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$160+ 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 4/8. Fares are subject to change and may not be available on all flights or dates of travel.
MBJ — CHI
Feb 27 — Mar 61
Thu 2/27
Thu 3/6
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 February 22, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$305
(Cheapflightsfares)

One-way from

$160
(Mytrip)

Popular in

January

Cheapest in

April

Average price

$480

Good round-trip deal

$400 or less

Good one-way deal

$322 or less
Provider with most accurate pricing for Montego Bay Sangster Intl-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Montego Bay Sangster Intl-Chicago (CHI) flights.
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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. 12% potential increase in price ($64 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($15 potential savings vs. average RT price).
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Average for round-trip flights in February 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 February 22, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 2/21. 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 5/112:00 pmMBJ - ORD
1 stop12h 41mSpirit Airlines
Thu 5/86:34 pmORD - MBJ
1 stop14h 40mSpirit Airlines
Deal found 2/21$305
This Frontier deal was found by Cheapflights users on 2/21. 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.
Sat 5/3110:57 amMBJ - ORD
2 stops13h 11mFrontier
Sat 8/96:00 amORD - MBJ
1 stop8h 13mFrontier
Deal found 2/21$342
This Booking.com deal was found by Cheapflights users on 2/21. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/3112:11 pmMBJ - ORD
1 stop7h 47mMultiple Airlines
Sat 8/96:00 amORD - MBJ
1 stop8h 13mMultiple Airlines
Deal found 2/21$366
This Kiwi.com deal was found by Cheapflights users on 2/22. 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.
Wed 4/2312:00 pmMBJ - MDW
2 stops27h 46mMultiple Airlines
Wed 5/72:12 pmMDW - MBJ
1 stop22h 49mMultiple Airlines
Deal found 2/22$369
This Delta deal was found by Cheapflights users on 2/22. 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 3/2012:09 pmMBJ - ORD
1 stop8h 49mDelta
Fri 3/285:45 amORD - MBJ
1 stop9h 38mDelta
Deal found 2/22$425
This Delta deal was found by Cheapflights users on 2/22. 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 3/207:00 amMBJ - MDW
2 stops11h 02mDelta
Fri 3/2812:51 pmMDW - MBJ
1 stop7h 46mDelta
Deal found 2/22$425
This American Airlines deal was found by Cheapflights users on 2/21. 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 8/122:15 pmMBJ - ORD
Nonstop4h 35mAmerican Airlines
Sun 8/318:05 amORD - MBJ
Nonstop4h 00mAmerican Airlines
Deal found 2/21$440
This United Airlines deal was found by Cheapflights users on 2/22. 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 2/263:55 pmMBJ - ORD
1 stop8h 14mUnited Airlines
Fri 2/284:10 pmORD - MBJ
1 stop23h 06mUnited Airlines
Deal found 2/22$462
This Southwest deal was found by Cheapflights users on 2/22. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/262:00 pmMBJ - MDW
1 stop8h 25mSouthwest
Fri 2/288:35 pmMDW - MBJ
2 stops14h 35mSouthwest
Deal found 2/22$532
This Air Canada deal was found by Cheapflights users on 2/21. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/128:20 pmMBJ - ORD
2 stops15h 04mAir Canada
Sun 8/3110:00 amORD - MBJ
1 stop9h 25mAir Canada
Deal found 2/21$626

Find flights from Montego Bay to Chicago within your budget

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 February 22, 2025.

