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Simpson Bay

$139+ Cheap flights from Illinois 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 4/25. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — SXM
Apr 7 — Apr 141
Mon 4/7
Mon 4/14
1 adult, Economy
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Cheap flight deals from Illinois to Simpson Bay

Keep the following information in mind while searching for Illinois to Simpson Bay flight deals. Data was last updated April 2, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$377
(Cheapflightsfares)

One-way from

$139
(Cheapflightsfares)

Popular in

March

Cheapest in

September

Average price

$727

Good round-trip deal

$795 or less
Provider with most accurate pricing for Chicago (CHI)-Simpson Bay Princess Juliana flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Simpson Bay Princess Juliana flights.
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From Illinois to Simpson Bay Princess Juliana
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One-way flight from Illinois to Simpson Bay Princess Juliana
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Highest demand for flights based on searches. 2% potential increase in price ($17 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($9 potential savings vs. average RT price).
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Average for round-trip flights in April 2025
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Price to beat on a round-trip flight from Illinois to Simpson Bay Princess Juliana.
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Find flight deals from Illinois to Simpson Bay

Cheapest flights from Illinois to Simpson Bay
Explore the most affordable flight options available from Illinois to Simpson Bay. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 2, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 4/1. 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 4/187:47 pmORD - SXM
1 stop17h 13mSpirit Airlines
Sat 5/33:05 pmSXM - ORD
1 stop10h 53mSpirit Airlines
Deal found 4/1$377
This Booking.com deal was found by Cheapflights users on 4/1. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/175:05 amORD - SXM
1 stop7h 55mMultiple Airlines
Sat 5/2412:34 pmSXM - ORD
1 stop20h 48mMultiple Airlines
Deal found 4/1$403
This Frontier deal was found by Cheapflights users on 4/1. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/309:12 pmMDW - SXM
1 stop13h 12mFrontier
Sat 6/1412:36 pmSXM - MDW
1 stop8h 41mFrontier
Deal found 4/1$431
This CheapOair deal was found by Cheapflights users on 4/1. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/35:10 amORD - SXM
2 stops53h 18mFrontier
Mon 7/76:26 pmSXM - ORD
2 stops30h 02mFrontier
Deal found 4/1$499
This deal was found by Cheapflights users on 4/1. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/276:00 amSTL - SXM
1 stop7h 05mDelta
Thu 5/11:46 pmSXM - STL
1 stop10h 50mDelta
Deal found 4/1$531
This American Airlines deal was found by Cheapflights users on 3/31. 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 5/185:12 amSTL - SXM
1 stop7h 03mAmerican Airlines
Sat 5/242:24 pmSXM - STL
1 stop8h 55mAmerican Airlines
Deal found 3/31$554
This Air Canada deal was found by Cheapflights users on 4/1. 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.
Fri 4/118:25 pmORD - SXM
1 stop18h 20mAir Canada
Mon 4/144:15 pmSXM - ORD
1 stop17h 40mAir Canada
Deal found 4/1$571
This Booking.com deal was found by Cheapflights users on 4/1. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/297:37 pmSTL - SXM
1 stop17h 24mMultiple Airlines
Sat 8/212:36 pmSXM - STL
1 stop12h 07mMultiple Airlines
Deal found 4/1$593
This Delta deal was found by Cheapflights users on 4/1. 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.
Tue 5/135:30 amORD - SXM
1 stop7h 24mDelta
Tue 5/203:19 pmSXM - ORD
1 stop9h 39mDelta
Deal found 4/1$622
This American Airlines deal was found by Cheapflights users on 4/1. 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 5/37:17 pmORD - SXM
1 stop16h 57mAmerican Airlines
Wed 5/73:24 pmSXM - ORD
2 stops16h 02mAmerican Airlines
Deal found 4/1$627
This Copa Airlines deal was found by Cheapflights users on 4/1. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/81:07 amORD - SXM
1 stop9h 17mCopa Airlines
Sun 7/1312:23 pmSXM - ORD
1 stop12h 57mCopa Airlines
Deal found 4/1$783
This Delta deal was found by Cheapflights users on 4/1. 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 4/266:04 amMDW - SXM
1 stop7h 01mDelta
Sat 5/31:46 pmSXM - MDW
1 stop9h 36mDelta
Deal found 4/1$792

Cheapflights Fare Finder

Customize your flight search to find flights from Illinois 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 April 2, 2025.
Use the filters below to find and compare flights from Illinois to Simpson Bay that are best for you.

