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

Flying on Delta is currently your cheapest option to Montego Bay, with prices starting at $393. Additional round-trip tickets that might be worth considering are offered by Frontier and Southwest, with the lowest prices starting at $409 and $410, respectively. Delta is currently priced 47% below the average price you’ll pay for this route.

What are the cheapest airlines to fly from Chicago Midway Airport to Montego Bay one-way?

The cheapest airlines for a one-way flight from Chicago Midway Airport to Montego Bay are Delta ($152), Southwest ($164), and Frontier ($165).

What is the cheapest day to fly from Chicago Midway Airport to Montego Bay?

Travelers seeking maximum savings on their Chicago Midway Airport to Montego Bay flight should consider departing on Thursday afternoons when fares are most often at their lowest. Thursday mornings flights should be avoided if possible as fares are typically the most expensive at this time.

What are the cheapest flights from Chicago Midway Airport to Montego Bay?

The cheapest flight price from Chicago Midway Airport to Montego Bay is $501. On average you can expect to pay $712. The most popular route, (Chicago Midway - Montego Bay Sangster Intl), can usually be booked for $351.

What are the most popular airlines that fly from Chicago Midway Airport to Montego Bay?

Consider Delta, Frontier or Southwest when booking your flight. These represent the most popular airlines when flying from Chicago Midway Airport to Montego Bay.

What is the cheapest day to fly round-trip from Chicago Midway Airport to Montego Bay?

Departing on a Thursday is a good option for securing a great price. You can expect to save up to 29% when planning your travel around this day of the week.

How far in advance should I book a flight from Chicago Midway Airport to Montego Bay?

Travelers have found it’s best to book a flight 56 days in advance to save up to 47% compared to booking the same week of travel. As your travel date approaches, the cost of this flight route may potentially increase. While opting to book 56 days out may not be an option for all, there are still additional ways to secure a deal in the near future. You might find a flight from Chicago Midway Airport to Montego Bay 1-2 weeks in advance for as low as $506, or $600 for flights within the next 24 hours.

What is the cheapest month to fly from Chicago Midway Airport to Montego Bay?

Due to multiple factors, expect to potentially pay more when booking in March. For low rates, January can be a great choice for travel to Montego Bay. Flights to Montego Bay from Chicago Midway Airport in January are about $584 on average during January, but can be found for as low as $332.

What airport do you fly into for flights to Montego Bay from Chicago Midway?

Montego Bay Sangster Intl (MBJ), located 2.3 mi from the city center, is the airport you fly into when you book flights from Chicago Midway to Montego Bay. 3 airlines have flights to Sangster Intl from Chicago Midway on a regular basis. Booking flights from Chicago Midway to Montego Bay Sangster Intl should not be difficult; the airport handles an average of 0 inbound flights from Chicago Midway per day.

Can I find deals for flights from Midway to Montego Bay that include hotel bookings?

Yes. In addition to deals on Midway to Montego Bay flights, Cheapflights offers vacation packages that include both flights and hotel.

How can I find direct flights from Midway to Montego Bay?

After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Midway to Montego Bay.

Can I find deals for business class flights from Midway to Montego Bay?

Yes. Cheapflights offers flight deals from Midway to Montego Bay by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

$152+ Flights from Chicago Midway Airport to Montego Bay

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Cheapflights Tip: The best prices from Chicago Midway to Montego Bay Sangster Intl are usually found in July or November, booked 85 days in advance, depart on a Thursday or Friday and return on a Monday

Cheap flight deals from Midway to Montego Bay

Round-trip from	$393 (Delta)
One-way from	$152 (Delta)
Popular in	December
Cheapest in	July
Average price	$763
Good round-trip deal	$523 or less

From Chicago Midway to Montego Bay Sangster Intl

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One-way flight from Chicago Midway to Montego Bay Sangster Intl

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Highest demand for flights based on searches. 2% potential increase in price ($21 potential increase over avg. RT price).

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Cheapest flight prices on average. 3% potential price decrease ($24 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 Chicago Midway to Montego Bay Sangster Intl.

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Find flight deals from Midway to Montego Bay

Cheapest flights from Midway to Montego Bay
Explore the most affordable flight options available from Midway to Montego Bay. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 12, 2025.