Fly from

Montego Bay

Fly to

Chicago

Route

Depart

Return

Price

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Thu 5/1

12:00 pm-12:41 am

1 stop12h 41m

Chicago O'Hare Intl

Thu 5/8

6:34 pm-9:14 am

1 stop14h 40m

$305

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Sat 5/31

10:57 am-12:08 am

2 stops13h 11m

Chicago O'Hare Intl

Sat 8/9

6:00 am-2:13 pm

1 stop8h 13m

$342

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Sat 5/31

12:11 pm-7:58 pm

1 stop7h 47m

Chicago O'Hare Intl

Sat 8/9

6:00 am-2:13 pm

1 stop8h 13m

$366

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Wed 4/23

12:00 pm-3:46 pm

2 stops27h 46m

Chicago Midway

Wed 5/7

2:12 pm-1:01 pm

1 stop22h 49m

$369

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Thu 3/20

12:09 pm-8:58 pm

1 stop8h 49m

Chicago O'Hare Intl

Fri 3/28

5:45 am-3:23 pm

1 stop9h 38m

$425

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Thu 3/20

7:00 am-4:14 pm

1 stop9h 14m

Chicago Midway

Fri 3/28

12:51 pm-8:37 pm

1 stop7h 46m

$425

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Tue 8/12

2:15 pm-6:50 pm

Nonstop4h 35m

Chicago O'Hare Intl

Sun 8/31

8:05 am-12:05 pm

Nonstop4h 00m

$440

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Sat 8/2

1:51 pm-6:20 pm

Nonstop4h 29m

Chicago O'Hare Intl

Sat 8/30

6:00 am-1:25 pm

1 stop7h 25m

$494

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Tue 8/12

8:20 pm-11:24 am

2 stops15h 04m

Chicago O'Hare Intl

Sun 8/31

10:00 am-7:25 pm

1 stop9h 25m

$626

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Wed 4/23

12:35 pm-11:10 pm

2 stops10h 35m

Chicago Midway

Wed 5/14

7:35 pm-1:55 pm

2 stops18h 20m

$662

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/21

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 February.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
AranGrantPrice Accuracy3 starsTrust Score*1 star
PricelinePrice Accuracy1 starTrust 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.

Travel insights for flights from Montego Bay to Chicago

Get recent, data-driven insights about flights from Montego Bay to Chicago including ideal travel times, pricing trends, and more.

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 February 22, 2025.

It’s optimal to fly from Montego Bay to Chicago in the morning. By choosing this option you can save up to 2% on the cost of your flight, compared to a flight at noon.

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 February 22, 2025.

The most flights from MBJ to CHI are scheduled on a Saturday (6 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (1 on average).

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 February 22, 2025.
Southwest
8.1
Very good
4,395 reviews

Boarding

8.2

Comfort

8.1

Overall

8.1

Food

7.1

Entertainment

7.6

Crew

8.7

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Southwest
8.1
Very good
4,395 reviews
Southwest
8.1
Very good
4,395 reviews

Boarding

8.2

Comfort

8.1

Overall

8.1

Food

7.1

Entertainment

7.6

Crew

8.7

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Delta
8.0
Very good
8,203 reviews
Southwest
8.1
Very good
4,395 reviews

Boarding

8.2

Comfort

8.1

Overall

8.1

Food

7.1

Entertainment

7.6

Crew

8.7

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

JetBlue
7.4
Good
3,068 reviews
Southwest
8.1
Very good
4,395 reviews

Boarding

8.2

Comfort

8.1

Overall

8.1

Food

7.1

Entertainment

7.6

Crew

8.7

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

United Airlines
7.4
Good
8,754 reviews
Southwest
8.1
Very good
4,395 reviews

Boarding

8.2

Comfort

8.1

Overall

8.1

Food

7.1

Entertainment

7.6

Crew

8.7

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

American Airlines
7.2
Good
10,000 reviews
Southwest
8.1
Very good
4,395 reviews

Boarding

8.2

Comfort

8.1

Overall

8.1

Food

7.1

Entertainment

7.6

Crew

8.7

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

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 3 outbound flights 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.

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

    According to our current data, Spirit Airlines ($305), Frontier ($342), and Delta ($425) offers the cheapest pricing from Montego Bay to Chicago. These flights start at 31% 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 $160. Users have also found prices from $172 and $248 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 American Airlines (71%), United Airlines (63%) and British Airways (56%).

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

    Looking at all options, your cheapest flight can be booked for $256. While the most popular route (Montego Bay Sangster Intl - Chicago O'Hare Intl) can be booked for $276 on average our data indicates $435 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 Montego Bay?

Book flights to Montego Bay if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
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.
Montego Bay to O'Hare Intl flights
Kingston to O'Hare Intl flights
Montego Bay to Midway 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 February 22, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$251Average$309FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$255Average$436FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$357Average$471FlexibilityNo cancel feeOn-time71%
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