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Cheap flights from Midway (MDW) to Jamaica from $99

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 5/14. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
MDW — MBJ
May 11 — May 181
From?
To?
Sat 5/11
Sat 5/18
1 adult, Economy
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What is the cheapest month to fly from Chicago Midway Airport to Jamaica?

August is one of the best times of the year to fly to Jamaica from Chicago Midway Airport. Prices for August average $533 per person but you can even find prices for as low as $239. The most expensive prices can be found in the month of December. Opting for a August flight can save you 32% on your journey compared to booking in December

When is the cheapest time to fly from Chicago Midway Airport to Jamaica (MDW - JM)?

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Chicago Midway Airport to Jamaica as you normally would.

Cheap Frontier flights from Midway to Jamaica

Explore cheap flight options specifically provided by Frontier for the route between Midway and Jamaica. Find affordable fares and compare prices with other airlines to secure the best deal for your journey. Over the last 7 days, Cheapflights users made 2,719,943 searches. Data last updated May 6, 2024.
Peruse some of the lowest-priced Frontier flights we've found from Chicago to Jamaica. Make sure to check back often as deals are often changing.
Sat 7/66:00 amMDW - MBJ
1 stop24h 57mFrontier
Tue 7/92:35 pmMBJ - MDW
1 stop6h 35mFrontier
Deal found 5/5$286
Thu 9/59:44 pmMDW - MBJ
1 stop9h 13mFrontier
Tue 9/108:07 amMBJ - MDW
1 stop12h 42mFrontier
Deal found 5/5$320
Mon 5/134:56 pmMDW - MBJ
2 stops38h 24mFrontier
Fri 5/1710:07 amMBJ - MDW
2 stops25h 06mFrontier
Deal found 5/5$347
Sun 5/2612:14 pmMDW - MBJ
1 stop20h 41mFrontier
Sat 6/18:07 amMBJ - MDW
1 stop12h 53mFrontier
Deal found 5/5$362
Sun 6/29:53 pmMDW - MBJ
1 stop11h 02mFrontier
Sat 6/84:49 pmMBJ - MDW
1 stop13h 11mFrontier
Deal found 5/5$386
Fri 6/77:30 amMDW - MBJ
1 stop8h 08mFrontier
Wed 6/123:15 pmMBJ - MDW
1 stop14h 45mFrontier
Deal found 5/5$390
Fri 5/106:08 pmMDW - MBJ
1 stop16h 30mFrontier
Tue 5/148:32 amMBJ - MDW
1 stop10h 43mFrontier
Deal found 5/5$410
Sat 6/17:53 amMDW - MBJ
1 stop7h 42mFrontier
Mon 6/31:43 pmMBJ - MDW
2 stops16h 07mFrontier
Deal found 5/4$416
Fri 6/217:30 amMDW - MBJ
1 stop8h 08mFrontier
Wed 6/263:15 pmMBJ - MDW
1 stop14h 45mFrontier
Deal found 5/5$420