Thu 10/167:23 pmMDW - MBJ

1 stop12h 30mFrontier

Mon 10/209:13 amMBJ - MDW

1 stop9h 05mFrontier

Deal found 6/12

$393

Mon 6/309:00 amMDW - MBJ

Nonstop4h 00mSouthwest

Wed 7/92:20 pmMBJ - MDW

Nonstop4h 10mSouthwest

Deal found 6/10

$410

Sun 8/106:00 amMDW - MBJ

1 stop7h 04mDelta

Tue 8/122:30 pmMBJ - MDW

1 stop7h 19mDelta

Deal found 6/9

$468

Fri 8/11:11 pmMDW - MBJ

3 stops21h 54mMultiple Airlines

Mon 8/412:45 pmMBJ - MDW

1 stop27h 39mMultiple Airlines

Deal found 6/10

$532

Best flights from Midway to Montego Bay
Discover carefully curated flight deals from Midway to Montego Bay that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated June 12, 2025.

Mon 9/86:00 amMDW - MBJ

1 stop9h 36mDelta

Sat 9/132:23 pmMBJ - MDW

1 stop7h 21mDelta

Deal found 6/11

$393

Fri 7/256:40 pmMDW - MBJ

1 stop16h 09mFrontier

Fri 8/13:53 pmMBJ - MDW

1 stop7h 24mFrontier

Deal found 6/10

$409

Mon 6/309:00 amMDW - MBJ

Nonstop4h 00mSouthwest

Wed 7/92:20 pmMBJ - MDW

Nonstop4h 10mSouthwest

Deal found 6/10

$410

Fri 8/11:11 pmMDW - MBJ

3 stops21h 54mMultiple Airlines

Mon 8/412:45 pmMBJ - MDW

1 stop27h 39mMultiple Airlines

Deal found 6/10

$532

Last-minute flights from Midway to Montego Bay
Discover last-minute flight deals from Midway to Montego Bay. Data last updated June 12, 2025 and is based on user searches.

Sat 6/146:20 amMDW - MBJ

1 stop8h 23mFrontier

Mon 6/163:53 pmMBJ - MDW

1 stop7h 25mFrontier

Deal found 6/10

$409

Tue 6/179:21 amMDW - MBJ

2 stops25h 49mMultiple Airlines

Tue 6/2412:05 pmMBJ - MDW

3 stops27h 32mMultiple Airlines

Deal found 6/10

$959

Wed 6/186:00 amMDW - MBJ

1 stop9h 25mDelta

Wed 6/252:29 pmMBJ - MDW

1 stop7h 16mDelta

Deal found 6/10

$1,241

Sat 6/216:20 amMDW - MBJ

1 stop25h 38mFrontier

Thu 6/269:18 amMBJ - MDW

1 stop14h 00mFrontier

Deal found 6/11

$502

Sun 6/229:00 amMDW - MBJ

Nonstop4h 00mSouthwest

Thu 6/262:20 pmMBJ - MDW

Nonstop4h 10mSouthwest

Deal found 6/10

$455

Mon 6/309:00 amMDW - MBJ

Nonstop4h 00mSouthwest

Wed 7/92:20 pmMBJ - MDW

Nonstop4h 10mSouthwest

Deal found 6/10

$410

Thu 7/39:12 pmMDW - MBJ

2 stops13h 50mMultiple Airlines

Thu 7/109:05 amMBJ - MDW

1 stop14h 12mMultiple Airlines

Deal found 6/10

$546

Wed 7/306:00 amMDW - MBJ

1 stop9h 34mDelta

Wed 8/61:14 pmMBJ - MDW

1 stop8h 28mDelta

Deal found 6/9

$551

One-way flights from Midway to Montego Bay
Search for one-way flight options from Midway to Montego Bay. Find affordable one-way fares based on user searches. Data last updated June 12, 2025.

