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$178+ 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 4/30. Fares are subject to change and may not be available on all flights or dates of travel.
MBJ — CHI
Apr 17 — Apr 241
Fri 4/17
Fri 4/24
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 March 18, 2026.

This Cheapflightsfares deal was found by Cheapflights users on 3/15. 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 5/71:21 pm
MBJ
-
ORD
1 stop11h 06m
Spirit Airlines
Tue 5/125:05 am
ORD
-
MBJ
1 stop7h 11m
Spirit Airlines
Deal found 3/15$270
This Cheapflightsfares deal was found by Cheapflights users on 3/17. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/281:21 pm
MBJ
-
ORD
1 stop11h 03m
Spirit Airlines
Tue 5/125:05 am
ORD
-
MBJ
1 stop7h 11m
Spirit Airlines
Deal found 3/17$278
This American Airlines deal was found by Cheapflights users on 3/13. 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 5/81:15 pm
MBJ
-
ORD
Nonstop4h 40m
American Airlines
Sat 5/167:15 am
ORD
-
MBJ
1 stop6h 10m
American Airlines
Deal found 3/13$281
This United Airlines deal was found by Cheapflights users on 3/15. 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 5/161:52 pm
MBJ
-
ORD
Nonstop4h 23m
United Airlines
Tue 5/195:30 am
ORD
-
MBJ
1 stop8h 00m
United Airlines
Deal found 3/15$286
This United Airlines deal was found by Cheapflights users on 3/16. 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.
Sat 5/162:40 pm
MBJ
-
ORD
1 stop18h 20m
United Airlines
Mon 5/189:56 pm
ORD
-
MBJ
1 stop15h 34m
United Airlines
Deal found 3/16$291
This American Airlines deal was found by Cheapflights users on 3/13. 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 5/1310:17 am
MBJ
-
ORD
1 stop7h 41m
American Airlines
Wed 5/279:20 am
ORD
-
MBJ
Nonstop4h 10m
American Airlines
Deal found 3/13$297
This American Airlines deal was found by Cheapflights users on 3/13. 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 4/2212:56 pm
MBJ
-
ORD
1 stop8h 42m
American Airlines
Wed 4/296:40 am
ORD
-
MBJ
1 stop7h 35m
American Airlines
Deal found 3/13$301
This American Airlines deal was found by Cheapflights users on 3/15. 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.
Sun 5/173:20 pm
MBJ
-
ORD
1 stop8h 14m
American Airlines
Sat 9/129:02 pm
ORD
-
MBJ
2 stops12h 08m
American Airlines
Deal found 3/15$306
This Cheapflightsfares deal was found by Cheapflights users on 3/17. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/121:21 pm
MBJ
-
ORD
1 stop11h 06m
Spirit Airlines
Wed 5/137:45 pm
ORD
-
MBJ
1 stop16h 31m
Spirit Airlines
Deal found 3/17$307
This United Airlines deal was found by Cheapflights users on 3/18. 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.
Thu 4/302:40 pm
MBJ
-
ORD
1 stop10h 05m
United Airlines
Thu 5/74:25 pm
ORD
-
MBJ
1 stop22h 45m
United Airlines
Deal found 3/18$312
This Frontier deal was found by Cheapflights users on 3/17. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/131:16 pm
MBJ
-
MDW
1 stop8h 46m
Frontier
Wed 5/276:00 am
MDW
-
MBJ
1 stop6h 11m
Frontier
Deal found 3/17$376
This Expedia deal was found by Cheapflights users on 3/17. 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.
Sat 5/91:16 pm
MBJ
-
MDW
1 stop21h 56m
Frontier
Tue 9/19:16 pm
MDW
-
MBJ
1 stop15h 26m
Frontier
Deal found 3/17$435

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 March 18, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$270
(Cheapflightsfares)

One-way from

$178
(Super.com)

Popular in

March

Cheapest in

November

Average price

$786

Good round-trip deal

$301 or less

Good one-way deal

$192 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 ($79 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 March 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 March 18, 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

