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Simpson Bay

$113+ Cheap flights from Michigan 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 1/28. Fares are subject to change and may not be available on all flights or dates of travel.
DTW — SXM
Nov 29 — Dec 61
Sat 11/29
Sat 12/6
1 adult, Economy
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Cheap flight deals from Michigan to Simpson Bay

Keep the following information in mind while searching for Michigan to Simpson Bay flight deals. Data was last updated October 30, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$298
(Cheapflightsfares)

One-way from

$113
(Cheapflightsfares)

Popular in

December

Cheapest in

September

Average price

$609
Provider with most accurate pricing for Detroit (DTT)-Simpson Bay Princess Juliana flight deals.
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Provider most trusted by Cheapflights users for Detroit (DTT)-Simpson Bay Princess Juliana flights.
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From Michigan to Simpson Bay Princess Juliana
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One-way flight from Michigan to Simpson Bay Princess Juliana
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Highest demand for flights based on searches. 17% potential increase in price ($158 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($24 potential savings vs. average RT price).
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Average for round-trip flights in October 2025
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Find flight deals from Michigan to Simpson Bay

Cheapest flights from Michigan to Simpson Bay
Explore the most affordable flight options available from Michigan to Simpson Bay. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 30, 2025.

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.
Sat 12/135:00 amORD - SXM
1 stop7h 15mSpirit Airlines
Wed 12/173:20 pmSXM - ORD
1 stop10h 49mSpirit Airlines
Deal found 10/29$314
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 12/143:20 pmORD - SXM
1 stop20h 55mMultiple Airlines
Wed 12/243:20 pmSXM - ORD
1 stop25h 42mMultiple Airlines
Deal found 10/28$318
This Priceline 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/135:00 amORD - SXM
1 stop7h 15mSpirit Airlines
Sat 12/203:20 pmSXM - ORD
1 stop11h 10mSpirit Airlines
Deal found 10/28$332
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.
Thu 12/116:15 amORD - SXM
1 stop30h 00mMultiple Airlines
Wed 12/173:20 pmSXM - ORD
1 stop10h 49mMultiple Airlines
Deal found 10/28$337
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.
Fri 11/285:00 amORD - SXM
1 stop7h 15mSpirit Airlines
Fri 12/53:20 pmSXM - ORD
1 stop10h 49mSpirit Airlines
Deal found 10/29$349
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 12/54:20 pmORD - SXM
1 stop19h 10mMultiple Airlines
Wed 12/103:20 pmSXM - ORD
1 stop10h 49mMultiple Airlines
Deal found 10/28$351
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/147:34 pmORD - SXM
2 stops16h 41mSpirit Airlines
Mon 11/173:20 pmSXM - ORD
1 stop11h 07mSpirit Airlines
Deal found 10/29$355
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/54:47 pmORD - SXM
2 stops19h 28mSpirit Airlines
Wed 12/103:20 pmSXM - ORD
1 stop10h 49mSpirit Airlines
Deal found 10/28$357
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 12/164:22 pmORD - SXM
2 stops19h 53mMultiple Airlines
Wed 1/73:20 pmSXM - ORD
1 stop30h 04mMultiple Airlines
Deal found 10/29$359
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.
Sat 12/137:07 pmORD - SXM
1 stop17h 13mAmerican Airlines
Sat 12/203:04 pmSXM - ORD
Nonstop5h 54mAmerican Airlines
Deal found 10/28$365
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/116:00 amMDW - SXM
1 stop6h 28mDelta
Wed 12/173:53 pmSXM - MDW
1 stop9h 54mDelta
Deal found 10/28$375
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/236:48 pmMDW - SXM
2 stops18h 07mDelta
Tue 11/254:20 pmSXM - MDW
2 stops18h 34mDelta
Deal found 10/27$380

Cheapflights Fare Finder

 
Customize your flight search to find flights from Michigan 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 October 30, 2025.
Use the filters below to find and compare flights from Michigan to Simpson Bay that are best for you.

