Montego Bay

$98+ 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 8/30. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MBJ
ago 5 — ago 121
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Cheapflights Tip: The best prices from Chicago to Montego Bay Sangster Intl are usually found in February or January, 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 julho 31, 2025.

Round-trip from

$381
(Kiwi.com)

One-way from

$117
(Booking.com)

Popular in

March

Cheapest in

February

Average price

$599

Good round-trip deal

$501 or less

Good one-way deal

$186 or less
From Chicago (CHI) to Montego Bay Sangster Intl
One-way flight from Chicago (CHI) to Montego Bay Sangster Intl
Highest demand for flights based on searches. 2% potential increase in price ($14 potential increase over avg. RT price).
Cheapest flight prices on average. 2% potential price decrease ($12 potential savings vs. average RT price).
Average for round-trip flights in July 2025
Price to beat on a round-trip flight from Chicago (CHI) to Montego Bay Sangster Intl.
Price to beat on a one-way flight from Chicago (CHI) to Montego Bay Sangster Intl.

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 julho 31, 2025.

This Frontier deal was found by Cheapflights users on 7/29. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb 9/206:15 amMDW - MBJ
1 stop6h 30mFrontier
dom 9/212:12 pmMBJ - MDW
1 stop9h 08mFrontier
Deal found 7/29$381
This Kiwi.com deal was found by Cheapflights users on 7/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb 10/45:05 amORD - MBJ
1 stop6h 00mSpirit Airlines
sex 10/1012:10 pmMBJ - ORD
1 stop22h 33mSpirit Airlines
Deal found 7/29$381
This CheapOair deal was found by Cheapflights users on 7/30. 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.
sex 8/158:12 pmORD - MBJ
1 stop15h 02mMultiple Airlines
seg 8/189:05 amMBJ - ORD
1 stop15h 17mMultiple Airlines
Deal found 7/30$383
This American Airlines deal was found by Cheapflights users on 7/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
seg 10/135:22 amORD - MBJ
1 stop10h 00mAmerican Airlines
ter 10/212:30 pmMBJ - ORD
1 stop6h 52mAmerican Airlines
Deal found 7/30$384
This Southwest deal was found by Cheapflights users on 7/29. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
seg 10/135:50 amMDW - MBJ
1 stop7h 45mSouthwest
qui 10/1612:20 pmMBJ - MDW
1 stop8h 15mSouthwest
Deal found 7/29$385
This Delta deal was found by Cheapflights users on 7/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
seg 9/225:30 amORD - MBJ
1 stop7h 39mDelta
qui 9/251:25 pmMBJ - ORD
1 stop8h 00mDelta
Deal found 7/29$385
This Delta deal was found by Cheapflights users on 7/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom 9/216:00 amMDW - MBJ
1 stop9h 34mDelta
qui 9/251:25 pmMBJ - MDW
2 stops19h 15mDelta
Deal found 7/29$389
This Frontier deal was found by Cheapflights users on 7/29. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sex 9/195:10 amORD - MBJ
1 stop7h 35mFrontier
dom 9/212:12 pmMBJ - ORD
1 stop9h 58mFrontier
Deal found 7/29$399

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 julho 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

