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Simpson Bay

$154+ 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 6/21. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — SXM
May 6 — May 131
Tue 5/6
Tue 5/13
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 May 1, 2025.

Most accurate provider

AranGrant
3 stars

Most trusted provider

AranGrant
3 stars

Round-trip from

$333
(Cheapflightsfares)

One-way from

$154
(Cheapflightsfares)

Popular in

March

Cheapest in

September

Average price

$714

Good round-trip deal

$1,125 or less

Good one-way deal

$560 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. 4% potential increase in price ($31 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($10 potential savings vs. average RT price).
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Average for round-trip flights in May 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 May 1, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 4/30. 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.
Mon 6/25:05 amORD - SXM
1 stop7h 55mSpirit Airlines
Mon 6/93:05 pmSXM - ORD
1 stop18h 45mSpirit Airlines
Deal found 4/30$333
This FlightHub deal was found by Cheapflights users on 5/1. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/65:08 pmORD - SXM
1 stop17h 15mMultiple Airlines
Sat 6/143:05 pmSXM - ORD
1 stop9h 40mMultiple Airlines
Deal found 5/1$369
This Frontier deal was found by Cheapflights users on 4/30. 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 4/30$411
This CheapOair deal was found by Cheapflights users on 5/1. 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.
Sat 8/25:01 amORD - SXM
2 stops11h 15mFrontier
Sat 8/96:26 pmSXM - ORD
2 stops30h 18mFrontier
Deal found 5/1$413
This Mytrip deal was found by Cheapflights users on 5/1. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/110:10 amSTL - SXM
1 stop26h 50mSpirit Airlines
Sat 6/73:05 pmSXM - STL
1 stop19h 10mSpirit Airlines
Deal found 5/1$465
This Mytrip deal was found by Cheapflights users on 5/1. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/15:15 pmSTL - SXM
3 stops19h 45mMultiple Airlines
Sat 6/73:05 pmSXM - STL
1 stop19h 10mMultiple Airlines
Deal found 5/1$515
This Delta deal was found by Cheapflights users on 5/1. 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.
Wed 11/266:00 amSTL - SXM
1 stop6h 35mDelta
Wed 12/34:00 pmSXM - STL
1 stop9h 39mDelta
Deal found 5/1$573
This American Airlines deal was found by Cheapflights users on 4/30. 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.
Thu 6/124:37 pmSTL - SXM
2 stops19h 57mAmerican Airlines
Thu 6/194:05 pmSXM - STL
2 stops18h 13mAmerican Airlines
Deal found 4/30$610
This American Airlines deal was found by Cheapflights users on 4/30. 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 6/106:00 amORD - SXM
1 stop8h 05mAmerican Airlines
Tue 6/172:20 pmSXM - ORD
1 stop10h 37mAmerican Airlines
Deal found 4/30$622
This JetBlue deal was found by Cheapflights users on 5/1. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/166:00 amORD - SXM
1 stop7h 41mJetBlue
Sat 8/2312:15 pmSXM - ORD
1 stop12h 10mJetBlue
Deal found 5/1$635
This Orbitz deal was found by Cheapflights users on 4/30. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/148:25 pmORD - SXM
1 stop17h 50mAir Canada
Sun 11/234:55 pmSXM - ORD
2 stops19h 00mAir Canada
Deal found 4/30$641
This United Airlines deal was found by Cheapflights users on 5/1. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/88:45 amORD - SXM
Nonstop5h 07mUnited Airlines
Sat 11/224:55 pmSXM - ORD
1 stop8h 17mUnited Airlines
Deal found 5/1$705

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 May 1, 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

Mon 6/2

5:05 am-2:00 pm

1 stop7h 55m

Simpson Bay Princess Juliana

Mon 6/9

3:05 pm-8:50 am

1 stop18h 45m

$333

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Fri 6/6

5:08 pm-11:23 am

1 stop17h 15m

Simpson Bay Princess Juliana

Sat 6/14

3:05 pm-11:45 pm

1 stop9h 40m

$369

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

$411

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sat 6/7

5:01 am-5:04 pm

2 stops11h 03m

Simpson Bay Princess Juliana

Sat 6/14

12:36 pm-7:09 am

1 stop19h 33m

$429

St. LouisSimpson Bay

STL - SXM

STLSXM

Lambert-St Louis

Sun 6/1

10:10 am-2:00 pm

1 stop26h 50m

Simpson Bay Princess Juliana

Sat 6/7

3:05 pm-9:15 am

1 stop19h 10m

$465

St. LouisSimpson Bay

STL - SXM

STLSXM

Lambert-St Louis

Sun 6/1

5:15 pm-2:00 pm

3 stops19h 45m

Simpson Bay Princess Juliana

Sat 6/7

3:05 pm-9:15 am

1 stop19h 10m

$515

St. LouisSimpson Bay

STL - SXM

STLSXM

Lambert-St Louis

Thu 6/12

4:37 pm-1:34 pm

2 stops19h 57m

Simpson Bay Princess Juliana

Thu 6/19

4:05 pm-9:18 am

2 stops18h 13m

$610

St. LouisSimpson Bay

STL - SXM

STLSXM

Lambert-St Louis

Fri 6/6

6:00 am-1:54 pm

1 stop6h 54m

Simpson Bay Princess Juliana

Thu 6/12

3:25 pm-11:51 pm

1 stop9h 26m

$612

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Tue 6/10

6:00 am-3:05 pm

1 stop8h 05m

Simpson Bay Princess Juliana

Tue 6/17

2:20 pm-11:57 pm

1 stop10h 37m

$622

St. LouisSimpson Bay

STL - SXM

STLSXM

Lambert-St Louis

Sat 6/14

1:00 pm-12:29 pm

1 stop22h 29m

Simpson Bay Princess Juliana

Wed 6/18

3:55 pm-3:30 pm

2 stops24h 35m

$711

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/1

Showing 1-10 of 16 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 July is currently the most expensive (average of $669). 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 May 1, 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 May 1, 2025.
Read reviews from past customers who have flown Delta, United Airlines and American 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
7,934 reviews

Crew

8.5

Overall

8.0

Food

7.3

Boarding

8.2

Entertainment

7.9

Comfort

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
7,934 reviews
Delta
8.0
Very good
7,934 reviews

Crew

8.5

Overall

8.0

Food

7.3

Boarding

8.2

Entertainment

7.9

Comfort

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
8,696 reviews
Delta
8.0
Very good
7,934 reviews

Crew

8.5

Overall

8.0

Food

7.3

Boarding

8.2

Entertainment

7.9

Comfort

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
7,934 reviews

Crew

8.5

Overall

8.0

Food

7.3

Boarding

8.2

Entertainment

7.9

Comfort

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.
Spirit Airlines
6.3
Okay
7,963 reviews
Delta
8.0
Very good
7,934 reviews

Crew

8.5

Overall

8.0

Food

7.3

Boarding

8.2

Entertainment

7.9

Comfort

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.
Frontier
6.0
Okay
3,287 reviews
Delta
8.0
Very good
7,934 reviews

Crew

8.5

Overall

8.0

Food

7.3

Boarding

8.2

Entertainment

7.9

Comfort

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 $154. However, be on the lookout for offers from Frontier 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 $328. While the most popular route (Chicago O'Hare Intl - Simpson Bay Princess Juliana) can be booked for $333 on average our data indicates $879 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 $669). 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 May 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$325Average$400FlexibilityNo cancel feeOn-time65%
DeltaCheapest$494Average$725FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$579Average$729FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$647Average$896FlexibilityNo cancel feeOn-time69%

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