Cheap Delta flights from Midway to Jamaica

Explore cheap flight options specifically provided by Delta for the route between Midway and Jamaica. Find affordable fares and compare prices with other airlines to secure the best deal for your journey. Over the last 7 days, Cheapflights users made 2,719,943 searches. Data last updated May 6, 2024.
Take a gander at the lowest prices we've found on Delta flights from Chicago to Jamaica. Ensure the flight price, dates, time, and airline match your criteria before you book.
Tue 7/212:45 pmMDW - MBJ
1 stop24h 20mDelta
Thu 7/112:25 pmMBJ - MDW
1 stop7h 16mDelta
Deal found 5/5$458
Wed 9/181:05 pmMDW - KIN
1 stop6h 42mDelta
Thu 9/269:00 amKIN - MDW
1 stop12h 44mDelta
Deal found 5/5$480
Mon 9/235:59 pmMDW - KIN
2 stops25h 48mDelta
Tue 10/19:00 amKIN - MDW
2 stops23h 45mDelta
Deal found 5/5$485
Mon 9/233:45 pmMDW - KIN
1 stop28h 02mDelta
Thu 9/269:00 amKIN - MDW
1 stop12h 44mDelta
Deal found 5/5$488
Mon 9/236:50 pmMDW - KIN
1 stop24h 57mDelta
Tue 10/19:00 amKIN - MDW
2 stops23h 45mDelta
Deal found 5/5$493
Sat 9/219:35 amMDW - KIN
2 stops34h 12mDelta
Fri 9/279:00 amKIN - MDW
1 stop8h 59mDelta
Deal found 5/5$498
Wed 9/181:10 pmMDW - KIN
2 stops30h 37mDelta
Sat 9/289:00 amKIN - MDW
2 stops27h 31mDelta
Deal found 5/5$504
Sat 5/256:00 amMDW - KIN
1 stop13h 56mDelta
Wed 5/299:00 amKIN - MDW
1 stop13h 01mDelta
Deal found 5/4$510
Sat 9/2110:11 amMDW - KIN
1 stop9h 36mDelta
Sat 9/289:00 amKIN - MDW
1 stop8h 16mDelta
Deal found 5/5$540

Cheap Midway to Jamaica flights in May & June 2024

Find cheap flight options from Midway to Jamaica specifically for the months of May and June 2024. Explore affordable fares based on user searches. Over the last 7 days, Cheapflights users made 2,719,943 searches. Prices were last updated on May 6, 2024.
Listed are some of the best fares we've found on flights departing from Chicago to Jamaica in 2024. Check back regularly for other flight deals.
Sun 6/29:53 pmMDW - MBJ
1 stop11h 02mMultiple Airlines
Sat 6/812:46 pmMBJ - MDW
2 stops9h 01mMultiple Airlines
Deal found 5/5$327
Mon 5/134:56 pmMDW - MBJ
2 stops38h 24mFrontier
Fri 5/1710:07 amMBJ - MDW
2 stops25h 06mFrontier
Deal found 5/5$347
Wed 5/87:00 amMDW - MBJ
1 stop24h 20mFrontier
Sat 5/1111:51 amMBJ - MDW
1 stop10h 50mFrontier
Deal found 5/5$357
Sun 5/2612:14 pmMDW - MBJ
1 stop20h 41mFrontier
Sat 6/18:07 amMBJ - MDW
1 stop12h 53mFrontier
Deal found 5/5$362
Sun 6/29:53 pmMDW - MBJ
1 stop11h 02mFrontier
Sat 6/84:49 pmMBJ - MDW
1 stop13h 11mFrontier
Deal found 5/5$386
Fri 6/77:30 amMDW - MBJ
1 stop8h 08mFrontier
Wed 6/123:15 pmMBJ - MDW
1 stop14h 45mFrontier
Deal found 5/5$390
Fri 5/106:08 pmMDW - MBJ
1 stop16h 30mFrontier
Tue 5/148:32 amMBJ - MDW
1 stop10h 43mFrontier
Deal found 5/5$410
Wed 5/87:00 amMDW - MBJ
1 stop24h 20mFrontier
Fri 5/108:32 amMBJ - MDW
2 stops35h 47mFrontier
Deal found 5/4$414
Sat 6/17:53 amMDW - MBJ
1 stop7h 42mFrontier
Mon 6/31:43 pmMBJ - MDW
2 stops16h 07mFrontier
Deal found 5/4$416

