of $403). Flying from Chicago to Montego Bay in July is currently the most expensive (average of $569). 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.

What is the cheapest time of day to fly from CHI to MBJ?

Find hourly flight availability from Chicago to Montego Bay. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated March 31, 2025.

It’s optimal to fly from Chicago to Montego Bay at noon. By choosing this option you can save up to 31% on the cost of your flight, compared to a flight in the morning.

What is the cheapest day to fly from Chicago to Montego Bay?

Use this chart to determine the cheapest time to fly round-trip from Chicago to Montego Bay. Price data was last updated on March 30, 2025.

Travelers seeking maximum savings on their Chicago to Montego Bay flight should consider departing on Tuesday evenings when fares are most often at their lowest. Thursday mornings flights should be avoided if possible as fares are typically the most expensive at this time.

Weekly flight availability from Chicago to Montego Bay

Explore weekly flight availability from Chicago to Montego Bay. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated March 31, 2025.

The most flights from CHI to MBJ are scheduled on a Sunday (3 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (1 on average).

Rainfall in Montego Bay by month

Plan your trip to Montego Bay by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Montego Bay ranges from 1.6 - 7.1 inches per month. October is typically the wettest month, when rainfall can reach 7.1 in. February is typically the driest time to visit Montego Bay when rainfall is around 1.6 in.

Temperature in Montego Bay by month

Plan your trip to Montego Bay by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Montego Bay, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 82.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 77.0 F).

Reviews of airlines servicing Montego Bay

Get insights into the airlines that provide service to Montego Bay. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Montego Bay. Reviews last updated March 31, 2025.
See what other customers who have flown with Southwest, Delta and Copa Airlines from Chicago to Montego Bay have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,276 reviews

Entertainment

7.6

Overall

8.0

Comfort

8.0

Boarding

8.2

Crew

8.6

Food

7.1

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Southwest
8.0
Very good
4,276 reviews
Southwest
8.0
Very good
4,276 reviews

Entertainment

7.6

Overall

8.0

Comfort

8.0

Boarding

8.2

Crew

8.6

Food

7.1

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Delta
8.0
Very good
7,899 reviews
Southwest
8.0
Very good
4,276 reviews

Entertainment

7.6

Overall

8.0

Comfort

8.0

Boarding

8.2

Crew

8.6

Food

7.1

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Copa Airlines
7.6
Good
1,400 reviews
Southwest
8.0
Very good
4,276 reviews

Entertainment

7.6

Overall

8.0

Comfort

8.0

Boarding

8.2

Crew

8.6

Food

7.1

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
SWISS
7.5
Good
1,570 reviews
Southwest
8.0
Very good
4,276 reviews

Entertainment

7.6

Overall

8.0

Comfort

8.0

Boarding

8.2

Crew

8.6

Food

7.1

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
United Airlines
7.4
Good
8,614 reviews
Southwest
8.0
Very good
4,276 reviews

Entertainment

7.6

Overall

8.0

Comfort

8.0

Boarding

8.2

Crew

8.6

Food

7.1

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

Related info for your journey

Find useful and relevant information for your journey from Chicago to Montego Bay. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to Montego Bay from Chicago?

    If you book a flight to Montego Bay from Chicago, you will be flying to Sangster Intl, which is the city’s only airport. Montego Bay Sangster Intl (MBJ) is located 2.3 mi from the center of Montego Bay. There is 1 flight from Chicago to Sangster Intl per day from 6 different airlines.

  • What are the cheapest airlines flying from Chicago to Montego Bay round-trip?

    Our cheapest airline available from Chicago to Montego Bay is Delta. Our recent data shows that you can find tickets from as low as $463 on this airline. Additional options worth looking into are American Airlines and Frontier, starting at $464 and $465 round-trip. Delta is 18% cheaper than the average price of flights available within the next 90 days to this destination.

  • What are the cheapest airlines to fly from Chicago to Montego Bay one-way?

    One-way options have recently been found by users for as low as $111 on Spirit Airlines. Other airlines that offer cheap prices include Frontier from $191 and American Airlines from $196 one-way.

  • What are the cheapest flights from Chicago to Montego Bay?

    Looking for the cheapest flight from Chicago to Montego Bay? While on average our users pay $434, our data indicates the cheapest price to be $196. The most popular route (Chicago O'Hare Intl - Montego Bay Sangster Intl), is priced around $301.

  • Can I find deals for flights from Chicago to Montego Bay that include hotel bookings?

    Yes. In addition to deals on Chicago to Montego Bay flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Montego Bay?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Montego Bay.

  • Can I find deals for business class flights from Chicago to Montego Bay?

    Yes. Cheapflights offers flight deals from Chicago to Montego Bay by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chicago to Montego Bay?

    Currently, January is the cheapest month in which you can book a flight from Chicago to Montego Bay (average of $403). Flying from Chicago to Montego Bay in July is currently the most expensive (average of $569). 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.

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Top 6 airlines flying from Chicago to Montego Bay

Discover the top 6 airlines that operate flights from Chicago to Montego Bay. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated March 31, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$205Average$265FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$273Average$482FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$393Average$581FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$393Average$610FlexibilityNo cancel feeOn-time69%
DeltaCheapest$427Average$813FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$579Average$735FlexibilityNo cancel feeOn-time63%
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