How long is the flight from Wisconsin to Jamaica?

Flight times from Wisconsin to Jamaica vary, but if you’re flying out of Milwaukee and flying into Montego Bay (one of the most popular routes), then the duration is 5h 55m on average. Another popular route from Wisconsin to Jamaica is flying from Madison to Montego Bay, which will take roughly 6h. Keep in mind that layovers or delays could extend your travel time.

What is the cheapest airline that flies from Wisconsin to Jamaica?

Delta, American Airlines, and United Airlines are the most popular carriers operating from Wisconsin to Jamaica

What airlines fly to Jamaica?

American Airlines, Delta and Southwest are the top three most popular airlines that fly to Jamaica from Wisconsin according to our data. American Airlines is the first choice among our users, with 64% of people opting to fly with this airline when traveling to Jamaica. Keep in mind that there are 3 different airlines that fly to Jamaica on a routine basis, so you have a few additional options to choose from.

When did momondo last update prices for flights from Wisconsin to Jamaica?

Prices for flights from Wisconsin to Jamaica were last updated today.

How many operators does momondo search for flights from Wisconsin to Jamaica?

As of September 2026, there are 3 operators available to choose from for flights from Wisconsin to Jamaica.

How old do you have to be to fly from Wisconsin to Jamaica?

The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Wisconsin to Jamaica.

What documentation or ID do you need to fly to Jamaica?

The necessary travel and health documents for your Jamaica trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

$182 Cheap Flights from Wisconsin to Jamaica in 2026/27

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Wisconsin to Jamaica

Round-trip

One-way

Last minute

Cheap round-trip flights

Enter your travel dates to find the best prices.