Midway to Jamaica 2024 flight deals

Discover exclusive flight deals for travel between Midway and Jamaica in 2024. Find excellent offers based on user searches. Over the last 7 days, Cheapflights users made 2,719,943 searches. Data last updated May 6, 2024.
Listed are some of the best fares we've found on flights departing from Chicago to Jamaica in 2024. Check back regularly for other flight deals.
Sat 7/66:00 amMDW - MBJ
1 stop24h 57mFrontier
Tue 7/92:35 pmMBJ - MDW
1 stop6h 35mFrontier
Deal found 5/5$286
Thu 9/59:44 pmMDW - MBJ
1 stop9h 13mFrontier
Tue 9/108:07 amMBJ - MDW
1 stop12h 42mFrontier
Deal found 5/5$320
Sun 6/29:53 pmMDW - MBJ
1 stop11h 02mMultiple Airlines
Sat 6/812:46 pmMBJ - MDW
2 stops9h 01mMultiple Airlines
Deal found 5/5$327
Mon 5/134:56 pmMDW - MBJ
2 stops38h 24mFrontier
Fri 5/1710:07 amMBJ - MDW
2 stops25h 06mFrontier
Deal found 5/5$347
Wed 5/87:00 amMDW - MBJ
1 stop24h 20mFrontier
Sat 5/1111:51 amMBJ - MDW
1 stop10h 50mFrontier
Deal found 5/5$357
Sun 5/2612:14 pmMDW - MBJ
1 stop20h 41mFrontier
Sat 6/18:07 amMBJ - MDW
1 stop12h 53mFrontier
Deal found 5/5$362
Sun 6/29:53 pmMDW - MBJ
1 stop11h 02mFrontier
Sat 6/84:49 pmMBJ - MDW
1 stop13h 11mFrontier
Deal found 5/5$386
Fri 6/77:30 amMDW - MBJ
1 stop8h 08mFrontier
Wed 6/123:15 pmMBJ - MDW
1 stop14h 45mFrontier
Deal found 5/5$390
Fri 5/106:08 pmMDW - MBJ
1 stop16h 30mFrontier
Tue 5/148:32 amMBJ - MDW
1 stop10h 43mFrontier
Deal found 5/5$410

Midway to Jamaica flights leaving soon

Find last-minute flight options from Midway to Jamaica for spontaneous travel. Discover available flights and compare prices based on user searches. Secure great deals and offers for spontaneous trips with quick booking options. Over the last 7 days, Cheapflights users made 2,719,943 searches. Data last updated May 6, 2024.
Check out these flights departing soon from Chicago to Jamaica. Users should examine the flight details to ensure there are no surprises.
Mon 5/134:56 pmMDW - MBJ
2 stops38h 24mFrontier
Fri 5/1710:07 amMBJ - MDW
2 stops25h 06mFrontier
Deal found 5/5$347
Fri 5/106:08 pmMDW - MBJ
1 stop16h 30mFrontier
Tue 5/148:32 amMBJ - MDW
1 stop10h 43mFrontier
Deal found 5/5$410
Mon 5/136:55 amMDW - MBJ
1 stop24h 25mFrontier
Fri 5/1710:07 amMBJ - MDW
2 stops25h 06mFrontier
Deal found 5/5$440
Fri 5/103:44 pmMDW - MBJ
2 stops46h 15mFrontier
Tue 5/148:32 amMBJ - MDW
1 stop10h 43mFrontier
Deal found 5/5$498
Sun 5/128:45 amMDW - KIN
1 stop11h 11mDelta
Sun 5/199:00 amKIN - MDW
1 stop13h 01mDelta
Deal found 5/5$909
Sun 5/129:32 amMDW - KIN
2 stops10h 24mDelta
Sun 5/199:00 amKIN - MDW
1 stop8h 58mDelta
Deal found 5/5$914
Mon 5/136:00 amMDW - MBJ
1 stop9h 34mDelta
Fri 5/171:05 pmMBJ - MDW
1 stop8h 56mDelta
Deal found 5/5$1,000
Sun 5/126:00 amMDW - KIN
2 stops13h 05mMultiple Airlines
Sun 5/198:35 amKIN - MDW
1 stop13h 02mMultiple Airlines
Deal found 5/5$1,138
Fri 5/106:00 amMDW - MBJ
2 stops12h 26mWestJet
Tue 5/1412:55 pmMBJ - MDW
2 stops26h 55mWestJet
Deal found 5/5$3,675

