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Simpson Bay

$83+ Cheap flights from Chicago (CHI) 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 1/25. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SXM
Jan 27 — Feb 31
Tue 1/27
Tue 2/3
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Simpson Bay Princess Juliana are usually found in August or September, booked 10 days in advance, depart on a Monday or Tuesday and return on a Monday

Cheap flight deals from Chicago to Simpson Bay

Cheapest flights from Chicago to Simpson Bay
Explore the most affordable flight options available from Chicago to Simpson Bay. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 28, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 12/27. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/315:00 amORD - SXM
1 stop7h 15mSpirit Airlines
Fri 1/23:20 pmSXM - ORD
1 stop11h 10mSpirit Airlines
Deal found 12/27$921
This Mytrip deal was found by Cheapflights users on 12/27. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/315:00 amORD - SXM
1 stop7h 15mMultiple Airlines
Fri 1/211:35 amSXM - ORD
3 stops22h 56mMultiple Airlines
Deal found 12/27$932
This Expedia deal was found by Cheapflights users on 12/26. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/316:00 pmORD - SXM
2 stops44h 00mMultiple Airlines
Mon 1/53:20 pmSXM - ORD
1 stop11h 10mMultiple Airlines
Deal found 12/26$970
This Priceline deal was found by Cheapflights users on 12/26. 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 12/296:00 pmORD - SXM
2 stops20h 00mMultiple Airlines
Fri 1/23:20 pmSXM - ORD
1 stop11h 10mMultiple Airlines
Deal found 12/26$1,051
This Air Canada deal was found by Cheapflights users on 12/26. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/276:00 pmORD - SXM
2 stops18h 40mAir Canada
Thu 1/13:40 pmSXM - ORD
2 stops29h 13mAir Canada
Deal found 12/26$1,091
This Kiwi.com deal was found by Cheapflights users on 12/26. 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 12/308:00 amORD - SXM
1 stop28h 15mMultiple Airlines
Sun 1/411:30 amSXM - ORD
2 stops13h 55mMultiple Airlines
Deal found 12/26$1,129
This Kiwi.com deal was found by Cheapflights users on 12/26. 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.
Wed 12/315:00 amORD - SXM
1 stop7h 15mMultiple Airlines
Sun 1/411:30 amSXM - ORD
2 stops54h 49mMultiple Airlines
Deal found 12/26$1,228
This FlightHub deal was found by Cheapflights users on 12/26. 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.
Sat 12/277:05 amORD - SXM
1 stop29h 35mMultiple Airlines
Thu 1/12:05 pmSXM - ORD
1 stop30h 41mMultiple Airlines
Deal found 12/26$1,251
This Delta deal was found by Cheapflights users on 12/26. 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 12/296:00 amMDW - SXM
1 stop6h 50mDelta
Fri 1/21:45 pmSXM - MDW
1 stop10h 37mDelta
Deal found 12/26$1,857
This Delta deal was found by Cheapflights users on 12/26. 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 12/276:00 amMDW - SXM
1 stop6h 50mDelta
Thu 1/11:45 pmSXM - MDW
1 stop10h 37mDelta
Deal found 12/26$1,875
This Kiwi.com deal was found by Cheapflights users on 12/27. 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.
Mon 12/294:15 pmMDW - SXM
1 stop18h 00mMultiple Airlines
Sat 1/310:25 amSXM - MDW
2 stops25h 45mMultiple Airlines
Deal found 12/27$1,939
This Kiwi.com deal was found by Cheapflights users on 12/27. 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.
Wed 12/313:10 pmMDW - SXM
2 stops17h 15mMultiple Airlines
Fri 1/24:20 pmSXM - MDW
1 stop19h 50mMultiple Airlines
Deal found 12/27$2,347

Find flight deals from Chicago to Simpson Bay

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) 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 December 28, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$243
(Priceline)

One-way from

$83
(Super.com)

