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Simpson Bay

$164+ 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 8/2. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — SXM
Jun 28 — Jul 51
Sat 6/28
Sat 7/5
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 June 23, 2025.

Round-trip from

$377
(Cheapflightsfares)

One-way from

$164
(FlightHub)

Popular in

March

Cheapest in

September

Average price

$755

Good round-trip deal

$682 or less
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. 1% potential price decrease ($11 potential savings vs. average RT price).
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Average for round-trip flights in June 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 June 23, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 6/21. 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 8/165:05 amORD - SXM
1 stop8h 22mSpirit Airlines
Sat 8/233:32 pmSXM - ORD
1 stop9h 27mSpirit Airlines
Deal found 6/21$377
This CheapOair deal was found by Cheapflights users on 6/22. 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.
Fri 7/49:58 amORD - SXM
1 stop24h 30mMultiple Airlines
Fri 7/113:05 pmSXM - ORD
1 stop9h 48mMultiple Airlines
Deal found 6/22$400
This FlightHub deal was found by Cheapflights users on 6/21. 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.
Fri 7/185:40 pmSTL - SXM
1 stop16h 48mMultiple Airlines
Sat 7/263:05 pmSXM - STL
2 stops43h 47mMultiple Airlines
Deal found 6/21$470
This Mytrip deal was found by Cheapflights users on 6/21. 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 7/1810:47 amSTL - SXM
3 stops26h 13mSpirit Airlines
Sat 7/263:05 pmSXM - STL
2 stops19h 47mSpirit Airlines
Deal found 6/21$479
This Booking.com deal was found by Cheapflights users on 6/20. 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.
Thu 12/113:35 pmORD - SXM
2 stops22h 40mAir Canada
Mon 12/155:15 pmSXM - ORD
2 stops19h 24mAir Canada
Deal found 6/20$563
This American Airlines deal was found by Cheapflights users on 6/22. 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.
Mon 7/215:15 amORD - SXM
1 stop7h 10mAmerican Airlines
Wed 7/302:50 pmSXM - ORD
1 stop10h 27mAmerican Airlines
Deal found 6/22$581
This American Airlines deal was found by Cheapflights users on 6/22. 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 8/65:26 amSTL - SXM
1 stop8h 43mAmerican Airlines
Wed 8/133:25 pmSXM - STL
1 stop17h 39mAmerican Airlines
Deal found 6/22$585
This Delta deal was found by Cheapflights users on 6/21. 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 8/106:20 pmMDW - SXM
2 stops18h 36mDelta
Wed 8/203:21 pmSXM - MDW
2 stops22h 07mDelta
Deal found 6/21$592
This Delta deal was found by Cheapflights users on 6/22. 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 9/72:00 pmORD - SXM
2 stops22h 45mDelta
Fri 10/33:15 pmSXM - ORD
1 stop9h 38mDelta
Deal found 6/22$592
This Delta deal was found by Cheapflights users on 6/22. 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 10/116:00 amSTL - SXM
1 stop6h 47mDelta
Sat 10/183:15 pmSXM - STL
1 stop7h 44mDelta
Deal found 6/22$663
This United Airlines deal was found by Cheapflights users on 6/21. 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 12/2810:30 amSTL - SXM
2 stops25h 21mUnited Airlines
Wed 12/314:55 pmSXM - STL
2 stops21h 25mUnited Airlines
Deal found 6/21$1,014
This FlightHub deal was found by Cheapflights users on 6/21. 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.
Wed 12/244:15 pmSTL - SXM
2 stops19h 40mAir Canada
Tue 12/303:05 pmSXM - STL
2 stops26h 21mAir Canada
Deal found 6/21$1,845

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 June 23, 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

