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Montego Bay

$110+ Cheap flights from Wisconsin to Montego Bay (MBJ)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 4/18. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — MBJ
Nov 28 — Dec 51
Fri 11/28
Fri 12/5
1 adult, Economy
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Find flight deals from Wisconsin to Montego Bay

Cheapest flights from Wisconsin to Montego Bay
Explore the most affordable flight options available from Wisconsin to Montego Bay. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 29, 2025.

This Kiwi.com deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/75:00 amORD - MBJ
1 stop6h 10mMultiple Airlines
Sun 12/141:05 pmMBJ - ORD
1 stop10h 57mMultiple Airlines
Deal found 10/28$355
This United Airlines deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/208:42 amORD - MBJ
Nonstop4h 04mUnited Airlines
Sun 11/232:48 pmMBJ - ORD
Nonstop4h 25mUnited Airlines
Deal found 10/28$356
This Priceline deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/105:05 amORD - MBJ
1 stop9h 10mMultiple Airlines
Thu 11/131:07 pmMBJ - ORD
1 stop12h 20mMultiple Airlines
Deal found 10/27$358
This American Airlines deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/286:47 amORD - MBJ
1 stop7h 06mAmerican Airlines
Fri 12/53:12 pmMBJ - ORD
Nonstop4h 47mAmerican Airlines
Deal found 10/28$361
This Kiwi.com deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/25:00 amORD - MBJ
1 stop6h 02mMultiple Airlines
Sat 12/612:13 pmMBJ - ORD
1 stop25h 39mMultiple Airlines
Deal found 10/29$363
This Kiwi.com deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/185:10 amORD - MBJ
1 stop5h 52mMultiple Airlines
Mon 11/244:30 pmMBJ - ORD
1 stop8h 38mMultiple Airlines
Deal found 10/27$364
This Cheapflightsfares deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/45:10 amORD - MBJ
1 stop5h 52mSpirit Airlines
Sun 11/91:07 pmMBJ - ORD
1 stop12h 20mSpirit Airlines
Deal found 10/29$365
This American Airlines deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/3012:52 amORD - MBJ
1 stop12h 58mAmerican Airlines
Sun 12/72:30 pmMBJ - ORD
Nonstop4h 47mAmerican Airlines
Deal found 10/27$366
This American Airlines deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/108:05 amORD - MBJ
Nonstop3h 59mAmerican Airlines
Sat 11/154:22 pmMBJ - ORD
1 stop17h 22mAmerican Airlines
Deal found 10/27$367
This Gotogate deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/145:11 amORD - MBJ
1 stop9h 04mMultiple Airlines
Thu 11/201:07 pmMBJ - ORD
1 stop11h 06mMultiple Airlines
Deal found 10/28$368
This Cheapflightsfares deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/135:10 amORD - MBJ
1 stop5h 52mSpirit Airlines
Thu 11/201:07 pmMBJ - ORD
1 stop11h 06mSpirit Airlines
Deal found 10/28$369
This American Airlines deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/48:50 pmORD - MBJ
1 stop16h 49mAmerican Airlines
Thu 12/113:57 pmMBJ - ORD
1 stop8h 29mAmerican Airlines
Deal found 10/29$371

Cheap flight deals from Wisconsin to Montego Bay

Keep the following information in mind while searching for Wisconsin to Montego Bay flight deals. Data was last updated October 29, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$353
(Kiwi.com)

One-way from

$110
(Sun Country Air)

Popular in

June

Cheapest in

March

Average price

$560
Provider with most accurate pricing for Milwaukee-Mitchell-Montego Bay Sangster Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for Milwaukee-Mitchell-Montego Bay Sangster Intl flights.
Search Deals
From Wisconsin to Montego Bay Sangster Intl
Search Deals
One-way flight from Wisconsin to Montego Bay Sangster Intl
Search Deals
Highest demand for flights based on searches. 10% potential increase in price ($71 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($17 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Wisconsin to Montego Bay 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, Cheapflights users made 2,558,603 searches. Data last updated October 29, 2025.
Use the filters below to find and compare flights from Wisconsin to Montego Bay that are best for you.

