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Montego Bay

$99+ 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 10/7. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MBJ
Oct 16 — Oct 231
Thu 10/16
Thu 10/23
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 September, 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 September 16, 2025.

Round-trip from

$376
(American Airlines)

One-way from

$99
(Cheapflightsfares)

Popular in

March

Cheapest in

February

Average price

$540

Good round-trip deal

$491 or less

Good one-way deal

$201 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. 2% potential increase in price ($15 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($13 potential savings vs. average RT price).
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Average for round-trip flights in September 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 September 16, 2025.

This United Airlines deal was found by Cheapflights users on 9/16. 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.
Sat 11/88:42 amORD - MBJ
Nonstop4h 04mUnited Airlines
Sat 11/152:48 pmMBJ - ORD
Nonstop4h 25mUnited Airlines
Deal found 9/16$376
This Cheapflightsfares deal was found by Cheapflights users on 9/15. 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.
Wed 10/155:05 amORD - MBJ
1 stop5h 55mSpirit Airlines
Sat 10/1812:09 pmMBJ - ORD
1 stop11h 36mSpirit Airlines
Deal found 9/15$377
This Kiwi.com deal was found by Cheapflights users on 9/15. 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.
Thu 11/135:05 amORD - MBJ
1 stop6h 00mSpirit Airlines
Tue 11/181:12 pmMBJ - ORD
1 stop8h 48mSpirit Airlines
Deal found 9/15$378
This Kiwi.com deal was found by Cheapflights users on 9/15. 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.
Sun 11/165:05 amORD - MBJ
1 stop6h 00mSpirit Airlines
Mon 11/171:12 pmMBJ - ORD
1 stop8h 48mSpirit Airlines
Deal found 9/15$379
This American Airlines deal was found by Cheapflights users on 9/14. 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.
Tue 10/148:44 amORD - MBJ
Nonstop4h 01mAmerican Airlines
Fri 10/1710:20 amMBJ - ORD
1 stop11h 04mAmerican Airlines
Deal found 9/14$380
This Kiwi.com deal was found by Cheapflights users on 9/15. 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.
Thu 10/306:20 amMDW - MBJ
1 stop8h 55mFrontier
Thu 11/64:30 pmMBJ - MDW
1 stop27h 09mFrontier
Deal found 9/15$380
This Kiwi.com deal was found by Cheapflights users on 9/16. 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.
Thu 10/211:57 amORD - MBJ
2 stops21h 50mSpirit Airlines
Sun 10/512:09 pmMBJ - ORD
1 stop11h 36mSpirit Airlines
Deal found 9/16$382
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 10/155:05 amORD - MBJ
1 stop5h 55mSpirit Airlines
Thu 10/1612:09 pmMBJ - ORD
1 stop6h 29mSpirit Airlines
Deal found 9/15$383
This Booking.com deal was found by Cheapflights users on 9/15. 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.
Tue 11/185:05 amORD - MBJ
1 stop6h 00mMultiple Airlines
Sun 11/307:05 pmMBJ - ORD
2 stops24h 50mMultiple Airlines
Deal found 9/15$384
This Mytrip deal was found by Cheapflights users on 9/16. 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.
Sun 9/285:05 amORD - MBJ
1 stop6h 00mSpirit Airlines
Wed 10/112:10 pmMBJ - ORD
3 stops30h 40mSpirit Airlines
Deal found 9/16$385
This Delta deal was found by Cheapflights users on 9/15. 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.
Mon 9/296:00 amMDW - MBJ
1 stop7h 09mDelta
Thu 10/21:25 pmMBJ - MDW
1 stop8h 11mDelta
Deal found 9/15$385
This American Airlines deal was found by Cheapflights users on 9/15. 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.
Fri 10/318:44 amORD - MBJ
Nonstop4h 01mAmerican Airlines
Fri 11/711:12 amMBJ - ORD
1 stop14h 25mAmerican Airlines
Deal found 9/15$386

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 September 16, 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

