Chicago

$166+ 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 9/4. Fares are subject to change and may not be available on all flights or dates of travel.
MBJ — CHI
Jul 8 — Jul 151
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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 July 3, 2025.

Round-trip from

$238
(FlightHub)

One-way from

$166
(Cheapflightsfares)

Popular in

January

Cheapest in

September

Average price

$421

Good round-trip deal

$366 or less

Good one-way deal

$264 or less
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. 10% potential increase in price ($52 potential increase over avg. RT price).
Cheapest flight prices on average. 3% potential price decrease ($14 potential savings vs. average RT price).
Average for round-trip flights in July 2025
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).

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 July 3, 2025.

This FlightHub deal was found by Cheapflights users on 7/1. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/2410:48 amMBJ - ORD
1 stop13h 05mSpirit Airlines
Mon 8/45:05 amORD - MBJ
1 stop6h 00mSpirit Airlines
Deal found 7/1$238
This American Airlines deal was found by Cheapflights users on 7/1. 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 8/12:30 pmMBJ - ORD
Nonstop4h 30mAmerican Airlines
Sat 8/210:05 pmORD - MBJ
1 stop16h 43mAmerican Airlines
Deal found 7/1$338
This Delta deal was found by Cheapflights users on 7/1. 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 9/182:35 pmMBJ - MDW
1 stop7h 01mDelta
Tue 9/306:00 amMDW - MBJ
1 stop7h 09mDelta
Deal found 7/1$339
This Booking.com deal was found by Cheapflights users on 7/2. 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.
Tue 8/53:45 pmMBJ - MDW
1 stop18h 55mFrontier
Wed 9/38:00 amMDW - MBJ
1 stop28h 45mFrontier
Deal found 7/2$365
This United Airlines deal was found by Cheapflights users on 7/2. 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 7/304:12 pmMBJ - ORD
1 stop7h 18mUnited Airlines
Sat 8/168:42 amORD - MBJ
Nonstop4h 07mUnited Airlines
Deal found 7/2$367
This Booking.com deal was found by Cheapflights users on 7/2. 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.
Mon 8/189:05 amMBJ - ORD
1 stop15h 17mFrontier
Thu 8/215:10 amORD - MBJ
1 stop26h 45mFrontier
Deal found 7/2$385
This Kiwi.com deal was found by Cheapflights users on 7/2. 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.
Fri 7/1812:10 pmMBJ - MDW
2 stops11h 07mMultiple Airlines
Fri 7/2512:50 pmMDW - MBJ
1 stop21h 40mMultiple Airlines
Deal found 7/2$431
This Southwest deal was found by Cheapflights users on 7/1. 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.
Thu 9/183:00 pmMBJ - MDW
2 stops16h 10mSouthwest
Tue 9/306:15 amMDW - MBJ
1 stop5h 40mSouthwest
Deal found 7/1$448

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 July 3, 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

Thu 7/24

10:48 am-11:53 pm

1 stop13h 05m

Chicago O'Hare Intl

Mon 8/4

5:05 am-11:05 am

1 stop6h 00m

$238

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Fri 8/1

2:30 pm-7:00 pm

Nonstop4h 30m

Chicago O'Hare Intl

Sat 8/2

10:05 pm-2:48 pm

1 stop16h 43m

$338

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Thu 9/18

2:35 pm-9:36 pm

1 stop7h 01m

Chicago Midway

Tue 9/30

6:00 am-1:09 pm

1 stop7h 09m

$339

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Tue 8/5

3:45 pm-10:40 am

1 stop18h 55m

Chicago Midway

Wed 9/3

8:00 am-12:45 pm

1 stop28h 45m

$365

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Wed 7/30

4:12 pm-11:30 pm

1 stop7h 18m

Chicago O'Hare Intl

Sat 8/16

7:40 pm-3:10 pm

1 stop19h 30m

$367

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Mon 8/18

9:05 am-12:22 am

1 stop15h 17m

Chicago O'Hare Intl

Thu 8/21

5:10 am-7:55 am

1 stop26h 45m

$385

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Fri 7/18

12:10 pm-11:17 pm

2 stops11h 07m

Chicago Midway

Fri 7/25

12:50 pm-10:30 am

1 stop21h 40m

$431

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Thu 9/18

3:00 pm-7:10 am

2 stops16h 10m

Chicago Midway

Tue 9/30

6:15 am-11:55 am

1 stop5h 40m

$448

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Thu 9/4

12:15 pm-10:48 pm

1 stop10h 33m

$166

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Thu 9/18

2:05 pm-11:20 pm

1 stop9h 15m

$177

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/2

Showing 1-10 of 19 results
1
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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 July 3, 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.

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 July 3, 2025.
See what other customers who have flown with Southwest, Delta, and Copa 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

7.6

Overall

8.0

Comfort

8.0

Crew

8.6

Boarding

8.2

Food

7.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

Entertainment

7.6

Overall

8.0

Comfort

8.0

Crew

8.6

Boarding

8.2

Food

7.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
8.0
Very good

Entertainment

7.6

Overall

8.0

Comfort

8.0

Crew

8.6

Boarding

8.2

Food

7.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

Entertainment

7.6

Overall

8.0

Comfort

8.0

Crew

8.6

Boarding

8.2

Food

7.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

Entertainment

7.6

Overall

8.0

Comfort

8.0

Crew

8.6

Boarding

8.2

Food

7.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

Entertainment

7.6

Overall

8.0

Comfort

8.0

Crew

8.6

Boarding

8.2

Food

7.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

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 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.

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

    According to our current data, Spirit Airlines ($238), American Airlines ($338), and Delta ($339) offers the cheapest pricing from Montego Bay to Chicago. These flights start at 48% 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 $166. Users have also found prices from $177 and $210 on Frontier 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 American Airlines (88%), British Airways (88%) and United Airlines (86%).

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

    Looking at all options, your cheapest flight can be booked for $192. While the most popular route (Montego Bay Sangster Intl - Chicago O'Hare Intl) can be booked for $290 on average our data indicates $356 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
Lansing
Benton Harbor
Porter
Hammond
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.

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 July 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$251Average$314FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$255Average$477FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$376Average$490FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$509Average$608FlexibilityNo cancel feeOn-time63%

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