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Jamaica

$918+ Cheap flights from Oshkosh, WI to Jamaica

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 3/17. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — MBJ
Dec 3 — Dec 101
Wed 12/3
Wed 12/10
1 adult, Economy
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Find flight deals from Oshkosh to Jamaica

Best flights from Oshkosh to Jamaica
Discover carefully curated flight deals from Oshkosh to Jamaica that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated November 3, 2025.

This American Airlines deal was found by Cheapflights users on 10/31. 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.
Tue 3/175:00 amATW - KIN
2 stops8h 05mAmerican Airlines
Wed 3/182:50 pmKIN - ATW
2 stops19h 57mAmerican Airlines
Deal found 10/31$918

Cheap flight deals from Oshkosh to Jamaica

Keep the following information in mind while searching for Oshkosh to Jamaica flight deals. Data was last updated November 3, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$918
(American Airlines)

Popular in

June

Cheapest in

August

Average price

$634
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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Highest demand for flights based on searches. 8% potential increase in price ($62 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 November 2025
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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 November 3, 2025.
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

Tue 3/17

5:00 am-1:05 pm

2 stops8h 05m

Kingston Norman Manley

Wed 3/18

2:50 pm-10:47 am

2 stops19h 57m

$918

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/31

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 $595). 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 OS9 to JM?

Find hourly flight availability from Oshkosh 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 November 3, 2025.

It’s typically best to fly out from Oshkosh to Jamaica at noon. Doing so could potentially save you 40% on the flight price compared to flying in the evening, which is usually more expensive.

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 November 3, 2025.
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
8,001 reviews

Boarding

8.2

Entertainment

7.9

Comfort

7.9

Overall

7.9

Food

7.3

Crew

8.5

Reviews

1 / 20
8.0
Excellent

Lane,Nov 2025

MEM - ATL

The crew was very friendly, but they only came around and offered the better Delta Comfort snacks one time. I thought they would come around more frequently on a 5 hour flight. They did do two beverage services though, which was nice.
Delta
7.9
Good
8,001 reviews
Delta
7.9
Good
8,001 reviews

Boarding

8.2

Entertainment

7.9

Comfort

7.9

Overall

7.9

Food

7.3

Crew

8.5

Reviews

1 / 20
8.0
Excellent

Lane,Nov 2025

MEM - ATL

The crew was very friendly, but they only came around and offered the better Delta Comfort snacks one time. I thought they would come around more frequently on a 5 hour flight. They did do two beverage services though, which was nice.
United Airlines
7.4
Good
8,997 reviews
Delta
7.9
Good
8,001 reviews

Boarding

8.2

Entertainment

7.9

Comfort

7.9

Overall

7.9

Food

7.3

Crew

8.5

Reviews

1 / 20
8.0
Excellent

Lane,Nov 2025

MEM - ATL

The crew was very friendly, but they only came around and offered the better Delta Comfort snacks one time. I thought they would come around more frequently on a 5 hour flight. They did do two beverage services though, which was nice.
American Airlines
7.2
Good
11,034 reviews
Delta
7.9
Good
8,001 reviews

Boarding

8.2

Entertainment

7.9

Comfort

7.9

Overall

7.9

Food

7.3

Crew

8.5

Reviews

1 / 20
8.0
Excellent

Lane,Nov 2025

MEM - ATL

The crew was very friendly, but they only came around and offered the better Delta Comfort snacks one time. I thought they would come around more frequently on a 5 hour flight. They did do two beverage services though, which was nice.

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 8h 05m. Fly via American Airlines to get the fastest option. Oshkosh and Jamaica are separated by a distance of 1941 mi.

  • 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 $595). 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 6 airlines flying from Oshkosh to Jamaica

Discover the top 6 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 November 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$328Average$403FlexibilityNo cancel feeOn-time65%
DeltaCheapest$499Average$637FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$514Average$642FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$529Average$745FlexibilityNo cancel feeOn-time69%
Sun Country AirCheapest$540Average$540FlexibilityNo cancel feeOn-time83%
SouthwestCheapest$571Average$720FlexibilityNo cancel feeOn-time63%

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