Sat 8/16

5:05 am-2:27 pm

1 stop8h 22m

Simpson Bay Princess Juliana

Sat 8/23

3:32 pm-11:59 pm

1 stop9h 27m

$377

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Fri 7/4

9:58 am-11:28 am

1 stop24h 30m

Simpson Bay Princess Juliana

Fri 7/11

3:05 pm-11:53 pm

1 stop9h 48m

$400

St. LouisSimpson Bay

STL - SXM

STLSXM

Lambert-St Louis

Fri 7/18

5:40 pm-11:28 am

1 stop16h 48m

Simpson Bay Princess Juliana

Sat 7/26

3:05 pm-9:52 am

2 stops43h 47m

$470

St. LouisSimpson Bay

STL - SXM

STLSXM

Lambert-St Louis

Fri 7/18

10:47 am-2:00 pm

3 stops26h 13m

Simpson Bay Princess Juliana

Sat 7/26

3:05 pm-9:52 am

2 stops19h 47m

$479

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Thu 12/11

3:35 pm-4:15 pm

2 stops22h 40m

Simpson Bay Princess Juliana

Mon 12/15

5:15 pm-10:39 am

2 stops19h 24m

$563

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Mon 7/21

5:15 am-1:25 pm

1 stop7h 10m

Simpson Bay Princess Juliana

Wed 7/30

2:50 pm-12:17 am

1 stop10h 27m

$581

St. LouisSimpson Bay

STL - SXM

STLSXM

Lambert-St Louis

Wed 8/6

5:26 am-3:09 pm

1 stop8h 43m

Simpson Bay Princess Juliana

Wed 8/13

3:25 pm-8:04 am

1 stop17h 39m

$585

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Sun 8/10

6:20 pm-1:56 pm

2 stops18h 36m

Simpson Bay Princess Juliana

Wed 8/20

3:21 pm-12:28 pm

2 stops22h 07m

$592

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sun 9/7

9:10 am-1:45 pm

2 stops27h 35m

Simpson Bay Princess Juliana

Wed 10/1

3:15 pm-9:25 am

2 stops19h 10m

$592

St. LouisSimpson Bay

STL - SXM

STLSXM

Lambert-St Louis

Sun 7/6

6:00 am-2:43 pm

1 stop7h 43m

Simpson Bay Princess Juliana

Sun 7/13

1:35 pm-11:43 pm

1 stop11h 08m

$1,055

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/22

Showing 1-10 of 20 results
1
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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 March is currently the most expensive (average of $656). 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 June 23, 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 June 23, 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
7,966 reviews

Comfort

7.9

Crew

8.5

Boarding

8.2

Overall

8.0

Entertainment

7.9

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Delta
8.0
Very good
7,966 reviews
Delta
8.0
Very good
7,966 reviews

Comfort

7.9

Crew

8.5

Boarding

8.2

Overall

8.0

Entertainment

7.9

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Copa Airlines
7.5
Good
1,460 reviews
Delta
8.0
Very good
7,966 reviews

Comfort

7.9

Crew

8.5

Boarding

8.2

Overall

8.0

Entertainment

7.9

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
United Airlines
7.4
Good
8,831 reviews
Delta
8.0
Very good
7,966 reviews

Comfort

7.9

Crew

8.5

Boarding

8.2

Overall

8.0

Entertainment

7.9

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,966 reviews

Comfort

7.9

Crew

8.5

Boarding

8.2

Overall

8.0

Entertainment

7.9

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
WestJet
7.2
Good
2,887 reviews
Delta
8.0
Very good
7,966 reviews

Comfort

7.9

Crew

8.5

Boarding

8.2

Overall

8.0

Entertainment

7.9

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

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 $164. However, be on the lookout for offers from Frontier and Delta, 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 $607. While the most popular route (Chicago O'Hare Intl - Simpson Bay Princess Juliana) can be booked for $372 on average our data indicates $752 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 March is currently the most expensive (average of $656). 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

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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 June 23, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$330Average$400FlexibilityNo cancel feeOn-time65%
DeltaCheapest$425Average$686FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$579Average$740FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$654Average$897FlexibilityNo cancel feeOn-time69%

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