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 6h 09m on average. Another popular route from Wisconsin to Jamaica is flying from Madison to Montego Bay, which will take roughly 7h 14m. Keep in mind that layovers or delays could extend your travel time.

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

Spirit Airlines, Frontier, and United Airlines are the most popular carriers operating from Wisconsin to Jamaica

What airlines fly to Jamaica?

American Airlines, Delta and Sun Country Air 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 56% of people opting to fly with this airline when traveling to Jamaica. Keep in mind that there are 6 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 2025, there are 6 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.

$105 Cheap Flights from Wisconsin to Jamaica in 2025/26

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Find the cheapest flights from Wisconsin to Jamaica

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

5:59 pm - 12:13 pmORD-KIN

17h 14m1 stop

1:28 pm - 9:00 pmKIN-ORD

8h 32m1 stop

$342Spirit Airlines

Find Deal

Tue, Nov 11 - Wed, Dec 3

5:59 pm - 12:13 pmORD-KIN

17h 14m1 stop

1:28 pm - 11:42 pmKIN-ORD

11h 14m1 stop

$346Spirit Airlines

Find Deal

Sat, Nov 15 - Wed, Nov 19

8:42 am - 1:46 pmORD-MBJ

4h 04mnonstop

2:48 pm - 6:13 pmMBJ-ORD

4h 25mnonstop

$381United Airlines

Find Deal

Fri, Dec 5 - Fri, Dec 12

6:00 am - 2:46 pmORD-MBJ

8h 46m1 stop

3:51 pm - 11:39 pmMBJ-ORD

7h 48m1 stop

$382Frontier

Find Deal

Sat, Oct 18 - Thu, Oct 23

5:05 am - 12:05 pmORD-MBJ

6h 00m1 stop

5:06 pm - 12:12 amMBJ-ORD

8h 06m1 stop

$383Multiple Airlines

Find Deal

Tue, Jan 13 - Sat, Jan 17

5:00 am - 2:50 pmORD-MBJ

8h 50m1 stop

2:14 pm - 5:50 pmMBJ-ORD

4h 36mnonstop

$386American Airlines

Find Deal

Sun, Nov 2 - Sat, Nov 8

6:58 pm - 11:00 amORD-MBJ

16h 02m2 stops

1:40 pm - 11:18 amMBJ-ORD

21h 38m2 stops

$387Multiple Airlines

Find Deal

Sat, Oct 18 - Tue, Oct 28

10:15 am - 3:28 pmORD-MBJ

4h 13mnonstop

11:12 am - 12:37 amMBJ-ORD

14h 25m1 stop

$391American Airlines

Find Deal

Mon, Nov 10 - Sat, Nov 15

6:00 am - 2:37 pmORD-MBJ

7h 37m1 stop

1:25 pm - 9:06 pmMBJ-ORD

8h 41m1 stop

$393United Airlines

Find Deal

Mon, Jan 5 - Fri, Jan 9

5:05 am - 2:46 pmORD-MBJ

9h 41m1 stop

4:06 pm - 12:01 amMBJ-ORD

7h 55m1 stop

$399Frontier

Find Deal

Tue, Mar 10 - Wed, Mar 11

Frontier flights from Wisconsin to Jamaica

Our best Frontier deals on Wisconsin to Jamaica flight tickets

Frontier

Oct 18

ORD6:00 amChicago O'Hare Intl

8h 46m

1 stop

MBJ2:46 pmMontego Bay Sangster Intl

Oct 23

MBJ3:51 pmMontego Bay Sangster Intl

7h 48m

1 stop

ORD11:39 pmChicago O'Hare Intl

$382

Find similar

Frontier

Mar 10

ORD5:05 amChicago O'Hare Intl

9h 41m

1 stop

MBJ2:46 pmMontego Bay Sangster Intl

Mar 11

MBJ4:06 pmMontego Bay Sangster Intl

7h 55m

1 stop

ORD12:01 amChicago O'Hare Intl

$399

Find similar

Frontier

Dec 11

MSP9:47 pmMinneapolis St Paul

16h 46m

2 stops

MBJ3:33 pmMontego Bay Sangster Intl

Dec 14

MBJ4:53 pmMontego Bay Sangster Intl

15h 53m

2 stops

MSP7:46 amMinneapolis St Paul

$446

Find similar

American Airlines flights from Wisconsin to Jamaica

