Cheap flights from Midway (MDW) to Jamaica from $109

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 5/7. 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
Feb 27 — Mar 51

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

When searching for a good deal, it’s best to be prepared for potential fluctuations in price. We recommend booking at least 47 days in advance, which can save you up to 35% on flights from Chicago Midway Airport to Jamaica compared to booking the week you need them. Waiting 47 days out may not be for everyone, so we have options available for flights within the next two weeks, with the lowest price starting at $440. For sooner than that we have options available in the next 3 days from $627.

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 $559 per person but you can even find prices for as low as $227. The most expensive prices can be found in the month of December. Opting for a August flight can save you 31% 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 3,442,422 searches. Data last updated February 22, 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.
Thu 4/117:00 amMDW - MBJ
1 stop6h 59mFrontier
Tue 4/168:32 amMBJ - MDW
1 stop12h 01mFrontier
Deal found 2/22$263
Thu 4/117:00 amMDW - MBJ
1 stop6h 59mFrontier
Tue 4/168:32 amMBJ - MDW
2 stops15h 44mFrontier
Deal found 2/22$275
Thu 4/117:00 amMDW - MBJ
1 stop6h 59mFrontier
Sat 4/2011:51 amMBJ - MDW
1 stop10h 50mFrontier
Deal found 2/22$276
Thu 4/117:00 amMDW - MBJ
1 stop6h 59mFrontier
Mon 4/153:34 pmMBJ - MDW
1 stop28h 59mFrontier
Deal found 2/22$279
Sun 5/126:45 amMDW - MBJ
1 stop7h 14mFrontier
Sat 5/188:07 amMBJ - MDW
1 stop13h 45mFrontier
Deal found 2/22$283
Thu 4/1810:22 pmMDW - MBJ
1 stop8h 58mFrontier
Mon 4/223:34 pmMBJ - MDW
1 stop28h 15mFrontier
Deal found 2/21$284
Tue 4/93:16 pmMDW - MBJ
2 stops16h 04mFrontier
Tue 4/168:32 amMBJ - MDW
1 stop12h 01mFrontier
Deal found 2/22$285
Mon 4/226:55 amMDW - MBJ
1 stop24h 25mFrontier
Mon 4/298:32 amMBJ - MDW
2 stops24h 19mFrontier
Deal found 2/22$291
Thu 4/186:33 pmMDW - MBJ
1 stop12h 47mFrontier
Mon 4/223:34 pmMBJ - MDW
1 stop28h 59mFrontier
Deal found 2/20$292

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 3,442,422 searches. Data last updated February 22, 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.
Wed 3/1310:43 amMDW - KIN
1 stop9h 17mDelta
Thu 3/219:00 amKIN - MDW
1 stop7h 31mDelta
Deal found 2/20$358
Mon 3/412:47 pmMDW - KIN
1 stop7h 22mDelta
Wed 3/69:24 amKIN - MDW
1 stop7h 38mDelta
Deal found 2/21$360
Sun 3/179:26 amMDW - KIN
2 stops10h 34mDelta
Wed 3/209:00 amKIN - MDW
1 stop12h 52mDelta
Deal found 2/22$363
Mon 3/412:47 pmMDW - KIN
1 stop7h 22mDelta
Wed 3/69:24 amKIN - MDW
2 stops28h 05mDelta
Deal found 2/21$365
Sat 3/26:00 amMDW - KIN
1 stop14h 09mDelta
Tue 3/59:24 amKIN - MDW
2 stops9h 38mDelta
Deal found 2/21$375
Fri 5/1010:00 amMDW - KIN
1 stop9h 48mDelta
Mon 5/139:00 amKIN - MDW
1 stop8h 58mDelta
Deal found 2/21$378
Sun 3/176:00 amMDW - KIN
1 stop14h 00mDelta
Wed 3/209:00 amKIN - MDW
1 stop12h 52mDelta
Deal found 2/22$419
Wed 3/139:26 amMDW - KIN
2 stops10h 34mDelta
Thu 3/219:00 amKIN - MDW
1 stop7h 31mDelta
Deal found 2/20$454
Mon 2/269:58 amMDW - MBJ
1 stop5h 34mDelta
Wed 2/285:57 pmMBJ - MDW
1 stop16h 11mDelta
Deal found 2/20$468

