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 39m on average. Another popular route from Wisconsin to Jamaica is flying from Madison to Montego Bay, which will take roughly 6h 12m. Keep in mind that layovers or delays could extend your travel time.

What airlines fly to Jamaica?

American Airlines, Delta and United Airlines 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 60% of people opting to fly with this airline when traveling to Jamaica. Keep in mind that there are 4 different airlines that fly to Jamaica on a routine basis, so you have a few additional options to choose from.

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

United Airlines, Delta, and American Airlines are the most popular carriers operating 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 November 2026, there are 4 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.

$202 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.

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

6h 00m1 stop Chicago Midway

1:25 pm - 6:55 pmMBJ Montego Bay Sangster Intl-MKE Milwaukee-Mitchell

6h 30m1 stop Chicago Midway

$454Southwest

Sat, Jan 30 - Sat, Feb 6

5:19 pm - 11:13 amMSN Madison Truax Field-MBJ Montego Bay Sangster Intl

16h 54m1 stop Philadelphia

3:59 pm - 8:14 amMBJ Montego Bay Sangster Intl-MSN Madison Truax Field

17h 15m1 stop Chicago O'Hare Intl

$463American Airlines

Fri, Dec 4 - Thu, Dec 10

5:10 am - 2:45 pmMKE Milwaukee-Mitchell-MBJ Montego Bay Sangster Intl

8h 35m1 stop Orlando

1:00 pm - 9:25 pmMBJ Montego Bay Sangster Intl-MKE Milwaukee-Mitchell

9h 25m1 stop Baltimore/Washington

$463Southwest

Sun, Dec 6 - Wed, Dec 9

5:19 pm - 11:13 amMSN Madison Truax Field-MBJ Montego Bay Sangster Intl

16h 54m1 stop Philadelphia

3:59 pm - 8:14 amMBJ Montego Bay Sangster Intl-MSN Madison Truax Field

17h 15m1 stop Chicago O'Hare Intl

$463American Airlines

Fri, Dec 4 - Thu, Dec 10

6:40 pm - 10:05 amMKE Milwaukee-Mitchell-MBJ Montego Bay Sangster Intl

15h 25m1 stop Atlanta Hartsfield-Jackson

5:00 pm - 9:22 amMBJ Montego Bay Sangster Intl-MKE Milwaukee-Mitchell

16h 22m1 stop Atlanta Hartsfield-Jackson

$464Delta

Sat, Mar 27 - Wed, Mar 31

6:40 pm - 10:05 amMKE Milwaukee-Mitchell-MBJ Montego Bay Sangster Intl

15h 25m1 stop Atlanta Hartsfield-Jackson

5:00 pm - 9:22 amMBJ Montego Bay Sangster Intl-MKE Milwaukee-Mitchell

16h 22m1 stop Atlanta Hartsfield-Jackson

$464Delta

Thu, Mar 25 - Wed, Mar 31

5:00 am - 4:19 pmMKE Milwaukee-Mitchell-MBJ Montego Bay Sangster Intl

10h 19m2 stops Chicago O'Hare Intl Washington, D.C. Dulles Intl

3:45 pm - 10:45 pmMBJ Montego Bay Sangster Intl-MKE Milwaukee-Mitchell

8h 00m1 stop Houston George Bush Intcntl

$474United Airlines

Sat, Jan 30 - Sat, Feb 6

6:29 pm - 12:13 pmMKE Milwaukee-Mitchell-MBJ Montego Bay Sangster Intl

16h 44m1 stop Newark

2:54 pm - 10:31 pmMBJ Montego Bay Sangster Intl-MKE Milwaukee-Mitchell

8h 37m1 stop Chicago O'Hare Intl

$474United Airlines

Wed, Jan 27 - Wed, Feb 3

12:05 pm - 2:37 pmMKE Milwaukee-Mitchell-MBJ Montego Bay Sangster Intl

25h 32m2 stops Orlando Minneapolis St Paul

2:59 pm - 5:56 pmMBJ Montego Bay Sangster Intl-MKE Milwaukee-Mitchell

27h 57m3 stops Atlanta Hartsfield-Jackson Dallas/Fort Worth Minneapolis St Paul

$1,474Multiple Airlines

Fri, Dec 25 - Fri, Jan 1

4:38 pm - 6:35 pmMKE Milwaukee-Mitchell-MBJ Montego Bay Sangster Intl

25h 57m2 stops Orlando Toronto Pearson Intl

1:25 pm - 11:27 pmMBJ Montego Bay Sangster Intl-MKE Milwaukee-Mitchell

34h 02m3 stops Toronto Pearson Intl Montreal Pierre Elliott Trudeau Intl Orlando

$1,478Multiple Airlines

Sat, Mar 27 - Sat, Apr 3

Cheap last minute flights

Enter your travel dates to find the best prices.

