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$219+ Cheap flights from Montego Bay (MBJ) to Chicago (CHI)

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 11/2. Fares are subject to change and may not be available on all flights or dates of travel.
MBJ — CHI
Aug 27 — Sep 31
Thu 8/27
Thu 9/3
1 adult, Economy
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Cheap flight deals from Montego Bay to Chicago

Cheapest flights from Montego Bay to Chicago
Explore the most affordable flight options available from Montego Bay to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 28, 2026.

This American Airlines deal was found by Cheapflights users on 7/26. 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 9/42:12 pm
MBJ
-
ORD
Nonstop4h 43m
American Airlines
Fri 9/115:48 pm
ORD
-
MBJ
1 stop17h 29m
American Airlines
Deal found 7/26$396
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/174:50 pm
MBJ
-
ORD
2 stops15h 06m
Delta
Tue 9/225:30 am
ORD
-
MBJ
1 stop6h 18m
Delta
Deal found 7/27$397
This Delta deal was found by Cheapflights users on 7/25. 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.
Thu 10/292:26 pm
MBJ
-
MDW
1 stop8h 07m
Delta
Tue 12/296:00 am
MDW
-
MBJ
1 stop13h 41m
Delta
Deal found 7/25$397
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.
Fri 8/215:08 pm
MBJ
-
ORD
1 stop7h 27m
American Airlines
Mon 8/246:45 am
ORD
-
MBJ
1 stop7h 38m
American Airlines
Deal found 7/27$406
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.
Thu 9/171:54 pm
MBJ
-
ORD
2 stops10h 05m
American Airlines
Tue 9/226:00 am
ORD
-
MBJ
1 stop5h 56m
American Airlines
Deal found 7/27$411
This Air Canada deal was found by Cheapflights users on 7/26. 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.
Mon 11/236:20 pm
MBJ
-
ORD
1 stop16h 03m
Air Canada
Sun 11/294:30 pm
ORD
-
MBJ
1 stop23h 50m
Air Canada
Deal found 7/26$425
This United Airlines deal was found by Cheapflights users on 7/25. 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.
Mon 11/232:54 pm
MBJ
-
ORD
Nonstop4h 26m
United Airlines
Sun 11/298:40 am
ORD
-
MBJ
Nonstop4h 08m
United Airlines
Deal found 7/25$432
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/172:15 pm
MBJ
-
MDW
2 stops8h 10m
Southwest
Tue 9/226:30 am
MDW
-
MBJ
1 stop6h 25m
Southwest
Deal found 7/27$444
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.
Mon 11/231:10 pm
MBJ
-
ORD
1 stop10h 18m
American Airlines
Sun 11/299:40 am
ORD
-
MBJ
Nonstop4h 15m
American Airlines
Deal found 7/27$445
This American Airlines deal was found by Cheapflights users on 7/23. 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 8/225:08 pm
MBJ
-
ORD
1 stop14h 26m
American Airlines
Mon 8/249:00 am
ORD
-
MBJ
Nonstop4h 12m
American Airlines
Deal found 7/23$454
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/222:26 pm
MBJ
-
MDW
1 stop8h 10m
Delta
Mon 8/246:05 am
MDW
-
MBJ
1 stop9h 29m
Delta
Deal found 7/28$531
This Southwest deal was found by Cheapflights users on 7/25. 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 8/2211:40 am
MBJ
-
MDW
1 stop8h 50m
Southwest
Mon 8/247:25 am
MDW
-
MBJ
1 stop5h 50m
Southwest
Deal found 7/25$554

Find flight deals from Montego Bay to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Montego Bay (MBJ) to Chicago (CHI). 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 July 28, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$396
(American Airlines)

One-way from

$219
(American Airlines)

Good round-trip deal

$385 or less

Good one-way deal

$245 or less
Provider with most accurate pricing for Montego Bay Sangster Intl-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Montego Bay Sangster Intl-Chicago (CHI) flights.
Search Deals
From Montego Bay Sangster Intl to Chicago (CHI)
Search Deals
One-way flight from Montego Bay Sangster Intl to Chicago (CHI)
Search Deals
Price to beat on a round-trip flight from Montego Bay Sangster Intl to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from Montego Bay Sangster Intl to Chicago (CHI).
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Montego Bay to Chicago 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 July 28, 2026.
Use the filters below to find and compare flights from Montego Bay to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Thu 9/17

