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$187+ 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 7/12. Fares are subject to change and may not be available on all flights or dates of travel.
MBJ — CHI
jun. 17 — jun. 241
mar. 6/17
mar. 6/24
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 junio 12, 2025.

Round-trip from

$303
(Cheapflightsfares)

One-way from

$187
(SmartFares)

Popular in

January

Cheapest in

September

Average price

$597

Good round-trip deal

$463 or less

Good one-way deal

$262 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. 8% potential increase in price ($42 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 June 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 junio 12, 2025.

This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 7/2312:10 pmMBJ - ORD
1 stop11h 03mSpirit Airlines
sáb. 8/25:38 pmORD - MBJ
1 stop16h 15mSpirit Airlines
Deal found 6/11$303
This American 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 6/272:23 pmMBJ - ORD
Nonstop4h 37mAmerican Airlines
lun. 6/308:44 amORD - MBJ
Nonstop3h 58mAmerican Airlines
Deal found 6/11$334
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.
dom. 7/271:51 pmMBJ - ORD
Nonstop4h 29mUnited Airlines
dom. 8/38:42 amORD - MBJ
Nonstop4h 07mUnited Airlines
Deal found 6/11$359
This Booking.com deal was found by Cheapflights users on 6/12. 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.
vie. 8/13:53 pmMBJ - ORD
1 stop18h 32mFrontier
sáb. 8/25:07 pmORD - MBJ
1 stop14h 48mFrontier
Deal found 6/12$375
This SmartFares deal was found by Cheapflights users on 6/10. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 6/159:18 amMBJ - MDW
1 stop14h 00mFrontier
sáb. 6/216:20 amMDW - MBJ
1 stop8h 23mFrontier
Deal found 6/10$384
This Delta deal was found by Cheapflights users on 6/10. 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.
mié. 6/111:09 pmMBJ - ORD
1 stop10h 48mDelta
lun. 8/115:45 amORD - MBJ
1 stop9h 53mDelta
Deal found 6/10$422
This Mytrip deal was found by Cheapflights users on 6/10. 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.
jue. 7/33:05 pmMBJ - ORD
2 stops29h 18mMultiple Airlines
sáb. 7/125:05 amORD - MBJ
1 stop6h 00mMultiple Airlines
Deal found 6/10$440
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 6/182:55 pmMBJ - MDW
1 stop8h 50mSouthwest
lun. 6/237:45 amMDW - MBJ
1 stop5h 35mSouthwest
Deal found 6/11$486
This Air Canada deal was found by Cheapflights users on 6/12. 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.
mié. 6/1812:05 pmMBJ - ORD
1 stop21h 04mAir Canada
jue. 8/143:35 pmORD - MBJ
2 stops19h 30mAir Canada
Deal found 6/12$527
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 6/2812:07 pmMBJ - MDW
2 stops10h 21mMultiple Airlines
mar. 7/811:39 amMDW - MBJ
1 stop20h 16mMultiple Airlines
Deal found 6/11$547
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 7/11:09 pmMBJ - MDW
1 stop8h 36mDelta
mar. 7/86:00 amMDW - MBJ
1 stop9h 34mDelta
Deal found 6/11$646
This Copa Airlines deal was found by Cheapflights users on 6/10. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 7/1312:14 pmMBJ - ORD
1 stop12h 06mCopa Airlines
sáb. 8/21:07 amORD - MBJ
1 stop10h 08mCopa Airlines
Deal found 6/10$1,132