5:50 am - 2:52 pmGRB Green Bay Austin-Straubel-MBJ Montego Bay Sangster Intl

8h 02m1 stop Chicago O'Hare Intl

3:49 pm - 12:07 amMBJ Montego Bay Sangster Intl-GRB Green Bay Austin-Straubel

9h 18m1 stop Chicago O'Hare Intl

$558American Airlines

Mon, Nov 9 - Thu, Nov 19

2:40 pm - 10:15 amGRB Green Bay Austin-Straubel-MBJ Montego Bay Sangster Intl

18h 35m2 stops Chicago O'Hare Intl Miami

3:49 pm - 12:07 amMBJ Montego Bay Sangster Intl-GRB Green Bay Austin-Straubel

9h 18m1 stop Chicago O'Hare Intl

$562American Airlines

Mon, Nov 9 - Thu, Nov 19

2:40 pm - 10:15 amGRB Green Bay Austin-Straubel-MBJ Montego Bay Sangster Intl

18h 35m2 stops Chicago O'Hare Intl Miami

6:09 pm - 2:00 pmMBJ Montego Bay Sangster Intl-GRB Green Bay Austin-Straubel

20h 51m2 stops Miami Chicago O'Hare Intl

$562American Airlines

Mon, Nov 9 - Thu, Nov 19

5:50 am - 2:52 pmGRB Green Bay Austin-Straubel-MBJ Montego Bay Sangster Intl

8h 02m1 stop Chicago O'Hare Intl

3:49 pm - 12:07 amMBJ Montego Bay Sangster Intl-GRB Green Bay Austin-Straubel

9h 18m1 stop Chicago O'Hare Intl

$568American Airlines

Mon, Nov 9 - Thu, Nov 19

6:54 pm - 12:21 pmGRB Green Bay Austin-Straubel-MBJ Montego Bay Sangster Intl

16h 27m2 stops Chicago O'Hare Intl Miami

1:45 pm - 9:32 amMBJ Montego Bay Sangster Intl-GRB Green Bay Austin-Straubel

20h 47m2 stops Philadelphia Chicago O'Hare Intl

$572American Airlines

Mon, Nov 9 - Thu, Nov 19

2:40 pm - 10:15 amGRB Green Bay Austin-Straubel-MBJ Montego Bay Sangster Intl

18h 35m2 stops Chicago O'Hare Intl Miami

3:49 pm - 12:07 amMBJ Montego Bay Sangster Intl-GRB Green Bay Austin-Straubel

9h 18m1 stop Chicago O'Hare Intl

$572American Airlines

Mon, Nov 9 - Thu, Nov 19

5:50 am - 2:52 pmGRB Green Bay Austin-Straubel-MBJ Montego Bay Sangster Intl

8h 02m1 stop Chicago O'Hare Intl

3:49 pm - 12:07 amMBJ Montego Bay Sangster Intl-GRB Green Bay Austin-Straubel

9h 18m1 stop Chicago O'Hare Intl

$617American Airlines

Mon, Nov 9 - Thu, Nov 19

7:00 am - 2:28 pmMKE Milwaukee-Mitchell-MBJ Montego Bay Sangster Intl

6h 28m1 stop Charlotte Douglas

6:09 pm - 11:30 amMBJ Montego Bay Sangster Intl-MKE Milwaukee-Mitchell

18h 21m2 stops Miami Dallas/Fort Worth

$621American Airlines

Fri, Nov 13 - Mon, Nov 16

5:00 am - 1:48 pmMKE Milwaukee-Mitchell-MBJ Montego Bay Sangster Intl

7h 48m1 stop Chicago O'Hare Intl

2:54 pm - 8:36 amMBJ Montego Bay Sangster Intl-MKE Milwaukee-Mitchell

18h 42m1 stop Chicago O'Hare Intl

$622United Airlines

Fri, Nov 13 - Mon, Nov 16

7:00 pm - 12:13 pmMSN Madison Truax Field-MBJ Montego Bay Sangster Intl

16h 13m2 stops Chicago O'Hare Intl Newark

2:54 pm - 9:05 pmMBJ Montego Bay Sangster Intl-MSN Madison Truax Field

7h 11m1 stop Chicago O'Hare Intl

$672United Airlines

Thu, Nov 12 - Mon, Nov 16

