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Cheap flights from Wisconsin to Jamaica from $125

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 5/16. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Wisconsin to Jamaica

Cheap round-trip flights

Enter your travel dates to find the best prices.
Frontier Logo
7:15 am - 12:11 pm
ORD
-
MBJ
28h 56m
1 stop
Frontier Logo
1:16 pm - 7:55 am
MBJ
-
ORD
18h 39m
1 stop
$297Frontier
Tue, May 5 - Tue, May 12
Frontier Logo
4:05 pm - 12:11 pm
ORD
-
MBJ
20h 06m
2 stops
Frontier Logo
1:16 pm - 7:55 am
MBJ
-
ORD
18h 39m
1 stop
$301Frontier
Tue, May 5 - Tue, May 12
American Airlines Logo
8:05 am - 12:13 pm
ORD
-
MBJ
4h 08mnonstop
American Airlines Logo
2:30 pm - 7:15 pm
MBJ
-
ORD
4h 45mnonstop
$318American Airlines
Mon, May 18 - Thu, May 21
Spirit Airlines Logo
5:05 am - 12:16 pm
ORD
-
MBJ
7h 11m
1 stop
Spirit Airlines Logo
1:36 pm - 11:15 pm
MBJ
-
ORD
9h 39m
1 stop
$320Spirit Airlines
Tue, Apr 28 - Thu, May 7
American Airlines Logo
6:05 am - 1:25 pm
ORD
-
MBJ
7h 20m
1 stop
American Airlines Logo
2:30 pm - 7:15 pm
MBJ
-
ORD
4h 45mnonstop
$322American Airlines
Mon, May 18 - Thu, May 21
United Airlines Logo
5:10 am - 12:50 pm
MKE
-
MBJ
7h 40m
1 stop
United Airlines Logo
2:40 pm - 10:45 pm
MBJ
-
MKE
8h 05m
1 stop
$432United Airlines
Sat, May 16 - Sat, May 23
Air Canada Logo
10:30 am - 11:20 am
MSP
-
MBJ
24h 50m
1 stop
Air Canada Logo
12:30 pm - 8:40 pm
MBJ
-
MSP
32h 10m
2 stops
$462Air Canada
Mon, Jun 1 - Sun, Jun 7
Air Canada Logo
3:55 pm - 11:20 am
MSP
-
MBJ
19h 25m
1 stop
Air Canada Logo
12:30 pm - 12:10 pm
MBJ
-
MSP
23h 40m
1 stop
$466Air Canada
Mon, Jun 1 - Sun, Jun 7
Spirit Airlines Logo
5:05 am - 11:07 am
ORD
-
KIN
6h 02m
1 stop
Spirit Airlines Logo
12:12 pm - 11:15 pm
KIN
-
ORD
11h 03m
1 stop
$476Spirit Airlines
Wed, Jun 3 - Wed, Jun 10
United Airlines Logo
6:00 am - 12:50 pm
MSP
-
MBJ
6h 50m
1 stop
United Airlines Logo
2:40 pm - 10:43 pm
MBJ
-
MSP
8h 03m
1 stop
$492United Airlines
Sat, May 9 - Thu, May 14

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Frontier flights from Wisconsin to Jamaica

Our best Frontier deals on Wisconsin to Jamaica flight tickets
Frontier
May 5
ORD7:15 amChicago O'Hare Intl
28h 56m
1 stop
MBJ12:11 pmMontego Bay Sangster Intl
May 12
MBJ1:16 pmMontego Bay Sangster Intl
18h 39m
1 stop
ORD7:55 amChicago O'Hare Intl
$297
Frontier
May 5
ORD4:05 pmChicago O'Hare Intl
20h 06m
2 stops
MBJ12:11 pmMontego Bay Sangster Intl
May 12
MBJ1:16 pmMontego Bay Sangster Intl
18h 39m
1 stop
ORD7:55 amChicago O'Hare Intl
$301
Frontier
May 9
ORD6:55 amChicago O'Hare Intl
29h 16m
1 stop
MBJ12:11 pmMontego Bay Sangster Intl
May 11
MBJ1:16 pmMontego Bay Sangster Intl
33h 57m
2 stops
ORD11:13 pmChicago O'Hare Intl
$303

