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$157+ 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 2/24. Fares are subject to change and may not be available on all flights or dates of travel.
MBJ — CHI
Jan 3 — Jan 101
Sat 1/3
Sat 1/10
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 December 4, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 12/2. 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.
Tue 12/91:05 pmMBJ - ORD
1 stop12h 04mSpirit Airlines
Tue 1/65:00 amORD - MBJ
1 stop6h 05mSpirit Airlines
Deal found 12/2$255
This Kiwi.com deal was found by Cheapflights users on 12/2. 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.
Thu 12/111:05 pmMBJ - ORD
1 stop7h 56mSpirit Airlines
Tue 1/65:00 amORD - MBJ
1 stop6h 05mSpirit Airlines
Deal found 12/2$282
This Kiwi.com deal was found by Cheapflights users on 12/2. 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.
Tue 12/91:05 pmMBJ - ORD
1 stop7h 56mSpirit Airlines
Thu 1/88:43 pmORD - MBJ
1 stop14h 19mSpirit Airlines
Deal found 12/2$287
This Kiwi.com deal was found by Cheapflights users on 12/2. 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.
Tue 12/91:05 pmMBJ - ORD
1 stop7h 56mSpirit Airlines
Mon 1/55:00 amORD - MBJ
1 stop6h 05mSpirit Airlines
Deal found 12/2$303
This Frontier deal was found by Cheapflights users on 12/4. 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.
Sat 12/203:34 pmMBJ - ORD
1 stop8h 12mFrontier
Sat 1/36:10 amORD - MBJ
1 stop7h 19mFrontier
Deal found 12/4$307
This Frontier deal was found by Cheapflights users on 12/4. 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.
Sat 12/203:34 pmMBJ - MDW
1 stop7h 38mFrontier
Sat 1/36:12 amMDW - MBJ
1 stop7h 17mFrontier
Deal found 12/4$307
This Kiwi.com deal was found by Cheapflights users on 12/2. 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.
Tue 12/91:05 pmMBJ - ORD
1 stop7h 56mSpirit Airlines
Fri 1/95:15 amORD - MBJ
1 stop5h 47mSpirit Airlines
Deal found 12/2$325
This Frontier deal was found by Cheapflights users on 12/4. 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.
Sat 12/203:34 pmMBJ - MDW
1 stop7h 38mFrontier
Thu 12/256:12 amMDW - MBJ
1 stop7h 17mFrontier
Deal found 12/4$331
This Kiwi.com deal was found by Cheapflights users on 12/2. 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.
Tue 12/91:05 pmMBJ - ORD
1 stop7h 56mSpirit Airlines
Sat 1/35:00 amORD - MBJ
1 stop6h 05mSpirit Airlines
Deal found 12/2$342
This Frontier deal was found by Cheapflights users on 12/3. 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 12/183:47 pmMBJ - ORD
1 stop7h 37mFrontier
Thu 12/256:00 amORD - MBJ
1 stop7h 29mFrontier
Deal found 12/3$346
This Frontier deal was found by Cheapflights users on 12/4. 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.
Wed 12/243:49 pmMBJ - ORD
1 stop7h 35mFrontier
Tue 12/306:00 amORD - MBJ
1 stop7h 29mFrontier
Deal found 12/4$351
This Frontier deal was found by Cheapflights users on 12/4. 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.
Sat 12/203:34 pmMBJ - MDW
1 stop7h 38mFrontier
Sat 12/276:12 amMDW - MBJ
1 stop7h 17mFrontier
Deal found 12/4$351

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 December 4, 2025.

Most accurate provider

Mytrip
3 stars

Most trusted provider

Mytrip
3 stars

Round-trip from

$263
(Spirit Airlines)

One-way from

$157
(Cheapflightsfares)

Popular in

February

Cheapest in

November

Average price

$446

Good round-trip deal

$387 or less

Good one-way deal

$257 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. 7% potential increase in price ($38 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($13 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
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 December 4, 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

Thu 1/22

12:57 pm-7:38 pm

1 stop7h 41m

Chicago O'Hare Intl

Mon 1/26

5:15 am-12:02 pm

1 stop5h 47m

$263

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Tue 1/6

1:05 pm-10:39 pm

2 stops34h 34m

Chicago O'Hare Intl

Sun 1/11

7:30 am-12:02 pm

1 stop27h 32m

$296

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Fri 1/16

12:57 pm-9:03 pm

1 stop9h 06m

Chicago O'Hare Intl

Fri 1/23

5:15 am-12:02 pm

1 stop5h 47m

$306

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Sat 12/20

3:34 pm-10:12 pm

1 stop7h 38m

Chicago Midway

Sat 1/3

6:12 am-2:29 pm

1 stop7h 17m

$307

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Thu 2/26

4:51 pm-11:35 pm

1 stop7h 44m

Chicago O'Hare Intl

Thu 3/5

5:05 am-3:31 pm

1 stop9h 26m

$324

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Thu 2/26

4:51 pm-11:25 pm

1 stop7h 34m

Chicago Midway

Thu 3/5

6:00 am-3:31 pm

1 stop8h 31m

$324

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Tue 1/6

1:05 pm-12:39 pm

2 stops24h 34m

Chicago O'Hare Intl

Wed 1/14

5:32 pm-12:02 pm

1 stop17h 30m

$332

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Sat 12/20

3:34 pm-10:12 pm

1 stop7h 38m

Chicago Midway

Sat 12/27

6:12 am-2:29 pm

1 stop7h 17m

$351

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Wed 12/24

3:49 pm-10:12 pm

1 stop7h 23m

Chicago Midway

Tue 12/30

6:14 am-2:29 pm

1 stop7h 15m

$357

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Thu 1/8

4:05 pm-8:40 am

1 stop17h 35m

Chicago O'Hare Intl

Tue 1/13

5:30 am-12:54 pm

1 stop6h 24m

$362

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/4

Showing 1-10 of 41 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 December.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars
MytripPrice 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 Mytrip to be most consistent on Cheapflights vs. Mytrip Users can find the same prices on Montego Bay-Chicago flight deals on Cheapflights vs. Mytrip >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 Mytrip the most. Mytrip 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 March is currently the most expensive (average of $477). 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 December 4, 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 December 4, 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).

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

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
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 December 4, 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
11,047 reviews

Comfort

7.2

Overall

7.2

Boarding

7.5

Crew

8.0

Food

6.5

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
11,047 reviews
American Airlines
7.2
Good
11,047 reviews

Comfort

7.2

Overall

7.2

Boarding

7.5

Crew

8.0

Food

6.5

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 Spirit Airlines, Frontier, and Delta fly from Montego Bay to Chicago in about 7h 38m. The time it takes to get you to your destination can typically vary by up to 2h 48m. Montego Bay and Chicago are separated by a distance of 1709 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 ($256), American Airlines ($348), and United Airlines ($349) offers the cheapest pricing from Montego Bay to Chicago. These flights start at 42% 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 $182. Users have also found prices from $215 and $217 on United Airlines and American Airlines, respectively.

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

    Looking at all options, your cheapest flight can be booked for $233. While the most popular route (Montego Bay Sangster Intl - Chicago O'Hare Intl) can be booked for $296 on average, our data indicates $427 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 March is currently the most expensive (average of $477). 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
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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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
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 December 4, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$256Average$337FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$348Average$476FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$349Average$480FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$392Average$536FlexibilityNo cancel feeOn-time63%

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