Sun 8/176:04 amMDW - MBJ

1 stop9h 34mDelta

Deal found 6/10

$152

Sun 7/139:00 amMDW - MBJ

Nonstop4h 00mSouthwest

Deal found 6/9

$164

Thu 9/47:23 pmMDW - MBJ

1 stop12h 30mFrontier

Deal found 6/12

$165

Mon 9/812:50 pmMDW - MBJ

2 stops20h 24mMultiple Airlines

Deal found 6/11

$180

Wed 8/279:15 amMDW - MBJ

3 stops26h 27mWestJet

Deal found 6/10

$378

Cheapflights Fare Finder

Use the filters below to find and compare flights from Chicago Midway Airport to Montego Bay that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Mon 9/8

6:00 am-3:36 pm

1 stop9h 36m

Montego Bay Sangster Intl

Sat 9/13

2:23 pm-9:44 pm

1 stop7h 21m

$393

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Fri 7/25

6:40 pm-10:49 am

1 stop16h 09m

Montego Bay Sangster Intl

Fri 8/1

3:53 pm-11:17 pm

1 stop7h 24m

$409

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Mon 6/30

9:00 am-1:00 pm

Nonstop4h 00m

Montego Bay Sangster Intl

Wed 7/9

2:20 pm-6:30 pm

Nonstop4h 10m

$410

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Fri 8/1

1:11 pm-11:05 am

3 stops21h 54m

Montego Bay Sangster Intl

Mon 8/4

12:45 pm-4:24 pm

1 stop27h 39m

$532

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sun 8/17

6:04 am-3:38 pm

1 stop9h 34m

$152

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sun 7/13

9:00 am-1:00 pm

Nonstop4h 00m

$164

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Thu 9/4

7:23 pm-7:53 am

1 stop12h 30m

$165

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Mon 9/8

12:50 pm-9:14 am

2 stops20h 24m

$180

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Wed 8/27

9:15 am-11:42 am

3 stops26h 27m

$378

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/10

Best time to book a flight from Midway to Montego Bay

Have a flexible travel schedule? Discover the best time to fly to Montego Bay from Midway 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 Chicago Midway Airport to Montego Bay

How far ahead should I book a flight from Chicago Midway Airport to Montego Bay?

The price you pay for your flight from Chicago Midway Airport to Montego Bay may vary depending on when you book. For the best chance of a lower fare, look to book 84 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

What is the cheapest month to book a flight from Chicago Midway Airport to Montego Bay?

Currently, January is the cheapest month in which you can book a flight from Chicago Midway Airport to Montego Bay (average of $403). Flying from Chicago Midway Airport to Montego Bay in July is currently the most expensive (average of $569). 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 MDW to MBJ?

It’s optimal to fly from Chicago Midway Airport to Montego Bay at noon. By choosing this option you can save up to 42% on the cost of your flight, compared to a flight in the morning.

Rainfall in Montego Bay by month

In terms of precipitation, rainfall in Montego Bay ranges from 1.6 - 7.1 inches per month. October is typically the wettest month, when rainfall can reach 7.1 in. February is typically the driest time to visit Montego Bay when rainfall is around 1.6 in.

Temperature in Montego Bay by month

If weather is an important factor for your trip to Montego Bay, 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 82.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 77.0 F).

Reviews of airlines servicing Montego Bay

To help decide which airline to fly from Chicago to Montego Bay, see what other customers have to say about Southwest, Delta and WestJet. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.

Southwest

8.0

Very good

4,287 reviews

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

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

7,950 reviews

Southwest

8.0

Very good

4,287 reviews

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.

WestJet

7.2

Good

2,868 reviews

Southwest

8.0

Very good

4,287 reviews

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.

