HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Chicago

$162+ 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 11/6. Fares are subject to change and may not be available on all flights or dates of travel.
MBJ — CHI
Nov 19 — Nov 261
Wed 11/19
Wed 11/26
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Montego Bay to Chicago 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

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Find 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 October 20, 2025.

This American Airlines deal was found by Cheapflights users on 10/19. 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 12/33:12 pmMBJ - ORD
Nonstop4h 47mAmerican Airlines
Wed 12/106:45 amORD - MBJ
1 stop8h 04mAmerican Airlines
Deal found 10/19$325
This Expedia deal was found by Cheapflights users on 10/19. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/2112:10 pmMBJ - ORD
2 stops30h 44mMultiple Airlines
Tue 11/115:10 amORD - MBJ
1 stop5h 52mMultiple Airlines
Deal found 10/19$344
This American Airlines deal was found by Cheapflights users on 10/19. 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 12/204:27 pmMBJ - ORD
Nonstop4h 37mAmerican Airlines
Sat 1/37:35 pmORD - MBJ
1 stop16h 48mAmerican Airlines
Deal found 10/19$358
This Delta deal was found by Cheapflights users on 10/19. 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.
Wed 12/33:38 pmMBJ - MDW
1 stop9h 09mDelta
Wed 12/106:00 amMDW - MBJ
1 stop9h 33mDelta
Deal found 10/19$359
This American Airlines deal was found by Cheapflights users on 10/19. 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 10/211:50 pmMBJ - ORD
Nonstop4h 33mAmerican Airlines
Tue 11/1110:15 amORD - MBJ
Nonstop4h 13mAmerican Airlines
Deal found 10/19$388
This American Airlines deal was found by Cheapflights users on 10/20. 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 12/122:30 pmMBJ - ORD
Nonstop4h 47mAmerican Airlines
Fri 1/28:05 amORD - MBJ
Nonstop4h 13mAmerican Airlines
Deal found 10/20$405
This Delta deal was found by Cheapflights users on 10/19. 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.
Fri 12/122:29 pmMBJ - ORD
1 stop8h 27mDelta
Fri 1/26:45 amORD - MBJ
1 stop12h 56mDelta
Deal found 10/19$411
This Delta deal was found by Cheapflights users on 10/19. 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 12/203:38 pmMBJ - MDW
1 stop7h 44mDelta
Sat 1/39:50 amMDW - MBJ
1 stop9h 51mDelta
Deal found 10/19$411
This United Airlines deal was found by Cheapflights users on 10/20. 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.
Wed 11/121:25 pmMBJ - ORD
1 stop8h 51mUnited Airlines
Fri 11/289:08 pmORD - MBJ
1 stop15h 57mUnited Airlines
Deal found 10/20$415
This Frontier deal was found by Cheapflights users on 10/19. 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.
Thu 11/202:43 pmMBJ - MDW
1 stop9h 00mFrontier
Sun 11/236:05 amMDW - MBJ
1 stop8h 30mFrontier
Deal found 10/19$432
This Kiwi.com deal was found by Cheapflights users on 10/19. 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 11/191:15 pmMBJ - MDW
2 stops27h 05mMultiple Airlines
Sun 11/236:05 amMDW - MBJ
1 stop8h 30mMultiple Airlines
Deal found 10/19$698
This Mytrip deal was found by Cheapflights users on 10/19. 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.
Sat 12/207:25 pmMBJ - MDW
2 stops16h 41mMultiple Airlines
Sat 1/311:48 amMDW - MBJ
2 stops22h 42mMultiple Airlines
Deal found 10/19$758

Cheap 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 October 20, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$325
(American Airlines)

One-way from

$162
(Cheapflightsfares)

Popular in

January

Cheapest in

September

Good round-trip deal

$293 or less

Good one-way deal

$217 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
Highest demand for flights based on searches. 13% potential increase in price ($75 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($14 potential savings vs. average RT price).
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 October 20, 2025.
Use the filters below to find and compare flights from Montego Bay to Chicago that are best for you.

