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Montego Bay

$193+ 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 9/8. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MBJ
Aug 31 — Sep 71
Mon 8/31
Mon 9/7
1 adult, Economy
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Find cheap flights from Chicago to Montego Bay with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

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Cheapflights Tip: The best prices from Chicago to Montego Bay Sangster Intl are usually found in September or April, booked 59 days in advance, depart on a Tuesday or Friday and return on a Wednesday

Cheap 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 August 1, 2026.

This Air Canada deal was found by Cheapflights users on 7/31. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/71:55 pm
ORD
-
MBJ
1 stop22h 30m
Air Canada
Sun 11/152:20 pm
MBJ
-
ORD
2 stops20h 03m
Air Canada
Deal found 7/31$420
This Air Canada deal was found by Cheapflights users on 7/31. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/88:50 pm
ORD
-
MBJ
1 stop15h 00m
Air Canada
Sat 11/146:20 pm
MBJ
-
ORD
1 stop16h 03m
Air Canada
Deal found 7/31$422
This Air Canada deal was found by Cheapflights users on 7/31. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/315:58 pm
ORD
-
MBJ
2 stops19h 27m
Air Canada
Sat 11/76:20 pm
MBJ
-
ORD
2 stops17h 47m
Air Canada
Deal found 7/31$424
This FlightHub deal was found by Cheapflights users on 7/31. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/226:21 pm
ORD
-
MBJ
2 stops40h 59m
Air Canada
Sun 10/251:20 pm
MBJ
-
ORD
1 stop21h 47m
Air Canada
Deal found 7/31$425
This United Airlines deal was found by Cheapflights users on 7/31. 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.
Sat 10/318:40 am
ORD
-
MBJ
Nonstop4h 08m
United Airlines
Sat 11/72:54 pm
MBJ
-
ORD
Nonstop4h 26m
United Airlines
Deal found 7/31$428
This Air Canada deal was found by Cheapflights users on 7/31. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/275:58 pm
ORD
-
MBJ
2 stops22h 22m
Air Canada
Tue 12/11:50 pm
MBJ
-
ORD
2 stops22h 17m
Air Canada
Deal found 7/31$430
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.
Mon 8/248:49 pm
ORD
-
MBJ
1 stop17h 34m
American Airlines
Thu 8/272:12 pm
MBJ
-
ORD
Nonstop4h 43m
American Airlines
Deal found 7/30$432
This American Airlines deal was found by Cheapflights users on 7/28. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/128:15 am
ORD
-
MBJ
1 stop8h 01m
American Airlines
Sat 9/195:16 pm
MBJ
-
ORD
1 stop7h 17m
American Airlines
Deal found 7/28$433
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/45:19 am
ORD
-
MBJ
1 stop6h 00m
American Airlines
Wed 11/113:57 pm
MBJ
-
ORD
Nonstop4h 49m
American Airlines
Deal found 7/29$437
This American Airlines deal was found by Cheapflights users on 7/27. 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 11/39:40 am
ORD
-
MBJ
Nonstop4h 17m
American Airlines
Tue 11/106:09 pm
MBJ
-
ORD
1 stop7h 35m
American Airlines
Deal found 7/27$438
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.
Mon 11/95:30 am
ORD
-
MBJ
1 stop10h 05m
Delta
Tue 11/176:00 pm
MBJ
-
ORD
1 stop16h 22m
Delta
Deal found 7/29$442
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.
Sun 11/156:00 am
MDW
-
MBJ
1 stop9h 35m
Delta
Sat 11/214:00 pm
MBJ
-
MDW
1 stop17h 50m
Delta
Deal found 7/29$442

Find 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 August 1, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$419
(Air Canada)

One-way from

$193
(American Airlines)

Popular in

December

Cheapest in

September

Average price

$532

Good round-trip deal

$547 or less

Good one-way deal

$196 or less
Provider with most accurate pricing for Chicago (CHI)-Montego Bay Sangster Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Montego Bay Sangster Intl flights.
Search Deals
From Chicago (CHI) to Montego Bay Sangster Intl
Search Deals
One-way flight from Chicago (CHI) to Montego Bay Sangster Intl
Search Deals
Highest demand for flights based on searches. 2% potential increase in price ($11 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($6 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in August 2026
Search Deals
Price to beat on a round-trip flight from Chicago (CHI) to Montego Bay Sangster Intl.
Search Deals
Price to beat on a one-way flight from Chicago (CHI) to Montego Bay Sangster Intl.
Search Deals

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 August 1, 2026.
Use the filters below to find and compare flights from Chicago to Montego Bay that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Sat 10/24

