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Simpson Bay

$589+ Cheap flights from Akron (CAK) to Simpson Bay (SXM)

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 5/14. Fares are subject to change and may not be available on all flights or dates of travel.
CAK — SXM
Feb 28 — Mar 71
Sat 2/28
Sat 3/7
1 adult, Economy
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Cheap flight deals from Akron to Simpson Bay

Cheapest flights from Akron to Simpson Bay
Explore the most affordable flight options available from Akron to Simpson Bay. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 29, 2026.

This United Airlines deal was found by Cheapflights users on 1/28. 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 5/141:55 pm
CAK
-
SXM
2 stops46h 38m
United Airlines
Tue 5/191:35 pm
SXM
-
CAK
2 stops23h 37m
United Airlines
Deal found 1/28$589
This United Airlines deal was found by Cheapflights users on 1/28. 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 5/141:55 pm
CAK
-
SXM
2 stops46h 38m
United Airlines
Fri 5/223:50 pm
SXM
-
CAK
2 stops45h 17m
United Airlines
Deal found 1/28$603
This United Airlines deal was found by Cheapflights users on 1/27. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/157:00 am
CAK
-
SXM
1 stop7h 57m
United Airlines
Sat 3/214:00 pm
SXM
-
CAK
2 stops25h 15m
United Airlines
Deal found 1/27$632
This United Airlines deal was found by Cheapflights users on 1/28. 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.
Fri 5/1510:30 am
CAK
-
SXM
2 stops26h 03m
United Airlines
Tue 5/191:35 pm
SXM
-
CAK
2 stops23h 37m
United Airlines
Deal found 1/28$639
This American Airlines deal was found by Cheapflights users on 1/28. 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.
Tue 4/75:53 pm
CAK
-
SXM
2 stops19h 23m
American Airlines
Mon 4/1312:41 pm
SXM
-
CAK
2 stops21h 53m
American Airlines
Deal found 1/28$645
This Kiwi.com deal was found by Cheapflights users on 1/27. 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.
Thu 5/217:25 am
CAK
-
SXM
2 stops29h 51m
Multiple Airlines
Tue 5/262:11 pm
SXM
-
CAK
1 stop24h 44m
Multiple Airlines
Deal found 1/27$648
This United Airlines deal was found by Cheapflights users on 1/28. 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.
Fri 5/1512:00 pm
CAK
-
SXM
2 stops24h 33m
United Airlines
Fri 5/223:50 pm
SXM
-
CAK
2 stops45h 17m
United Airlines
Deal found 1/28$653
This United Airlines deal was found by Cheapflights users on 1/28. 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 5/141:55 pm
CAK
-
SXM
2 stops46h 38m
United Airlines
Mon 5/253:50 pm
SXM
-
CAK
2 stops31h 50m
United Airlines
Deal found 1/28$670
This United Airlines deal was found by Cheapflights users on 1/28. 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 5/141:55 pm
CAK
-
SXM
2 stops46h 38m
United Airlines
Sun 5/243:50 pm
SXM
-
CAK
2 stops24h 47m
United Airlines
Deal found 1/28$715
This American Airlines deal was found by Cheapflights users on 1/28. 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.
Sun 5/176:17 am
CAK
-
SXM
1 stop7h 04m
American Airlines
Wed 5/202:24 pm
SXM
-
CAK
1 stop8h 58m
American Airlines
Deal found 1/28$743

Find flight deals from Akron to Simpson Bay

Discover tips and strategies to find the most affordable flight options for your journey from Akron (CAK) 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 January 29, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$589
(United Airlines)

Popular in

December

Cheapest in

May

Average price

$622
Provider with most accurate pricing for Akron/Canton-Simpson Bay Princess Juliana flight deals.
Search Deals
Provider most trusted by Cheapflights users for Akron/Canton-Simpson Bay Princess Juliana flights.
Search Deals
From Akron/Canton to Simpson Bay Princess Juliana
Search Deals
Highest demand for flights based on searches. 5% potential increase in price ($38 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($9 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Akron 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 January 29, 2026.
Use the filters below to find and compare flights from Akron to Simpson Bay that are best for you.