Cheap Midway to Jamaica flights in February & March 2024

Find cheap flight options from Midway to Jamaica specifically for the months of February and March 2024. Explore affordable fares based on user searches. Over the last 7 days, Cheapflights users made 3,442,422 searches. Prices were last updated on February 22, 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.
Thu 2/299:11 pmMDW - MBJ
1 stop13h 30mFrontier
Sun 3/310:06 amMBJ - MDW
2 stops45h 58mFrontier
Deal found 2/22$341
Wed 3/1310:43 amMDW - KIN
1 stop9h 17mDelta
Thu 3/219:00 amKIN - MDW
1 stop7h 31mDelta
Deal found 2/20$358
Mon 3/412:47 pmMDW - KIN
1 stop7h 22mDelta
Wed 3/69:24 amKIN - MDW
1 stop7h 38mDelta
Deal found 2/21$360
Sun 3/179:26 amMDW - KIN
2 stops10h 34mDelta
Wed 3/209:00 amKIN - MDW
1 stop12h 52mDelta
Deal found 2/22$363
Mon 3/412:47 pmMDW - KIN
1 stop7h 22mDelta
Wed 3/69:24 amKIN - MDW
2 stops28h 05mDelta
Deal found 2/20$365
Wed 3/274:20 pmMDW - MBJ
1 stop15h 33mFrontier
Tue 4/21:20 pmMBJ - MDW
1 stop8h 11mFrontier
Deal found 2/21$373
Sat 3/29:44 amMDW - KIN
2 stops10h 25mDelta
Tue 3/59:24 amKIN - MDW
2 stops9h 38mDelta
Deal found 2/21$375
Sat 3/28:54 pmMDW - MBJ
1 stop11h 02mMultiple Airlines
Thu 3/71:55 pmMBJ - MDW
2 stops11h 49mMultiple Airlines
Deal found 2/21$383
Thu 2/297:36 pmMDW - MBJ
1 stop19h 54mMultiple Airlines
Thu 3/71:55 pmMBJ - MDW
2 stops25h 20mMultiple Airlines
Deal found 2/21$384

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 3,442,422 searches. Data last updated February 22, 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.
Thu 4/117:00 amMDW - MBJ
1 stop6h 59mFrontier
Tue 4/168:32 amMBJ - MDW
1 stop12h 01mFrontier
Deal found 2/22$263
Thu 4/117:00 amMDW - MBJ
1 stop6h 59mFrontier
Tue 4/168:32 amMBJ - MDW
2 stops15h 44mFrontier
Deal found 2/22$275
Thu 4/2510:17 pmMDW - MBJ
1 stop9h 03mFrontier
Tue 4/308:32 amMBJ - MDW
1 stop10h 43mFrontier
Deal found 2/21$276
Tue 4/94:20 pmMDW - MBJ
1 stop15h 00mFrontier
Wed 4/173:34 pmMBJ - MDW
1 stop22h 19mFrontier
Deal found 2/22$279
Sun 5/126:45 amMDW - MBJ
1 stop7h 14mFrontier
Sat 5/188:07 amMBJ - MDW
1 stop13h 45mFrontier
Deal found 2/22$283
Thu 4/1810:22 pmMDW - MBJ
1 stop8h 58mFrontier
Mon 4/223:34 pmMBJ - MDW
1 stop28h 15mFrontier
Deal found 2/21$284
Tue 4/94:20 pmMDW - MBJ
1 stop15h 00mFrontier
Wed 4/178:32 amMBJ - MDW
2 stops14h 51mFrontier
Deal found 2/22$285
Sat 4/276:45 amMDW - MBJ
1 stop8h 34mFrontier
Tue 5/78:32 amMBJ - MDW
2 stops15h 44mFrontier
Deal found 2/22$288
Mon 4/226:55 amMDW - MBJ
1 stop24h 25mFrontier
Mon 4/298:32 amMBJ - MDW
2 stops24h 19mFrontier
Deal found 2/22$291

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 3,442,422 searches. Data last updated February 22, 2024.
Check out these flights departing soon from Chicago to Jamaica. Users should examine the flight details to ensure there are no surprises.
Mon 3/412:47 pmMDW - KIN
1 stop7h 22mDelta
Wed 3/69:24 amKIN - MDW
1 stop7h 38mDelta
Deal found 2/21$360
Mon 3/412:47 pmMDW - KIN
1 stop7h 22mDelta
Wed 3/69:24 amKIN - MDW
2 stops28h 05mDelta
Deal found 2/21$365
Sat 3/26:00 amMDW - KIN
1 stop14h 09mDelta
Tue 3/59:24 amKIN - MDW
2 stops9h 38mDelta
Deal found 2/21$375
Sat 3/28:54 pmMDW - MBJ
1 stop11h 02mMultiple Airlines
Thu 3/71:55 pmMBJ - MDW
2 stops11h 49mMultiple Airlines
Deal found 2/21$383
Thu 2/297:36 pmMDW - MBJ
1 stop19h 54mMultiple Airlines
Thu 3/71:55 pmMBJ - MDW
2 stops25h 20mMultiple Airlines
Deal found 2/21$384
Sat 2/248:54 pmMDW - MBJ
1 stop11h 02mFrontier
Sat 3/212:46 pmMBJ - MDW
1 stop8h 18mFrontier
Deal found 2/22$400
Sun 3/38:10 amMDW - MBJ
1 stop7h 20mMultiple Airlines
Sun 3/1012:55 pmMBJ - MDW
2 stops11h 02mMultiple Airlines
Deal found 2/21$440
Thu 2/298:45 amMDW - MBJ
1 stop6h 45mMultiple Airlines
Thu 3/710:03 amMBJ - MDW
1 stop29h 12mMultiple Airlines
Deal found 2/21$461
Mon 2/269:58 amMDW - MBJ
1 stop5h 34mDelta
Wed 2/285:57 pmMBJ - MDW
1 stop16h 11mDelta
Deal found 2/20$468

