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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 9/17. Fares are subject to change and may not be available on all flights or dates of travel.
MBJ — CHI
Aug 23 — Aug 301
Sat 8/23
Sat 8/30
1 adult, Economy
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Cheap 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 August 18, 2025.

Round-trip from

$275
(Priceline)

One-way from

$149
(Cheapflightsfares)

Popular in

January

Cheapest in

September

Average price

$400

Good round-trip deal

$410 or less

Good one-way deal

$292 or less
From Montego Bay Sangster Intl to Chicago (CHI)
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One-way flight from Montego Bay Sangster Intl to Chicago (CHI)
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Highest demand for flights based on searches. 10% potential increase in price ($53 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($14 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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Price to beat on a round-trip flight from Montego Bay Sangster Intl to Chicago (CHI).
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Price to beat on a one-way flight from Montego Bay Sangster Intl to Chicago (CHI).
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Find 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 August 18, 2025.

This Priceline deal was found by Cheapflights users on 8/16. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/3012:10 pmMBJ - ORD
1 stop10h 38mSpirit Airlines
Tue 10/75:05 amORD - MBJ
1 stop5h 55mSpirit Airlines
Deal found 8/16$275
This Cheapflightsfares deal was found by Cheapflights users on 8/17. 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.
Wed 9/2412:10 pmMBJ - ORD
1 stop10h 38mSpirit Airlines
Wed 10/15:05 amORD - MBJ
1 stop6h 00mSpirit Airlines
Deal found 8/17$295
This Expedia deal was found by Cheapflights users on 8/17. 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.
Wed 10/112:10 pmMBJ - ORD
1 stop10h 38mSpirit Airlines
Wed 10/85:05 amORD - MBJ
1 stop5h 55mSpirit Airlines
Deal found 8/17$298
This Cheapflightsfares deal was found by Cheapflights users on 8/17. 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 9/2312:10 pmMBJ - ORD
1 stop10h 38mSpirit Airlines
Tue 9/305:05 amORD - MBJ
1 stop6h 00mSpirit Airlines
Deal found 8/17$318
This Expedia deal was found by Cheapflights users on 8/18. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/212:10 pmMBJ - ORD
1 stop10h 38mSpirit Airlines
Thu 10/97:29 pmORD - MBJ
1 stop15h 31mSpirit Airlines
Deal found 8/18$341
This Kiwi.com deal was found by Cheapflights users on 8/18. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/22:12 pmMBJ - MDW
1 stop9h 08mFrontier
Thu 10/99:26 pmMDW - MBJ
1 stop17h 10mFrontier
Deal found 8/18$375
This Expedia deal was found by Cheapflights users on 8/17. 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.
Sun 8/3110:22 amMBJ - ORD
1 stop13h 37mSpirit Airlines
Wed 9/35:05 amORD - MBJ
1 stop6h 09mSpirit Airlines
Deal found 8/17$398
This Mytrip deal was found by Cheapflights users on 8/18. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/212:10 pmMBJ - ORD
1 stop10h 38mMultiple Airlines
Thu 10/91:26 pmORD - MBJ
2 stops23h 54mMultiple Airlines
Deal found 8/18$404
This Delta deal was found by Cheapflights users on 8/16. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/301:25 pmMBJ - MDW
1 stop8h 11mDelta
Tue 10/76:00 amMDW - MBJ
1 stop7h 20mDelta
Deal found 8/16$637
This WestJet deal was found by Cheapflights users on 8/18. 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 WestJet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/210:30 amMBJ - MDW
2 stops23h 10mWestJet
Thu 10/912:48 pmMDW - MBJ
2 stops20h 38mWestJet
Deal found 8/18$1,487

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 August 18, 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

