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Simpson Bay

$142+ 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 1/10. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — SXM
Nov 13 — Nov 201
Thu 11/13
Thu 11/20
1 adult, Economy
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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 October 14, 2025.

This Frontier deal was found by Cheapflights users on 10/13. 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.
Sat 12/65:10 amORD - SXM
1 stop8h 10mFrontier
Sat 12/134:30 pmSXM - ORD
1 stop9h 38mFrontier
Deal found 10/13$365
This Cheapflightsfares deal was found by Cheapflights users on 10/12. 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 11/85:10 amORD - SXM
1 stop7h 05mSpirit Airlines
Fri 11/143:20 pmSXM - ORD
1 stop11h 07mSpirit Airlines
Deal found 10/12$370
This Kiwi.com deal was found by Cheapflights users on 10/12. 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 12/93:21 pmORD - SXM
1 stop20h 49mSpirit Airlines
Wed 12/173:15 pmSXM - ORD
1 stop10h 19mSpirit Airlines
Deal found 10/12$374
This Delta deal was found by Cheapflights users on 10/13. 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 11/246:00 amMDW - SXM
1 stop6h 55mDelta
Thu 11/274:20 pmSXM - MDW
1 stop9h 20mDelta
Deal found 10/13$375
This Delta deal was found by Cheapflights users on 10/13. 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 12/77:53 pmORD - SXM
1 stop16h 35mDelta
Wed 12/173:53 pmSXM - ORD
1 stop8h 50mDelta
Deal found 10/13$375
This Delta deal was found by Cheapflights users on 10/13. 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 11/236:48 pmMDW - SXM
2 stops18h 07mDelta
Tue 11/254:20 pmSXM - MDW
2 stops27h 48mDelta
Deal found 10/13$380
This Delta deal was found by Cheapflights users on 10/13. 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 12/77:53 pmORD - SXM
1 stop16h 35mDelta
Thu 12/184:15 pmSXM - ORD
2 stops26h 33mDelta
Deal found 10/13$380
This American Airlines deal was found by Cheapflights users on 10/12. 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 12/137:07 pmORD - SXM
1 stop19h 18mAmerican Airlines
Fri 12/191:39 pmSXM - ORD
1 stop13h 54mAmerican Airlines
Deal found 10/12$385
This Kiwi.com deal was found by Cheapflights users on 10/12. 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 12/107:41 pmORD - SXM
2 stops37h 47mMultiple Airlines
Wed 12/173:15 pmSXM - ORD
1 stop10h 19mMultiple Airlines
Deal found 10/12$388
This Kiwi.com deal was found by Cheapflights users on 10/12. 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 12/97:00 amORD - SXM
2 stops26h 28mMultiple Airlines
Wed 12/173:15 pmSXM - ORD
1 stop10h 19mMultiple Airlines
Deal found 10/12$389
This American Airlines deal was found by Cheapflights users on 10/13. 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 12/66:39 pmORD - SXM
1 stop17h 19mAmerican Airlines
Sat 12/203:04 pmSXM - ORD
Nonstop5h 54mAmerican Airlines
Deal found 10/13$390
This Kiwi.com deal was found by Cheapflights users on 10/12. 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.
Sun 11/910:52 amORD - SXM
1 stop25h 23mSpirit Airlines
Fri 11/143:20 pmSXM - ORD
1 stop21h 52mSpirit Airlines
Deal found 10/12$392

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 October 14, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$317
(Copa Airlines)

One-way from

$142
(Priceline)

Popular in

December

Cheapest in

August

Average price

$762

Good round-trip deal

$584 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 Illinois to Simpson Bay Princess Juliana
Search Deals
One-way flight from Illinois to Simpson Bay Princess Juliana
Search Deals
Highest demand for flights based on searches. 7% potential increase in price ($59 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($23 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
Search Deals
Price to beat on a round-trip flight from Illinois to Simpson Bay Princess Juliana.
Search Deals

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 October 14, 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 2/23

6:10 pm-12:15 pm

1 stop16h 05m

Simpson Bay Princess Juliana

Fri 2/27

4:26 pm-10:09 am

1 stop19h 43m

$329

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sun 1/25

6:05 am-3:51 pm

1 stop7h 46m

Simpson Bay Princess Juliana

Thu 1/29

2:52 pm-10:59 pm

1 stop10h 07m

$329

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sun 2/22

5:50 am-2:56 pm

1 stop7h 06m

Simpson Bay Princess Juliana

Thu 2/26

4:26 pm-10:09 am

1 stop19h 43m

$329

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Mon 1/12

3:50 pm-12:15 pm

2 stops18h 25m

Simpson Bay Princess Juliana

Fri 1/16

4:26 pm-12:41 pm

2 stops22h 15m

$334

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sun 2/22

6:10 pm-12:15 pm

1 stop16h 05m

Simpson Bay Princess Juliana

Fri 2/27

4:26 pm-1:23 pm

2 stops22h 57m

$334

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sat 1/24

2:13 pm-11:24 am

1 stop19h 11m

Simpson Bay Princess Juliana

Mon 2/2

12:25 pm-12:04 am

1 stop13h 39m

$347

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Fri 1/9

6:10 pm-12:15 pm

1 stop16h 05m

Simpson Bay Princess Juliana

Thu 1/15

4:26 pm-10:09 am

1 stop19h 43m

$354

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Mon 12/8

6:00 am-2:28 pm

1 stop6h 28m

Simpson Bay Princess Juliana

Thu 12/18

1:45 pm-11:49 pm

1 stop12h 04m

$375

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Tue 11/25

6:00 am-2:55 pm

1 stop6h 55m

Simpson Bay Princess Juliana

Thu 11/27

4:20 pm-11:40 pm

1 stop9h 20m

$375

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Tue 12/9

6:00 am-2:28 pm

1 stop6h 28m

Simpson Bay Princess Juliana

Wed 12/17

3:53 pm-11:49 pm

1 stop9h 56m

$375

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/14

Showing 1-10 of 50 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 $312). Flying from Illinois 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 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 October 14, 2025.

It’s optimal to fly from Illinois to Simpson Bay at noon. By choosing this option you can save up to 25% on the cost of your flight, compared to a flight in the evening.

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

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.

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

    Delta, United Airlines, and Air Canada can get you from Illinois to Simpson Bay in just under 7h 46m. Your travel time can differ by up to 36h 49m. Airlines will cover a distance of 2204 mi. This flight may include one or multiple stops.

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

    The cheapest airline one-way is Frontier, with whom users have recently found tickets for as low as $142. However, be on the lookout for offers from Spirit Airlines and Air Canada, 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 $480. While the most popular route (Chicago O'Hare Intl - Simpson Bay Princess Juliana) can be booked for $329 on average, our data indicates $713 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 $312). Flying from Illinois 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 Illinois to Simpson Bay

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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 October 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$316Average$399FlexibilityNo cancel feeOn-time65%
DeltaCheapest$318Average$721FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$597Average$929FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$618Average$713FlexibilityNo cancel feeOn-time71%

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