Chicago

$183+ 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 12/11. Fares are subject to change and may not be available on all flights or dates of travel.
MBJ — CHI
Jul 16 — Jul 231
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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 June 16, 2026.

This United Airlines deal was found by Cheapflights users on 6/14. 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.
Sun 11/12:48 pm
MBJ
-
ORD
Nonstop4h 28m
United Airlines
Sat 11/78:42 am
ORD
-
MBJ
Nonstop4h 04m
United Airlines
Deal found 6/14$311
This United Airlines deal was found by Cheapflights users on 6/14. 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.
Sun 11/12:48 pm
MBJ
-
ORD
Nonstop4h 28m
United Airlines
Mon 11/98:00 pm
ORD
-
MBJ
1 stop15h 07m
United Airlines
Deal found 6/14$316
This Delta deal was found by Cheapflights users on 6/14. 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.
Tue 11/31:50 pm
MBJ
-
ORD
1 stop8h 43m
Delta
Tue 11/107:10 am
ORD
-
MBJ
1 stop6h 05m
Delta
Deal found 6/14$317
This Delta deal was found by Cheapflights users on 6/14. 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 11/55:59 pm
MBJ
-
ORD
2 stops15h 01m
Delta
Fri 11/137:40 pm
ORD
-
MBJ
1 stop17h 55m
Delta
Deal found 6/14$322
This Delta deal was found by Cheapflights users on 6/14. 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 11/55:59 pm
MBJ
-
MDW
2 stops19h 34m
Delta
Sun 11/86:00 am
MDW
-
MBJ
1 stop9h 34m
Delta
Deal found 6/14$322
This American Airlines deal was found by Cheapflights users on 6/14. 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.
Tue 11/31:55 pm
MBJ
-
ORD
1 stop10h 45m
American Airlines
Tue 11/105:00 am
ORD
-
MBJ
1 stop6h 42m
American Airlines
Deal found 6/14$326
This Delta deal was found by Cheapflights users on 6/14. 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 8/134:59 pm
MBJ
-
ORD
2 stops14h 57m
Delta
Mon 8/175:30 am
ORD
-
MBJ
1 stop6h 14m
Delta
Deal found 6/14$359
This JetBlue deal was found by Cheapflights users on 6/14. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/23:59 pm
MBJ
-
ORD
1 stop8h 45m
JetBlue
Mon 11/97:00 am
ORD
-
MBJ
1 stop6h 54m
JetBlue
Deal found 6/14$362
This Delta deal was found by Cheapflights users on 6/14. 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.
Tue 11/31:50 pm
MBJ
-
ORD
1 stop8h 43m
Delta
Fri 11/135:55 pm
ORD
-
MBJ
2 stops17h 30m
Delta
Deal found 6/14$365
This Delta deal was found by Cheapflights users on 6/14. 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 11/42:32 pm
MBJ
-
MDW
1 stop8h 38m
Delta
Mon 11/96:00 am
MDW
-
MBJ
1 stop7h 15m
Delta
Deal found 6/14$365
This Delta deal was found by Cheapflights users on 6/14. 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 11/42:32 pm
MBJ
-
MDW
1 stop8h 38m
Delta
Sun 11/86:00 am
MDW
-
MBJ
1 stop9h 34m
Delta
Deal found 6/14$368
This United Airlines deal was found by Cheapflights users on 6/11. 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.
Tue 8/44:12 pm
MBJ
-
ORD
1 stop7h 19m
United Airlines
Fri 8/76:30 am
ORD
-
MBJ
1 stop8h 40m
United Airlines
Deal found 6/11$369

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 June 16, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$311
(United Airlines)

One-way from

$183
(United Airlines)

Popular in

March

Cheapest in

July

Average price

$500

Good round-trip deal

$426 or less

Good one-way deal

$286 or less
Provider with most accurate pricing for Montego Bay Sangster Intl-Chicago (CHI) flight deals.
Provider most trusted by Cheapflights users for Montego Bay Sangster Intl-Chicago (CHI) flights.
From Montego Bay Sangster Intl to Chicago (CHI)
One-way flight from Montego Bay Sangster Intl to Chicago (CHI)
Highest demand for flights based on searches. 22% potential increase in price ($128 potential increase over avg. RT price).
Cheapest flight prices on average. 7% potential price decrease ($34 potential savings vs. average RT price).
Average for round-trip flights in June 2026
Price to beat on a round-trip flight from Montego Bay Sangster Intl to Chicago (CHI).
Price to beat on a one-way flight from Montego Bay Sangster Intl to Chicago (CHI).

