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Cheap flights from Wisconsin to Jamaica from $171

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 10/31. 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
1 adult, Economy, 0 bags

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Find the cheapest flights from Wisconsin to Jamaica

Cheap round-trip flights

Enter your travel dates to find the best prices.
American Airlines Logo
8:42 pm - 2:57 pmMSN  Madison Truax Field-MBJ Montego Bay Sangster Intl
17h 15m1 stop Chicago O'Hare Intl
American Airlines Logo
3:57 pm - 12:13 amMBJ  Montego Bay Sangster Intl-MSN Madison Truax Field
9h 16m1 stop Chicago O'Hare Intl
$392American Airlines
Sun, Nov 1 - Thu, Nov 5
Delta Logo
6:28 am - 2:35 pmMKE  Milwaukee-Mitchell-MBJ Montego Bay Sangster Intl
7h 07m1 stop Minneapolis St Paul
Delta Logo
2:20 pm - 9:03 pmMBJ  Montego Bay Sangster Intl-MKE Milwaukee-Mitchell
7h 43m1 stop Atlanta Hartsfield-Jackson
$392Delta
Sat, Nov 14 - Thu, Nov 19
United Airlines Logo
6:00 am - 1:46 pmMKE  Milwaukee-Mitchell-MBJ Montego Bay Sangster Intl
6h 46m1 stop Chicago O'Hare Intl
United Airlines Logo
3:55 pm - 9:49 amMBJ  Montego Bay Sangster Intl-MKE Milwaukee-Mitchell
18h 54m2 stops Newark Chicago O'Hare Intl
$392United Airlines
Fri, Jan 22 - Fri, Jan 29
United Airlines Logo
6:47 am - 4:19 pmMKE  Milwaukee-Mitchell-MBJ Montego Bay Sangster Intl
8h 32m2 stops Chicago O'Hare Intl Washington, D.C. Dulles Intl
United Airlines Logo
1:25 pm - 10:47 pmMBJ  Montego Bay Sangster Intl-MKE Milwaukee-Mitchell
10h 22m1 stop Newark
$392United Airlines
Sat, Nov 14 - Fri, Nov 20
American Airlines Logo
6:13 am - 1:44 pmMKE  Milwaukee-Mitchell-MBJ Montego Bay Sangster Intl
6h 31m1 stop Charlotte Douglas
American Airlines Logo
12:43 pm - 11:12 pmMBJ  Montego Bay Sangster Intl-MKE Milwaukee-Mitchell
11h 29m1 stop Charlotte Douglas
$392American Airlines
Tue, Jan 26 - Tue, Feb 9
Delta Logo
7:00 am - 4:29 pmMKE  Milwaukee-Mitchell-MBJ Montego Bay Sangster Intl
8h 29m1 stop Atlanta Hartsfield-Jackson
Delta Logo
6:00 pm - 9:11 amMBJ  Montego Bay Sangster Intl-MKE Milwaukee-Mitchell
16h 11m1 stop Atlanta Hartsfield-Jackson
$392Delta
Sun, Nov 8 - Sat, Nov 14
Air Canada Logo
3:45 pm - 1:25 pmORD  Chicago O'Hare Intl-MBJ Montego Bay Sangster Intl
20h 40m1 stop Montreal Pierre Elliott Trudeau Intl
Air Canada Logo
6:20 pm - 11:07 amMBJ  Montego Bay Sangster Intl-ORD Chicago O'Hare Intl
17h 47m2 stops Toronto Pearson Intl Montreal Pierre Elliott Trudeau Intl
$420Air Canada
Sat, Nov 14 - Mon, Nov 23
Air Canada Logo
8:40 pm - 11:20 amORD  Chicago O'Hare Intl-MBJ Montego Bay Sangster Intl
14h 40m1 stop Toronto Pearson Intl
Air Canada Logo
12:30 pm - 9:00 amMBJ  Montego Bay Sangster Intl-ORD Chicago O'Hare Intl
20h 30m1 stop Toronto Pearson Intl
$420Air Canada
Fri, Oct 16 - Fri, Oct 23
Multiple Airlines Logo
8:40 am - 1:55 pmORD  Chicago O'Hare Intl-KIN Kingston Norman Manley
29h 15m2 stops Montreal Pierre Elliott Trudeau Intl Toronto Pearson Intl
Multiple Airlines Logo
1:55 pm - 11:44 pmKIN  Kingston Norman Manley-ORD Chicago O'Hare Intl
9h 49m1 stop Fort Lauderdale
$465Multiple Airlines
Tue, Sep 1 - Thu, Sep 3
Multiple Airlines Logo
4:30 pm - 2:20 pmMSP  Minneapolis St Paul-MBJ Montego Bay Sangster Intl
20h 50m2 stops Toronto Pearson Intl Ottawa
Multiple Airlines Logo
3:40 pm - 7:39 pmMBJ  Montego Bay Sangster Intl-MSP Minneapolis St Paul
4h 59mnonstop
$510Multiple Airlines
Sat, Dec 12 - Sat, Dec 19

