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$195+ Cheap flights from Simpson Bay (SXM) to Illinois

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 11/14. Fares are subject to change and may not be available on all flights or dates of travel.
SXM — ORD
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
1 adult, Economy
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Cheap flight deals from Simpson Bay to Illinois

Keep the following information in mind while searching for Simpson Bay to Illinois flight deals. Data was last updated September 11, 2025.

Round-trip from

$347
(Priceline)

One-way from

$195
(Cheapflightsfares)

Good one-way deal

$399 or less
From Simpson Bay Princess Juliana to Illinois
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One-way flight from Simpson Bay Princess Juliana to Illinois
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Price to beat on a one-way flight from Simpson Bay Princess Juliana to Illinois.
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Find flight deals from Simpson Bay to Illinois

Cheapest flights from Simpson Bay to Illinois
Explore the most affordable flight options available from Simpson Bay to Illinois. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 11, 2025.

This Mytrip deal was found by Cheapflights users on 9/9. 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 10/313:05 pmSXM - ORD
1 stop10h 58mSpirit Airlines
Sat 11/15:05 amORD - SXM
1 stop7h 55mSpirit Airlines
Deal found 9/9$333
This Booking.com deal was found by Cheapflights users on 9/9. 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 10/313:05 pmSXM - ORD
1 stop10h 58mSpirit Airlines
Sun 11/27:43 pmORD - SXM
1 stop17h 16mSpirit Airlines
Deal found 9/9$335
This Priceline deal was found by Cheapflights users on 9/10. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/253:05 pmSXM - ORD
1 stop9h 40mSpirit Airlines
Sat 11/15:05 amORD - SXM
1 stop7h 55mSpirit Airlines
Deal found 9/10$347
This Booking.com deal was found by Cheapflights users on 9/9. 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 10/313:05 pmSXM - ORD
1 stop10h 58mSpirit Airlines
Mon 11/35:05 amORD - SXM
1 stop7h 54mSpirit Airlines
Deal found 9/9$355
This Kiwi.com deal was found by Cheapflights users on 9/9. 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.
Sat 11/13:05 pmSXM - ORD
1 stop10h 58mSpirit Airlines
Sun 11/27:43 pmORD - SXM
1 stop17h 16mSpirit Airlines
Deal found 9/9$383
This Booking.com deal was found by Cheapflights users on 9/9. 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 10/314:00 pmSXM - ORD
2 stops20h 18mMultiple Airlines
Sun 11/27:43 pmORD - SXM
1 stop17h 16mMultiple Airlines
Deal found 9/9$397
This Kiwi.com deal was found by Cheapflights users on 9/9. 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 10/2612:25 pmSXM - ORD
2 stops21h 57mMultiple Airlines
Sun 11/211:55 amORD - SXM
1 stop25h 04mMultiple Airlines
Deal found 9/9$398
This Booking.com deal was found by Cheapflights users on 9/9. 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 10/314:00 pmSXM - ORD
2 stops20h 18mMultiple Airlines
Mon 11/35:05 amORD - SXM
1 stop7h 54mMultiple Airlines
Deal found 9/9$416
This Kissandfly.com deal was found by Cheapflights users on 9/9. 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 Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/3012:25 pmSXM - ORD
2 stops21h 57mMultiple Airlines
Sun 11/27:43 pmORD - SXM
1 stop17h 16mMultiple Airlines
Deal found 9/9$449
This Delta deal was found by Cheapflights users on 9/9. 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.
Fri 10/313:14 pmSXM - MDW
1 stop8h 00mDelta
Mon 11/36:00 amMDW - SXM
1 stop6h 49mDelta
Deal found 9/9$598
This Delta deal was found by Cheapflights users on 9/9. 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 10/293:14 pmSXM - MDW
1 stop8h 00mDelta
Mon 11/36:00 amMDW - SXM
1 stop6h 49mDelta
Deal found 9/9$600
This Delta deal was found by Cheapflights users on 9/9. 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 10/293:14 pmSXM - MDW
1 stop8h 00mDelta
Sat 11/16:00 amMDW - SXM
1 stop6h 49mDelta
Deal found 9/9$757

Cheapflights Fare Finder

 
Customize your flight search to find flights from Simpson Bay to Illinois 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 September 11, 2025.
Use the filters below to find and compare flights from Simpson Bay to Illinois that are best for you.

