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$150+ 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 5/21. Fares are subject to change and may not be available on all flights or dates of travel.
MBJ — CHI
avr. 22 — avr. 291
mar. 4/22
mar. 4/29
1 adult, Economy
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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 avril 17, 2025.

Most accurate provider

AranGrant
3 stars

Most trusted provider

AranGrant
3 stars

Round-trip from

$291
(Cheapflightsfares)

One-way from

$150
(Cheapflightsfares)

Popular in

January

Cheapest in

May

Average price

$406

Good round-trip deal

$479 or less

Good one-way deal

$295 or less
Provider with most accurate pricing for Montego Bay Sangster Intl-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Montego Bay Sangster Intl-Chicago (CHI) flights.
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From Montego Bay Sangster Intl to Chicago (CHI)
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One-way flight from Montego Bay Sangster Intl to Chicago (CHI)
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Highest demand for flights based on searches. 8% potential increase in price ($45 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 April 2025
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Price to beat on a round-trip flight from Montego Bay Sangster Intl to Chicago (CHI).
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Price to beat on a one-way flight from Montego Bay Sangster Intl to Chicago (CHI).
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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 avril 17, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 4/16. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 6/1012:07 pmMBJ - ORD
1 stop10h 57mSpirit Airlines
mer. 6/255:05 amORD - MBJ
1 stop5h 57mSpirit Airlines
Deal found 4/16$291
This American Airlines deal was found by Cheapflights users on 4/16. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jeu. 5/82:25 pmMBJ - ORD
Nonstop4h 35mAmerican Airlines
lun. 5/199:00 amORD - MBJ
Nonstop4h 00mAmerican Airlines
Deal found 4/16$398
This Delta deal was found by Cheapflights users on 4/16. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ven. 5/212:11 pmMBJ - ORD
1 stop6h 49mDelta
mer. 5/77:10 amORD - MBJ
2 stops8h 20mDelta
Deal found 4/16$404
This Delta deal was found by Cheapflights users on 4/16. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ven. 5/212:11 pmMBJ - MDW
1 stop10h 11mDelta
mer. 5/76:00 amMDW - MBJ
1 stop6h 58mDelta
Deal found 4/16$404
This Booking.com deal was found by Cheapflights users on 4/16. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sam. 5/173:17 pmMBJ - MDW
1 stop22h 17mFrontier
ven. 5/238:55 pmMDW - MBJ
1 stop14h 58mFrontier
Deal found 4/16$412
This Expedia deal was found by Cheapflights users on 4/17. 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.
jeu. 6/1912:07 pmMBJ - ORD
1 stop11h 38mMultiple Airlines
jeu. 7/36:16 pmORD - MBJ
1 stop13h 42mMultiple Airlines
Deal found 4/17$414
This United Airlines deal was found by Cheapflights users on 4/16. 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.
sam. 8/21:51 pmMBJ - ORD
Nonstop4h 29mUnited Airlines
sam. 8/306:00 amORD - MBJ
1 stop7h 30mUnited Airlines
Deal found 4/16$520
This Southwest deal was found by Cheapflights users on 4/17. 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.
mer. 5/712:00 pmMBJ - MDW
1 stop7h 50mSouthwest
dim. 9/79:15 pmMDW - MBJ
2 stops16h 45mSouthwest
Deal found 4/17$548
This Air Canada deal was found by Cheapflights users on 4/16. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 8/1212:10 pmMBJ - ORD
2 stops19h 49mAir Canada
dim. 8/313:35 pmORD - MBJ
2 stops19h 40mAir Canada
Deal found 4/16$573

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 avril 17, 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