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 June 16, 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
Quickest round-trip

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Mon 11/23

2:48 pm-6:16 pm

Nonstop4h 28m

Chicago O'Hare Intl

Sun 11/29

8:42 am-1:46 pm

Nonstop4h 04m

$311

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Wed 11/4

2:48 pm-6:16 pm

Nonstop4h 28m

Chicago O'Hare Intl

Tue 11/10

5:00 am-2:29 pm

1 stop8h 29m

$316

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Thu 11/5

5:59 pm-12:33 pm

2 stops19h 34m

Chicago Midway

Mon 11/9

6:00 am-4:35 pm

1 stop9h 35m

$322

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Thu 8/13

4:59 pm-7:56 am

2 stops14h 57m

Chicago O'Hare Intl

Mon 8/17

5:30 am-11:44 am

1 stop6h 14m

$359

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Wed 11/4

2:32 pm-10:10 pm

1 stop8h 38m

Chicago Midway

Mon 11/9

6:00 am-2:15 pm

1 stop7h 15m

$365

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Wed 11/4

2:32 pm-10:10 pm

1 stop8h 38m

Chicago Midway

Sun 11/8

6:00 am-4:34 pm

1 stop9h 34m

$368

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Tue 8/4

4:12 pm-11:31 pm

1 stop7h 19m

Chicago O'Hare Intl

Fri 8/7

6:30 am-3:10 pm

1 stop8h 40m

$369

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Mon 11/23

6:00 pm-11:50 pm

1 stop6h 50m

Chicago O'Hare Intl

Sun 11/29

5:30 am-4:35 pm

1 stop10h 05m

$401

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Tue 8/4

1:32 pm-10:03 pm

1 stop8h 31m

Chicago Midway

Fri 8/7

6:05 am-12:27 pm

1 stop6h 22m

$435

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Tue 7/14

12:22 pm-1:57 pm

1 stop25h 35m

Chicago O'Hare Intl

Sat 7/25

8:02 am-11:15 am

1 stop27h 13m

$447

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/11

Showing 1-10 of 35 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 June.
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 June 16, 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 June 16, 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.

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.

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 June 16, 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.

Entertainment

6.8

Food

6.4

Overall

7.1

Crew

7.9

Boarding

7.5

Comfort

7.2

Reviews

1 / 20
10.0
Excellent

Beatriz,May 2026

HEL - DFW

Very modern and confortable plane. Dinner was delicious. Whole crew were polite and perfect.

Entertainment

6.8

Food

6.4

Overall

7.1

Crew

7.9

Boarding

7.5

Comfort

7.2

Reviews

1 / 20
10.0
Excellent

Beatriz,May 2026

HEL - DFW

Very modern and confortable plane. Dinner was delicious. Whole crew were polite and perfect.

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 2 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, Delta, and American Airlines fly from Montego Bay to Chicago in about 4h 28m. The time it takes to get you to your destination can typically vary by up to 6h 17m. 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, United Airlines ($280), and American Airlines ($281) 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 United Airlines. According to our data, you can fly for as low as $185. Users have also found prices from $192 and $198 on American Airlines and Frontier, respectively.

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

    Looking at all options, your cheapest flight can be booked for $204. While the most popular route (Montego Bay Sangster Intl - Chicago O'Hare Intl) can be booked for $311 on average, our data indicates $444 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

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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.

Top 2 airlines flying from Montego Bay to Chicago

Discover the top 2 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 June 16, 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$280Average$387FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$281Average$409FlexibilityNo cancel feeOn-time71%

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