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Montego Bay

$109+ 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 5/28. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MBJ
May 4 — May 111
Sun 5/4
Sun 5/11
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 April 29, 2025.

Most accurate provider

AranGrant
3 stars

Most trusted provider

AranGrant
3 stars

Round-trip from

$448
(Cheapflightsfares)

One-way from

$109
(Kiwi.com)

Popular in

March

Cheapest in

February

Average price

$540

Good round-trip deal

$543 or less

Good one-way deal

$252 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. 1% potential increase in price ($6 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($10 potential savings vs. average RT price).
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Average for round-trip flights in April 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 April 29, 2025.

This Mytrip deal was found by Cheapflights users on 4/28. 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 6/22:19 pmORD - MBJ
3 stops20h 43mSpirit Airlines
Tue 6/1012:07 pmMBJ - ORD
3 stops34h 32mSpirit Airlines
Deal found 4/28$448
This Booking.com deal was found by Cheapflights users on 4/28. 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 5/299:50 amMDW - MBJ
1 stop22h 00mFrontier
Sun 6/19:38 amMBJ - MDW
1 stop11h 54mFrontier
Deal found 4/28$448
This Delta deal was found by Cheapflights users on 4/28. 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 5/76:00 amMDW - MBJ
1 stop5h 37mDelta
Wed 5/141:02 pmMBJ - MDW
1 stop8h 26mDelta
Deal found 4/28$449
This American Airlines deal was found by Cheapflights users on 4/29. 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 8/205:00 amORD - MBJ
1 stop8h 30mAmerican Airlines
Tue 8/262:00 pmMBJ - ORD
Nonstop4h 30mAmerican Airlines
Deal found 4/29$451
This Booking.com deal was found by Cheapflights users on 4/28. 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.
Wed 6/42:45 pmORD - MBJ
1 stop17h 13mFrontier
Sun 6/89:18 amMBJ - ORD
1 stop25h 04mFrontier
Deal found 4/28$458
This Kiwi.com deal was found by Cheapflights users on 4/28. 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.
Wed 6/45:03 pmORD - MBJ
2 stops17h 59mMultiple Airlines
Fri 6/1312:07 pmMBJ - ORD
1 stop6h 37mMultiple Airlines
Deal found 4/28$459
This Southwest deal was found by Cheapflights users on 4/28. 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.
Sat 5/249:40 amMDW - MBJ
Nonstop4h 00mSouthwest
Thu 5/2912:00 pmMBJ - MDW
1 stop10h 00mSouthwest
Deal found 4/28$465
This Mytrip deal was found by Cheapflights users on 4/28. 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.
Sat 5/249:40 amMDW - MBJ
1 stop26h 02mMultiple Airlines
Thu 5/2912:07 pmMBJ - MDW
2 stops31h 07mMultiple Airlines
Deal found 4/28$467
This United Airlines deal was found by Cheapflights users on 4/28. 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.
Sun 7/136:00 amORD - MBJ
1 stop9h 10mUnited Airlines
Sun 7/201:51 pmMBJ - ORD
Nonstop4h 29mUnited Airlines
Deal found 4/28$506
This CheapOair deal was found by Cheapflights users on 4/28. 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.
Thu 9/118:25 pmORD - MBJ
1 stop14h 45mAir Canada
Mon 9/1512:05 pmMBJ - ORD
2 stops23h 18mAir Canada
Deal found 4/28$509
This Copa Airlines deal was found by Cheapflights users on 4/28. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/11:07 amORD - MBJ
1 stop10h 08mCopa Airlines
Sun 7/612:14 pmMBJ - ORD
1 stop12h 06mCopa Airlines
Deal found 4/28$519
This Delta deal was found by Cheapflights users on 4/28. 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.
Sat 8/237:00 amORD - MBJ
2 stops8h 36mDelta
Sat 8/305:01 pmMBJ - ORD
1 stop6h 54mDelta
Deal found 4/28$545

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 April 29, 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

