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Jamaica

$239+ Cheap flights from Oshkosh, WI to Jamaica

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 3/14. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — MBJ
Feb 28 — Mar 71
Sat 2/28
Sat 3/7
1 adult, Economy
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Cheap flight deals from Oshkosh to Jamaica

Cheapest flights from Oshkosh to Jamaica
Explore the most affordable flight options available from Oshkosh to Jamaica. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 29, 2026.

This Kiwi.com deal was found by Cheapflights users on 1/27. 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.
Sat 3/147:03 pm
ATW
-
KIN
1 stop15h 57m
Multiple Airlines
Sat 3/2112:17 pm
KIN
-
ATW
1 stop26h 08m
Multiple Airlines
Deal found 1/27$720
This American Airlines deal was found by Cheapflights users on 1/28. 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 2/201:25 pm
ATW
-
KIN
2 stops19h 57m
American Airlines
Sat 2/283:29 pm
KIN
-
ATW
2 stops18h 37m
American Airlines
Deal found 1/28$749
This American Airlines deal was found by Cheapflights users on 1/27. 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.
Sat 3/144:05 pm
ATW
-
KIN
2 stops21h 24m
American Airlines
Sat 3/216:32 am
KIN
-
ATW
2 stops17h 27m
American Airlines
Deal found 1/27$789
This United Airlines deal was found by Cheapflights users on 1/26. 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.
Mon 2/23:39 pm
ATW
-
KIN
2 stops45h 14m
United Airlines
Thu 2/53:00 pm
KIN
-
ATW
2 stops24h 09m
United Airlines
Deal found 1/26$938
This Delta deal was found by Cheapflights users on 1/28. 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.
Fri 2/205:25 am
ATW
-
KIN
1 stop13h 35m
Delta
Sat 2/289:00 am
KIN
-
ATW
1 stop13h 50m
Delta
Deal found 1/28$1,022
This United Airlines deal was found by Cheapflights users on 1/27. 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 10/215:35 pm
ATW
-
KIN
2 stops44h 23m
United Airlines
Thu 10/293:00 pm
KIN
-
ATW
2 stops28h 16m
United Airlines
Deal found 1/27$1,941
This WestJet deal was found by Cheapflights users on 1/27. 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 WestJet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/2311:10 am
ATW
-
KIN
2 stops27h 20m
WestJet
Fri 10/303:30 pm
KIN
-
ATW
2 stops25h 07m
WestJet
Deal found 1/27$3,927

Find flight deals from Oshkosh to Jamaica

Keep the following information in mind while searching for Oshkosh to Jamaica flight deals. Data was last updated January 29, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$720
(Kiwi.com)

One-way from

$239
(Kiwi.com)

Popular in

June

Cheapest in

August

Average price

$749
Provider with most accurate pricing for Appleton Intl-Montego Bay Sangster Intl flight deals.
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Provider most trusted by Cheapflights users for Appleton Intl-Montego Bay Sangster Intl flights.
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From Oshkosh to Jamaica
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One-way flight from Oshkosh to Jamaica
Search Deals
Highest demand for flights based on searches. 7% potential increase in price ($58 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($18 potential savings vs. average RT price).
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Average for round-trip flights in January 2026
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Cheapflights Fare Finder

 
Customize your flight search to find flights from Oshkosh 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 2,558,603 searches. Data last updated January 29, 2026.
Use the filters below to find and compare flights from Oshkosh to Jamaica that are best for you.

Fly from

Oshkosh

Fly to

Jamaica

Route

Depart

Return

Price

AppletonKingston

ATW - KIN

ATWKIN

Appleton Intl

Sat 3/14

7:03 pm-11:00 am

1 stop15h 57m

Kingston Norman Manley

Sat 3/21

12:17 pm-2:25 pm

1 stop26h 08m

$720

AppletonKingston

ATW - KIN

ATWKIN

Appleton Intl

Fri 2/20

1:25 pm-10:22 am

2 stops19h 57m

Kingston Norman Manley

Sat 2/28

3:29 pm-9:06 am

2 stops18h 37m

$749

AppletonKingston

ATW - KIN

ATWKIN

Appleton Intl

Sat 3/14

4:05 pm-1:29 pm

2 stops21h 24m

Kingston Norman Manley

Sat 3/21

6:32 am-11:59 pm

2 stops17h 27m

$789

AppletonKingston

ATW - KIN

ATWKIN

Appleton Intl

Fri 2/20

5:25 am-8:00 pm

1 stop13h 35m

Kingston Norman Manley

Sat 2/28

9:00 am-9:50 pm

1 stop13h 50m

$1,022

AppletonKingston

ATW - KIN

ATWKIN

Appleton Intl

Sat 3/14

7:03 pm-11:00 am

1 stop15h 57m

$239

AppletonKingston

ATW - KIN

ATWKIN

Appleton Intl

Sat 3/14

4:05 pm-9:22 am

2 stops17h 17m

$347

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/27

Best time to book a flight from Oshkosh to Jamaica

Have a flexible travel schedule? Discover the best time to fly to Jamaica from Oshkosh 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 Oshkosh to Jamaica

What is the cheapest month to book a flight from Oshkosh to Jamaica?

Currently, October is the cheapest month in which you can book a flight from Oshkosh to Jamaica (average of $312). Flying from Oshkosh to Jamaica in July is currently the most expensive (average of $637). 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.

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 January 29, 2026.
See what other customers who have flown with Delta, United Airlines, and American Airlines from Oshkosh to Jamaica have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
7.9
Good
8,128 reviews

Entertainment

7.8

Crew

8.5

Comfort

7.9

Overall

7.9

Boarding

8.1

Food

7.2

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Delta
7.9
Good
8,128 reviews
Delta
7.9
Good
8,128 reviews

Entertainment

7.8

Crew

8.5

Comfort

7.9

Overall

7.9

Boarding

8.1

Food

7.2

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
United Airlines
7.4
Good
9,215 reviews
Delta
7.9
Good
8,128 reviews

Entertainment

7.8

Crew

8.5

Comfort

7.9

Overall

7.9

Boarding

8.1

Food

7.2

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
American Airlines
7.2
Good
11,205 reviews
Delta
7.9
Good
8,128 reviews

Entertainment

7.8

Crew

8.5

Comfort

7.9

Overall

7.9

Boarding

8.1

Food

7.2

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.

Related info for your journey

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

  • How long is the flight from Oshkosh to Jamaica?

    There are many flights that can get you from Oshkosh to Jamaica in 13h 35m. Fly via American Airlines or Delta to get the fastest option. Oshkosh and Jamaica are separated by a distance of 1941 mi. This flight may include one or multiple stops.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Oshkosh 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.

  • What is the cheapest month to book a flight from Oshkosh to Jamaica?

    Currently, October is the cheapest month in which you can book a flight from Oshkosh to Jamaica (average of $312). Flying from Oshkosh to Jamaica in July is currently the most expensive (average of $637). 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

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.

Alternative routes for Oshkosh to Jamaica

See prices for flight routes from nearby airports that may be better suited for you.
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Top 5 airlines flying from Oshkosh to Jamaica

Discover the top 5 airlines that operate flights from Oshkosh 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 2,558,603 searches. Data last updated January 29, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$470Average$632FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$490Average$623FlexibilityNo cancel feeOn-time71%
Sun Country AirCheapest$540Average$540FlexibilityNo cancel feeOn-time83%
United AirlinesCheapest$563Average$739FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$571Average$698FlexibilityNo cancel feeOn-time63%

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