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Montego Bay

$109+ 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 1/22. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — MBJ
Jan 14 — Jan 211
Wed 1/14
Wed 1/21
1 adult, Economy
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Cheap 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 December 15, 2025.

This American Airlines deal was found by Cheapflights users on 12/13. 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 12/1510:15 amORD - MBJ
Nonstop4h 07mAmerican Airlines
Thu 12/184:27 pmMBJ - ORD
Nonstop4h 37mAmerican Airlines
Deal found 12/13$376
This American Airlines deal was found by Cheapflights users on 12/13. 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.
Sat 12/138:50 pmORD - MBJ
1 stop16h 49mAmerican Airlines
Thu 12/184:27 pmMBJ - ORD
Nonstop4h 37mAmerican Airlines
Deal found 12/13$381
This Delta deal was found by Cheapflights users on 12/13. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/155:30 amORD - MBJ
1 stop7h 43mDelta
Thu 12/1812:35 pmMBJ - ORD
1 stop7h 08mDelta
Deal found 12/13$391
This Delta deal was found by Cheapflights users on 12/12. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/289:41 amORD - MBJ
2 stops24h 24mDelta
Wed 12/318:00 amMBJ - ORD
1 stop17h 02mDelta
Deal found 12/12$396
This American Airlines deal was found by Cheapflights users on 12/13. 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 12/1510:15 amORD - MBJ
Nonstop4h 07mAmerican Airlines
Mon 12/224:27 pmMBJ - ORD
Nonstop4h 37mAmerican Airlines
Deal found 12/13$406
This Gotogate deal was found by Cheapflights users on 12/13. 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.
Sat 12/138:30 pmORD - MBJ
2 stops20h 35mMultiple Airlines
Sat 12/201:05 pmMBJ - ORD
1 stop12h 25mMultiple Airlines
Deal found 12/13$408
This American Airlines deal was found by Cheapflights users on 12/13. 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.
Sat 12/138:50 pmORD - MBJ
1 stop16h 49mAmerican Airlines
Sat 12/204:27 pmMBJ - ORD
Nonstop4h 37mAmerican Airlines
Deal found 12/13$411
This Priceline deal was found by Cheapflights users on 12/12. 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.
Fri 12/265:15 amORD - MBJ
1 stop29h 40mMultiple Airlines
Sun 12/281:05 pmMBJ - ORD
1 stop12h 25mMultiple Airlines
Deal found 12/12$415
This Delta deal was found by Cheapflights users on 12/13. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/207:55 pmORD - MBJ
1 stop14h 10mDelta
Wed 12/242:23 pmMBJ - ORD
1 stop10h 39mDelta
Deal found 12/13$421
This Priceline deal was found by Cheapflights users on 12/14. 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.
Fri 12/265:15 amORD - MBJ
1 stop29h 40mFrontier
Mon 12/2910:14 amMBJ - ORD
1 stop13h 10mFrontier
Deal found 12/14$435
This Delta deal was found by Cheapflights users on 12/14. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/215:50 pmMKE - MBJ
1 stop16h 15mDelta
Wed 12/2412:30 pmMBJ - MKE
1 stop6h 29mDelta
Deal found 12/14$473
This Delta deal was found by Cheapflights users on 12/14. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/226:15 pmMKE - MBJ
2 stops18h 12mDelta
Tue 12/304:15 pmMBJ - MKE
2 stops17h 34mDelta
Deal found 12/14$478

Find 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 December 15, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$359
(Kiwi.com)

One-way from

$109
(FlightHub)

Popular in

June

Cheapest in

October

Average price

$697
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. 8% potential increase in price ($59 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($16 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 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 December 15, 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

Mon 12/29

6:35 am-2:50 pm

1 stop7h 15m

Montego Bay Sangster Intl

Wed 12/31

4:15 pm-9:25 am

1 stop18h 10m

$391

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Tue 1/20

7:30 pm-12:32 pm

1 stop16h 02m

Montego Bay Sangster Intl

Fri 1/30

12:38 pm-6:49 pm

1 stop7h 11m

$391

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Tue 2/3

5:30 am-12:54 pm

1 stop6h 24m

Montego Bay Sangster Intl

Thu 2/12

4:44 pm-8:38 am

1 stop16h 54m

$391

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Mon 1/5

6:15 am-2:40 pm

1 stop7h 25m

Montego Bay Sangster Intl

Wed 1/14

4:45 pm-11:59 pm

1 stop8h 14m

$391

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Tue 2/3

5:59 pm-11:13 am

1 stop16h 14m

Montego Bay Sangster Intl

Wed 2/11

12:38 pm-11:56 pm

1 stop12h 18m

$391

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Tue 3/3

6:45 am-3:19 pm

1 stop7h 34m

Montego Bay Sangster Intl

Tue 3/10

11:35 am-7:52 pm

1 stop8h 17m

$391

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Sun 12/28

9:41 am-11:05 am

2 stops24h 24m

Montego Bay Sangster Intl

Wed 12/31

8:00 am-12:02 am

1 stop17h 02m

$396

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Tue 1/20

1:58 pm-11:13 am

2 stops20h 15m

Montego Bay Sangster Intl

Wed 1/28

4:45 pm-11:56 pm

1 stop8h 11m

$396

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Wed 1/14

1:55 pm-11:13 am

2 stops20h 18m

Montego Bay Sangster Intl

Tue 2/3

4:45 pm-8:43 am

1 stop16h 58m

$396

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Tue 2/3

2:50 pm-12:32 pm

2 stops20h 42m

Montego Bay Sangster Intl

Fri 2/13

4:44 pm-11:57 pm

1 stop8h 13m

$396

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/12

Showing 1-10 of 59 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 $637). 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 December 15, 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.

How much does it cost to fly round-trip from Wisconsin to Montego Bay?

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 Delta, American Airlines, and United Airlines fly from Wisconsin to Montego Bay in about 7h 15m. The time it takes to get you to your destination can typically vary by up to 14h 24m. 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 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 $637). 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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O'Hare Intl to Kingston flights
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Top 5 airlines flying from Wisconsin to Montego Bay

Discover the top 5 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 December 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$473Average$615FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$514Average$644FlexibilityNo cancel feeOn-time71%
Sun Country AirCheapest$540Average$541FlexibilityNo cancel feeOn-time83%
United AirlinesCheapest$563Average$759FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$571Average$727FlexibilityNo cancel feeOn-time63%

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