5:27 am-1:00 pm

1 stop7h 33m

Montego Bay Sangster Intl

Wed 10/28

12:59 pm-9:43 pm

1 stop8h 44m

$442

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Tue 9/22

6:30 am-12:55 pm

1 stop6h 25m

Montego Bay Sangster Intl

Tue 9/29

12:55 pm-9:25 pm

1 stop8h 30m

$442

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sun 12/6

6:00 am-4:35 pm

1 stop9h 35m

Montego Bay Sangster Intl

Thu 12/10

3:40 pm-10:56 pm

1 stop8h 16m

$442

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sat 8/29

5:55 am-12:25 pm

1 stop6h 30m

Montego Bay Sangster Intl

Wed 9/2

1:55 pm-8:45 pm

1 stop6h 50m

$442

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Wed 11/11

6:00 am-4:35 pm

1 stop9h 35m

Montego Bay Sangster Intl

Tue 11/24

3:40 pm-10:56 pm

1 stop8h 16m

$442

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Fri 12/4

6:00 am-4:35 pm

1 stop9h 35m

Montego Bay Sangster Intl

Wed 12/9

3:40 pm-10:56 pm

1 stop8h 16m

$442

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Sat 10/24

7:10 am-3:35 pm

2 stops8h 25m

Montego Bay Sangster Intl

Thu 10/29

4:44 pm-7:41 am

2 stops14h 57m

$447

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Mon 8/24

6:40 am-3:34 pm

1 stop8h 54m

Montego Bay Sangster Intl

Thu 8/27

4:59 pm-7:56 am

2 stops14h 57m

$447

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Wed 11/11

6:00 am-4:35 pm

1 stop9h 35m

Montego Bay Sangster Intl

Mon 11/23

6:00 pm-9:42 am

2 stops16h 42m

$447

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Sat 9/12

8:05 am-3:35 pm

1 stop7h 30m

Montego Bay Sangster Intl

Sat 9/19

1:14 pm-8:56 pm

1 stop7h 42m

$480

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/28

Showing 1-10 of 38 resultsSorted by cheapest first
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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 August.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
OvagoPrice Accuracy3 starsTrust Score*3 stars
AranGrantPrice 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

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

Currently, April is the cheapest month in which you can book a flight from Chicago to Montego Bay (average of $473). Flying from Chicago to Montego Bay in December is currently the most expensive (average of $658). 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 August 1, 2026.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Chicago to Montego Bay as you normally would.

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 August 1, 2026.

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

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

Airfare is below average for this route at the moment.
Chicago to Montego Bay flights typically cost between $455 and $640 in October.
The cheapest round-trip price found within the last 5 days was $419 on Air Canada (Oct 28-Nov 1).

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.

Charlotte (CLT) – chosen by Cheapflights users on 40% 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.

New York (JFK) is the most affordable 1-stop option, with an average round-trip price of $549.

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 Miami (MIA) have the shortest average one-way travel time for 1-stop routes: 5h 40m.

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 Charlotte (CLT) offer the fastest connection on this route, with an average layover time of 1h 20m.

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

The best time to book flights from Chicago to Montego Bay is 87 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.

The best insider tips for Chicago to Montego Bay flights

AI-powered summary based on content written by travel experts. AI can make mistakes.
Cheapflights partnered with top experts to bring you the best recommendations for your Chicago to Montego Bay trip
Our travel experts
Ramsey Qubein

Ramsey Qubein

Expert on ORD

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 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

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 August 1, 2026.
Read reviews from past customers who have flown Southwest,Delta, andUnited 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
4,229 reviews

Food

7.0

Boarding

8.1

Comfort

8.0

Overall

8.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Libby,Jun 2026

TUS - LAS

One delay in a 2 layover flight=a good trip. The crew was great.
Southwest
8.0
Very good
4,229 reviews
Southwest
8.0
Very good
4,229 reviews

Food

7.0

Boarding

8.1

Comfort

8.0

Overall

8.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Libby,Jun 2026

TUS - LAS

One delay in a 2 layover flight=a good trip. The crew was great.
Delta
7.8
Good
8,497 reviews
Southwest
8.0
Very good
4,229 reviews

Food

7.0

Boarding

8.1

Comfort

8.0

Overall

8.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Libby,Jun 2026

TUS - LAS

One delay in a 2 layover flight=a good trip. The crew was great.
United Airlines
7.4
Good
10,062 reviews
Southwest
8.0
Very good
4,229 reviews

Food

7.0

Boarding

8.1

Comfort

8.0

Overall

8.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Libby,Jun 2026

TUS - LAS

One delay in a 2 layover flight=a good trip. The crew was great.
American Airlines
7.1
Good
11,845 reviews
Southwest
8.0
Very good
4,229 reviews

Food

7.0

Boarding

8.1

Comfort

8.0

Overall

8.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Libby,Jun 2026

TUS - LAS

One delay in a 2 layover flight=a good trip. The crew was great.
Frontier
5.6
Fair
2,740 reviews
Southwest
8.0
Very good
4,229 reviews

Food

7.0

Boarding

8.1

Comfort

8.0

Overall

8.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Libby,Jun 2026

TUS - LAS

One delay in a 2 layover flight=a good trip. The crew was great.

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.

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

    A quick flight from Chicago to Montego Bay can take about 6h 25m. Delta provides one of the quickest options available for as low as $442. The distance between Chicago and Montego Bay is about 1709 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 Frontier. Our recent data shows that you can find tickets from as low as $144 on this airline. Additional options worth looking into are Delta and JetBlue, starting at $162 and $297 round-trip. Frontier is 73% 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 $108 on Frontier. Other airlines that offer cheap prices include American Airlines from $138 and United Airlines from $138 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 $466, our data indicates the cheapest price to be $172. The most popular route (Chicago O'Hare Intl - Montego Bay Sangster Intl), is priced around $428.

  • 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, April is the cheapest month in which you can book a flight from Chicago to Montego Bay (average of $473). Flying from Chicago to Montego Bay in December is currently the most expensive (average of $658). 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
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 August 1, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$144Average$686FlexibilityNo cancel feeOn-time62%
DeltaCheapest$162Average$575FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$297Average$510FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$302Average$529FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$317Average$542FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$467Average$653FlexibilityNo cancel feeOn-time63%

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