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

American Airlines flights from Wisconsin to Jamaica

Our best American Airlines deals on Wisconsin to Jamaica flight tickets

American Airlines

Dec 4

MSN5:19 pmMadison Truax Field

16h 54m

1 stop

MBJ11:13 amMontego Bay Sangster Intl

Dec 10

MBJ3:59 pmMontego Bay Sangster Intl

17h 15m

1 stop

MSN8:14 amMadison Truax Field

$463

American Airlines

Apr 10

MSN8:24 pmMadison Truax Field

15h 49m

1 stop

MBJ12:13 pmMontego Bay Sangster Intl

Apr 20

MBJ12:14 pmMontego Bay Sangster Intl

10h 12m

1 stop

MSN10:26 pmMadison Truax Field

$464

American Airlines

Feb 6

LSE8:32 pmLa Crosse

17h 46m

1 stop

MBJ3:18 pmMontego Bay Sangster Intl

Feb 13

MBJ2:35 pmMontego Bay Sangster Intl

29h 17m

1 stop

LSE6:52 pmLa Crosse

$465

United Airlines flights from Wisconsin to Jamaica

Our best United Airlines deals on Wisconsin to Jamaica flight tickets

United Airlines

Jan 30

MKE5:00 amMilwaukee-Mitchell

10h 19m

2 stops

MBJ4:19 pmMontego Bay Sangster Intl

Feb 6

MBJ3:45 pmMontego Bay Sangster Intl

8h 00m

1 stop

MKE10:45 pmMilwaukee-Mitchell

$474

United Airlines

Feb 23

ATW5:00 amAppleton Intl

7h 48m

1 stop

MBJ1:48 pmMontego Bay Sangster Intl

Mar 4

MBJ2:54 pmMontego Bay Sangster Intl

9h 14m

1 stop

ATW11:08 pmAppleton Intl

$521

United Airlines

Nov 15

MKE7:03 pmMilwaukee-Mitchell

16h 10m

1 stop

MBJ12:13 pmMontego Bay Sangster Intl

Nov 20

MBJ2:54 pmMontego Bay Sangster Intl

6h 56m

1 stop

MKE8:50 pmMilwaukee-Mitchell

$522

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

Quickest round-trip

MilwaukeeMontego Bay

MKE Milwaukee-Mitchell - MBJ Montego Bay Sangster Intl

MKEMBJ

Milwaukee-Mitchell

Sat 1/30

5:50 am-12:50 pm

1 stop6h 00m

Montego Bay Sangster Intl

Sat 2/6

1:25 pm-6:55 pm

1 stop6h 30m

$454

MadisonMontego Bay

MSN Madison Truax Field - MBJ Montego Bay Sangster Intl

MSNMBJ

Madison Truax Field

Fri 12/4

5:19 pm-11:13 am

1 stop16h 54m

Montego Bay Sangster Intl

Thu 12/10

3:59 pm-8:14 am

1 stop17h 15m

$463

MilwaukeeMontego Bay

MKE Milwaukee-Mitchell - MBJ Montego Bay Sangster Intl

MKEMBJ

Milwaukee-Mitchell

Sun 12/6

5:10 am-2:45 pm

1 stop8h 35m

Montego Bay Sangster Intl

Wed 12/9

1:00 pm-9:25 pm

1 stop9h 25m

$463

MadisonMontego Bay

MSN Madison Truax Field - MBJ Montego Bay Sangster Intl

MSNMBJ

Madison Truax Field

Fri 12/4

5:19 pm-11:13 am

1 stop16h 54m

Montego Bay Sangster Intl

Thu 12/10

3:59 pm-8:14 am

1 stop17h 15m

$463

MilwaukeeMontego Bay

MKE Milwaukee-Mitchell - MBJ Montego Bay Sangster Intl

MKEMBJ

Milwaukee-Mitchell

Sat 3/27

6:40 pm-10:05 am

1 stop15h 25m

Montego Bay Sangster Intl

Wed 3/31

5:00 pm-9:22 am

1 stop16h 22m

$464

MilwaukeeMontego Bay

