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Montego Bay

$123+ 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 8/20. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MBJ
juin 17 — juin 241
mar. 6/17
mar. 6/24
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Montego Bay Sangster Intl are usually found in January or February, 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 juin 12, 2025.

Round-trip from

$393
(Cheapflightsfares)

One-way from

$123
(FlightHub)

Popular in

March

Cheapest in

January

Average price

$642

Good round-trip deal

$523 or less

Good one-way deal

$242 or less
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 ($8 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($12 potential savings vs. average RT price).
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Average for round-trip flights in June 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 juin 12, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 6/11. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ven. 7/115:40 pmORD - MBJ
1 stop17h 25mSpirit Airlines
mar. 7/1512:10 pmMBJ - ORD
2 stops11h 01mSpirit Airlines
Deal found 6/11$393
This Frontier deal was found by Cheapflights users on 6/12. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jeu. 10/167:23 pmMDW - MBJ
1 stop12h 30mFrontier
lun. 10/209:13 amMBJ - MDW
1 stop9h 05mFrontier
Deal found 6/12$393
This FlightHub deal was found by Cheapflights users on 6/12. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jeu. 9/116:16 pmORD - MBJ
1 stop13h 37mFrontier
lun. 9/159:13 amMBJ - ORD
1 stop28h 12mFrontier
Deal found 6/12$394
This Booking.com deal was found by Cheapflights users on 6/12. 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.
sam. 6/286:16 pmORD - MBJ
1 stop13h 42mMultiple Airlines
mer. 7/212:07 pmMBJ - ORD
1 stop11h 38mMultiple Airlines
Deal found 6/12$397
This American Airlines deal was found by Cheapflights users on 6/12. 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.
jeu. 7/310:05 pmORD - MBJ
1 stop16h 25mAmerican Airlines
jeu. 7/102:26 pmMBJ - ORD
Nonstop4h 34mAmerican Airlines
Deal found 6/12$400
This Southwest deal was found by Cheapflights users on 6/10. 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.
lun. 6/309:00 amMDW - MBJ
Nonstop4h 00mSouthwest
mer. 7/92:20 pmMBJ - MDW
Nonstop4h 10mSouthwest
Deal found 6/10$410
This Delta deal was found by Cheapflights users on 6/10. 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.
lun. 11/177:10 amORD - MBJ
1 stop5h 57mDelta
lun. 11/245:58 pmMBJ - ORD
1 stop6h 55mDelta
Deal found 6/10$446
This deal was found by Cheapflights users on 6/9. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dim. 8/106:00 amMDW - MBJ
1 stop7h 04mDelta
mar. 8/122:30 pmMBJ - MDW
1 stop7h 19mDelta
Deal found 6/9$468
This United Airlines deal was found by Cheapflights users on 6/9. 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.
lun. 7/79:31 pmORD - MBJ
1 stop17h 39mUnited Airlines
ven. 7/111:51 pmMBJ - ORD
Nonstop4h 29mUnited Airlines
Deal found 6/9$478
This Air Canada deal was found by Cheapflights users on 6/12. 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.
lun. 6/168:25 pmORD - MBJ
1 stop14h 45mAir Canada
mer. 6/1812:05 pmMBJ - ORD
1 stop21h 04mAir Canada
Deal found 6/12$481
This Mytrip deal was found by Cheapflights users on 6/10. 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.
ven. 8/11:11 pmMDW - MBJ
3 stops21h 54mMultiple Airlines
lun. 8/412:45 pmMBJ - MDW
1 stop27h 39mMultiple Airlines
Deal found 6/10$532

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 juin 12, 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

