Montego Bay

$111+ 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 2/24. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MBJ
Mar 13 — Mar 201
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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 January or September, booked 28 days in advance, depart on a Tuesday or Sunday 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 February 11, 2026.

This Mytrip deal was found by Cheapflights users on 2/9. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/312:44 pm
ORD
-
MBJ
3 stops22h 18m
Spirit Airlines
Tue 3/1011:57 am
MBJ
-
ORD
1 stop7h 14m
Spirit Airlines
Deal found 2/9$364
This CheapOair deal was found by Cheapflights users on 2/9. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/174:28 pm
ORD
-
MBJ
1 stop19h 44m
Multiple Airlines
Tue 4/2112:00 pm
MBJ
-
ORD
1 stop11h 41m
Multiple Airlines
Deal found 2/9$365
This American Airlines deal was found by Cheapflights users on 2/9. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/167:15 am
ORD
-
MBJ
1 stop6h 10m
American Airlines
Wed 4/2210:17 am
MBJ
-
ORD
1 stop13h 37m
American Airlines
Deal found 2/9$366
This CheapOair deal was found by Cheapflights users on 2/10. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/18:42 pm
ORD
-
MBJ
2 stops14h 20m
Spirit Airlines
Fri 3/61:00 pm
MBJ
-
ORD
1 stop11h 47m
Spirit Airlines
Deal found 2/10$367
This Kiwi.com deal was found by Cheapflights users on 2/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/278:16 pm
ORD
-
MBJ
1 stop14h 46m
Spirit Airlines
Mon 3/21:00 pm
MBJ
-
ORD
1 stop23h 22m
Spirit Airlines
Deal found 2/10$369
This CheapOair deal was found by Cheapflights users on 2/10. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/288:16 pm
ORD
-
MBJ
1 stop14h 46m
Spirit Airlines
Tue 3/31:00 pm
MBJ
-
ORD
2 stops31h 47m
Spirit Airlines
Deal found 2/10$370
This American Airlines deal was found by Cheapflights users on 2/10. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/88:05 am
ORD
-
MBJ
Nonstop4h 06m
American Airlines
Sat 3/141:14 pm
MBJ
-
ORD
Nonstop4h 41m
American Airlines
Deal found 2/10$371
This Southwest deal was found by Cheapflights users on 2/10. 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.
Sat 4/189:55 am
MDW
-
MBJ
Nonstop3h 50m
Southwest
Thu 4/232:55 pm
MBJ
-
MDW
1 stop7h 25m
Southwest
Deal found 2/10$372
This CheapOair deal was found by Cheapflights users on 2/10. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/88:16 pm
ORD
-
MBJ
1 stop14h 46m
Multiple Airlines
Sat 3/143:32 pm
MBJ
-
ORD
1 stop19h 20m
Multiple Airlines
Deal found 2/10$373
This Southwest deal was found by Cheapflights users on 2/9. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/116:30 am
MDW
-
MBJ
1 stop8h 00m
Southwest
Sun 3/1512:30 pm
MBJ
-
MDW
Nonstop4h 20m
Southwest
Deal found 2/9$375
This American Airlines deal was found by Cheapflights users on 2/9. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/710:15 pm
ORD
-
MBJ
1 stop14h 49m
American Airlines
Sat 3/141:14 pm
MBJ
-
ORD
Nonstop4h 41m
American Airlines
Deal found 2/9$375
This Air Canada deal was found by Cheapflights users on 2/9. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/175:35 pm
ORD
-
MBJ
1 stop17h 45m
Air Canada
Sun 6/2112:30 pm
MBJ
-
ORD
1 stop20h 30m
Air Canada
Deal found 2/9$376

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 February 11, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$364
(Mytrip)

One-way from

$111
(Cheapflightsfares)

Popular in

June

Cheapest in

January

Average price

$546

Good round-trip deal

$484 or less

Good one-way deal

$224 or less
Provider with most accurate pricing for Chicago (CHI)-Montego Bay Sangster Intl flight deals.
Provider most trusted by Cheapflights users for Chicago (CHI)-Montego Bay Sangster Intl flights.
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. 7% potential increase in price ($46 potential increase over avg. RT price).
Cheapest flight prices on average. 1% potential price decrease ($11 potential savings vs. average RT price).
Average for round-trip flights in February 2026
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.

