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$149+ 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 2/14. Fares are subject to change and may not be available on all flights or dates of travel.
MBJ — CHI
Feb 26 — Mar 51
Thu 2/26
Thu 3/5
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 January 27, 2026.

This Cheapflightsfares deal was found by Cheapflights users on 1/25. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/2912:57 pm
MBJ
-
ORD
1 stop11h 49m
Spirit Airlines
Mon 2/25:15 am
ORD
-
MBJ
1 stop5h 47m
Spirit Airlines
Deal found 1/25$296
This Cheapflightsfares deal was found by Cheapflights users on 1/26. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/2912:57 pm
MBJ
-
ORD
1 stop11h 49m
Spirit Airlines
Sat 2/145:15 am
ORD
-
MBJ
1 stop5h 47m
Spirit Airlines
Deal found 1/26$299
This Priceline deal was found by Cheapflights users on 1/25. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/1111:57 am
MBJ
-
ORD
1 stop11h 50m
Spirit Airlines
Wed 3/188:41 pm
ORD
-
MBJ
1 stop14h 17m
Spirit Airlines
Deal found 1/25$319
This American Airlines deal was found by Cheapflights users on 1/27. 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 5/141:15 pm
MBJ
-
ORD
Nonstop4h 43m
American Airlines
Mon 5/188:10 am
ORD
-
MBJ
Nonstop4h 05m
American Airlines
Deal found 1/27$320
This FlightHub deal was found by Cheapflights users on 1/24. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/2612:00 pm
MBJ
-
ORD
1 stop7h 46m
Spirit Airlines
Mon 3/308:41 pm
ORD
-
MBJ
1 stop14h 17m
Spirit Airlines
Deal found 1/24$327
This American Airlines deal was found by Cheapflights users on 1/26. 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.
Thu 5/141:15 pm
MBJ
-
ORD
Nonstop4h 43m
American Airlines
Sun 5/178:10 am
ORD
-
MBJ
Nonstop4h 05m
American Airlines
Deal found 1/26$345
This United Airlines deal was found by Cheapflights users on 1/25. 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.
Wed 3/111:48 pm
MBJ
-
ORD
Nonstop4h 25m
United Airlines
Wed 3/189:15 pm
ORD
-
MBJ
1 stop15h 50m
United Airlines
Deal found 1/25$349
This Delta deal was found by Cheapflights users on 1/27. 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 5/144:55 pm
MBJ
-
ORD
2 stops14h 31m
Delta
Mon 5/187:10 am
ORD
-
MBJ
1 stop6h 06m
Delta
Deal found 1/27$351
This Delta deal was found by Cheapflights users on 1/27. 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 5/142:40 pm
MBJ
-
MDW
1 stop7h 05m
Delta
Mon 5/186:00 am
MDW
-
MBJ
1 stop7h 16m
Delta
Deal found 1/27$351
This Delta deal was found by Cheapflights users on 1/25. 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.
Wed 3/1111:15 am
MBJ
-
MDW
1 stop11h 16m
Delta
Wed 3/186:00 am
MDW
-
MBJ
1 stop9h 28m
Delta
Deal found 1/25$508
This Delta deal was found by Cheapflights users on 1/25. 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.
Sun 6/282:30 pm
MBJ
-
MDW
1 stop7h 15m
Delta
Sat 7/46:00 am
MDW
-
MBJ
1 stop7h 05m
Delta
Deal found 1/25$982
This Delta deal was found by Cheapflights users on 1/25. 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.
Sun 6/282:30 pm
MBJ
-
MDW
1 stop7h 15m
Delta
Sun 7/56:00 am
MDW
-
MBJ
1 stop9h 25m
Delta
Deal found 1/25$1,061

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 January 27, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$319
(Priceline)

One-way from

$149
(Super.com)

Popular in

June

Cheapest in

November

Average price

$449

Good round-trip deal

$365 or less

Good one-way deal

$282 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. 14% potential increase in price ($73 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($12 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
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 January 27, 2026.
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 3/11