ven. 7/11

5:40 pm-11:05 am

1 stop17h 25m

Montego Bay Sangster Intl

mar. 7/15

12:10 pm-11:11 pm

2 stops11h 01m

$393

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

lun. 9/8

6:00 am-3:36 pm

1 stop9h 36m

Montego Bay Sangster Intl

sam. 9/13

2:23 pm-9:44 pm

1 stop7h 21m

$393

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

jeu. 9/11

6:16 pm-7:53 am

1 stop13h 37m

Montego Bay Sangster Intl

lun. 9/15

9:13 am-1:25 pm

1 stop28h 12m

$394

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

sam. 6/28

6:16 pm-7:58 am

1 stop13h 42m

Montego Bay Sangster Intl

mer. 7/2

12:07 pm-11:45 pm

1 stop11h 38m

$397

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

jeu. 7/3

10:05 pm-2:30 pm

1 stop16h 25m

Montego Bay Sangster Intl

jeu. 7/10

2:26 pm-7:00 pm

Nonstop4h 34m

$400

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

ven. 7/25

6:40 pm-10:49 am

1 stop16h 09m

Montego Bay Sangster Intl

ven. 8/1

3:53 pm-11:17 pm

1 stop7h 24m

$409

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

lun. 6/30

9:00 am-1:00 pm

Nonstop4h 00m

Montego Bay Sangster Intl

mer. 7/9

2:20 pm-6:30 pm

Nonstop4h 10m

$410

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

lun. 7/14

8:52 am-3:10 pm

1 stop6h 18m

Montego Bay Sangster Intl

sam. 7/19

1:51 pm-6:20 pm

Nonstop4h 29m

$412

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

lun. 12/1

6:00 am-4:33 pm

1 stop9h 33m

Montego Bay Sangster Intl

sam. 12/6

5:58 pm-11:53 pm

1 stop6h 55m

$446

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

dim. 10/26

3:35 pm-12:05 pm

2 stops20h 30m

Montego Bay Sangster Intl

dim. 11/2

7:05 pm-10:39 am

1 stop16h 34m

$530

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/12

Showing 1-10 of 24 results
1
2
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The best insider tips for Chicago to Montego Bay flights

Snippets provided in this section are AI-generated based on a summarization of Cheapflights-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.
Cheapflights partnered with top experts to bring you the best recommendations for your Chicago to Montego Bay trip
Airports
ORD

For a smooth departure from ORD, consider taking the “L” train to avoid Chicago traffic delays.

Read more about ORDby Ramsey Qubein
MBJ

Fill out the immigration form online before arriving at MBJ to save time and avoid long lines.

Read more about MBJby Mark Chesnut
Our travel experts
Ramsey Qubein

Ramsey Qubein

Expert on ORD

Ramsey Qubein

Ramsey Qubein

An avid traveler and aviation expert who has visited 173 countries, all 50 states and seven continents, Ramsey Qubein flies nearly 400,000 miles a year. As a North Carolina-based freelance journalist for publications including Conde Nast Traveler, Forbes, USA Today and Bloomberg among others, he explores the latest trends in aviation, hospitality, cruises and business.

Read more
Mark Chesnut

Mark Chesnut

Expert on MBJ

Mark Chesnut

Mark Chesnut

Mark Chesnut is a travel writer and public speaker with more than 30 years of experience. The 2019 winner of the NLGJA Excellence in Travel Writing Award, Mark is the author of the book “Prepare for Departure” and has covered air travel for multiple top consumer and trade media outlets.

Read more

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 June 9, 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 juin 12, 2025.

It’s optimal to fly from Chicago to Montego Bay at noon. By choosing this option you can save up to 34% 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 June 8, 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 juin 12, 2025.

The most flights from CHI to MBJ are scheduled on a Monday (2 on average). You will have fewer flight options on Saturday, 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 juin 12, 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
4,287 reviews

Overall

8.0

Food

7.1

Boarding

8.2

Comfort

8.0

Entertainment

7.6

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Southwest
8.0
Very good
4,287 reviews
Southwest
8.0
Very good
4,287 reviews

Overall

8.0

Food

7.1

Boarding

8.2

Comfort

8.0

Entertainment

7.6

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Delta
8.0
Very good
7,946 reviews
Southwest
8.0
Very good
4,287 reviews

Overall

8.0

Food

7.1

Boarding

8.2

Comfort

8.0

Entertainment

7.6

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Copa Airlines
7.5
Good
1,451 reviews
Southwest
8.0
Very good
4,287 reviews

Overall

8.0

Food

7.1

Boarding

8.2

Comfort

8.0

Entertainment

7.6

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
United Airlines
7.4
Good
8,790 reviews
Southwest
8.0
Very good
4,287 reviews

Overall

8.0

Food

7.1

Boarding

8.2

Comfort

8.0

Entertainment

7.6

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,287 reviews

Overall

8.0

Food

7.1

Boarding

8.2

Comfort

8.0

Entertainment

7.6

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

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 Spirit Airlines. Our recent data shows that you can find tickets from as low as $393 on this airline. Additional options worth looking into are Delta and American Airlines, starting at $393 and $400 round-trip. Spirit Airlines is 32% 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 $123 on Spirit Airlines. Other airlines that offer cheap prices include Delta from $152 and United Airlines from $164 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 $711, our data indicates the cheapest price to be $217. The most popular route (Chicago O'Hare Intl - Montego Bay Sangster Intl), is priced around $319.

  • 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.

See more FAQs

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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 juin 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$276Average$470FlexibilityNo cancel feeOn-time65%
FrontierCheapest$338Average$436FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$410Average$621FlexibilityNo cancel feeOn-time69%
DeltaCheapest$427Average$786FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$427Average$600FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$579Average$741FlexibilityNo cancel feeOn-time63%

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