mar. 6/10

12:07 pm-11:04 pm

1 stop10h 57m

Chicago O'Hare Intl

mer. 6/25

5:05 am-11:02 am

1 stop5h 57m

$291

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

jeu. 5/8

2:25 pm-7:00 pm

Nonstop4h 35m

Chicago O'Hare Intl

lun. 5/19

9:00 am-1:00 pm

Nonstop4h 00m

$398

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

ven. 5/2

12:11 pm-7:00 pm

1 stop6h 49m

Chicago O'Hare Intl

mer. 5/7

7:10 am-3:30 pm

2 stops8h 20m

$404

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

ven. 5/2

12:11 pm-10:22 pm

1 stop10h 11m

Chicago Midway

mer. 5/7

6:00 am-12:58 pm

1 stop6h 58m

$404

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

sam. 5/17

3:17 pm-1:34 pm

1 stop22h 17m

Chicago Midway

ven. 5/23

8:55 pm-11:53 am

1 stop14h 58m

$412

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

jeu. 6/19

12:07 pm-11:45 pm

1 stop11h 38m

Chicago O'Hare Intl

jeu. 7/3

6:16 pm-7:58 am

1 stop13h 42m

$414

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

sam. 8/2

2:40 pm-11:12 pm

1 stop8h 32m

Chicago O'Hare Intl

sam. 8/30

6:00 am-1:30 pm

1 stop7h 30m

$473

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

mer. 5/7

12:00 pm-7:50 pm

1 stop7h 50m

Chicago Midway

dim. 9/7

9:15 pm-2:00 pm

2 stops16h 45m

$548

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

mar. 6/10

12:10 pm-6:53 pm

2 stops30h 43m

Chicago O'Hare Intl

mer. 6/25

8:40 am-11:15 am

2 stops26h 35m

$550

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

mer. 5/21

12:07 pm-11:04 pm

1 stop10h 57m

$150

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/17

Showing 1-10 of 23 results
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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 April.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*2 stars
eDreamsPrice 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 Montego Bay-Chicago flights, users find the pricing of AranGrant to be most consistent on Cheapflights vs. AranGrant Users can find the same prices on Montego Bay-Chicago flight deals on Cheapflights vs. AranGrant >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 AranGrant the most. AranGrant 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.

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

For international arrivals at ORD, immigration lines can be extensive. Prepare for long walks to reach immigration.

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

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, August is the cheapest month in which you can book a flight from Montego Bay to Chicago (average of $245). Flying from Montego Bay to Chicago in March is currently the most expensive (average of $321). 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 avril 17, 2025.

It’s optimal to fly from Montego Bay to Chicago at noon. By choosing this option you can save up to 2% on the cost of your flight, compared to a flight in the morning.

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 avril 17, 2025.

The most flights from MBJ to CHI are scheduled on a Monday (3 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (2 on average).

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 avril 17, 2025.
Read reviews from past customers who have flown Southwest, Delta and Copa Airlines from Montego Bay to Chicago. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,280 reviews

Food

7.1

Comfort

8.0

Entertainment

7.6

Boarding

8.2

Overall

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Southwest
8.0
Very good
4,280 reviews
Southwest
8.0
Very good
4,280 reviews

Food

7.1

Comfort

8.0

Entertainment

7.6

Boarding

8.2

Overall

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Delta
8.0
Very good
7,916 reviews
Southwest
8.0
Very good
4,280 reviews

Food

7.1

Comfort

8.0

Entertainment

7.6

Boarding

8.2

Overall

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Copa Airlines
7.6
Good
1,409 reviews
Southwest
8.0
Very good
4,280 reviews

Food

7.1

Comfort

8.0

Entertainment

7.6

Boarding

8.2

Overall

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Avelo Airlines
7.5
Good
Southwest
8.0
Very good
4,280 reviews

Food

7.1

Comfort

8.0

Entertainment

7.6

Boarding

8.2

Overall

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
United Airlines
7.4
Good
8,667 reviews
Southwest
8.0
Very good
4,280 reviews

Food

7.1

Comfort

8.0

Entertainment

7.6

Boarding

8.2

Overall

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

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 2 outbound flights 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.

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

    According to our current data, Spirit Airlines ($291), American Airlines ($398), and Delta ($404) offers the cheapest pricing from Montego Bay to Chicago. These flights start at 37% 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 Spirit Airlines. According to our data, you can fly for as low as $150. Users have also found prices from $242 and $242 on United Airlines and Frontier, 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 (74%), British Airways (74%) and United Airlines (70%).

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

    Looking at all options, your cheapest flight can be booked for $221. While the most popular route (Montego Bay Sangster Intl - Chicago O'Hare Intl) can be booked for $291 on average our data indicates $454 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, August is the cheapest month in which you can book a flight from Montego Bay to Chicago (average of $245). Flying from Montego Bay to Chicago in March is currently the most expensive (average of $321). 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
Merrillville
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

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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.
Kingston to O'Hare Intl flights
Montego Bay 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 avril 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$251Average$309FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$255Average$480FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$357Average$483FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$451Average$744FlexibilityNo cancel feeOn-time63%

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