Fly from

Illinois

Fly to

Simpson Bay

Route

Depart

Return

Price

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Fri 4/18

7:47 pm-2:00 pm

1 stop17h 13m

Simpson Bay Princess Juliana

Sat 5/3

3:05 pm-12:58 am

1 stop10h 53m

$377

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sat 5/17

5:05 am-2:00 pm

1 stop7h 55m

Simpson Bay Princess Juliana

Sat 5/24

12:34 pm-8:22 am

1 stop20h 48m

$403

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Fri 5/30

9:12 pm-11:24 am

1 stop13h 12m

Simpson Bay Princess Juliana

Sat 6/14

12:36 pm-8:17 pm

1 stop8h 41m

$431

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Thu 7/3

5:10 am-11:28 am

2 stops53h 18m

Simpson Bay Princess Juliana

Mon 7/7

6:26 pm-11:28 pm

2 stops30h 02m

$499

St. LouisSimpson Bay

STL - SXM

STLSXM

Lambert-St Louis

Sun 4/27

6:00 am-2:05 pm

1 stop7h 05m

Simpson Bay Princess Juliana

Wed 4/30

1:46 pm-11:36 pm

1 stop10h 50m

$531

St. LouisSimpson Bay

STL - SXM

STLSXM

Lambert-St Louis

Sun 5/18

5:12 am-1:15 pm

1 stop7h 03m

Simpson Bay Princess Juliana

Sat 5/24

2:24 pm-10:19 pm

1 stop8h 55m

$554

St. LouisSimpson Bay

STL - SXM

STLSXM

Lambert-St Louis

Tue 7/29

7:37 pm-2:01 pm

1 stop17h 24m

Simpson Bay Princess Juliana

Sat 8/2

12:36 pm-11:43 pm

1 stop12h 07m

$593

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Tue 5/13

5:30 am-1:54 pm

1 stop7h 24m

Simpson Bay Princess Juliana

Tue 5/20

3:19 pm-11:58 pm

1 stop9h 39m

$622

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sat 5/3

7:17 pm-1:14 pm

1 stop16h 57m

Simpson Bay Princess Juliana

Wed 5/7

3:24 pm-6:26 am

2 stops16h 02m

$627

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Tue 7/8

1:07 am-11:24 am

1 stop9h 17m

Simpson Bay Princess Juliana

Sun 7/13

12:23 pm-12:20 am

1 stop12h 57m

$783

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/1

Showing 1-10 of 25 results
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Best time to book a flight from Illinois to Simpson Bay

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

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

Currently, September is the cheapest month in which you can book a flight from Illinois to Simpson Bay (average of $459). Flying from Illinois to Simpson Bay in July is currently the most expensive (average of $675). 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 IL to SXM?

Find hourly flight availability from Illinois 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 April 2, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Illinois to Simpson Bay as you normally would.

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 April 2, 2025.
Read reviews from past customers who have flown Delta, Copa Airlines and United Airlines from Illinois to Simpson Bay. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,899 reviews

Boarding

8.2

Overall

8.0

Comfort

8.0

Food

7.3

Crew

8.5

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
Delta
8.0
Very good
7,899 reviews
Delta
8.0
Very good
7,899 reviews

Boarding

8.2

Overall

8.0

Comfort

8.0

Food

7.3

Crew

8.5

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
Copa Airlines
7.6
Good
1,400 reviews
Delta
8.0
Very good
7,899 reviews

Boarding

8.2

Overall

8.0

Comfort

8.0

Food

7.3

Crew

8.5

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
United Airlines
7.4
Good
8,615 reviews
Delta
8.0
Very good
7,899 reviews

Boarding

8.2

Overall

8.0

Comfort

8.0

Food

7.3

Crew

8.5

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,899 reviews

Boarding

8.2

Overall

8.0

Comfort

8.0

Food

7.3

Crew

8.5

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
WestJet
7.2
Good
2,789 reviews
Delta
8.0
Very good
7,899 reviews

Boarding

8.2

Overall

8.0

Comfort

8.0

Food

7.3

Crew

8.5

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

Related info for your journey

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

    If you book a flight to Simpson Bay from Illinois, you will be flying to Princess Juliana, which is the city’s only airport. Simpson Bay Princess Juliana (SXM) is located 0.5 mi from the center of Simpson Bay.

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

    The cheapest airline one-way is Spirit Airlines, with whom users have recently found tickets for as low as $139. However, be on the lookout for offers from Delta and American Airlines, as they are both options that can get you from Illinois to Simpson Bay for a low price.

  • What are the most popular routes from Illinois to Simpson Bay?

    Most travelers choose Chicago O'Hare Intl - Simpson Bay Princess Juliana, Chicago Midway - Simpson Bay Princess Juliana or Lambert-St Louis - Simpson Bay Princess Juliana when deciding on the best route from Illinois to Simpson Bay.

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

    Looking at all options, your cheapest flight can be booked for $757. While the most popular route (Chicago O'Hare Intl - Simpson Bay Princess Juliana) can be booked for $337 on average our data indicates $1,043 when flying from Illinois to Simpson Bay.

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

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

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

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

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

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

    Currently, September is the cheapest month in which you can book a flight from Illinois to Simpson Bay (average of $459). Flying from Illinois to Simpson Bay in July is currently the most expensive (average of $675). 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.

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Alternative routes for Illinois to Simpson Bay

See prices for flight routes from nearby airports that may be better suited for you.
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Top 4 airlines flying from Illinois to Simpson Bay

Discover the top 4 airlines that operate flights from Illinois 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 April 2, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$325Average$401FlexibilityNo cancel feeOn-time65%
DeltaCheapest$494Average$754FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$579Average$765FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$610Average$896FlexibilityNo cancel feeOn-time69%

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