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Simpson Bay

$111+ 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 3/23. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — SXM
Feb 25 — Mar 41
Tue 2/25
Tue 3/4
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 February 20, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$353
(FlightHub)

One-way from

$111
(Priceline)

Popular in

December

Cheapest in

September

Average price

$670

Good round-trip deal

$666 or less

Good one-way deal

$438 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. 5% potential increase in price ($40 potential increase over avg. RT price).
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Cheapest flight prices on average. 0% potential price decrease ($7 potential savings vs. average RT price).
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Average for round-trip flights in February 2025
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Price to beat on a round-trip flight from Illinois to Simpson Bay Princess Juliana.
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Price to beat on a one-way 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 February 20, 2025.

This FlightHub deal was found by Cheapflights users on 2/19. 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.
Tue 5/66:11 pmSTL - SXM
1 stop18h 50mSpirit Airlines
Wed 5/142:56 pmSXM - STL
1 stop28h 36mSpirit Airlines
Deal found 2/19$353
This Cheapflightsfares deal was found by Cheapflights users on 2/20. 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 4/265:10 amORD - SXM
1 stop7h 17mSpirit Airlines
Fri 5/22:34 pmSXM - ORD
1 stop11h 07mSpirit Airlines
Deal found 2/20$385
This Kiwi.com deal was found by Cheapflights users on 2/20. 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 5/84:15 pmORD - SXM
2 stops23h 46mMultiple Airlines
Sun 5/1111:55 amSXM - ORD
1 stop9h 55mMultiple Airlines
Deal found 2/20$424
This Mytrip deal was found by Cheapflights users on 2/18. 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.
Tue 3/256:47 pmSTL - SXM
1 stop17h 41mMultiple Airlines
Sat 4/53:05 pmSXM - STL
3 stops28h 36mMultiple Airlines
Deal found 2/18$432
This Booking.com deal was found by Cheapflights users on 2/20. 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.
Fri 6/64:21 pmORD - SXM
1 stop17h 37mFrontier
Sat 6/1412:18 pmSXM - ORD
2 stops12h 50mFrontier
Deal found 2/20$470
This Frontier deal was found by Cheapflights users on 2/20. 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 stop12h 46mFrontier
Sat 6/1412:18 pmSXM - MDW
2 stops12h 37mFrontier
Deal found 2/20$474
This Delta deal was found by Cheapflights users on 2/18. 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.
Wed 3/196:00 amSTL - SXM
1 stop7h 01mDelta
Wed 3/261:40 pmSXM - STL
1 stop10h 51mDelta
Deal found 2/18$545
This American Airlines deal was found by Cheapflights users on 2/18. 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.
Wed 3/195:01 amSTL - SXM
1 stop8h 19mAmerican Airlines
Wed 3/264:15 pmSXM - STL
2 stops17h 33mAmerican Airlines
Deal found 2/18$550
This United Airlines deal was found by Cheapflights users on 2/18. 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 4/41:12 pmSTL - SXM
1 stop26h 37mUnited Airlines
Fri 4/111:35 pmSXM - STL
2 stops23h 45mUnited Airlines
Deal found 2/18$617
This American Airlines deal was found by Cheapflights users on 2/20. 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 3/236:30 pmORD - SXM
1 stop17h 25mAmerican Airlines
Thu 4/33:20 pmSXM - ORD
1 stop10h 00mAmerican Airlines
Deal found 2/20$622
This Delta deal was found by Cheapflights users on 2/20. 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.
Wed 4/96:00 amMDW - SXM
1 stop6h 59mDelta
Tue 4/151:46 pmSXM - MDW
1 stop9h 40mDelta
Deal found 2/20$632
This Mytrip deal was found by Cheapflights users on 2/19. 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.
Sat 4/1912:55 pmMDW - SXM
1 stop24h 21mMultiple Airlines
Sat 4/2612:25 pmSXM - MDW
1 stop22h 55mMultiple Airlines
Deal found 2/19$646

Find flights from Illinois to Simpson Bay within your budget

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 February 20, 2025.