Tue 9/30

12:10 pm-10:48 pm

1 stop10h 38m

Chicago O'Hare Intl

Tue 10/7

5:05 am-11:00 am

1 stop5h 55m

$275

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Wed 9/24

12:10 pm-10:48 pm

1 stop10h 38m

Chicago O'Hare Intl

Wed 10/1

5:05 am-11:05 am

1 stop6h 00m

$295

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Wed 10/1

12:10 pm-10:48 pm

1 stop10h 38m

Chicago O'Hare Intl

Wed 10/8

5:05 am-11:00 am

1 stop5h 55m

$298

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Tue 9/23

12:10 pm-10:48 pm

1 stop10h 38m

Chicago O'Hare Intl

Tue 9/30

5:05 am-11:05 am

1 stop6h 00m

$318

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Thu 10/2

2:12 pm-11:20 pm

1 stop9h 08m

Chicago Midway

Thu 10/9

9:26 pm-2:36 pm

1 stop17h 10m

$375

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Sun 8/31

10:22 am-11:59 pm

1 stop13h 37m

Chicago O'Hare Intl

Wed 9/3

5:05 am-11:14 am

1 stop6h 09m

$398

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Tue 9/30

2:38 pm-11:49 pm

1 stop9h 11m

Chicago O'Hare Intl

Tue 10/7

8:40 am-12:41 pm

Nonstop4h 01m

$422

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Tue 9/30

1:25 pm-9:36 pm

1 stop8h 11m

Chicago Midway

Tue 10/7

6:00 am-1:20 pm

1 stop7h 20m

$637

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Thu 10/2

10:30 am-9:40 am

2 stops23h 10m

Chicago Midway

Thu 10/9

12:48 pm-9:26 am

2 stops20h 38m

$1,487

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Wed 9/17

12:10 pm-10:48 pm

1 stop10h 38m

$149

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/18

Showing 1-10 of 26 results
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The best insider tips for Montego Bay to Chicago flights

Snippets provided in this section are AI-generated based on a summarization of Cheapflights-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.
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

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, August is the cheapest month in which you can book a flight from Montego Bay to Chicago (average of $245). Flying from Montego Bay to Chicago in March is currently the most expensive (average of $321). 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 August 18, 2025.

It’s optimal to fly from Montego Bay to Chicago at noon. By choosing this option you can save up to 3% on the cost of your flight, compared to a flight in the morning.

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 August 18, 2025.

The most flights from MBJ to CHI are scheduled on a Monday (2 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (2 on average).

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 August 18, 2025.
See what other customers who have flown with United Airlines and 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.
United Airlines
7.4
Good
8,925 reviews

Crew

8.1

Boarding

7.7

Comfort

7.3

Food

6.6

Overall

7.4

Entertainment

7.1

Reviews

1 / 20
4.0
Okay

Thomas,Apr 2025

TPE - SFO

The boarding experience was okay. The dietary food choices were limited, the midway snacks were hard and dry. The seat was uncomfortable - stiff seat cushion, seat back kept springing back to the upright position, narrow seat width. Love the app and the ability to track my luggage. Flight crew was efficient.
United Airlines
7.4
Good
8,925 reviews
United Airlines
7.4
Good
8,925 reviews

Crew

8.1

Boarding

7.7

Comfort

7.3

Food

6.6

Overall

7.4

Entertainment

7.1

Reviews

1 / 20
4.0
Okay

Thomas,Apr 2025

TPE - SFO

The boarding experience was okay. The dietary food choices were limited, the midway snacks were hard and dry. The seat was uncomfortable - stiff seat cushion, seat back kept springing back to the upright position, narrow seat width. Love the app and the ability to track my luggage. Flight crew was efficient.
American Airlines
7.2
Good
10,000 reviews
United Airlines
7.4
Good
8,925 reviews

Crew

8.1

Boarding

7.7

Comfort

7.3

Food

6.6

Overall

7.4

Entertainment

7.1

Reviews

1 / 20
4.0
Okay

Thomas,Apr 2025

TPE - SFO

The boarding experience was okay. The dietary food choices were limited, the midway snacks were hard and dry. The seat was uncomfortable - stiff seat cushion, seat back kept springing back to the upright position, narrow seat width. Love the app and the ability to track my luggage. Flight crew was efficient.

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 Spirit Airlines, Frontier, and Delta fly from Montego Bay to Chicago in about 8h 11m. The time it takes to get you to your destination can typically vary by up to 2h 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, Spirit Airlines ($251), American Airlines ($370), and United Airlines ($383) offers the cheapest pricing from Montego Bay to Chicago. These flights start at 45% 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 $149. Users have also found prices from $202 and $215 on Frontier and Delta, 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 (100%), American Airlines (81%) and British Airways (81%).

  • 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 $295 on average our data indicates $423 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, August is the cheapest month in which you can book a flight from Montego Bay to Chicago (average of $245). Flying from Montego Bay to Chicago in March is currently the most expensive (average of $321). 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
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

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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 August 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$251Average$316FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$370Average$488FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$383Average$480FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$392Average$550FlexibilityNo cancel feeOn-time63%

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