Sat 5/16

1:52 pm-6:15 pm

Nonstop4h 23m

Chicago O'Hare Intl

Tue 5/19

5:30 am-1:30 pm

1 stop8h 00m

$286

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Sat 5/16

1:52 pm-6:15 pm

Nonstop4h 23m

Chicago O'Hare Intl

Mon 5/18

11:00 pm-1:30 pm

1 stop14h 30m

$286

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Thu 4/16

1:52 pm-6:15 pm

Nonstop4h 23m

Chicago O'Hare Intl

Thu 4/30

9:35 pm-3:10 pm

1 stop17h 35m

$292

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Sat 5/9

4:12 pm-11:44 pm

1 stop7h 32m

Chicago O'Hare Intl

Sat 5/16

8:40 am-12:50 pm

Nonstop4h 10m

$292

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Tue 5/19

3:20 pm-11:34 pm

1 stop8h 14m

Chicago O'Hare Intl

Mon 8/17

6:34 am-1:58 pm

1 stop7h 24m

$296

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Wed 5/13

2:40 pm-11:15 pm

1 stop8h 35m

Chicago O'Hare Intl

Wed 5/27

6:30 am-1:30 pm

1 stop7h 00m

$296

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Wed 5/13

10:17 am-5:58 pm

1 stop7h 41m

Chicago O'Hare Intl

Wed 5/27

9:20 am-1:30 pm

Nonstop4h 10m

$297
Quickest round-trip

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Sat 5/9

11:35 am-3:45 pm

Nonstop4h 10m

Chicago Midway

Tue 9/1

6:15 am-11:55 am

1 stop5h 40m

$439

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Wed 5/13

12:15 pm-7:10 am

2 stops18h 55m

Chicago Midway

Wed 5/27

7:00 am-1:55 pm

1 stop6h 55m

$491

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Tue 4/28

12:15 pm-9:25 pm

1 stop9h 10m

Chicago Midway

Tue 5/12

7:00 am-1:55 pm

1 stop6h 55m

$539

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/15

Showing 1-10 of 31 resultsSorted by cheapest first
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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 March.
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, April is the cheapest month in which you can book a flight from Montego Bay to Chicago (average of $184). Flying from Montego Bay to Chicago in January is currently the most expensive (average of $448). 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 March 18, 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 March 18, 2026.

The most flights from MBJ to CHI are scheduled on a Monday (3 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (1 on average).

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 March 18, 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
7.1
Good
11,468 reviews

Boarding

7.5

Overall

7.1

Entertainment

6.9

Food

6.4

Crew

7.9

Comfort

7.2

Reviews

1 / 20
2.0
Mediocre

Anonymous,Mar 2026

MIA - SFO

Horrible. When they power flights for other airlines there is nothing they can do to change or accommodate any changes
American Airlines
7.1
Good
11,468 reviews
American Airlines
7.1
Good
11,468 reviews

Boarding

7.5

Overall

7.1

Entertainment

6.9

Food

6.4

Crew

7.9

Comfort

7.2

Reviews

1 / 20
2.0
Mediocre

Anonymous,Mar 2026

MIA - SFO

Horrible. When they power flights for other airlines there is nothing they can do to change or accommodate any changes

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.

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

    Airlines like United Airlines and Southwest fly from Montego Bay to Chicago in about 4h 10m. The time it takes to get you to your destination is usually consistent. Montego Bay and Chicago are separated by a distance of 1709 mi. All flights are typically nonstop.

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

    According to our current data, Spirit Airlines ($146), American Airlines ($305), and United Airlines ($306) offers the cheapest pricing from Montego Bay to Chicago. These flights start at 68% 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 $195 and $198 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 Qatar Airways (71%), American Airlines (68%) and United Airlines (50%).

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

    Looking at all options, your cheapest flight can be booked for $172. While the most popular route (Montego Bay Sangster Intl - Chicago O'Hare Intl) can be booked for $270 on average, our data indicates $329 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 $184). Flying from Montego Bay to Chicago in January is currently the most expensive (average of $448). 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

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 March 18, 2026.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$146Average$337FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$305Average$464FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$306Average$469FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$392Average$536FlexibilityNo cancel feeOn-time63%

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