United Airlines flights from Wisconsin to Jamaica

Our best United Airlines deals on Wisconsin to Jamaica flight tickets
United Airlines
Apr 19
ORD8:40 amChicago O'Hare Intl
4h 10m
MBJ12:50 pmMontego Bay Sangster Intl
Apr 25
MBJ1:52 pmMontego Bay Sangster Intl
4h 23m
ORD6:15 pmChicago O'Hare Intl
$318
United Airlines
Apr 19
ORD6:00 amChicago O'Hare Intl
9h 10m
1 stop
MBJ3:10 pmMontego Bay Sangster Intl
Apr 25
MBJ1:52 pmMontego Bay Sangster Intl
4h 23m
ORD6:15 pmChicago O'Hare Intl
$322
United Airlines
Apr 27
ORD8:40 amChicago O'Hare Intl
4h 10m
MBJ12:50 pmMontego Bay Sangster Intl
May 4
MBJ2:40 pmMontego Bay Sangster Intl
10h 47m
1 stop
ORD1:27 amChicago O'Hare Intl
$394

momondo Fare Finder

 
Customize your flight search to find flights from Wisconsin 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, momondo users made 832,500 searches. Data last updated April 19, 2026.
Use the filters below to find and compare flights from Wisconsin to Jamaica that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Tue 5/5

7:15 am-12:11 pm

1 stop28h 56m

Montego Bay Sangster Intl

Tue 5/12

1:16 pm-7:55 am

1 stop18h 39m

$297

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Tue 5/5

4:05 pm-12:11 pm

2 stops20h 06m

Montego Bay Sangster Intl

Tue 5/12

1:16 pm-7:55 am

1 stop18h 39m

$301
Quickest round-trip

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Mon 5/18

8:05 am-12:13 pm

Nonstop4h 08m

Montego Bay Sangster Intl

Thu 5/21

2:30 pm-7:15 pm

Nonstop4h 45m

$318

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Tue 4/28

5:05 am-12:16 pm

1 stop7h 11m

Montego Bay Sangster Intl

Thu 5/7

1:36 pm-11:15 pm

1 stop9h 39m

$320

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Mon 5/18

6:05 am-1:25 pm

1 stop7h 20m

Montego Bay Sangster Intl

Thu 5/21

2:30 pm-7:15 pm

Nonstop4h 45m

$322

MilwaukeeMontego Bay

MKE - MBJ

MKEMBJ

Milwaukee-Mitchell

Sat 5/16

5:10 am-12:50 pm

1 stop7h 40m

Montego Bay Sangster Intl

Sat 5/23

2:40 pm-10:45 pm

1 stop8h 05m

$432

MinneapolisMontego Bay

MSP - MBJ

MSPMBJ

Minneapolis St Paul

Mon 6/1

10:30 am-11:20 am

1 stop24h 50m

Montego Bay Sangster Intl

Sun 6/7

12:30 pm-8:40 pm

2 stops32h 10m

$462

MinneapolisMontego Bay

MSP - MBJ

MSPMBJ

Minneapolis St Paul

Mon 6/1

3:55 pm-11:20 am

1 stop19h 25m

Montego Bay Sangster Intl

Sun 6/7

12:30 pm-12:10 pm

1 stop23h 40m

$466

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Wed 6/3

5:05 am-11:07 am

1 stop6h 02m

Kingston Norman Manley

Wed 6/10

12:12 pm-11:15 pm

1 stop11h 03m

$476

MinneapolisMontego Bay

MSP - MBJ

MSPMBJ

Minneapolis St Paul

Sat 5/9

6:00 am-12:50 pm

1 stop6h 50m

Montego Bay Sangster Intl

Thu 5/14

2:40 pm-10:43 pm

1 stop8h 03m

$492

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Jamaica from

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?

The cheapest month to fly to Jamaica from Wisconsin is in January. Flight prices, which tend to average around $551, 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 January, then flying in May is also cheap. Prices for this month can be found on momondo for an average of $558.

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

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 37% 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

4h 01m

Direct flights

Every day

Airports in Jamaica

11 airports
The fastest flight from Wisconsin to Jamaica takes 4h 01m
Direct flights go from Wisconsin to Jamaica every day.
There are 11 airports in Jamaica. From Wisconsin there are direct flights to Montego Bay Sangster Intl (MBJ).
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?

  • 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?

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
DeltaPriceFrom $277Free CancellationRating
7.9
8,422 reviews
Search Delta flights
American AirlinesPriceFrom $336Free CancellationRating
7.1
11,621 reviews
Search American Airlines flights
SouthwestPriceFrom $571Free CancellationRating
8.0
4,328 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.

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