Popular in

December

Cheapest in

August

Average price

$988

Good round-trip deal

$556 or less
Provider with most accurate pricing for Chicago (CHI)-Simpson Bay Princess Juliana flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Simpson Bay Princess Juliana flights.
Search Deals
From Chicago (CHI) to Simpson Bay Princess Juliana
Search Deals
One-way flight from Chicago (CHI) to Simpson Bay Princess Juliana
Search Deals
Highest demand for flights based on searches. 6% potential increase in price ($52 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($26 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals
Price to beat on a round-trip flight from Chicago (CHI) to Simpson Bay Princess Juliana.
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago 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 December 28, 2025.
Use the filters below to find and compare flights from Chicago to Simpson Bay that are best for you.

Fly from

Chicago

Fly to

Simpson Bay

Route

Depart

Return

Price

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sun 1/25

8:43 pm-2:10 pm

1 stop15h 27m

Simpson Bay Princess Juliana

Fri 1/30

3:15 pm-11:46 pm

1 stop10h 31m

$250

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sun 2/15

3:40 pm-2:15 pm

1 stop20h 35m

Simpson Bay Princess Juliana

Mon 2/23

3:20 pm-11:47 pm

1 stop10h 27m

$275

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Fri 1/30

8:43 pm-2:10 pm

1 stop15h 27m

Simpson Bay Princess Juliana

Sun 2/1

3:20 pm-11:47 pm

1 stop10h 27m

$300

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sat 2/14

12:06 pm-2:15 pm

1 stop24h 09m

Simpson Bay Princess Juliana

Sun 2/22

3:20 pm-11:22 am

1 stop22h 02m

$301

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sat 2/14

12:06 pm-2:15 pm

1 stop24h 09m

Simpson Bay Princess Juliana

Mon 2/23

3:20 pm-11:47 pm

1 stop10h 27m

$301

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Fri 2/13

3:29 pm-2:15 pm

1 stop20h 46m

Simpson Bay Princess Juliana

Sat 2/21

3:20 pm-11:47 pm

1 stop10h 27m

$346

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Fri 2/13

3:29 pm-2:15 pm

1 stop20h 46m

Simpson Bay Princess Juliana

Mon 2/23

3:20 pm-11:47 pm

1 stop10h 27m

$346

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Fri 1/30

8:43 pm-2:10 pm

1 stop15h 27m

Simpson Bay Princess Juliana

Sun 2/1

3:20 pm-11:59 pm

2 stops10h 39m

$359

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sat 2/14

3:55 pm-2:40 pm

2 stops20h 45m

Simpson Bay Princess Juliana

Sat 2/21

3:20 pm-11:47 pm

1 stop10h 27m

$393

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Sun 1/25

6:00 am-2:55 pm

1 stop6h 55m

Simpson Bay Princess Juliana

Fri 1/30

1:55 pm-10:22 pm

1 stop10h 27m

$501

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/26

Showing 1-10 of 34 results
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Compare providers for flights from Chicago to Simpson Bay

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Chicago to Simpson Bay in December.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars
AranGrantPrice Accuracy2 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Chicago-Simpson Bay flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Chicago-Simpson Bay flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Chicago-Simpson Bay flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago-Simpson Bay flights, Cheapflights users trust eDreams the most. eDreams 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 Chicago-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 Chicago to Simpson Bay

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

How far ahead should I book a flight from Chicago to Simpson Bay?

Use this chart to determine the optimal time to book a round-trip flight from Chicago to Simpson Bay. Price data was last updated on December 19, 2025.

The price you pay for your flight from Chicago to Simpson Bay may vary depending on when you book. For the best chance of a lower fare, look to book 9 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

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

Currently, September is the cheapest month in which you can book a flight from Chicago to Simpson Bay (average of $312). Flying from Chicago to Simpson Bay in June 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 CHI to SXM?

Find hourly flight availability from Chicago 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 December 28, 2025.

When flying from Chicago to Simpson Bay, the time of day you fly usually plays a role in the price. Save by searching for a flight at noon, which can drop the price by up to 47% versus a flight in the evening.

