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Simpson Bay

$178+ Cheap flights from Milwaukee (MKE) to Simpson Bay (SXM)

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 7/11. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — SXM
Jun 17 — Jun 241
Tue 6/17
Tue 6/24
1 adult, Economy
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Cheap flight deals from Milwaukee to Simpson Bay

Discover tips and strategies to find the most affordable flight options for your journey from Milwaukee (MKE) to Simpson Bay (SXM). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated June 12, 2025.

Round-trip from

$571
(FlightHub)

One-way from

$178
(Trip.com)

Popular in

June

Cheapest in

May

Average price

$1,991
From Milwaukee-Mitchell to Simpson Bay Princess Juliana
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One-way flight from Milwaukee-Mitchell to Simpson Bay Princess Juliana
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Highest demand for flights based on searches. 23% potential increase in price ($253 potential increase over avg. RT price).
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Cheapest flight prices on average. 16% potential price decrease ($118 potential savings vs. average RT price).
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Average for round-trip flights in June 2025
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Find flight deals from Milwaukee to Simpson Bay

Cheapest flights from Milwaukee to Simpson Bay
Explore the most affordable flight options available from Milwaukee to Simpson Bay. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 12, 2025.

This FlightHub deal was found by Cheapflights users on 6/12. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/34:37 pmMKE - SXM
2 stops20h 23mSpirit Airlines
Fri 8/83:05 pmSXM - MKE
2 stops49h 37mSpirit Airlines
Deal found 6/12$571
This American Airlines deal was found by Cheapflights users on 6/10. 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 10/205:19 pmMKE - SXM
2 stops18h 56mAmerican Airlines
Fri 10/244:10 pmSXM - MKE
2 stops20h 34mAmerican Airlines
Deal found 6/10$610
This Delta deal was found by Cheapflights users on 6/11. 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 9/136:00 amMKE - SXM
1 stop6h 50mDelta
Sat 9/203:15 pmSXM - MKE
1 stop9h 10mDelta
Deal found 6/11$637
This Mytrip deal was found by Cheapflights users on 6/12. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/263:07 pmMKE - SXM
3 stops45h 53mMultiple Airlines
Thu 7/32:10 pmSXM - MKE
3 stops32h 29mMultiple Airlines
Deal found 6/12$1,087

Cheapflights Fare Finder

Customize your flight search to find flights from Milwaukee to Simpson 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 June 12, 2025.
Use the filters below to find and compare flights from Milwaukee to Simpson Bay that are best for you.

Fly from

Milwaukee

Fly to

Simpson Bay

Route

Depart

Return

Price

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Sun 8/3

4:37 pm-2:00 pm

2 stops20h 23m

Simpson Bay Princess Juliana

Fri 8/8

3:05 pm-3:42 pm

2 stops49h 37m

$571

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Mon 10/20

5:19 pm-1:15 pm

2 stops18h 56m

Simpson Bay Princess Juliana

Fri 10/24

4:10 pm-11:44 am

2 stops20h 34m

$610

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Sat 9/13

6:00 am-1:50 pm

1 stop6h 50m

Simpson Bay Princess Juliana

Sat 9/20

3:15 pm-11:25 pm

1 stop9h 10m

$637

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Thu 6/26

3:07 pm-2:00 pm

3 stops45h 53m

Simpson Bay Princess Juliana

Thu 7/3

2:10 pm-9:39 pm

3 stops32h 29m

$1,087

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Fri 7/11

4:37 pm-11:28 am

1 stop17h 51m

$178

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Tue 7/15

4:37 pm-2:00 pm

2 stops20h 23m

$200

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Wed 7/9

5:40 am-1:56 pm

1 stop7h 16m

$293

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Sat 7/26

4:16 pm-1:25 pm

1 stop20h 09m

$309

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/11

Best time to book a flight from Milwaukee to Simpson Bay

Have a flexible travel schedule? Discover the best time to fly to Simpson Bay from Milwaukee 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 Milwaukee to Simpson Bay

What is the cheapest month to book a flight from Milwaukee to Simpson Bay?

Currently, September is the cheapest month in which you can book a flight from Milwaukee to Simpson Bay (average of $459). Flying from Milwaukee to Simpson Bay in March is currently the most expensive (average of $657). 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 MKE to SXM?

Find hourly flight availability from Milwaukee to Simpson Bay. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated June 12, 2025.

Unlike in the morning, when flights are generally more expensive, you can save up to 9% on flights from Milwaukee to Simpson Bay by exploring options for tickets at noon.

Reviews of airlines servicing Simpson Bay

Get insights into the airlines that provide service to Simpson Bay. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Simpson Bay. Reviews last updated June 12, 2025.
Delta
8.0
Very good
7,946 reviews

Crew

8.5

Overall

8.0

Boarding

8.2

Comfort

7.9

Food

7.3

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Delta
8.0
Very good
7,946 reviews
Delta
8.0
Very good
7,946 reviews

Crew

8.5

Overall

8.0

Boarding

8.2

Comfort

7.9

Food

7.3

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,946 reviews

Crew

8.5

Overall

8.0

Boarding

8.2

Comfort

7.9

Food

7.3

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Spirit Airlines
6.3
Okay
8,052 reviews
Delta
8.0
Very good
7,946 reviews

Crew

8.5

Overall

8.0

Boarding

8.2

Comfort

7.9

Food

7.3

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

Related info for your journey

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

  • What are the cheapest airlines flying from Milwaukee to Simpson Bay round-trip?

    Spirit Airlines, at $571, was found to be the cheapest airline from Milwaukee to Simpson Bay.Alternate airlines to your destination round-trip include American Airlines and Delta. You may be able to fly from Milwaukee to Simpson Bay for 30% less than the average price by searching for these airlines.

  • What are the cheapest airlines to fly from Milwaukee to Simpson Bay one-way?

    $200 is the cheapest one-way deal found within the past few days, from Spirit Airlines. You may also be able to find cheap deals on Delta and American Airlines, with prices starting from $293 and $309, respectively.

  • Can I find deals for flights from Milwaukee to Simpson Bay that include hotel bookings?

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

  • How can I find direct flights from Milwaukee to Simpson Bay?

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

  • Can I find deals for business class flights from Milwaukee to Simpson Bay?

    Yes. Cheapflights offers flight deals from Milwaukee to Simpson 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 Milwaukee to Simpson Bay?

    Currently, September is the cheapest month in which you can book a flight from Milwaukee to Simpson Bay (average of $459). Flying from Milwaukee to Simpson Bay in March is currently the most expensive (average of $657). 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

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Alternative routes for Milwaukee to Simpson Bay

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Simpson Bay flights
Minneapolis to Simpson Bay flights
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Eau Claire to Simpson Bay flights

Top 2 airlines flying from Milwaukee to Simpson Bay

Discover the top 2 airlines that operate flights from Milwaukee to Simpson 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 June 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$509Average$673FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$534Average$721FlexibilityNo cancel feeOn-time71%

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