Fly from

Illinois

Fly to

Simpson Bay

Route

Depart

Return

Price

St. LouisSimpson Bay

STL - SXM

STLSXM

Lambert-St Louis

Tue 5/6

6:11 pm-2:01 pm

1 stop18h 50m

Simpson Bay Princess Juliana

Wed 5/14

2:56 pm-6:32 pm

1 stop28h 36m

$353

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sat 4/26

5:10 am-1:27 pm

1 stop7h 17m

Simpson Bay Princess Juliana

Fri 5/2

2:34 pm-12:41 am

1 stop11h 07m

$385

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Thu 5/8

4:15 pm-5:01 pm

2 stops23h 46m

Simpson Bay Princess Juliana

Sun 5/11

11:55 am-8:50 pm

1 stop9h 55m

$424

St. LouisSimpson Bay

STL - SXM

STLSXM

Lambert-St Louis

Tue 3/25

6:47 pm-1:28 pm

1 stop17h 41m

Simpson Bay Princess Juliana

Sat 4/5

3:05 pm-6:41 pm

3 stops28h 36m

$432

St. LouisSimpson Bay

STL - SXM

STLSXM

Lambert-St Louis

Wed 3/19

6:00 am-2:01 pm

1 stop7h 01m

Simpson Bay Princess Juliana

Wed 3/26

1:40 pm-11:31 pm

1 stop10h 51m

$545

St. LouisSimpson Bay

STL - SXM

STLSXM

Lambert-St Louis

Wed 3/19

5:01 am-2:20 pm

1 stop8h 19m

Simpson Bay Princess Juliana

Wed 3/26

4:15 pm-8:48 am

2 stops17h 33m

$550

St. LouisSimpson Bay

STL - SXM

STLSXM

Lambert-St Louis

Fri 4/4

5:35 pm-12:29 pm

2 stops17h 54m

Simpson Bay Princess Juliana

Fri 4/11

1:35 pm-11:03 am

2 stops22h 28m

$610

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sun 3/23

6:30 pm-12:55 pm

1 stop17h 25m

Simpson Bay Princess Juliana

Thu 4/3

3:20 pm-12:20 am

1 stop10h 00m

$622

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Wed 4/9

6:00 am-1:59 pm

1 stop6h 59m

Simpson Bay Princess Juliana

Tue 4/15

1:46 pm-10:26 pm

1 stop9h 40m

$632

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Sat 4/19

12:55 pm-2:16 pm

1 stop24h 21m

Simpson Bay Princess Juliana

Sat 4/26

12:25 pm-10:20 am

1 stop22h 55m

$646

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/19

Showing 1-10 of 27 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.

Travel insights for flights from Illinois to Simpson Bay

Get recent, data-driven insights about flights from Illinois to Simpson Bay including ideal travel times, pricing trends, and more.

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 $684). 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 February 20, 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 February 20, 2025.
Read reviews from past customers who have flown Delta, KLM 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
8,220 reviews

Entertainment

7.9

Boarding

8.2

Food

7.3

Comfort

8.0

Overall

8.0

Crew

8.5

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
8,220 reviews
Delta
8.0
Very good
8,220 reviews

Entertainment

7.9

Boarding

8.2

Food

7.3

Comfort

8.0

Overall

8.0

Crew

8.5

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.

KLM
7.8
Good
1,333 reviews
Delta
8.0
Very good
8,220 reviews

Entertainment

7.9

Boarding

8.2

Food

7.3

Comfort

8.0

Overall

8.0

Crew

8.5

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
8,766 reviews
Delta
8.0
Very good
8,220 reviews

Entertainment

7.9

Boarding

8.2

Food

7.3

Comfort

8.0

Overall

8.0

Crew

8.5

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
8,220 reviews

Entertainment

7.9

Boarding

8.2

Food

7.3

Comfort

8.0

Overall

8.0

Crew

8.5

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
2,801 reviews
Delta
8.0
Very good
8,220 reviews

Entertainment

7.9

Boarding

8.2

Food

7.3

Comfort

8.0

Overall

8.0

Crew

8.5

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 $111. However, be on the lookout for offers from Air Canada 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, Lambert-St Louis - Simpson Bay Princess Juliana or Chicago Midway - 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 $378. While the most popular route (Chicago O'Hare Intl - Simpson Bay Princess Juliana) can be booked for $323 on average our data indicates $697 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 $684). 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 February 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$319Average$438FlexibilityNo cancel feeOn-time65%
DeltaCheapest$494Average$746FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$579Average$802FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$614Average$892FlexibilityNo cancel feeOn-time69%
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