Fly from

Simpson Bay

Fly to

Illinois

Route

Depart

Return

Price

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sat 10/25

3:05 pm-11:45 pm

1 stop9h 40m

Chicago O'Hare Intl

Sat 11/1

5:05 am-2:00 pm

1 stop7h 55m

$347

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sat 11/1

3:05 pm-1:03 am

1 stop10h 58m

Chicago O'Hare Intl

Sun 11/2

7:43 pm-2:59 pm

1 stop17h 16m

$383

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Fri 10/31

4:00 pm-11:18 am

2 stops20h 18m

Chicago O'Hare Intl

Sun 11/2

7:43 pm-2:59 pm

1 stop17h 16m

$397

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sun 10/26

12:25 pm-9:22 am

2 stops21h 57m

Chicago O'Hare Intl

Sun 11/2

11:55 am-2:59 pm

1 stop25h 04m

$398

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Fri 10/31

4:00 pm-11:18 am

2 stops20h 18m

Chicago O'Hare Intl

Mon 11/3

5:05 am-2:59 pm

1 stop7h 54m

$416

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Thu 10/30

12:25 pm-9:22 am

2 stops21h 57m

Chicago O'Hare Intl

Sun 11/2

7:43 pm-2:59 pm

1 stop17h 16m

$449

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Thu 10/30

1:52 pm-11:34 pm

1 stop10h 42m

Chicago O'Hare Intl

Sun 11/2

8:45 am-3:57 pm

Nonstop5h 12m

$493

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Tue 10/28

1:52 pm-11:34 pm

1 stop10h 42m

Chicago O'Hare Intl

Sun 11/2

8:45 am-3:57 pm

Nonstop5h 12m

$493

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Wed 10/29

1:52 pm-11:34 pm

1 stop10h 42m

Chicago O'Hare Intl

Sun 11/2

8:45 am-3:57 pm

Nonstop5h 12m

$493

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Wed 10/1

9:17 am-10:52 am

2 stops26h 35m

Chicago O'Hare Intl

Fri 10/3

6:44 pm-2:00 pm

1 stop18h 16m

$508

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/8

Showing 1-10 of 33 results
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Best time to book a flight from Simpson Bay to Illinois

Have a flexible travel schedule? Discover the best time to fly to Illinois from Simpson Bay 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 Simpson Bay to Illinois
No data available for this route at this time. Please check back soon.

Related info for your journey

Find useful and relevant information for your journey from Simpson Bay to Illinois. 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 from for flights from Simpson Bay to Illinois?

    Located just 0.5 mi from the city center, Simpson Bay Princess Juliana (SXM) is the airport most travelers will use when flying to Illinois from Simpson Bay.

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

    Airlines like Spirit Airlines and Delta fly from Simpson Bay to Illinois in about 8h. The time it takes to get you to your destination can typically vary by up to 1h 40m. Simpson Bay and Illinois are separated by a distance of 2189 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

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

    For one-way options, check prices for Spirit Airlines. According to our data, you can fly for as low as $195. Users have also found prices from $380 and $380 on WestJet and Delta, respectively.

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

    While on average a flight from Simpson Bay to Illinois is generally $479, our data shows the cheapest flight currently is $376. When looking at the most popular route, (Simpson Bay Princess Juliana - Chicago O'Hare Intl), you can expect to pay $347 for that flight.

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

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

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

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

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

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

    Currently, August is the cheapest month in which you can book a flight from Simpson Bay to Illinois (average of $245). Flying from Simpson Bay to Illinois in March is currently the most expensive (average of $321). 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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