Fly from

Akron

Fly to

Simpson Bay

Route

Depart

Return

Price

AkronSimpson Bay

CAK - SXM

CAKSXM

Akron/Canton

Thu 5/14

1:55 pm-12:33 pm

2 stops46h 38m

Simpson Bay Princess Juliana

Tue 5/19

1:35 pm-1:12 pm

2 stops23h 37m

$589

AkronSimpson Bay

CAK - SXM

CAKSXM

Akron/Canton

Thu 5/14

1:55 pm-12:33 pm

2 stops46h 38m

Simpson Bay Princess Juliana

Sat 5/23

3:50 pm-1:07 pm

2 stops21h 17m

$589

AkronSimpson Bay

CAK - SXM

CAKSXM

Akron/Canton

Thu 5/14

1:55 pm-12:33 pm

2 stops46h 38m

Simpson Bay Princess Juliana

Fri 5/22

3:50 pm-1:07 pm

2 stops45h 17m

$603

AkronSimpson Bay

CAK - SXM

CAKSXM

Akron/Canton

Sun 3/15

7:00 am-2:57 pm

1 stop7h 57m

Simpson Bay Princess Juliana

Sat 3/21

4:00 pm-5:15 pm

2 stops25h 15m

$632

AkronSimpson Bay

CAK - SXM

CAKSXM

Akron/Canton

Fri 5/15

12:00 pm-12:33 pm

2 stops24h 33m

Simpson Bay Princess Juliana

Sat 5/23

3:50 pm-1:07 pm

2 stops21h 17m

$639

AkronSimpson Bay

CAK - SXM

CAKSXM

Akron/Canton

Fri 5/15

10:30 am-12:33 pm

2 stops26h 03m

Simpson Bay Princess Juliana

Tue 5/19

1:35 pm-1:12 pm

2 stops23h 37m

$639

AkronSimpson Bay

CAK - SXM

CAKSXM

Akron/Canton

Tue 4/7

5:53 pm-1:16 pm

2 stops19h 23m

Simpson Bay Princess Juliana

Mon 4/13

12:41 pm-10:34 am

2 stops21h 53m

$645

AkronSimpson Bay

CAK - SXM

CAKSXM

Akron/Canton

Thu 5/21

7:25 am-1:16 pm

2 stops29h 51m

Simpson Bay Princess Juliana

Tue 5/26

2:11 pm-2:55 pm

1 stop24h 44m

$648

AkronSimpson Bay

CAK - SXM

CAKSXM

Akron/Canton

Fri 5/15

12:00 pm-12:33 pm

2 stops24h 33m

Simpson Bay Princess Juliana

Fri 5/22

3:50 pm-1:07 pm

2 stops45h 17m

$653

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/28

  • Most accurate provider: When it comes to deals on Akron-Simpson Bay flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Akron-Simpson Bay flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Akron-Simpson Bay flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Akron-Simpson Bay flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Akron-Simpson Bay flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Akron to Simpson Bay

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

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

Currently, March is the cheapest month in which you can book a flight from Akron to Simpson Bay (average of $194). Flying from Akron to Simpson Bay in June is currently the most expensive (average of $435). 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.

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 January 29, 2026.
Read through reviews of airlines operating flights from Akron to Simpson Bay, such as American Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
American Airlines
7.2
Good
11,206 reviews

Comfort

7.2

Crew

8.0

Boarding

7.5

Food

6.4

Entertainment

6.9

Overall

7.2

Reviews

1 / 20
2.0
Mediocre

Susie,Jan 2026

CLT - TPA

This flight was delayed 3 or 4 times. We had boarded the plane, sat on plane for a good 30 minutes, then we had to board the aircraft, walk to a different gate, wait and then board another aircraft. We arrived in Tampa 4 hours later than the original booking. I feel there should have been some sort of compensation especially for the advantage members.
American Airlines
7.2
Good
11,206 reviews
American Airlines
7.2
Good
11,206 reviews

Comfort

7.2

Crew

8.0

Boarding

7.5

Food

6.4

Entertainment

6.9

Overall

7.2

Reviews

1 / 20
2.0
Mediocre

Susie,Jan 2026

CLT - TPA

This flight was delayed 3 or 4 times. We had boarded the plane, sat on plane for a good 30 minutes, then we had to board the aircraft, walk to a different gate, wait and then board another aircraft. We arrived in Tampa 4 hours later than the original booking. I feel there should have been some sort of compensation especially for the advantage members.

Related info for your journey

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

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

    Airlines like United Airlines fly from Akron to Simpson Bay in about 46h 38m. The time it takes to get you to your destination can typically vary by up to . Akron and Simpson Bay are separated by a distance of 1917 mi.

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

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

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

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

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

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

    Currently, March is the cheapest month in which you can book a flight from Akron to Simpson Bay (average of $194). Flying from Akron to Simpson Bay in June is currently the most expensive (average of $435). 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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Top airline flying from Akron to Simpson Bay

Discover the top airline that operate flights from Akron 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 January 29, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$612Average$1,000FlexibilityNo cancel feeOn-time71%

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