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Air Canada flights from Wisconsin to Jamaica

Our best Air Canada deals on Wisconsin to Jamaica flight tickets
Air Canada
Nov 14
ORD3:45 pmChicago O'Hare Intl
20h 40m
1 stop
MBJ1:25 pmMontego Bay Sangster Intl
Nov 23
MBJ6:20 pmMontego Bay Sangster Intl
17h 47m
2 stops
ORD11:07 amChicago O'Hare Intl
$420
Air Canada
Nov 3
ORD4:30 pmChicago O'Hare Intl
19h 20m
1 stop
MBJ12:50 pmMontego Bay Sangster Intl
Nov 7
MBJ6:20 pmMontego Bay Sangster Intl
24h 23m
1 stop
ORD5:43 pmChicago O'Hare Intl
$421
Air Canada
Dec 3
ORD7:05 amChicago O'Hare Intl
29h 20m
1 stop
MBJ1:25 pmMontego Bay Sangster Intl
Dec 11
MBJ2:20 pmMontego Bay Sangster Intl
30h 32m
1 stop
ORD7:52 pmChicago O'Hare Intl
$422

American Airlines flights from Wisconsin to Jamaica

Our best American Airlines deals on Wisconsin to Jamaica flight tickets
American Airlines
Nov 1
MSN8:42 pmMadison Truax Field
17h 15m
1 stop
MBJ2:57 pmMontego Bay Sangster Intl
Nov 5
MBJ3:57 pmMontego Bay Sangster Intl
9h 16m
1 stop
MSN12:13 amMadison Truax Field
$392
American Airlines
Nov 14
MKE7:24 pmMilwaukee-Mitchell
15h 55m
2 stops
MBJ12:19 pmMontego Bay Sangster Intl
Nov 20
MBJ6:22 pmMontego Bay Sangster Intl
16h 42m
2 stops
MKE10:04 amMilwaukee-Mitchell
$397
American Airlines
Jan 26
MKE3:53 pmMilwaukee-Mitchell
18h 50m
2 stops
MBJ11:43 amMontego Bay Sangster Intl
Feb 9
MBJ2:19 pmMontego Bay Sangster Intl
18h 48m
2 stops
MKE8:07 amMilwaukee-Mitchell
$398

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 August 8, 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