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 3,442,422 searches. Data last updated February 22, 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 5/77:00 amMDW - MBJ
1 stop7h 53mFrontier
Deal found 2/21$109
Sat 3/28:54 pmMDW - MBJ
1 stop11h 02mFrontier
Deal found 2/21$121
Fri 3/19:07 pmMDW - MBJ
1 stop13h 19mFrontier
Deal found 2/21$126
Tue 2/276:10 pmMDW - MBJ
1 stop16h 31mFrontier
Deal found 2/21$140
Sun 3/38:10 amMDW - MBJ
1 stop7h 20mMultiple Airlines
Deal found 2/21$145
Tue 5/78:16 pmMDW - MBJ
2 stops15h 24mMultiple Airlines
Deal found 2/21$146
Tue 2/276:10 pmMDW - MBJ
1 stop16h 31mFrontier
Deal found 2/22$152
Wed 2/2812:58 pmMDW - MBJ
2 stops18h 58mFrontier
Deal found 2/21$155
Thu 2/297:36 pmMDW - MBJ
1 stop19h 54mMultiple Airlines
Deal found 2/21$164

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 3,442,422 searches. Data last updated February 22, 2024.

Fly from

Any airport

Fly to

Any airport

Budget

$263 - $391

Route

Depart

Return

Price

Chicago MidwayMontego Bay Sangster Intl

MDW - MBJ

MDWMBJ

Chicago Midway

Thu 4/11

1 stop6h 59m

Montego Bay Sangster Intl

Tue 4/16

1 stop12h 01m

$263

Chicago MidwayMontego Bay Sangster Intl

MDW - MBJ

MDWMBJ

Chicago Midway

Thu 4/11

1 stop6h 59m

Montego Bay Sangster Intl

Tue 4/16

2 stops15h 44m

$275

Chicago MidwayMontego Bay Sangster Intl

MDW - MBJ

MDWMBJ

Chicago Midway

Thu 4/11

1 stop6h 59m

Montego Bay Sangster Intl

Sat 4/20

1 stop10h 50m

$276

Chicago MidwayMontego Bay Sangster Intl

MDW - MBJ

MDWMBJ

Chicago Midway

Thu 4/11

1 stop6h 59m

Montego Bay Sangster Intl

Mon 4/15

1 stop28h 59m

$279

Chicago MidwayMontego Bay Sangster Intl

MDW - MBJ

MDWMBJ

Chicago Midway

Sun 5/12

1 stop7h 14m

Montego Bay Sangster Intl

Sat 5/18

1 stop13h 45m

$283

Chicago MidwayKingston Norman Manley

MDW - KIN

MDWKIN

Chicago Midway

Wed 3/13

1 stop9h 17m

Kingston Norman Manley

Thu 3/21

1 stop7h 31m

$358

Chicago MidwayKingston Norman Manley

MDW - KIN

MDWKIN

Chicago Midway

Mon 3/4

1 stop7h 22m

Kingston Norman Manley

Wed 3/6

1 stop7h 38m

$360

Chicago MidwayKingston Norman Manley

MDW - KIN

MDWKIN

Chicago Midway

Sun 3/17

2 stops10h 34m

Kingston Norman Manley

Wed 3/20

1 stop12h 52m

$363

Chicago MidwayMontego Bay Sangster Intl

MDW - MBJ

MDWMBJ

Chicago Midway

Thu 4/18

2 stops13h 47m

Montego Bay Sangster Intl

Mon 4/22

1 stop9h 27m

$391

Flights are sorted by cheapest first

Deals found on 2/22

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 February 22, 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.
8.1
Very good
11,921 reviews

Overall

8.1

Comfort

7.9

Food

7.5

Entertainment

8.1

Boarding

8.2

Crew

8.6

Reviews

1 / 10

It was a good experience other than a short delay.

8.1
Very good
11,921 reviews
8.1
Very good
11,921 reviews

Overall

8.1

Comfort

7.9

Food

7.5

Entertainment

8.1

Boarding

8.2

Crew

8.6

Reviews

1 / 10

It was a good experience other than a short delay.

7.6
Good
3,161 reviews
8.1
Very good
11,921 reviews

Overall

8.1

Comfort

7.9

Food

7.5

Entertainment

8.1

Boarding

8.2

Crew

8.6

Reviews

1 / 10

It was a good experience other than a short delay.

6.4
Okay
4,512 reviews
8.1
Very good
11,921 reviews

Overall

8.1

Comfort

7.9

Food

7.5

Entertainment

8.1

Boarding

8.2

Crew

8.6

Reviews

1 / 10

It was a good experience other than a short delay.

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 $263, but on average you can expect to pay $295.

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

There are currently 20+ open flights from Chicago Midway Airport to Jamaica within the next 7 days for less than $400.

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.

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

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 3,442,422 searches. Data last updated February 22, 2024.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$244Average$364FlexibilityNo cancel feeOn-time62%
Search Frontier flights
DeltaCheapest$485Average$808FlexibilityNo cancel feeOn-timeN/A
Search Delta flights

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.

Book a flight to one of these trending destinations

User searches for flights to these destinations increased 20% or more in the past 90 days compared to other destinations

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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