Fri 11/14

8:42 am-1:46 pm

Nonstop4h 04m

Montego Bay Sangster Intl

Mon 11/17

2:48 pm-6:13 pm

Nonstop4h 25m

$376

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Sun 11/30

8:42 am-1:46 pm

Nonstop4h 04m

Montego Bay Sangster Intl

Sat 12/6

2:48 pm-6:13 pm

Nonstop4h 25m

$376

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Mon 11/3

8:42 am-1:46 pm

Nonstop4h 04m

Montego Bay Sangster Intl

Fri 11/7

2:48 pm-6:13 pm

Nonstop4h 25m

$376

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Sat 11/8

8:48 am-4:12 pm

1 stop6h 24m

Montego Bay Sangster Intl

Sat 11/15

2:48 pm-6:13 pm

Nonstop4h 25m

$381

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Sat 11/1

6:00 am-1:05 pm

1 stop7h 05m

Montego Bay Sangster Intl

Fri 11/7

2:48 pm-6:13 pm

Nonstop4h 25m

$381

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Sat 11/1

6:00 am-1:05 pm

1 stop7h 05m

Montego Bay Sangster Intl

Sat 11/8

2:48 pm-6:13 pm

Nonstop4h 25m

$381

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Sat 11/8

6:00 am-2:05 pm

1 stop7h 05m

Montego Bay Sangster Intl

Wed 11/12

2:48 pm-6:13 pm

Nonstop4h 25m

$381

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sat 10/18

6:25 am-1:35 pm

1 stop7h 10m

Montego Bay Sangster Intl

Tue 10/21

1:00 pm-12:05 am

2 stops11h 05m

$389

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Fri 10/3

8:45 pm-2:00 pm

2 stops17h 15m

Montego Bay Sangster Intl

Tue 10/7

1:00 pm-10:35 pm

1 stop9h 35m

$389

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Sun 1/4

8:42 am-1:46 pm

Nonstop4h 04m

Montego Bay Sangster Intl

Fri 1/9

2:48 pm-6:13 pm

Nonstop4h 25m

$390

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/14

Showing 1-10 of 44 results
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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 September 12, 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 $561). 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 September 16, 2025.

It’s optimal to fly from Chicago to Montego Bay at noon. By choosing this option you can save up to 35% 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 September 14, 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 69% 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 September 16, 2025.
Read reviews from past customers who have flown Southwest, Delta, and United 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.
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Food

7.0

Entertainment

7.5

Overall

8.0

Boarding

8.1

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,242 reviews
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Food

7.0

Entertainment

7.5

Overall

8.0

Boarding

8.1

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Delta
8.0
Very good
7,957 reviews
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Food

7.0

Entertainment

7.5

Overall

8.0

Boarding

8.1

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
United Airlines
7.4
Good
8,924 reviews
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Food

7.0

Entertainment

7.5

Overall

8.0

Boarding

8.1

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Food

7.0

Entertainment

7.5

Overall

8.0

Boarding

8.1

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Spirit Airlines
6.3
Okay
8,019 reviews
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Food

7.0

Entertainment

7.5

Overall

8.0

Boarding

8.1

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

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 are 0 flights from Chicago to Sangster Intl per day from 6 different airlines.

  • How long is the flight from Chicago to Montego Bay?

    A quick flight from Chicago to Montego Bay can take about 4h 04m. United Airlines provides one of the quickest options available for as low as $376. The distance between Chicago and Montego Bay is about 1724 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • 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 $258 on this airline. Additional options worth looking into are Frontier and United Airlines, starting at $370 and $408 round-trip. Spirit Airlines is 56% 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 $150 on Frontier. Other airlines that offer cheap prices include Southwest 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 $661, our data indicates the cheapest price to be $164. The most popular route (Chicago O'Hare Intl - Montego Bay Sangster Intl), is priced around $257.

  • 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 $561). 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 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 September 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$258Average$481FlexibilityNo cancel feeOn-time65%
FrontierCheapest$370Average$446FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$408Average$631FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$444Average$600FlexibilityNo cancel feeOn-time71%
DeltaCheapest$448Average$836FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$549Average$726FlexibilityNo cancel feeOn-time63%

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