MadisonMontego Bay

MSN Madison Truax Field - MBJ Montego Bay Sangster Intl

MSNMBJ

Madison Truax Field

Sun 11/1

8:42 pm-2:57 pm

1 stop17h 15m

Montego Bay Sangster Intl

Thu 11/5

3:57 pm-12:13 am

1 stop9h 16m

$392
Quickest round-trip

MilwaukeeMontego Bay

MKE Milwaukee-Mitchell - MBJ Montego Bay Sangster Intl

MKEMBJ

Milwaukee-Mitchell

Sat 11/14

6:28 am-2:35 pm

1 stop7h 07m

Montego Bay Sangster Intl

Thu 11/19

2:20 pm-9:03 pm

1 stop7h 43m

$392

MilwaukeeMontego Bay

MKE Milwaukee-Mitchell - MBJ Montego Bay Sangster Intl

MKEMBJ

Milwaukee-Mitchell

Fri 1/22

6:00 am-1:46 pm

1 stop6h 46m

Montego Bay Sangster Intl

Fri 1/29

3:55 pm-9:49 am

2 stops18h 54m

$392

MilwaukeeMontego Bay

MKE Milwaukee-Mitchell - MBJ Montego Bay Sangster Intl

MKEMBJ

Milwaukee-Mitchell

Sat 11/14

6:47 am-4:19 pm

2 stops8h 32m

Montego Bay Sangster Intl

Fri 11/20

1:25 pm-10:47 pm

1 stop10h 22m

$392

MilwaukeeMontego Bay

MKE Milwaukee-Mitchell - MBJ Montego Bay Sangster Intl

MKEMBJ

Milwaukee-Mitchell

Tue 1/26

6:13 am-1:44 pm

1 stop6h 31m

Montego Bay Sangster Intl

Tue 2/9

12:43 pm-11:12 pm

1 stop11h 29m

$392

MilwaukeeMontego Bay

MKE Milwaukee-Mitchell - MBJ Montego Bay Sangster Intl

MKEMBJ

Milwaukee-Mitchell

Sun 11/8

7:00 am-4:29 pm

1 stop8h 29m

Montego Bay Sangster Intl

Sat 11/14

6:00 pm-9:11 am

1 stop16h 11m

$392

ChicagoMontego Bay

ORD Chicago O'Hare Intl - MBJ Montego Bay Sangster Intl

ORDMBJ

Chicago O'Hare Intl

Sat 11/14

3:45 pm-1:25 pm

1 stop20h 40m

Montego Bay Sangster Intl

Mon 11/23

6:20 pm-11:07 am

2 stops17h 47m

$420

ChicagoMontego Bay

ORD Chicago O'Hare Intl - MBJ Montego Bay Sangster Intl

ORDMBJ

Chicago O'Hare Intl

Fri 10/16

8:40 pm-11:20 am

1 stop14h 40m

Montego Bay Sangster Intl

Fri 10/23

12:30 pm-9:00 am

1 stop20h 30m

$420

ChicagoKingston

ORD Chicago O'Hare Intl - KIN Kingston Norman Manley

ORDKIN

Chicago O'Hare Intl

Tue 9/1

8:40 am-1:55 pm

2 stops29h 15m

Kingston Norman Manley

Thu 9/3

1:55 pm-11:44 pm

1 stop9h 49m

$465

MinneapolisMontego Bay

MSP Minneapolis St Paul - MBJ Montego Bay Sangster Intl

MSPMBJ

Minneapolis St Paul

Sat 12/12

4:30 pm-2:20 pm

2 stops20h 50m

Montego Bay Sangster Intl

Sat 12/19

3:40 pm-7:39 pm

Nonstop4h 59m

$510

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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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?

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

Fastest flight time

4h 04m

Direct flights

Every day

Airports in Jamaica

11 airports
The fastest flight from Wisconsin to Jamaica takes 4h 04m
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).
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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.

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 AirlinesPriceFrom $336Free CancellationRating
7.1
11,885 reviews
Search American Airlines flights
DeltaPriceFrom $362Free CancellationRating
7.8
8,504 reviews
Search Delta flights
United AirlinesPriceFrom $390Free CancellationRating
7.4
10,085 reviews
Search United Airlines flights
SouthwestPriceFrom $615Free CancellationRating
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.

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