Our best American Airlines deals on Wisconsin to Jamaica flight tickets

American Airlines

Nov 2

ORD5:00 amChicago O'Hare Intl

8h 50m

1 stop

MBJ2:50 pmMontego Bay Sangster Intl

Nov 8

MBJ2:14 pmMontego Bay Sangster Intl

4h 36m

ORD5:50 pmChicago O'Hare Intl

$386

Find similar

American Airlines

Oct 7

ORD8:44 amChicago O'Hare Intl

4h 01m

MBJ12:45 pmMontego Bay Sangster Intl

Oct 11

MBJ12:27 pmMontego Bay Sangster Intl

10h 04m

1 stop

ORD10:31 pmChicago O'Hare Intl

$391

Find similar

American Airlines

Oct 4

ORD7:15 pmChicago O'Hare Intl

16h 50m

1 stop

MBJ12:05 pmMontego Bay Sangster Intl

Oct 8

MBJ1:50 pmMontego Bay Sangster Intl

4h 33m

ORD6:23 pmChicago O'Hare Intl

$397

Find similar

Fly from

Fly to

Route

Depart

Return

Price

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Tue 11/11

5:59 pm-12:13 pm

1 stop17h 14m

Kingston Norman Manley

Wed 12/3

1:28 pm-9:00 pm

1 stop8h 32m

$342

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Sat 11/15

5:59 pm-12:13 pm

1 stop17h 14m

Kingston Norman Manley

Wed 11/19

1:28 pm-11:42 pm

1 stop11h 14m

$346

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Fri 12/5

8:42 am-1:46 pm

Nonstop4h 04m

Montego Bay Sangster Intl

Fri 12/12

2:48 pm-6:13 pm

Nonstop4h 25m

$381

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Sat 10/18

6:00 am-2:46 pm

1 stop8h 46m

Montego Bay Sangster Intl

Thu 10/23

3:51 pm-11:39 pm

1 stop7h 48m

$382

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Tue 1/13

5:05 am-12:05 pm

1 stop6h 00m

Montego Bay Sangster Intl

Sat 1/17

5:06 pm-12:12 am

1 stop8h 06m

$383

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Sun 11/2

5:00 am-2:50 pm

1 stop8h 50m

Montego Bay Sangster Intl

Sat 11/8

2:14 pm-5:50 pm

Nonstop4h 36m

$386

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Sat 10/18

6:58 pm-11:00 am

2 stops16h 02m

Montego Bay Sangster Intl

Tue 10/28

1:40 pm-11:18 am

2 stops21h 38m

$387

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Mon 11/10

10:15 am-3:28 pm

Nonstop4h 13m

Montego Bay Sangster Intl

Sat 11/15

11:12 am-12:37 am

1 stop14h 25m

$391

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Mon 1/5

6:00 am-2:37 pm

1 stop7h 37m

Montego Bay Sangster Intl

Fri 1/9

1:25 pm-9:06 pm

1 stop8h 41m

$393

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Tue 3/10

5:05 am-2:46 pm

1 stop9h 41m

Montego Bay Sangster Intl

Wed 3/11

4:06 pm-12:01 am

1 stop7h 55m

$399

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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 March. Flight prices, which tend to average around $543, 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 March, then flying in October is also cheap. Prices for this month can be found on momondo for an average of $555.

What is the cheapest day to depart on your flight to Jamaica?

The cheapest day to depart on your flight to Jamaica is on a Tuesday when prices can be found for as low as $509. This is often the case because there is less demand to fly during this day of the week. On the other hand, Sunday is the most expensive day to depart from Wisconsin because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $585.

What is the cheapest time of day to depart on your flight to Jamaica?