Fly from

Michigan

Fly to

Simpson Bay

Route

Depart

Return

Price

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Thu 12/11

6:15 am-2:15 pm

1 stop30h 00m

Simpson Bay Princess Juliana

Wed 12/17

3:20 pm-12:09 am

1 stop10h 49m

$337

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sun 12/14

8:45 am-3:57 pm

Nonstop5h 12m

Simpson Bay Princess Juliana

Sun 12/21

5:00 pm-11:44 pm

1 stop8h 44m

$371

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Sun 12/14

6:00 am-2:28 pm

1 stop6h 28m

Simpson Bay Princess Juliana

Wed 12/24

1:45 pm-10:22 pm

1 stop10h 37m

$375

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Wed 12/17

6:00 am-2:28 pm

1 stop6h 28m

Simpson Bay Princess Juliana

Tue 12/23

1:45 pm-10:22 pm

1 stop10h 37m

$375

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Thu 12/11

5:30 am-2:28 pm

1 stop6h 58m

Simpson Bay Princess Juliana

Tue 12/16

3:53 pm-10:43 pm

1 stop8h 50m

$375

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Wed 12/3

5:30 am-2:28 pm

1 stop6h 58m

Simpson Bay Princess Juliana

Fri 12/5

3:53 pm-12:01 am

1 stop10h 08m

$375

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Wed 12/10

5:30 am-2:28 pm

1 stop6h 58m

Simpson Bay Princess Juliana

Tue 12/16

3:53 pm-10:43 pm

1 stop8h 50m

$375

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Mon 12/1

5:23 am-2:55 pm

1 stop7h 32m

Simpson Bay Princess Juliana

Fri 12/5

3:53 pm-12:01 am

1 stop10h 08m

$375

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Wed 12/17

5:30 am-2:28 pm

1 stop6h 58m

Simpson Bay Princess Juliana

Tue 12/23

1:45 pm-9:14 pm

1 stop9h 29m

$375

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Wed 12/3

5:30 am-2:28 pm

1 stop6h 58m

Simpson Bay Princess Juliana

Sat 12/6

3:25 pm-10:43 pm

1 stop9h 18m

$375

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/28

Showing 1-10 of 50 results
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Best time to book a flight from Michigan to Simpson Bay

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

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

Currently, November is the cheapest month in which you can book a flight from Michigan to Simpson Bay (average of $282). Flying from Michigan to Simpson Bay in December is currently the most expensive (average of $543). 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 MI to SXM?

Find hourly flight availability from Michigan 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 October 30, 2025.

One of the essential ways to save on airfare from Michigan to Simpson Bay is to remain as flexible as possible. Flights that are in the morning tend to be the most expensive. A flight in the evening could potentially save you up to 35% on airfare.

How much does it cost to fly round-trip from Michigan to Simpson Bay?

Related info for your journey

Find useful and relevant information for your journey from Michigan 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 airport do you fly into for flights to Simpson Bay from Michigan?

    Simpson Bay Princess Juliana (SXM) is the airport you will fly into if you book a flight from Michigan to Simpson Bay. It is only a 0.5 mi journey from Princess Juliana (SXM) to Simpson Bay’s city center.

  • How long is the flight from Michigan to Simpson Bay?

    There are many flights that can get you from Michigan to Simpson Bay in 5h 12m. Fly via United Airlines, Delta, or Spirit Airlines to get the fastest option. The distance between Michigan and Simpson Bay is about 2204 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 Michigan to Simpson Bay?

    While some choose either Chicago Midway - Simpson Bay Princess Juliana or Detroit Metropolitan Wayne County - Simpson Bay Princess Juliana, Chicago O'Hare Intl - Simpson Bay Princess Juliana is the most popular route from Michigan to Simpson Bay.

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

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

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

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

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

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

    Currently, November is the cheapest month in which you can book a flight from Michigan to Simpson Bay (average of $282). Flying from Michigan to Simpson Bay in December is currently the most expensive (average of $543). 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 Simpson Bay?

Book flights to Simpson Bay if you plan to visit one of these locations
Philipsburg

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Alternative routes for Michigan to Simpson Bay

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Top 5 airlines flying from Michigan to Simpson Bay

Discover the top 5 airlines that operate flights from Michigan 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 October 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$357Average$459FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$448Average$656FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$555Average$749FlexibilityNo cancel feeOn-time71%
DeltaCheapest$585Average$852FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$658Average$1,046FlexibilityNo cancel feeOn-time69%

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