sáb 10/4

5:05 am-11:05 am

1 stop6h 00m

Montego Bay Sangster Intl

sex 10/10

12:10 pm-10:43 am

1 stop22h 33m

$381

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

sáb 9/20

6:15 am-12:45 pm

1 stop6h 30m

Montego Bay Sangster Intl

dom 9/21

2:12 pm-11:20 pm

1 stop9h 08m

$381

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

sex 8/15

8:12 pm-11:14 am

1 stop15h 02m

Montego Bay Sangster Intl

seg 8/18

9:05 am-12:22 am

1 stop15h 17m

$383

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

seg 10/13

5:22 am-3:22 pm

1 stop10h 00m

Montego Bay Sangster Intl

ter 10/21

2:30 pm-9:22 pm

1 stop6h 52m

$384

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

seg 9/22

5:30 am-1:09 pm

1 stop7h 39m

Montego Bay Sangster Intl

qui 9/25

1:25 pm-9:25 pm

1 stop8h 00m

$385

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

seg 10/13

5:00 am-1:55 pm

1 stop8h 55m

Montego Bay Sangster Intl

qui 10/16

12:50 pm-8:40 pm

2 stops7h 50m

$385

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

dom 9/21

6:00 am-3:34 pm

1 stop9h 34m

Montego Bay Sangster Intl

sex 9/26

4:59 pm-12:28 pm

2 stops19h 29m

$389

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

sex 9/19

5:10 am-12:45 pm

1 stop7h 35m

Montego Bay Sangster Intl

dom 9/21

2:12 pm-12:10 am

1 stop9h 58m

$399

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

sáb 8/30

8:12 pm-9:17 am

1 stop13h 05m

$98

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

sáb 9/13

6:15 am-12:45 pm

1 stop6h 30m

$161

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/31

Showing 1-10 of 17 results
1
2

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 July 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 $562). 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 julho 31, 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 July 27, 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.

How much does it cost to fly round-trip from Chicago to Montego Bay?

What’s the top layover airport for flights from Chicago to Montego Bay?

Share of 1-stop round-trip flights from Chicago to Montego Bay chosen by Cheapflights users in the past 12 months, using the same layover each way.

Fort Lauderdale (FLL) – chosen by Cheapflights users on 71% of 1-stop itineraries from Chicago to Montego Bay on Cheapflights.

What’s the cheapest layover airport for flights from Chicago to Montego Bay?

Average round-trip fare for 1-stop flights from Chicago to Montego Bay, chosen by Cheapflights users in the past 12 months, with the same layover each way.

Atlanta (ATL) is the most affordable 1-stop option, with an average round-trip price of $370.

What’s the fastest layover option from Chicago to Montego Bay?

Shortest average travel time for 1-stop one-way flights from Chicago to Montego Bay, based on itineraries clicked by Cheapflights users over the past 12 months, grouped by layover airport.

Flights via Orlando (MCO) have the shortest average one-way travel time for 1-stop routes: 6h 05m.

Which airport typically offers the quickest layover for flights from Chicago to Montego Bay?

Average layover duration for 1-stop one-way flights from Chicago to Montego Bay, chosen by Cheapflights users in the last 12 months, grouped by stopover airport.

Flights via Baltimore (BWI) offer the fastest connection on this route, with an average layover time of 1h 20m.

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 julho 31, 2025.
Read reviews from past customers who have flown Southwest, Delta, and American Airlines from Chicago to Montego Bay. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.

Entertainment

7.5

Comfort

8.0

Boarding

8.1

Food

7.0

Overall

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.

Entertainment

7.5

Comfort

8.0

Boarding

8.1

Food

7.0

Overall

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
8.0
Very good

Entertainment

7.5

Comfort

8.0

Boarding

8.1

Food

7.0

Overall

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.

Entertainment

7.5

Comfort

8.0

Boarding

8.1

Food

7.0

Overall

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.

Entertainment

7.5

Comfort

8.0

Boarding

8.1

Food

7.0

Overall

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.

Entertainment

7.5

Comfort

8.0

Boarding

8.1

Food

7.0

Overall

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.

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 $381 on this airline. Additional options worth looking into are Frontier and American Airlines, starting at $381 and $384 round-trip. Spirit Airlines is 34% 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 $117 on Spirit Airlines. Other airlines that offer cheap prices include Frontier from $161 and American 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 $658, our data indicates the cheapest price to be $164. The most popular route (Chicago O'Hare Intl - Montego Bay Sangster Intl), is priced around $282.

  • 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 $562). 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

Traveling to a place near Montego Bay?

Book flights to Montego Bay if you plan to visit one of these locations
Whitehouse
Lucea

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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 julho 31, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$266Average$488FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$410Average$622FlexibilityNo cancel feeOn-time69%
DeltaCheapest$427Average$796FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$432Average$591FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$555Average$724FlexibilityNo cancel feeOn-time63%

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