Our most recent data shows that the best time of day to fly to Jamaica is at noon. Flights from Wisconsin to Jamaica during this time can be as low as $534. In the afternoon is when there is more demand to fly to Jamaica, so prices are often more expensive at around $566 per ticket.

What is the cheapest Wisconsin to Jamaica flight route?

Fly from Milwaukee-Mitchell to Montego Bay Sangster Intl for the best Wisconsin - Jamaica flight prices

How far in advance should I book a flight to Jamaica?

You are more likely to see cheaper flights to Jamaica from Wisconsin when booking weeks ahead of your departure date. In general, you can expect to find flights to Jamaica for around $620 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Jamaica from Wisconsin for as low as $514 on momondo.

What cabin class options are available on Wisconsin to Jamaica flights?

There is only 1 cabin class available to choose from on Wisconsin to Jamaica flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Wisconsin to Jamaica flights?

You could potentially save up to 12% 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

Fastest flight time	3h 59m
Direct flights	Every day
Airports in Jamaica	1 airport

The fastest flight from Wisconsin to Jamaica takes 3h 59m

Direct flights go from Wisconsin to Jamaica every day.

There is 1 airport near Jamaica: Montego Bay Sangster Intl (MBJ)

Search flight deals

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 2025, there are 6 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.
What is the most popular plane model from Wisconsin to Jamaica?
Based on momondo bookings for this flight route, the most popular plane model on flight routes from Wisconsin to Jamaica is Boeing 737-800 (71.43% of total bookings). The next most popular plane models are Boeing 737 MAX 8 (14.29%) and Boeing 737-800 Passenger/BBJ2 (winglets) (14.29%).

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
Spirit Airlines	PriceFrom $328	Free Cancellation	Rating 6.3 8,045 reviews	Search Spirit Airlines flights
United Airlines	PriceFrom $443	Free Cancellation	Rating 7.4 8,928 reviews	Search United Airlines flights
Delta	PriceFrom $490	Free Cancellation	Rating 7.9 7,973 reviews	Search Delta flights
American Airlines	PriceFrom $514	Free Cancellation	Rating 7.2 10,000 reviews	Search American Airlines flights
Sun Country Air	PriceFrom $540	Free Cancellation	Rating 6.9 333 reviews	Search Sun Country Air flights
Southwest	PriceFrom $571	Free Cancellation	Rating 8.0 4,246 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.

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Find better results for your trip to Jamaica

Popular cities in Jamaica

Flights to Montego Bayfrom $211

Flights to Kingstonfrom $225

Flights to Ocho Rios

Cheap flights from Wisconsin to Jamaica from $105

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 10/7. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

Big names and deals

Big names and deals

Filter for what you want

Filter for what you want

Trusted and free

Trusted and free

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Price Alerts

Find the cheapest flights from Wisconsin to Jamaica

Cheap round-trip flights

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Cheap last minute flights

Cheap direct flights

Frontier flights from Wisconsin to Jamaica

Our best Frontier 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

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

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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

What is the cheapest month to fly to Jamaica?

What is the cheapest day to depart on your flight to Jamaica?

What is the cheapest time of day to depart on your flight to Jamaica?

Our most recent data shows that the best time of day to fly to Jamaica is at noon. Flights from Wisconsin to Jamaica during this time can be as low as $534. In the afternoon is when there is more demand to fly to Jamaica, so prices are often more expensive at around $566 per ticket.

What is the cheapest Wisconsin to Jamaica flight route?

Fly from Milwaukee-Mitchell to Montego Bay Sangster Intl for the best Wisconsin - Jamaica flight prices

How far in advance should I book a flight to Jamaica?

What cabin class options are available on Wisconsin to Jamaica flights?

There is only 1 cabin class available to choose from on Wisconsin to Jamaica flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Wisconsin to Jamaica flights?

You could potentially save up to 12% on your flight if you consider stops on a Wisconsin to Jamaica flight.

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

Spirit Airlines, Frontier, and United Airlines are the most popular carriers operating 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

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

Fastest flight time

Direct flights

Airports in Jamaica

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

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

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

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

What is the most popular plane model 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?

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

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

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

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

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