Frontier

5.9

Fair

3,295 reviews

Southwest

8.0

Very good

4,287 reviews

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

What airport do you fly into for flights to Montego Bay from Chicago Midway?
Montego Bay Sangster Intl (MBJ), located 2.3 mi from the city center, is the airport you fly into when you book flights from Chicago Midway to Montego Bay. 3 airlines have flights to Sangster Intl from Chicago Midway on a regular basis. Booking flights from Chicago Midway to Montego Bay Sangster Intl should not be difficult; the airport handles an average of 0 inbound flights from Chicago Midway per day.
What are the cheapest airlines flying from Chicago Midway Airport to Montego Bay round-trip?
Flying on Delta is currently your cheapest option to Montego Bay, with prices starting at $393. Additional round-trip tickets that might be worth considering are offered by Frontier and Southwest, with the lowest prices starting at $409 and $410, respectively. Delta is currently priced 47% below the average price you’ll pay for this route.
What are the cheapest airlines to fly from Chicago Midway Airport to Montego Bay one-way?
The cheapest airlines for a one-way flight from Chicago Midway Airport to Montego Bay are Delta ($152), Southwest ($164), and Frontier ($165).
What are the cheapest flights from Chicago Midway Airport to Montego Bay?
The cheapest flight price from Chicago Midway Airport to Montego Bay is $501. On average you can expect to pay $712. The most popular route, (Chicago Midway - Montego Bay Sangster Intl), can usually be booked for $351.
Can I find deals for flights from Midway to Montego Bay that include hotel bookings?
Yes. In addition to deals on Midway to Montego Bay flights, Cheapflights offers vacation packages that include both flights and hotel.
How can I find direct flights from Midway to Montego Bay?
After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Midway to Montego Bay.
Can I find deals for business class flights from Midway to Montego Bay?
Yes. Cheapflights offers flight deals from Midway to Montego Bay 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 Chicago Midway Airport to Montego Bay?
Currently, January is the cheapest month in which you can book a flight from Chicago Midway Airport to Montego Bay (average of $403). Flying from Chicago Midway Airport to Montego Bay in July is currently the most expensive (average of $569). 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

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Top 3 airlines flying from Midway to Montego Bay

Airline	Cheapest	Average	Flexibility	On-time
Frontier	Cheapest$338	Average$436	FlexibilityNo cancel fee	On-time62%
Delta	Cheapest$452	Average$815	FlexibilityNo cancel fee	On-timeN/A
Southwest	Cheapest$579	Average$741	FlexibilityNo cancel fee	On-time63%

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$152+ Cheap flights from Midway (MDW) to Montego Bay (MBJ)

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 8/17. Fares are subject to change and may not be available on all flights or dates of travel.

Find cheap flights from Midway to Montego Bay with Cheapflights

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3. Compare prices and book

Cheapflights Tip: The best prices from Chicago Midway to Montego Bay Sangster Intl are usually found in July or November, booked 85 days in advance, depart on a Thursday or Friday and return on a Monday

Cheap flight deals from Midway to Montego Bay

Round-trip from

One-way from

Popular in

Cheapest in

Average price

Good round-trip deal

Find flight deals from Midway to Montego Bay

Cheapest flights from Midway to Montego BayExplore the most affordable flight options available from Midway to Montego Bay. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 12, 2025.

Explore the most affordable flight options available from Midway to Montego Bay. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 12, 2025.

Cheapflights Fare Finder

Use the filters below to find and compare flights from Chicago Midway Airport to Montego Bay that are best for you.

Best time to book a flight from Midway to Montego Bay

Have a flexible travel schedule? Discover the best time to fly to Montego Bay from Midway with our price prediction graph.

Cheapflights Insights

Everything you need to know about your flight from Chicago Midway Airport to Montego Bay

How far ahead should I book a flight from Chicago Midway Airport to Montego Bay?

Use this chart to determine the optimal time to book a round-trip flight from Midway to Montego Bay. Price data was last updated on June 9, 2025.

What is the cheapest month to book a flight from Chicago Midway Airport to Montego Bay?

What is the cheapest time of day to fly from MDW to MBJ?

Find hourly flight availability from Midway to Montego Bay. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated June 12, 2025.

Rainfall in Montego Bay by month

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

Temperature in Montego Bay by month

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

Reviews of airlines servicing Montego Bay

Related info for your journey

Find useful and relevant information for your journey from Midway to Montego Bay. 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 into for flights to Montego Bay from Chicago Midway?

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

What are the cheapest airlines to fly from Chicago Midway Airport to Montego Bay one-way?

What are the cheapest flights from Chicago Midway Airport to Montego Bay?

Can I find deals for flights from Midway to Montego Bay that include hotel bookings?

How can I find direct flights from Midway to Montego Bay?

Can I find deals for business class flights from Midway to Montego Bay?

What is the cheapest month to book a flight from Chicago Midway Airport to Montego Bay?

Traveling to a place near Chicago Midway Airport?

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Alternative routes for Midway to Montego Bay

See prices for flight routes from nearby airports that may be better suited for you.

Top 3 airlines flying from Midway to Montego Bay

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Cheapest flights from Midway to Montego Bay
Explore the most affordable flight options available from Midway to Montego Bay. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 12, 2025.