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

How often are flights from Chicago to Simpson Bay delayed?

About 34% of weekly flights between Chicago and Simpson Bay have experienced delays in the past year, with the average delay time being 129 minutes.

What is the most punctual flight time for Chicago to Simpson Bay flights?

Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving in the morning tend to experience delays more often.

What day of the week experiences the fewest flight delays on this route?

Sunday tends to have the lowest number of delays on this route, whereas Saturday has historically faced a higher average of delays compared to other days of the week.

Which airline has the best punctuality record on Chicago to Simpson Bay flights?

Over the last year, United Airlines have had the lowest number of delays on this route, with just 33% of flights being delayed.

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 December 28, 2025.
See what other customers who have flown with Delta, United Airlines, and American Airlines from Chicago to Simpson Bay have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
7.9
Good
8,019 reviews

Entertainment

7.9

Boarding

8.1

Food

7.3

Crew

8.5

Overall

7.9

Comfort

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Delta
7.9
Good
8,019 reviews
Delta
7.9
Good
8,019 reviews

Entertainment

7.9

Boarding

8.1

Food

7.3

Crew

8.5

Overall

7.9

Comfort

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
United Airlines
7.4
Good
9,113 reviews
Delta
7.9
Good
8,019 reviews

Entertainment

7.9

Boarding

8.1

Food

7.3

Crew

8.5

Overall

7.9

Comfort

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
American Airlines
7.2
Good
11,072 reviews
Delta
7.9
Good
8,019 reviews

Entertainment

7.9

Boarding

8.1

Food

7.3

Crew

8.5

Overall

7.9

Comfort

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Spirit Airlines
6.3
Okay
8,212 reviews
Delta
7.9
Good
8,019 reviews

Entertainment

7.9

Boarding

8.1

Food

7.3

Crew

8.5

Overall

7.9

Comfort

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Frontier
5.8
Fair
3,065 reviews
Delta
7.9
Good
8,019 reviews

Entertainment

7.9

Boarding

8.1

Food

7.3

Crew

8.5

Overall

7.9

Comfort

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.

Related info for your journey

Find useful and relevant information for your journey from Chicago 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 Chicago?

    Most people fly into Simpson Bay Princess Juliana (SXM) if they book a flight to Simpson Bay from Chicago. On average, Princess Juliana has 0 inbound flights from Chicago per day from 5 airlines. Simpson Bay Princess Juliana is conveniently located just 0.5 mi from Simpson Bay’s city center.

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

    Departing from Chicago to Simpson Bay will take you 6h 55m. The distance between Chicago and Simpson Bay is about 2189 mi. Both multi-stop and nonstop flights can be found to your destination and back.

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

    According to our current data, Delta ($290), Spirit Airlines ($312), and United Airlines ($410) offers the cheapest pricing from Chicago to Simpson Bay. Users have found that Delta is 59% cheaper than the other options available to this destination.

  • What are the cheapest flights from Chicago to Simpson Bay?

    On average you can expect to pay $507 for a flight from Chicago to Simpson Bay. The cheapest flight overall is $313 while the most popular route, (Chicago O'Hare Intl - Simpson Bay Princess Juliana) is currently priced at $246.

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

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

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

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

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

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

    Currently, September is the cheapest month in which you can book a flight from Chicago to Simpson Bay (average of $312). Flying from Chicago to Simpson Bay in June 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 Simpson Bay?

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

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Alternative routes for Chicago 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
Midway to Simpson Bay flights
St. Louis to Simpson Bay flights

Top 5 airlines flying from Chicago to Simpson Bay

Discover the top 5 airlines that operate flights from Chicago 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 December 28, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$292Average$687FlexibilityNo cancel feeOn-timeN/A
Spirit AirlinesCheapest$312Average$398FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$410Average$789FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$525Average$695FlexibilityNo cancel feeOn-time71%
JetBlueCheapest$535Average$731FlexibilityNo cancel feeOn-time62%

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