One-way flights to Jamaica from Midway

Search for one-way flight options from Midway to Jamaica. Find affordable one-way fares based on user searches. Compare prices and availability to plan your one-way journey according to your preferred dates and budget. Over the last 7 days, Cheapflights users made 2,719,943 searches. Data last updated May 6, 2024.
Take a look at some of the best available options we've come across on one-way flights from Chicago to Jamaica. Users can also find round-trip Chicago to Jamaica flights by using the search form above.
Tue 5/148:16 pmMDW - MBJ
1 stop11h 04mFrontier
Deal found 5/5$99
Mon 6/37:53 amMDW - MBJ
1 stop23h 04mFrontier
Deal found 5/5$122
Sat 5/187:53 amMDW - MBJ
1 stop24h 18mFrontier
Deal found 5/5$135
Mon 6/37:53 amMDW - MBJ
2 stops27h 48mMultiple Airlines
Deal found 5/5$149
Sat 5/189:08 pmMDW - MBJ
2 stops14h 33mMultiple Airlines
Deal found 5/5$171
Sun 6/29:53 pmMDW - MBJ
1 stop11h 02mFrontier
Deal found 5/5$182
Mon 5/207:53 amMDW - MBJ
1 stop23h 04mFrontier
Deal found 5/5$204
Mon 7/87:27 amMDW - MBJ
1 stop23h 30mFrontier
Deal found 5/5$211
Mon 5/203:36 pmMDW - MBJ
2 stops20h 05mMultiple Airlines
Deal found 5/5$218

Find flights from Midway to Jamaica within your budget

Customize your flight search to find flights from Midway to Jamaica 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 2,719,943 searches. Data last updated May 6, 2024.

Fly from

Any airport

Fly to

Any airport

Budget

$286 - $480

Route

Depart

Return

Price

Chicago MidwayMontego Bay Sangster Intl

MDW - MBJ

MDWMBJ

Chicago Midway

Sat 7/6

1 stop24h 57m

Montego Bay Sangster Intl

Tue 7/9

1 stop6h 35m

$286

Chicago MidwayMontego Bay Sangster Intl

MDW - MBJ

MDWMBJ

Chicago Midway

Thu 9/5

1 stop9h 13m

Montego Bay Sangster Intl

Tue 9/10

1 stop12h 42m

$320

Chicago MidwayMontego Bay Sangster Intl

MDW - MBJ

MDWMBJ

Chicago Midway

Sun 6/2

1 stop11h 02m

Montego Bay Sangster Intl

Sat 6/8

2 stops9h 01m

$327

Chicago MidwayMontego Bay Sangster Intl

MDW - MBJ

MDWMBJ

Chicago Midway

Sun 5/26

1 stop20h 41m

Montego Bay Sangster Intl

Sat 6/1

1 stop12h 53m

$362

Chicago MidwayMontego Bay Sangster Intl

MDW - MBJ

MDWMBJ

Chicago Midway

Sun 6/2

1 stop11h 02m

Montego Bay Sangster Intl

Sat 6/8

1 stop13h 11m

$386

Chicago MidwayMontego Bay Sangster Intl

MDW - MBJ

MDWMBJ

Chicago Midway

Fri 6/7

1 stop8h 08m

Montego Bay Sangster Intl

Wed 6/12

1 stop14h 45m

$390

Chicago MidwayMontego Bay Sangster Intl

MDW - MBJ

MDWMBJ

Chicago Midway

Wed 7/3

2 stops26h 48m

Montego Bay Sangster Intl

Tue 7/9

1 stop6h 35m

$411

Chicago MidwayMontego Bay Sangster Intl

MDW - MBJ

MDWMBJ

Chicago Midway

Tue 7/2

1 stop24h 20m

Montego Bay Sangster Intl

Thu 7/11

1 stop7h 16m

$458

Chicago MidwayKingston Norman Manley

MDW - KIN

MDWKIN

Chicago Midway

Wed 9/18

1 stop6h 42m

Kingston Norman Manley

Thu 9/26

1 stop12h 44m

$480

Flights are sorted by cheapest first

Deals found on 5/5

No data available for this route at this time. Please check back soon.