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 junio 12, 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

mié. 7/23

12:10 pm-11:13 pm

1 stop11h 03m

Chicago O'Hare Intl

sáb. 8/2

5:38 pm-9:53 am

1 stop16h 15m

$303

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

vie. 6/27

2:23 pm-7:00 pm

Nonstop4h 37m

Chicago O'Hare Intl

lun. 6/30

8:44 am-12:42 pm

Nonstop3h 58m

$334

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

dom. 7/27

1:51 pm-6:20 pm

Nonstop4h 29m

Chicago O'Hare Intl

dom. 8/3

8:42 am-12:49 pm

Nonstop4h 07m

$359

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

vie. 8/1

3:53 pm-10:25 am

1 stop18h 32m

Chicago O'Hare Intl

sáb. 8/2

5:07 pm-7:55 am

1 stop14h 48m

$375

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

dom. 6/15

9:18 am-11:18 pm

1 stop14h 00m

Chicago Midway

sáb. 6/21

6:20 am-2:43 pm

1 stop8h 23m

$384

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

jue. 7/3

3:05 pm-8:23 pm

2 stops29h 18m

Chicago O'Hare Intl

sáb. 7/12

5:05 am-11:05 am

1 stop6h 00m

$440

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

mié. 6/18

2:55 pm-11:45 pm

1 stop8h 50m

Chicago Midway

lun. 6/23

7:45 am-1:20 pm

1 stop5h 35m

$486

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

mié. 6/18

12:05 pm-9:09 am

1 stop21h 04m

Chicago O'Hare Intl

jue. 8/14

3:35 pm-11:05 am

2 stops19h 30m

$527

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

sáb. 6/28

12:07 pm-10:28 pm

2 stops10h 21m

Chicago Midway

mar. 7/8

11:39 am-7:55 am

1 stop20h 16m

$547

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

mar. 7/1

1:09 pm-9:45 pm

1 stop8h 36m

Chicago Midway

mar. 7/8

6:00 am-3:34 pm

1 stop9h 34m

$646

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/9

Showing 1-10 of 24 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 junio 12, 2025.

It’s optimal to fly from Montego Bay to Chicago at noon. By choosing this option you can save up to 14% 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 junio 12, 2025.

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 (2 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 junio 12, 2025.
Read reviews from past customers who have flown Southwest, Delta and Copa Airlines from Montego Bay to Chicago. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,287 reviews

Overall

8.0

Entertainment

7.6

Comfort

8.0

Food

7.1

Boarding

8.2

Crew

8.6

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.
Southwest
8.0
Very good
4,287 reviews
Southwest
8.0
Very good
4,287 reviews

Overall

8.0

Entertainment

7.6

Comfort

8.0

Food

7.1

Boarding

8.2

Crew

8.6

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.
Delta
8.0
Very good
7,946 reviews
Southwest
8.0
Very good
4,287 reviews

Overall

8.0

Entertainment

7.6

Comfort

8.0

Food

7.1

Boarding

8.2

Crew

8.6

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.
Copa Airlines
7.5
Good
1,451 reviews
Southwest
8.0
Very good
4,287 reviews

Overall

8.0

Entertainment

7.6

Comfort

8.0

Food

7.1

Boarding

8.2

Crew

8.6

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.
United Airlines
7.4
Good
8,790 reviews
Southwest
8.0
Very good
4,287 reviews

Overall

8.0

Entertainment

7.6

Comfort

8.0

Food

7.1

Boarding

8.2

Crew

8.6

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.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,287 reviews

Overall

8.0

Entertainment

7.6

Comfort

8.0

Food

7.1

Boarding

8.2

Crew

8.6

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 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.

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

    According to our current data, Spirit Airlines ($303), American Airlines ($334), and United Airlines ($359) offers the cheapest pricing from Montego Bay to Chicago. These flights start at 35% 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 $187. Users have also found prices from $210 and $210 on American Airlines and Southwest, 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 (92%), British Airways (92%) and United Airlines (83%).

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

    Looking at all options, your cheapest flight can be booked for $240. While the most popular route (Montego Bay Sangster Intl - Chicago O'Hare Intl) can be booked for $306 on average our data indicates $409 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.
Montego Bay to O'Hare Intl flights
Montego Bay to Midway 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 junio 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$251Average$309FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$255Average$480FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$357Average$489FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$509Average$608FlexibilityNo cancel feeOn-time63%

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