7:14 am - 4:12 pmMKE Milwaukee-Mitchell-MBJ Montego Bay Sangster Intl

8h 58m1 stop Dallas/Fort Worth

12:13 pm - 11:57 pmMBJ Montego Bay Sangster Intl-MKE Milwaukee-Mitchell

11h 44m1 stop Charlotte Douglas

$412American Airlines

Sat, Oct 24 - Fri, Oct 30

7:40 am - 2:52 pmMKE Milwaukee-Mitchell-MBJ Montego Bay Sangster Intl

6h 12m1 stop Chicago O'Hare Intl

1:02 pm - 11:06 pmMBJ Montego Bay Sangster Intl-MKE Milwaukee-Mitchell

11h 04m1 stop Charlotte Douglas

$412American Airlines

Mon, Dec 7 - Mon, Dec 14

6:00 am - 1:48 pmMKE Milwaukee-Mitchell-MBJ Montego Bay Sangster Intl

6h 48m1 stop Chicago O'Hare Intl

2:54 pm - 9:55 pmMBJ Montego Bay Sangster Intl-MKE Milwaukee-Mitchell

8h 01m1 stop Chicago O'Hare Intl

$412United Airlines

Sun, Dec 6 - Wed, Dec 9

6:00 am - 1:48 pmMKE Milwaukee-Mitchell-MBJ Montego Bay Sangster Intl

6h 48m1 stop Chicago O'Hare Intl

2:54 pm - 10:55 pmMBJ Montego Bay Sangster Intl-MKE Milwaukee-Mitchell

9h 01m1 stop Chicago O'Hare Intl

$412United Airlines

Sun, Dec 6 - Thu, Dec 10

5:30 am - 4:57 pmMSN Madison Truax Field-MBJ Montego Bay Sangster Intl

10h 27m1 stop Atlanta Hartsfield-Jackson

3:28 pm - 10:52 pmMBJ Montego Bay Sangster Intl-MSN Madison Truax Field

8h 24m1 stop Atlanta Hartsfield-Jackson

$412Delta

Mon, Dec 7 - Thu, Dec 10

5:04 am - 2:52 pmMKE Milwaukee-Mitchell-MBJ Montego Bay Sangster Intl

8h 48m1 stop Chicago O'Hare Intl

3:56 pm - 10:37 pmMBJ Montego Bay Sangster Intl-MKE Milwaukee-Mitchell

7h 41m1 stop Chicago O'Hare Intl

$412American Airlines

Sun, Nov 8 - Fri, Nov 13

6:00 am - 1:48 pmMKE Milwaukee-Mitchell-MBJ Montego Bay Sangster Intl

6h 48m1 stop Chicago O'Hare Intl

2:54 pm - 10:55 pmMBJ Montego Bay Sangster Intl-MKE Milwaukee-Mitchell

9h 01m1 stop Chicago O'Hare Intl

$412United Airlines

Sun, Dec 6 - Thu, Dec 10

6:40 pm - 11:10 amMKE Milwaukee-Mitchell-MBJ Montego Bay Sangster Intl

15h 30m1 stop Atlanta Hartsfield-Jackson

12:35 pm - 9:08 pmMBJ Montego Bay Sangster Intl-MKE Milwaukee-Mitchell

9h 33m1 stop Atlanta Hartsfield-Jackson

$413Delta

Thu, Jan 28 - Fri, Feb 5

5:55 am - 2:45 pmMKE Milwaukee-Mitchell-MBJ Montego Bay Sangster Intl

7h 50m1 stop Orlando

1:50 pm - 9:00 pmMBJ Montego Bay Sangster Intl-MKE Milwaukee-Mitchell

8h 10m1 stop Orlando

$1,253Southwest

Thu, Dec 24 - Fri, Jan 1

5:55 am - 12:50 pmMKE Milwaukee-Mitchell-MBJ Montego Bay Sangster Intl

5h 55m1 stop Orlando

1:50 pm - 10:10 pmMBJ Montego Bay Sangster Intl-MKE Milwaukee-Mitchell

9h 20m2 stops Orlando Chicago Midway

$1,284Southwest

Thu, Dec 24 - Fri, Jan 1

Save money when you book flights with momondo

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Not ready to book? to track prices.