Reviews of airlines servicing Jamaica

Get insights into the airlines that provide service to Jamaica. 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 Jamaica. Reviews last updated May 6, 2024.
To help decide which airline to fly from Chicago to Jamaica, see what other customers have to say about Frontier, Delta and WestJet. In addition to providing an overall rating, users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.1
Very good
10,826 reviews
Check prices

Comfort

7.9

Food

7.4

Overall

8.1

Crew

8.6

Entertainment

8.0

Boarding

8.2

Reviews

1 / 10

Bad experience with the staff boarding the gate. I couldn’t board with my carry on, personal item and a funny bag. I had to put my passport inside my pockets and put the funny bag inside the personal item. Then after passing the staff pull out everything again.

Delta
8.1
Very good
10,826 reviews
Delta
8.1
Very good
10,826 reviews
Check prices

Comfort

7.9

Food

7.4

Overall

8.1

Crew

8.6

Entertainment

8.0

Boarding

8.2

Reviews

1 / 10

Bad experience with the staff boarding the gate. I couldn’t board with my carry on, personal item and a funny bag. I had to put my passport inside my pockets and put the funny bag inside the personal item. Then after passing the staff pull out everything again.

WestJet
7.6
Good
2,957 reviews
Delta
8.1
Very good
10,826 reviews
Check prices

Comfort

7.9

Food

7.4

Overall

8.1

Crew

8.6

Entertainment

8.0

Boarding

8.2

Reviews

1 / 10

Bad experience with the staff boarding the gate. I couldn’t board with my carry on, personal item and a funny bag. I had to put my passport inside my pockets and put the funny bag inside the personal item. Then after passing the staff pull out everything again.

Frontier
6.3
Okay
4,090 reviews
Delta
8.1
Very good
10,826 reviews
Check prices

Comfort

7.9

Food

7.4

Overall

8.1

Crew

8.6

Entertainment

8.0

Boarding

8.2

Reviews

1 / 10

Bad experience with the staff boarding the gate. I couldn’t board with my carry on, personal item and a funny bag. I had to put my passport inside my pockets and put the funny bag inside the personal item. Then after passing the staff pull out everything again.

Related info for your journey

Find useful and relevant information for your journey from Midway to Jamaica. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • Can I find flights from Chicago Midway Airport to Jamaica for under $300 on Cheapflights?

    Yes, there are multiple flights from Chicago Midway Airport to Jamaica for under $300. The cheapest flight booked recently is on Frontier for just $286, but on average you can expect to pay $424.

  • Are there last-minute flights available from Chicago Midway Airport to Jamaica for under $400?

    There are currently 9+ open flights from Chicago Midway Airport to Jamaica within the next 7 days for less than $400.

  • What are the cheapest airlines to fly from Chicago Midway Airport to Jamaica one-way?

    One-way options have recently been found by users for as low as $99 on Frontier. Other airlines that offer cheap prices include Delta from $267 and WestJet from $1,913 one-way.

  • What does MDW to MBJ mean?

    MDW and MBJ are unique codes to identify airports used in the aviation industry. They are defined by IATA (International Air Transport Association) and are commonly called IATA codes. MDW to MBJ refers to a flight route from Chicago Midway Airport to Montego Bay Sangster Intl Airport. Kingston Norman Manley Airport (KIN), Ocho Rios Boscobel Airport (OCJ), Negril Airport (NEG) are some additional IATA codes for airports related to your trip.

  • Can I find deals for flights from Midway to Jamaica that include extra baggage allowance?