11:57 am-11:47 pm

1 stop11h 50m

Chicago O'Hare Intl

Wed 3/18

8:41 pm-10:58 am

1 stop14h 17m

$319

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Thu 5/14

3:20 pm-11:53 pm

1 stop8h 33m

Chicago O'Hare Intl

Mon 5/18

6:58 pm-11:51 am

1 stop16h 53m

$335

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Wed 3/11

1:48 pm-6:13 pm

Nonstop4h 25m

Chicago O'Hare Intl

Wed 3/18

8:42 am-12:46 pm

Nonstop4h 04m

$345

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Thu 5/14

1:15 pm-5:58 pm

Nonstop4h 43m

Chicago O'Hare Intl

Sun 5/17

8:10 am-12:15 pm

Nonstop4h 05m

$345

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Thu 5/14

12:55 pm-11:55 pm

1 stop11h 00m

Chicago O'Hare Intl

Sun 5/17

6:00 am-3:29 pm

1 stop9h 29m

$351

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Thu 5/14

4:55 pm-7:26 am

2 stops14h 31m

Chicago O'Hare Intl

Mon 5/18

7:10 am-1:16 pm

1 stop6h 06m

$351

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Wed 3/11

11:15 am-10:31 pm

1 stop11h 16m

Chicago Midway

Wed 3/18

6:00 am-3:28 pm

1 stop9h 28m

$508

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Wed 3/11

1:55 pm-5:22 pm

2 stops27h 27m

Chicago Midway

Wed 3/18

9:35 am-12:49 pm

2 stops27h 14m

$1,412

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Sat 2/28

12:40 pm-10:39 pm

1 stop10h 59m

$181

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Sat 2/28

12:40 pm-9:39 pm

1 stop9h 59m

$181

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/25

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 January.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
MytripPrice 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, October is the cheapest month in which you can book a flight from Montego Bay to Chicago (average of $289). Flying from Montego Bay to Chicago in March is currently the most expensive (average of $455). 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 January 27, 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.

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 January 27, 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
7.2
Good
11,197 reviews

Entertainment

6.9

Crew

8.0

Food

6.4

Overall

7.2

Comfort

7.2

Boarding

7.5

Reviews

1 / 20
2.0
Mediocre

Susie,Jan 2026

CLT - TPA

This flight was delayed 3 or 4 times. We had boarded the plane, sat on plane for a good 30 minutes, then we had to board the aircraft, walk to a different gate, wait and then board another aircraft. We arrived in Tampa 4 hours later than the original booking. I feel there should have been some sort of compensation especially for the advantage members.
American Airlines
7.2
Good
11,197 reviews
American Airlines
7.2
Good
11,197 reviews

Entertainment

6.9

Crew

8.0

Food

6.4

Overall

7.2

Comfort

7.2

Boarding

7.5

Reviews

1 / 20
2.0
Mediocre

Susie,Jan 2026

CLT - TPA

This flight was delayed 3 or 4 times. We had boarded the plane, sat on plane for a good 30 minutes, then we had to board the aircraft, walk to a different gate, wait and then board another aircraft. We arrived in Tampa 4 hours later than the original booking. I feel there should have been some sort of compensation especially for the advantage members.

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 0 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.

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

    Airlines like Spirit Airlines, American Airlines, and United Airlines fly from Montego Bay to Chicago in about 4h 25m. The time it takes to get you to your destination can typically vary by up to 7h 25m. 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 ($256), American Airlines ($348), and United Airlines ($349) offers the cheapest pricing from Montego Bay to Chicago. These flights start at 40% 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 $198 and $213 on Frontier 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 $236. While the most popular route (Montego Bay Sangster Intl - Chicago O'Hare Intl) can be booked for $296 on average, our data indicates $396 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, October is the cheapest month in which you can book a flight from Montego Bay to Chicago (average of $289). Flying from Montego Bay to Chicago in March is currently the most expensive (average of $455). 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.
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 January 27, 2026.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$256Average$337FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$348Average$472FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$349Average$480FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$392Average$536FlexibilityNo cancel feeOn-time63%

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