MKE Milwaukee-Mitchell - MBJ Montego Bay Sangster Intl

MKEMBJ

Milwaukee-Mitchell

Thu 3/25

6:40 pm-10:05 am

1 stop15h 25m

Montego Bay Sangster Intl

Wed 3/31

5:00 pm-9:22 am

1 stop16h 22m

$464

MilwaukeeMontego Bay

MKE Milwaukee-Mitchell - MBJ Montego Bay Sangster Intl

MKEMBJ

Milwaukee-Mitchell

Sat 1/30

5:00 am-4:19 pm

2 stops10h 19m

Montego Bay Sangster Intl

Sat 2/6

3:45 pm-10:45 pm

1 stop8h 00m

$474

MilwaukeeMontego Bay

MKE Milwaukee-Mitchell - MBJ Montego Bay Sangster Intl

MKEMBJ

Milwaukee-Mitchell

Wed 1/27

6:29 pm-12:13 pm

1 stop16h 44m

Montego Bay Sangster Intl

Wed 2/3

2:54 pm-10:31 pm

1 stop8h 37m

$474

MilwaukeeMontego Bay

MKE Milwaukee-Mitchell - MBJ Montego Bay Sangster Intl

MKEMBJ

Milwaukee-Mitchell

Fri 12/25

12:05 pm-2:37 pm

2 stops25h 32m

Montego Bay Sangster Intl

Fri 1/1

2:59 pm-5:56 pm

3 stops27h 57m

$1,474

MilwaukeeMontego Bay

MKE Milwaukee-Mitchell - MBJ Montego Bay Sangster Intl

MKEMBJ

Milwaukee-Mitchell

Sat 3/27

4:38 pm-6:35 pm

2 stops25h 57m

Montego Bay Sangster Intl

Sat 4/3

1:25 pm-11:27 pm

3 stops34h 02m

$1,478

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 January is also cheap. Prices for this month can be found on momondo for an average of $550.

Can stopping save me money on Wisconsin to Jamaica flights?

You could potentially save up to 33% 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	$202
Fastest flight time	4h 08m
Direct flights	None

The best one-way flight to Jamaica from Wisconsin in the past 72 hours is $202. The best round-trip flight deal from Wisconsin to Jamaica found on momondo in the last 72 hours is $454.

The fastest flight from Wisconsin to Jamaica takes 4h 08m

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 November 2026, there are 4 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 $352	Free Cancellation	Rating 7.0 12,228 reviews	Search American Airlines flights
Delta	PriceFrom $362	Free Cancellation	Rating 7.8 8,698 reviews	Search Delta flights
United Airlines	PriceFrom $383	Free Cancellation	Rating 7.3 10,469 reviews	Search United Airlines flights
Southwest	PriceFrom $452	Free Cancellation	Rating 8.0 4,215 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

Tue 12/8

Tue 12/15

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 $238

Flights to Kingstonfrom $415

Flights to Ocho Rios

Cheap flights from Wisconsin to Jamaica from $202

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 2/9. 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

American Airlines flights from Wisconsin to Jamaica

Our best American Airlines deals on Wisconsin to Jamaica flight tickets

United Airlines flights from Wisconsin to Jamaica

Our best United 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