    The amount of baggage you can bring on your Midway to Jamaica flight depends on the airline and the type of fare you've chosen. After entering your flight details, you'll be able to view the specific baggage policies for each deal in the search results. Keep in mind that certain deals may offer additional baggage allowance.

  • Can I find deals on flights from Midway to Jamaica with specific airlines?

    Yes, Cheapflights allows you to browse and filter Midway to Jamaica flight deals by airline. After entering your origin and destination, use the available filters to view flights offered by airlines.

  • Can I find deals for flights from Midway to Jamaica that include hotel bookings?

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

  • How can I find direct flights from Midway to Jamaica?

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

  • Can I find deals for business class flights from Midway to Jamaica?

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

  • Can I find deals for flights from Midway to Jamaica that allow pets onboard?

    Many airlines flying from Midway to Jamaica offer the option to travel with pets. After selecting a flight deal, you can find more information about the airline's pet policy on their official website or by contacting the airline directly. Please note that additional fees and restrictions may apply.

  • Can I find deals on last-minute flights from Midway to Jamaica?

    Yes, you can often find last-minute deals on Midway to Jamaica flights on Cheapflights. However, these deals can vary and may not always be available. We recommend checking back frequently or signing up for price alerts for the most up-to-date deals.

  • How recently were the Chicago Midway Airport to Jamaica flight deals updated?

    The Chicago Midway Airport to Jamaica flight deals you see on this page were last updated on 5/5.

See more FAQs

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Alternative routes for Midway to Jamaica
See prices for flight routes from nearby airports that may be better suited for you.

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Midway to Georgetown flights
Midway to Santiago de los Caballeros flights
O'Hare Intl to Pointe-à-Pitre flights
O'Hare Intl to Fort-de-France flights
O'Hare Intl to Gustavia flights
O'Hare Intl to Marsh Harbour flights

Top 2 airlines flying from Midway to Jamaica

Discover the top 2 airlines that operate flights from Midway to Jamaica. 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 2,719,943 searches. Data last updated May 6, 2024.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$242Average$317FlexibilityNo cancel feeOn-time62%
Search Frontier flights
DeltaCheapest$474Average$650FlexibilityNo cancel feeOn-timeN/A
Search Delta flights
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Search flights from Midway to Jamaica by cabin class

Find flights from Midway to Jamaica, based on your preferred cabin class, be it economy, premium economy, business, or first class.
First Class
Business Class
Prem Econ Class
Economy Class

Hourly flight availability from Midway to Jamaica

Find hourly flight availability from Midway to Jamaica. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated May 6, 2024.
0%of flight departuresEarly morningMidnight to 6 am
100%of flight departuresMorning6 am to noon
0%of flight departuresAfternoonNoon to 6 pm
0%of flight departuresEvening6 pm to midnight
Midnight
6 AM
Noon
6 PM

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Fly with Cheapflights

Find the best flight deals on Cheapflights, where travelers can enjoy low prices and a wide availability of flights to their desired destinations.

How does Cheapflights help users find flights from Midway to Jamaica?

900+ travel sites are searched through when a user searches for a flight using Cheapflights. From the search interface, users can use filters to choose airlines, airports, flight times, cabin classes and more to their preference. Book your flight to Jamaica from Midway today with Cheapflights!

Why should you use Cheapflights to find cheap flight tickets from Midway to Jamaica?

Cheapflights taps into our reliable network of hundreds of airlines and travel agencies to find the best deals for flights from Midway to Jamaica for you. Better yet — we are completely free to use.

Can Cheapflights find flights from Midway to Jamaica with no change fees?

Yes, we can. To see specific flights from Midway to Jamaica with no change fees, users can toggle flexible booking options after using the search form above to find flights.

Can Cheapflights notify me if prices for flights from Midway to Jamaica become cheaper?

Yes, Cheapflights has a feature called Price Alert, which notifies users when flight prices change. Track prices for your flight to Jamaica from Midway today and book when prices fit your budget.

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