Fly from

Montego Bay

Fly to

Chicago

Route

Depart

Return

Price

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Wed 12/3

3:12 pm-6:59 pm

Nonstop4h 47m

Chicago O'Hare Intl

Wed 12/10

6:45 am-3:49 pm

1 stop8h 04m

$325

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Sat 12/20

4:27 pm-8:04 pm

Nonstop4h 37m

Chicago O'Hare Intl

Sat 1/3

7:35 pm-1:23 pm

1 stop16h 48m

$358

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Wed 12/3

3:38 pm-11:47 pm

1 stop9h 09m

Chicago Midway

Wed 12/10

6:00 am-4:33 pm

1 stop9h 33m

$359

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Fri 12/12

2:30 pm-6:17 pm

Nonstop4h 47m

Chicago O'Hare Intl

Fri 1/2

8:05 am-1:18 pm

Nonstop4h 13m

$405

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Wed 11/12

2:48 pm-6:13 pm

Nonstop4h 25m

Chicago O'Hare Intl

Fri 11/28

9:08 pm-2:05 pm

1 stop15h 57m

$410

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Wed 11/12

5:59 pm-8:06 am

2 stops15h 07m

Chicago O'Hare Intl

Thu 11/27

6:45 am-4:34 pm

2 stops8h 49m

$411

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Fri 12/12

2:29 pm-9:56 pm

1 stop8h 27m

Chicago O'Hare Intl

Fri 1/2

6:45 am-8:41 pm

1 stop12h 56m

$411

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Sat 12/20

3:38 pm-10:22 pm

1 stop7h 44m

Chicago Midway

Sat 1/3

9:50 am-8:41 pm

1 stop9h 51m

$411

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Thu 11/20

2:43 pm-10:43 pm

1 stop9h 00m

Chicago Midway

Sun 11/23

6:05 am-3:35 pm

1 stop8h 30m

$432

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Wed 11/19

1:15 pm-3:20 pm

2 stops27h 05m

Chicago Midway

Sun 11/23

6:05 am-3:35 pm

1 stop8h 30m

$698

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/18

Showing 1-10 of 33 results
1
2
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 October.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice 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 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 month to book a flight from Montego Bay to Chicago?

Currently, December is the cheapest month in which you can book a flight from Montego Bay to Chicago (average of $251). Flying from Montego Bay to Chicago in April is currently the most expensive (average of $440). 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 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 October 20, 2025.

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 October 20, 2025.

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

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 Montego Bay to Chicago trip
Airports
MBJ

Check-in lines at MBJ can be long; allow extra time if you need to check baggage.

Read more about MBJby Mark Chesnut
ORD

At ORD, immigration lines can be extensive. Prepare for a long walk to reach immigration after your flight.

Read more about ORDby Ramsey Qubein
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

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 October 20, 2025.
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
7.2
Good
11,024 reviews

Comfort

7.2

Food

6.4

Crew

8.0

Overall

7.2

Boarding

7.5

Entertainment

6.9

Reviews

1 / 20
2.0
Mediocre

Nordia,Sep 2025

KIN - MIA

We were to land in Miami sometime after 3pm but couldn’t due to bad weather, we flew around for 2 hrs until we had to land in Forth Myers to refuel, we had to sit another 2 hrs at Forth Myers until given the clearance to refuel, we were hungry, thirsty and frustrated at that point. All the had on the flight to offer was a small plastic glass of water and a pack of biscoff, I requested a cup of tea and was told none was there. We were basically at another airport and not one of the staff could consider that the passengers might be hungry or thirsty being on a plane for around 8 hrs, which you weren’t prepared for, at least find some hot water on board.
American Airlines
7.2
Good
11,024 reviews
American Airlines
7.2
Good
11,024 reviews

Comfort

7.2

Food

6.4

Crew

8.0

Overall

7.2

Boarding

7.5

Entertainment

6.9

Reviews

1 / 20
2.0
Mediocre

Nordia,Sep 2025

KIN - MIA

We were to land in Miami sometime after 3pm but couldn’t due to bad weather, we flew around for 2 hrs until we had to land in Forth Myers to refuel, we had to sit another 2 hrs at Forth Myers until given the clearance to refuel, we were hungry, thirsty and frustrated at that point. All the had on the flight to offer was a small plastic glass of water and a pack of biscoff, I requested a cup of tea and was told none was there. We were basically at another airport and not one of the staff could consider that the passengers might be hungry or thirsty being on a plane for around 8 hrs, which you weren’t prepared for, at least find some hot water on board.

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 4 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 American Airlines, Delta, and Frontier fly from Montego Bay to Chicago in about 4h 47m. The time it takes to get you to your destination can typically vary by up to 4h 22m. 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, Spirit Airlines ($251), American Airlines ($348), and Southwest ($392) offers the cheapest pricing from Montego Bay to Chicago. These flights start at 46% lower than the current average price 3 months from now.

  • 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 $203. Users have also found prices from $207 and $209 on Frontier and Delta, respectively.

  • What are the most reliable airlines from Montego Bay to Chicago?

    The top 3 most reliable airlines when flying from Montego Bay to Chicago are American Airlines (85%), British Airways (82%) and United Airlines (0%).

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

    Looking at all options, your cheapest flight can be booked for $203. While the most popular route (Montego Bay Sangster Intl - Chicago O'Hare Intl) can be booked for $344 on average, our data indicates $351 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.

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

    Currently, December is the cheapest month in which you can book a flight from Montego Bay to Chicago (average of $251). Flying from Montego Bay to Chicago in April is currently the most expensive (average of $440). 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 Chicago?

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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

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
Montego Bay to Midway flights

Top 4 airlines flying from Montego Bay to Chicago

Discover the top 4 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 October 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$251Average$316FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$348Average$479FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$392Average$536FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$409Average$484FlexibilityNo cancel feeOn-time69%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.