Mon 6/2

2:19 pm-11:02 am

3 stops20h 43m

Montego Bay Sangster Intl

Tue 6/10

12:07 pm-10:39 pm

3 stops34h 32m

$448

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Thu 5/29

9:50 am-7:50 am

1 stop22h 00m

Montego Bay Sangster Intl

Sun 6/1

9:38 am-9:32 pm

1 stop11h 54m

$448

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Wed 5/7

6:00 am-11:37 am

1 stop5h 37m

Montego Bay Sangster Intl

Wed 5/14

1:02 pm-9:28 pm

1 stop8h 26m

$449

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Sat 7/5

9:13 pm-12:20 pm

1 stop15h 07m

Montego Bay Sangster Intl

Wed 7/9

2:26 pm-7:00 pm

Nonstop4h 34m

$452

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Fri 5/9

5:31 pm-1:53 pm

1 stop20h 22m

Montego Bay Sangster Intl

Mon 5/12

2:08 pm-11:11 pm

1 stop9h 03m

$458

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Wed 6/4

5:03 pm-11:02 am

2 stops17h 59m

Montego Bay Sangster Intl

Fri 6/13

12:07 pm-6:44 pm

1 stop6h 37m

$459

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sat 5/24

9:40 am-1:40 pm

Nonstop4h 00m

Montego Bay Sangster Intl

Thu 5/29

12:00 pm-10:00 pm

1 stop10h 00m

$465

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sat 5/24

9:40 am-11:42 am

1 stop26h 02m

Montego Bay Sangster Intl

Thu 5/29

12:07 pm-7:14 pm

2 stops31h 07m

$467

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Sun 7/13

8:42 am-12:49 pm

Nonstop4h 07m

Montego Bay Sangster Intl

Sun 7/20

1:51 pm-6:20 pm

Nonstop4h 29m

$501

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Tue 6/17

9:14 pm-11:10 am

1 stop13h 56m

Montego Bay Sangster Intl

Sun 6/22

12:05 pm-7:59 am

1 stop19h 54m

$509

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/29

Showing 1-10 of 28 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 April.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*2 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
AranGrantPrice Accuracy3 starsTrust Score*3 stars
CheapflightsfaresPrice Accuracy3 starsTrust Score*2 stars
CheapOairPrice Accuracy3 starsTrust Score*3 stars
Justfly.comPrice Accuracy3 starsTrust Score*2 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 AranGrant to be most consistent on Cheapflights vs. AranGrant Users can find the same prices on Chicago-Montego Bay flight deals on Cheapflights vs. AranGrant >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 AranGrant the most. AranGrant 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 April 25, 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 April 29, 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 April 29, 2025.

The most flights from CHI to MBJ are scheduled on a Monday (2 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 April 29, 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
4,295 reviews

Entertainment

7.6

Boarding

8.2

Comfort

8.0

Food

7.1

Crew

8.6

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Southwest
8.0
Very good
4,295 reviews
Southwest
8.0
Very good
4,295 reviews

Entertainment

7.6

Boarding

8.2

Comfort

8.0

Food

7.1

Crew

8.6

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Delta
8.0
Very good
7,936 reviews
Southwest
8.0
Very good
4,295 reviews

Entertainment

7.6

Boarding

8.2

Comfort

8.0

Food

7.1

Crew

8.6

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Copa Airlines
7.5
Good
1,411 reviews
Southwest
8.0
Very good
4,295 reviews

Entertainment

7.6

Boarding

8.2

Comfort

8.0

Food

7.1

Crew

8.6

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
United Airlines
7.4
Good
8,696 reviews
Southwest
8.0
Very good
4,295 reviews

Entertainment

7.6

Boarding

8.2

Comfort

8.0

Food

7.1

Crew

8.6

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
JetBlue
7.3
Good
2,922 reviews
Southwest
8.0
Very good
4,295 reviews

Entertainment

7.6

Boarding

8.2

Comfort

8.0

Food

7.1

Crew

8.6

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!

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 5 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 Spirit Airlines. Our recent data shows that you can find tickets from as low as $448 on this airline. Additional options worth looking into are Frontier and American Airlines, starting at $448 and $449 round-trip. Spirit Airlines is 21% 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 $109 on Spirit Airlines. Other airlines that offer cheap prices include Frontier from $193 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 $702, our data indicates the cheapest price to be $252. The most popular route (Chicago O'Hare Intl - Montego Bay Sangster Intl), is priced around $277.

  • 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 5 airlines flying from Chicago to Montego Bay

Discover the top 5 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 April 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$273Average$481FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$393Average$592FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$396Average$620FlexibilityNo cancel feeOn-time69%
DeltaCheapest$427Average$801FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$579Average$748FlexibilityNo cancel feeOn-time63%

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