4:50 pm-7:56 am

2 stops15h 06m

Chicago O'Hare Intl

Tue 9/22

5:30 am-11:48 am

1 stop6h 18m

$397

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Thu 10/29

2:26 pm-10:33 pm

1 stop8h 07m

Chicago Midway

Tue 12/29

9:30 am-8:41 pm

2 stops10h 11m

$397

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Thu 9/17

1:14 pm-10:45 pm

1 stop9h 31m

Chicago Midway

Tue 9/22

6:05 am-11:48 am

1 stop5h 43m

$397

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Fri 9/4

12:47 pm-7:42 am

1 stop18h 55m

Chicago O'Hare Intl

Fri 9/11

5:48 pm-11:17 am

1 stop17h 29m

$406

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Fri 8/21

5:08 pm-12:35 am

1 stop7h 27m

Chicago O'Hare Intl

Mon 8/24

6:45 am-2:23 pm

1 stop7h 38m

$406

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Thu 9/17

1:54 pm-11:59 pm

2 stops10h 05m

Chicago O'Hare Intl

Tue 9/22

6:00 am-11:56 am

1 stop5h 56m

$411

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Mon 11/23

6:20 pm-9:23 am

1 stop16h 03m

Chicago O'Hare Intl

Sun 11/29

4:30 pm-5:20 pm

1 stop23h 50m

$425
Quickest round-trip

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Mon 11/23

2:54 pm-6:20 pm

Nonstop4h 26m

Chicago O'Hare Intl

Sun 11/29

8:40 am-1:48 pm

Nonstop4h 08m

$432

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Thu 9/17

2:15 pm-10:25 pm

2 stops8h 10m

Chicago Midway

Tue 9/22

6:30 am-12:55 pm

1 stop6h 25m

$444

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Mon 11/23

1:10 pm-10:28 pm

1 stop10h 18m

Chicago O'Hare Intl

Sun 11/29

9:40 am-2:55 pm

Nonstop4h 15m

$455

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/23

Showing 1-10 of 35 resultsSorted by cheapest first
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3
4

Compare providers for flights from Montego Bay to Chicago

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 Montego Bay to Chicago in July.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
MytripPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy2 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 Montego Bay-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Montego Bay-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Montego Bay-Chicago flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Montego Bay-Chicago 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 Montego Bay-Chicago 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 Montego Bay to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Montego Bay 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 Montego Bay to Chicago

What is the cheapest time of day to fly from MBJ to CHI?

Find hourly flight availability from Montego Bay to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated July 28, 2026.

When flying from Montego Bay to Chicago, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Weekly flight availability from Montego Bay to Chicago

Explore weekly flight availability from Montego Bay to Chicago. 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 July 28, 2026.

The most flights from MBJ to CHI 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).

The best insider tips for Montego Bay to Chicago 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 Montego Bay to Chicago 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 Chicago

Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated July 28, 2026.
See what other customers who have flown with American Airlines from Montego Bay to Chicago have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
American Airlines
7.1
Good
11,839 reviews

Entertainment

6.8

Comfort

7.2

Crew

7.9

Overall

7.1

Food

6.4

Boarding

7.5

Reviews

1 / 20
2.0
Mediocre

Anonymous,Aug 2025

BNA - ORD

My flight was 8 hours delayed, so I missed my connecting flight to Dublin. I understand it’s not the staff’s fault but the lack of sympathy and apology was appalling. I had been sat in the airport since 4am until 3pm and they did not seem understanding. Not good. Need better customer service.
American Airlines
7.1
Good
11,839 reviews
American Airlines
7.1
Good
11,839 reviews

Entertainment

6.8

Comfort

7.2

Crew

7.9

Overall

7.1

Food

6.4

Boarding

7.5

Reviews

1 / 20
2.0
Mediocre

Anonymous,Aug 2025

BNA - ORD

My flight was 8 hours delayed, so I missed my connecting flight to Dublin. I understand it’s not the staff’s fault but the lack of sympathy and apology was appalling. I had been sat in the airport since 4am until 3pm and they did not seem understanding. Not good. Need better customer service.

Related info for your journey

Find useful and relevant information for your journey from Montego Bay to Chicago. 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 from for flights from Montego Bay to Chicago?

    Montego Bay Sangster Intl (MBJ) is the airport you will fly out of if you book a flight from Montego Bay to Chicago. You should not have trouble finding flights to Chicago from Sangster Intl; the airport handles an average of 1 outbound flight to Chicago per day. You should also have plenty of airline options to choose from since 2 airlines have flights from the Montego Bay airport to Chicago. It is only a 2.3 mi journey to Sangster Intl (MBJ) from Montego Bay’s city center.

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

    Airlines like Delta, American Airlines, and Air Canada fly from Montego Bay to Chicago in about 15h 06m. The time it takes to get you to your destination can typically vary by up to 3h 49m. Montego Bay and Chicago are separated by a distance of 1724 mi. This flight may include one or multiple stops.

  • What are the cheapest airlines flying from Montego Bay to Chicago round-trip?

    According to our current data, United Airlines ($280), and American Airlines ($281) offers the cheapest pricing from Montego Bay to Chicago.

  • What are the cheapest airlines to fly from Montego Bay to Chicago one-way?

    For one-way options, check prices for United Airlines. According to our data, you can fly for as low as $185. Users have also found prices from $192 and $198 on American Airlines and Frontier, respectively.

  • What are the cheapest flights from Montego Bay to Chicago?

    Looking at all options, your cheapest flight can be booked for $204. While the most popular route (Montego Bay Sangster Intl - Chicago O'Hare Intl) can be booked for $413 on average, our data indicates $388 when flying from Montego Bay to Chicago.

  • Can I find deals for flights from Montego Bay to Chicago that include hotel bookings?

    Yes. In addition to deals on Montego Bay to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Montego Bay to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Montego Bay to Chicago.

  • Can I find deals for business class flights from Montego Bay to Chicago?

    Yes. Cheapflights offers flight deals from Montego Bay to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

See more FAQs

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Benton Harbor
Lansing
Merrillville
Valparaiso
Hammond
Saint Joseph
Porter

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Alternative routes for Montego Bay to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
Montego Bay to O'Hare Intl flights
Kingston to O'Hare Intl flights

Top 2 airlines flying from Montego Bay to Chicago

Discover the top 2 airlines that operate flights from Montego Bay to Chicago. 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 July 28, 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$280Average$431FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$281Average$402FlexibilityNo cancel feeOn-time71%

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