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 February 11, 2026.
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

Tue 4/14

7:00 am-3:17 pm

2 stops8h 17m

Montego Bay Sangster Intl

Wed 4/22

2:09 pm-9:25 pm

1 stop7h 16m

$367

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Fri 2/20

5:15 am-12:02 pm

1 stop5h 47m

Montego Bay Sangster Intl

Fri 2/27

1:00 pm-9:13 pm

1 stop9h 13m

$370

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sat 4/18

9:55 am-1:45 pm

Nonstop3h 50m

Montego Bay Sangster Intl

Thu 4/23

2:55 pm-10:20 pm

1 stop7h 25m

$372

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Thu 4/23

1:35 pm-11:02 am

2 stops21h 27m

Montego Bay Sangster Intl

Tue 4/28

12:00 pm-7:48 pm

1 stop7h 48m

$377

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sat 4/18

9:55 am-1:45 pm

Nonstop3h 50m

Montego Bay Sangster Intl

Tue 4/21

12:15 pm-9:25 pm

1 stop9h 10m

$381

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Sat 3/7

6:51 pm-2:04 pm

1 stop18h 13m

Montego Bay Sangster Intl

Sat 3/14

3:04 pm-9:45 am

1 stop18h 41m

$385

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Wed 3/11

6:00 am-3:28 pm

1 stop9h 28m

Montego Bay Sangster Intl

Wed 3/18

1:38 pm-10:31 pm

1 stop8h 53m

$388

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Tue 5/12

6:00 am-3:29 pm

1 stop9h 29m

Montego Bay Sangster Intl

Sun 5/17

4:55 pm-11:59 pm

1 stop7h 04m

$389

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Wed 4/29

6:00 am-12:54 pm

1 stop6h 54m

Montego Bay Sangster Intl

Sat 5/2

2:09 pm-10:28 pm

1 stop8h 19m

$389

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sat 4/25

6:00 am-12:54 pm

1 stop6h 54m

Montego Bay Sangster Intl

Wed 4/29

12:44 pm-10:28 pm

1 stop9h 44m

$389

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/9

Showing 1-10 of 37 results
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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 February.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
AranGrantPrice Accuracy2 starsTrust Score*2 stars
OvagoPrice Accuracy2 starsTrust Score*3 stars
CheapOairPrice Accuracy3 starsTrust Score*3 stars
CheapflightsfaresPrice Accuracy2 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 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

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 February 6, 2026.

The best time to book flights from Chicago to Montego Bay is 28 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 $95). Flying from Chicago to Montego Bay in August is currently the most expensive (average of $384). 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 February 11, 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.

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 63% 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 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.

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.

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.

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 February 11, 2026.
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.

Boarding

8.1

Crew

8.6

Overall

8.0

Entertainment

7.5

Comfort

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

Boarding

8.1

Crew

8.6

Overall

8.0

Entertainment

7.5

Comfort

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

Boarding

8.1

Crew

8.6

Overall

8.0

Entertainment

7.5

Comfort

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

Boarding

8.1

Crew

8.6

Overall

8.0

Entertainment

7.5

Comfort

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

Boarding

8.1

Crew

8.6

Overall

8.0

Entertainment

7.5

Comfort

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

Boarding

8.1

Crew

8.6

Overall

8.0

Entertainment

7.5

Comfort

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

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 3h 50m. Delta provides one of the quickest options available for as low as $372. 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 Spirit Airlines. Our recent data shows that you can find tickets from as low as $130 on this airline. Additional options worth looking into are Frontier and Delta, starting at $144 and $178 round-trip. Spirit Airlines is 77% 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 $98 on Spirit Airlines. Other airlines that offer cheap prices include United Airlines from $157 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 $390, our data indicates the cheapest price to be $170. The most popular route (Chicago O'Hare Intl - Montego Bay Sangster Intl), is priced around $276.

  • 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 $95). Flying from Chicago to Montego Bay in August is currently the most expensive (average of $384). 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
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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 February 11, 2026.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$130Average$384FlexibilityNo cancel feeOn-time65%
FrontierCheapest$144Average$662FlexibilityNo cancel feeOn-time62%
DeltaCheapest$178Average$563FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$356Average$601FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$412Average$576FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$518Average$719FlexibilityNo cancel feeOn-time63%

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