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$169+ 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 5/20. Fares are subject to change and may not be available on all flights or dates of travel.
MBJ — CHI
May 31 — Jun 71
Sun 5/31
Sun 6/7
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 May 1, 2026.

This American Airlines deal was found by Cheapflights users on 4/27. 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 40m
American Airlines
Mon 8/319:10 am
ORD
-
MBJ
Nonstop4h 07m
American Airlines
Deal found 4/27$281
This United Airlines deal was found by Cheapflights users on 4/28. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/21:52 pm
MBJ
-
ORD
Nonstop4h 23m
United Airlines
Mon 5/48:10 pm
ORD
-
MBJ
1 stop17h 20m
United Airlines
Deal found 4/28$283
This United Airlines deal was found by Cheapflights users on 4/27. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/202:40 pm
MBJ
-
ORD
1 stop10h 46m
United Airlines
Sat 9/127:05 am
ORD
-
MBJ
1 stop28h 38m
United Airlines
Deal found 4/27$290
This American Airlines deal was found by Cheapflights users on 4/27. 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.
Sat 5/210:13 am
MBJ
-
ORD
1 stop9h 09m
American Airlines
Mon 5/48:05 am
ORD
-
MBJ
Nonstop4h 08m
American Airlines
Deal found 4/27$292
This United Airlines deal was found by Cheapflights users on 4/28. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/164:12 pm
MBJ
-
ORD
1 stop7h 32m
United Airlines
Mon 5/189:56 pm
ORD
-
MBJ
1 stop15h 34m
United Airlines
Deal found 4/28$296
This American Airlines deal was found by Cheapflights users on 4/27. 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 5/212:08 pm
MBJ
-
ORD
1 stop10h 16m
American Airlines
Sat 9/129:02 pm
ORD
-
MBJ
2 stops12h 08m
American Airlines
Deal found 4/27$301
This American Airlines deal was found by Cheapflights users on 4/29. 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 40m
American Airlines
Sat 9/128:44 pm
ORD
-
MBJ
1 stop12h 26m
American Airlines
Deal found 4/29$306
This United Airlines deal was found by Cheapflights users on 4/30. 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 5/62:40 pm
MBJ
-
ORD
1 stop8h 35m
United Airlines
Fri 5/154:25 pm
ORD
-
MBJ
1 stop22h 45m
United Airlines
Deal found 4/30$311
This American Airlines deal was found by Cheapflights users on 4/30. 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 5/612:25 pm
MBJ
-
ORD
1 stop11h 29m
American Airlines
Sat 8/156:45 am
ORD
-
MBJ
1 stop6h 49m
American Airlines
Deal found 4/30$316
This American Airlines deal was found by Cheapflights users on 4/30. 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 5/295:17 pm
MBJ
-
ORD
1 stop7h 07m
American Airlines
Wed 9/29:10 am
ORD
-
MBJ
Nonstop4h 07m
American Airlines
Deal found 4/30$317
This Frontier deal was found by Cheapflights users on 4/28. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/101:16 pm
MBJ
-
MDW
1 stop8h 46m
Frontier
Mon 6/16:00 am
MDW
-
MBJ
1 stop6h 11m
Frontier
Deal found 4/28$336
This Priceline deal was found by Cheapflights users on 4/29. 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 8/261:26 pm
MBJ
-
MDW
1 stop8h 45m
Frontier
Sat 8/296:00 am
MDW
-
MBJ
1 stop6h 21m
Frontier
Deal found 4/29$348

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 May 1, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$281
(American Airlines)

One-way from

$172
(Trip.com)

Popular in

March

Cheapest in

July

Average price

$486

Good round-trip deal

$366 or less

Good one-way deal

$224 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. 20% potential increase in price ($121 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 7% potential price decrease ($33 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 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 May 1, 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

Tue 6/2

4:12 pm-7:27 am

1 stop15h 15m

Chicago O'Hare Intl

Fri 6/5

6:30 am-3:10 pm

1 stop8h 40m

$289

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Wed 5/20

4:12 pm-11:44 pm

1 stop7h 32m

Chicago O'Hare Intl

Fri 9/11

5:45 pm-1:30 pm

1 stop19h 45m

$290

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Fri 7/10

4:12 pm-11:26 pm

1 stop7h 14m

Chicago O'Hare Intl

Fri 7/24

9:40 pm-3:26 pm

1 stop17h 46m

$290

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Fri 7/24

4:12 pm-11:26 pm

1 stop7h 14m

Chicago O'Hare Intl

Fri 8/14

2:30 pm-3:10 pm

1 stop24h 40m

$290

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Sat 9/19

2:40 pm-9:09 am

1 stop18h 29m

Chicago O'Hare Intl

Fri 9/25

7:45 am-1:30 pm

1 stop29h 45m

$290

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Sat 5/16

2:40 pm-12:45 am

1 stop10h 05m

Chicago O'Hare Intl

Fri 5/29

8:40 am-3:10 pm

1 stop6h 30m

$296

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Sat 5/23

4:33 pm-10:20 am

1 stop17h 47m

Chicago O'Hare Intl

Sat 5/30

8:40 am-3:10 pm

1 stop6h 30m

$296

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Sun 7/19

4:33 pm-12:45 am

1 stop8h 12m

Chicago O'Hare Intl

Fri 7/24

9:40 pm-3:26 pm

1 stop17h 46m

$296

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Wed 6/17

4:12 pm-11:26 pm

1 stop7h 14m

Chicago O'Hare Intl

Sun 6/21

6:30 am-3:10 pm

1 stop8h 40m

$316

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Wed 8/26

1:26 pm-10:11 pm

1 stop8h 45m

Chicago Midway

Sat 8/29

6:00 am-12:21 pm

1 stop6h 21m

$348

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/27

Showing 1-10 of 37 resultsSorted by cheapest first
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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 May.
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 month to book a flight from Montego Bay to Chicago?

Currently, April is the cheapest month in which you can book a flight from Montego Bay to Chicago (average of $146). Flying from Montego Bay to Chicago in January is currently the most expensive (average of $397). 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 May 1, 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 May 1, 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).

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
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

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 3 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 United Airlines, Frontier, and Delta fly from Montego Bay to Chicago in about 6h 48m. The time it takes to get you to your destination can typically vary by up to 8h 27m. 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, United Airlines ($281), Southwest ($281), and American Airlines ($281) offers the cheapest pricing from Montego Bay to Chicago. These flights start at 38% 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 $185. Users have also found prices from $186 and $192 on Spirit Airlines and American Airlines, 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 Qatar Airways (82%), American Airlines (80%) and United Airlines (58%).

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

    Looking at all options, your cheapest flight can be booked for $182. While the most popular route (Montego Bay Sangster Intl - Chicago O'Hare Intl) can be booked for $296 on average, our data indicates $387 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, April is the cheapest month in which you can book a flight from Montego Bay to Chicago (average of $146). Flying from Montego Bay to Chicago in January is currently the most expensive (average of $397). 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
Benton Harbor
Lansing
Merrillville
Hammond
Porter

Browse thousands of different options on Cheapflights for your next trip

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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 3 airlines flying from Montego Bay to Chicago

Discover the top 3 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 May 1, 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$281Average$409FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$281Average$463FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$281Average$436FlexibilityNo cancel feeOn-time71%

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