Search flight deals

Delta flights from Wisconsin to Jamaica

Our best Delta deals on Wisconsin to Jamaica flight tickets

Delta

Dec 7

MSN5:30 amMadison Truax Field

10h 27m

1 stop

MBJ4:57 pmMontego Bay Sangster Intl

Dec 10

MBJ3:28 pmMontego Bay Sangster Intl

8h 24m

1 stop

MSN10:52 pmMadison Truax Field

$412

Delta

Jan 28

MSN5:17 pmMadison Truax Field

16h 53m

1 stop

MBJ11:10 amMontego Bay Sangster Intl

Feb 3

MBJ4:10 pmMontego Bay Sangster Intl

7h 45m

1 stop

MSN10:55 pmMadison Truax Field

$413

Delta

Jan 21

MSN1:45 pmMadison Truax Field

20h 25m

2 stops

MBJ11:10 amMontego Bay Sangster Intl

Jan 28

MBJ3:25 pmMontego Bay Sangster Intl

18h 25m

2 stops

MSN8:50 amMadison Truax Field

$418

American Airlines flights from Wisconsin to Jamaica

Our best American Airlines deals on Wisconsin to Jamaica flight tickets

American Airlines

Nov 8

ATW6:00 amAppleton Intl

10h 09m

1 stop

MBJ5:09 pmMontego Bay Sangster Intl

Nov 13

MBJ1:02 pmMontego Bay Sangster Intl

10h 52m

1 stop

ATW10:54 pmAppleton Intl

$412

American Airlines

Dec 6

MKE5:08 pmMilwaukee-Mitchell

16h 07m

2 stops

MBJ10:15 amMontego Bay Sangster Intl

Dec 10

MBJ3:56 pmMontego Bay Sangster Intl

16h 52m

1 stop

MKE7:48 amMilwaukee-Mitchell

$417

American Airlines

Jan 26

MKE6:52 amMilwaukee-Mitchell

9h 14m

1 stop

MBJ5:06 pmMontego Bay Sangster Intl

Feb 9

MBJ3:19 pmMontego Bay Sangster Intl

18h 52m

2 stops

MKE9:11 amMilwaukee-Mitchell

$418

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

MilwaukeeMontego Bay

MKE Milwaukee-Mitchell - MBJ Montego Bay Sangster Intl

MKEMBJ

Milwaukee-Mitchell

Sat 10/24

7:14 am-4:12 pm

1 stop8h 58m

Montego Bay Sangster Intl

Fri 10/30

12:13 pm-11:57 pm

1 stop11h 44m

$412

MilwaukeeMontego Bay

MKE Milwaukee-Mitchell - MBJ Montego Bay Sangster Intl

MKEMBJ

Milwaukee-Mitchell

Mon 12/7

7:40 am-2:52 pm

1 stop6h 12m

Montego Bay Sangster Intl

Mon 12/14

1:02 pm-11:06 pm

1 stop11h 04m

$412

Quickest round-trip

MilwaukeeMontego Bay

MKE Milwaukee-Mitchell - MBJ Montego Bay Sangster Intl

MKEMBJ

Milwaukee-Mitchell

Sun 12/6

6:00 am-1:48 pm

1 stop6h 48m

Montego Bay Sangster Intl

Wed 12/9

2:54 pm-9:55 pm

1 stop8h 01m

$412

MilwaukeeMontego Bay

MKE Milwaukee-Mitchell - MBJ Montego Bay Sangster Intl

MKEMBJ

Milwaukee-Mitchell

Sun 12/6

6:00 am-1:48 pm

1 stop6h 48m

Montego Bay Sangster Intl

Thu 12/10

2:54 pm-10:55 pm

1 stop9h 01m

$412

MadisonMontego Bay

MSN Madison Truax Field - MBJ Montego Bay Sangster Intl

MSNMBJ

Madison Truax Field

Mon 12/7

5:30 am-4:57 pm

1 stop10h 27m

Montego Bay Sangster Intl

Thu 12/10

3:28 pm-10:52 pm

1 stop8h 24m

$412

MilwaukeeMontego Bay

MKE Milwaukee-Mitchell - MBJ Montego Bay Sangster Intl

MKEMBJ

Milwaukee-Mitchell

Sun 11/8

5:04 am-2:52 pm

1 stop8h 48m

Montego Bay Sangster Intl

Fri 11/13

3:56 pm-10:37 pm

1 stop7h 41m

$412

MilwaukeeMontego Bay

MKE Milwaukee-Mitchell - MBJ Montego Bay Sangster Intl

MKEMBJ

Milwaukee-Mitchell

Sun 12/6

6:00 am-1:48 pm

1 stop6h 48m

Montego Bay Sangster Intl

Thu 12/10

2:54 pm-10:55 pm

1 stop9h 01m

$412

MilwaukeeMontego Bay

MKE Milwaukee-Mitchell - MBJ Montego Bay Sangster Intl

MKEMBJ

Milwaukee-Mitchell

Thu 1/28

6:40 pm-11:10 am

1 stop15h 30m

Montego Bay Sangster Intl

Fri 2/5

12:35 pm-9:08 pm

1 stop9h 33m

$413

MilwaukeeMontego Bay

MKE Milwaukee-Mitchell - MBJ Montego Bay Sangster Intl

MKEMBJ

Milwaukee-Mitchell

Thu 12/24

5:55 am-2:45 pm

1 stop7h 50m

Montego Bay Sangster Intl

Fri 1/1

1:50 pm-9:00 pm

1 stop8h 10m

$1,253

MilwaukeeMontego Bay

MKE Milwaukee-Mitchell - MBJ Montego Bay Sangster Intl

MKEMBJ

Milwaukee-Mitchell

Thu 12/24

5:55 am-12:50 pm

1 stop5h 55m

Montego Bay Sangster Intl

Fri 1/1

1:50 pm-10:10 pm

2 stops9h 20m

$1,284

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

How to get the cheapest flight ticket from Wisconsin to Jamaica

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

Prices

Airlines

Other information

What is the cheapest month to fly to Jamaica?

The cheapest month to fly to Jamaica from Wisconsin is in August. Flight prices, which tend to average around $432, are often lower during this time because this is during the off-season. If you aren’t able to travel to Jamaica during the month of August, then flying in May is also cheap. Prices for this month can be found on momondo for an average of $558.

Can stopping save me money on Wisconsin to Jamaica flights?

You could potentially save up to 8% on your flight if you consider stops on a Wisconsin to Jamaica flight.

Cheap Wisconsin to Jamaica flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Wisconsin to Jamaica

Best Price Found	$182
Fastest flight time	4h 04m
Direct flights	None

The best one-way flight to Jamaica from Wisconsin in the past 72 hours is $182. The best round-trip flight deal from Wisconsin to Jamaica found on momondo in the last 72 hours is $412.

The fastest flight from Wisconsin to Jamaica takes 4h 04m

There are no direct flights from Wisconsin to Jamaica. There are no popular flight routes from Wisconsin to Jamaica.