Fly from

Wisconsin

Fly to

Montego Bay

Route

Depart

Return

Price

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Thu 11/13

8:42 am-1:46 pm

Nonstop4h 04m

Montego Bay Sangster Intl

Sun 11/16

2:48 pm-6:13 pm

Nonstop4h 25m

$356

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Tue 12/2

8:42 am-1:46 pm

Nonstop4h 04m

Montego Bay Sangster Intl

Sat 12/6

2:48 pm-6:13 pm

Nonstop4h 25m

$356

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Wed 1/7

8:42 am-1:46 pm

Nonstop4h 04m

Montego Bay Sangster Intl

Wed 1/14

2:48 pm-6:13 pm

Nonstop4h 25m

$357

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Wed 11/19

6:50 am-2:53 pm

1 stop7h 03m

Montego Bay Sangster Intl

Wed 11/26

2:14 pm-5:50 pm

Nonstop4h 36m

$361

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Sun 1/4

7:59 pm-11:13 am

1 stop14h 14m

Montego Bay Sangster Intl

Fri 1/16

8:00 am-1:39 pm

1 stop6h 39m

$371

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Wed 2/18

9:30 am-8:25 pm

1 stop9h 55m

Montego Bay Sangster Intl

Wed 2/25

8:00 am-7:29 pm

1 stop12h 29m

$371

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Tue 1/6

5:55 pm-11:13 am

1 stop16h 18m

Montego Bay Sangster Intl

Mon 1/12

4:05 pm-8:40 am

1 stop17h 35m

$371

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Sun 1/4

5:30 am-2:13 pm

1 stop7h 43m

Montego Bay Sangster Intl

Tue 1/13

4:05 pm-8:40 am

1 stop17h 35m

$371

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Wed 11/19

6:45 am-4:34 pm

1 stop8h 49m

Montego Bay Sangster Intl

Wed 11/26

5:59 pm-12:02 am

1 stop7h 03m

$371

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Thu 1/8

7:05 am-8:36 pm

1 stop12h 31m

Montego Bay Sangster Intl

Sat 1/17

12:45 pm-9:04 pm

1 stop9h 19m

$371

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/29

Showing 1-10 of 60 results
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Best time to book a flight from Wisconsin to Montego Bay

Have a flexible travel schedule? Discover the best time to fly to Montego Bay from Wisconsin with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Wisconsin to Montego Bay

What is the cheapest month to book a flight from Wisconsin to Montego Bay?

Currently, October is the cheapest month in which you can book a flight from Wisconsin to Montego Bay (average of $312). Flying from Wisconsin to Montego Bay in July is currently the most expensive (average of $595). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from WI to MBJ?

Find hourly flight availability from Wisconsin to Montego Bay. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated October 29, 2025.

It’s typically best to fly out from Wisconsin to Montego Bay at noon. Doing so could potentially save you 51% on the flight price compared to flying in the evening, which is usually more expensive.

Related info for your journey

Find useful and relevant information for your journey from Wisconsin to Montego Bay. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to Montego Bay from Wisconsin?

    For a flight from Wisconsin to Montego Bay, you will be flying into Sangster Intl. Montego Bay Sangster Intl (MBJ) is just 2.3 mi from the center of the city.

  • How long is the flight from Wisconsin to Montego Bay?

    Airlines like United Airlines, American Airlines, and Sun Country Air fly from Wisconsin to Montego Bay in about 4h 04m. The time it takes to get you to your destination can typically vary by up to 2h 59m. The distance between Wisconsin and Montego Bay is about 1724 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What are the cheapest airlines to fly from Wisconsin to Montego Bay one-way?

    To fly one-way, consider booking your trip with Spirit Airlines, which is currently one of the cheapest options available, starting at $137. United Airlines flights start at $157 while deals on Southwest start at $256 one-way.

  • What are the most popular routes from Wisconsin to Montego Bay?

    The most popular flight routes from Wisconsin to Montego Bay are Chicago O'Hare Intl - Montego Bay Sangster Intl, Minneapolis St Paul - Montego Bay Sangster Intl and Milwaukee-Mitchell - Montego Bay Sangster Intl.

  • Can I find deals for flights from Wisconsin to Montego Bay that include hotel bookings?

    Yes. In addition to deals on Wisconsin to Montego Bay flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Wisconsin to Montego Bay?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Wisconsin to Montego Bay.

  • Can I find deals for business class flights from Wisconsin to Montego Bay?

    Yes. Cheapflights offers flight deals from Wisconsin to Montego Bay by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Wisconsin to Montego Bay?

    Currently, October is the cheapest month in which you can book a flight from Wisconsin to Montego Bay (average of $312). Flying from Wisconsin to Montego Bay in July is currently the most expensive (average of $595). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Montego Bay?

Book flights to Montego Bay if you plan to visit one of these locations
Whitehouse
Lucea

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Alternative routes for Wisconsin to Montego Bay

See prices for flight routes from nearby airports that may be better suited for you.
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Reagan-National to Kingston flights
St. Louis to Montego Bay flights
Dulles Intl to Kingston flights
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Hartford to Montego Bay flights
Seattle to Kingston flights
Indianapolis to Montego Bay flights
Los Angeles to Kingston flights
Baltimore to Kingston flights
Jacksonville to Montego Bay flights
Hobby to Kingston flights
Orlando to Kingston flights
Kansas City to Montego Bay flights

Top 6 airlines flying from Wisconsin to Montego Bay

Discover the top 6 airlines that operate flights from Wisconsin to Montego Bay. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated October 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$328Average$403FlexibilityNo cancel feeOn-time65%
DeltaCheapest$499Average$607FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$514Average$653FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$529Average$728FlexibilityNo cancel feeOn-time69%
Sun Country AirCheapest$540Average$540FlexibilityNo cancel feeOn-time83%
SouthwestCheapest$571Average$713FlexibilityNo cancel feeOn-time63%

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