Search flight deals

Frequently asked questions about flying from Wisconsin to Jamaica

When did momondo last update prices for flights from Wisconsin to Jamaica?
Prices for flights from Wisconsin to Jamaica were last updated today.
How many operators does momondo search for flights from Wisconsin to Jamaica?
As of September 2026, there are 3 operators available to choose from for flights from Wisconsin to Jamaica.
How old do you have to be to fly from Wisconsin to Jamaica?
The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Wisconsin to Jamaica.
What documentation or ID do you need to fly to Jamaica?
The necessary travel and health documents for your Jamaica trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

Best airlines flying from Wisconsin to Jamaica

Compare and see reviews for airlines that fly from Wisconsin to Jamaica with momondo

Airline	Rating	Free Cancellation	Price
American Airlines	PriceFrom $336	Free Cancellation	Rating 7.0 12,073 reviews	Search American Airlines flights
Delta	PriceFrom $362	Free Cancellation	Rating 7.8 8,593 reviews	Search Delta flights
Southwest	PriceFrom $615	Free Cancellation	Rating 8.0 4,199 reviews	Search Southwest flights

Why use momondo?

Why should I use momondo to find a flight deal from Wisconsin to Jamaica?

Finding the right flight to Jamaica from Wisconsin is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Jamaica quick and easy, saving you time and money.

Can I find flights from Wisconsin to Jamaica with flexible booking policies on momondo?

Flights from Wisconsin to Jamaica with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

How can momondo help me find flights from Wisconsin to Jamaica?

momondo provides multiple filters to help you find the best flight to Jamaica from Wisconsin. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

I’m not ready to book a flight from Wisconsin to Jamaica right now. Can momondo alert me if prices change?

If you are not ready to book a flight from Wisconsin to Jamaica now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Jamaica and let you know when they change.

An easier way to manage your Jamaica trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Start using Trips

Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

1 adult

Fri 10/23

Fri 10/30

Email me momondo's favorite deals

By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to Jamaica

Popular cities

Other flights from Wisconsin

Other flights to Jamaica

Airlines

Cabin classes

Complete your trip

Feeling lucky

Popular cities in Jamaica

Flights to Montego Bayfrom $303

Flights to Kingstonfrom $301

Flights to Ocho Rios

Cheap flights from Wisconsin to Jamaica from $182

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Wisconsin to Jamaica departing on 11/15. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

Find the cheapest flights from Wisconsin to Jamaica

Cheap round-trip flights

Cheap one-way flights

Cheap last minute flights

Big names and deals

Big names and deals

Filter for what you want

Filter for what you want

Trusted and free

Trusted and free

Price Alerts

Price Alerts

Delta flights from Wisconsin to Jamaica

Our best Delta deals on Wisconsin to Jamaica flight tickets

American Airlines flights from Wisconsin to Jamaica

Our best American Airlines deals on Wisconsin to Jamaica flight tickets

momondo Fare Finder

Use the filters below to find and compare flights from Wisconsin to Jamaica that are best for you.

See travel insights to Jamaica from

How to get the cheapest flight ticket from Wisconsin to Jamaica

What is the cheapest month to fly to Jamaica?

Can stopping save me money on Wisconsin to Jamaica flights?

What is the cheapest airline that flies from Wisconsin to Jamaica?

What airlines fly to Jamaica?

How long is the flight from Wisconsin to Jamaica?

Cheap Wisconsin to Jamaica flight deals and tips

Best Price Found

Fastest flight time

Direct flights

Frequently asked questions about flying from Wisconsin to Jamaica

Best airlines flying from Wisconsin to Jamaica

Compare and see reviews for airlines that fly from Wisconsin to Jamaica with momondo

Why use momondo?

An easier way to manage your Jamaica trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

Find better results for your trip to Jamaica

Popular cities in Jamaica

Popular flights according to clicks in the last 7 days on momondo

Wisconsin flight routes

According to popular flight searches on momondo this year

Jamaica flight routes

According to popular flight searches on momondo this year

Fly your favorite airline to Jamaica

Airlines are sorted and displayed according to clicks in the past 7 days on momondo

Cabin classes currently available on flights to Jamaica

List of cabin classes available on flights landing in Jamaica. Availability may vary depending on flight origin and airline.

Complete your trip to Jamaica

Explore popular destinations other users love

According to popular flight searches on momondo this year