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$185+ 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 12/13. Fares are subject to change and may not be available on all flights or dates of travel.
SXM — ORD
Nov 29 — Dec 61
Sat 11/29
Sat 12/6
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 October 30, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$368
(American Airlines)

One-way from

$185
(Cheapflightsfares)

Good one-way deal

$444 or less
Provider with most accurate pricing for Simpson Bay Princess Juliana-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Simpson Bay Princess Juliana-Chicago (CHI) flights.
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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 October 30, 2025.

This American Airlines deal was found by Cheapflights users on 10/29. 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 11/225:05 pmSXM - ORD
1 stop8h 35mAmerican Airlines
Sat 11/295:00 amORD - SXM
1 stop9h 22mAmerican Airlines
Deal found 10/29$368
This Kiwi.com deal was found by Cheapflights users on 10/29. 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.
Mon 12/13:20 pmSXM - ORD
2 stops25h 52mMultiple Airlines
Sun 12/73:20 pmORD - SXM
1 stop20h 55mMultiple Airlines
Deal found 10/29$371
This Mytrip deal was found by Cheapflights users on 10/30. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/223:20 pmSXM - ORD
2 stops19h 41mSpirit Airlines
Sat 11/295:00 amORD - SXM
1 stop7h 15mSpirit Airlines
Deal found 10/30$398
This Kissandfly.com deal was found by Cheapflights users on 10/29. 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.
Sat 11/222:40 pmSXM - ORD
Nonstop6h 00mLufthansa
Sat 11/298:45 amORD - SXM
Nonstop5h 12mLufthansa
Deal found 10/29$410
This Mytrip deal was found by Cheapflights users on 10/29. 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.
Mon 12/153:20 pmSXM - ORD
3 stops30h 49mSpirit Airlines
Mon 12/225:00 amORD - SXM
1 stop7h 15mSpirit Airlines
Deal found 10/29$442
This Delta deal was found by Cheapflights users on 10/30. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/224:30 pmSXM - ORD
1 stop19h 25mDelta
Sat 11/298:02 pmORD - SXM
1 stop16h 53mDelta
Deal found 10/30$454
This Mytrip deal was found by Cheapflights users on 10/29. 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.
Mon 12/13:20 pmSXM - ORD
3 stops23h 36mSpirit Airlines
Sun 12/74:38 pmORD - SXM
2 stops19h 37mSpirit Airlines
Deal found 10/29$461
This Kiwi.com deal was found by Cheapflights users on 10/29. 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.
Mon 12/14:20 pmSXM - MDW
1 stop19h 45mMultiple Airlines
Sun 12/76:37 pmMDW - SXM
2 stops17h 38mMultiple Airlines
Deal found 10/29$603
This Delta deal was found by Cheapflights users on 10/30. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/113:53 pmSXM - MDW
1 stop9h 54mDelta
Thu 12/186:00 amMDW - SXM
1 stop6h 50mDelta
Deal found 10/30$627
This Kiwi.com deal was found by Cheapflights users on 10/29. 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.
Mon 12/154:20 pmSXM - MDW
1 stop19h 45mMultiple Airlines
Mon 12/228:15 amMDW - SXM
2 stops52h 00mMultiple Airlines
Deal found 10/29$659
This Kiwi.com deal was found by Cheapflights users on 10/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/114:20 pmSXM - MDW
1 stop19h 45mMultiple Airlines
Thu 12/186:12 amMDW - SXM
2 stops30h 03mMultiple Airlines
Deal found 10/30$660
This Delta deal was found by Cheapflights users on 10/29. 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 12/14:20 pmSXM - MDW
1 stop19h 34mDelta
Sun 12/76:00 amMDW - SXM
1 stop6h 28mDelta
Deal found 10/29$727

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 October 30, 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 11/22

5:05 pm-11:40 pm

1 stop8h 35m

Chicago O'Hare Intl

Sat 11/29

5:00 am-4:22 pm

1 stop9h 22m

$368

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sat 1/17

4:30 pm-10:58 am

1 stop20h 28m

Chicago O'Hare Intl

Sat 1/24

5:05 am-3:10 pm

1 stop8h 05m

$381

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Mon 12/1

3:20 pm-9:17 am

1 stop19h 57m

Chicago O'Hare Intl

Sun 12/7

3:20 pm-2:15 pm

1 stop20h 55m

$390

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sat 1/17

2:03 pm-11:27 pm

2 stops11h 24m

Chicago O'Hare Intl

Sat 1/24

9:10 pm-1:45 pm

2 stops14h 35m

$396

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sat 11/22

2:40 pm-6:40 pm

Nonstop6h 00m

Chicago O'Hare Intl

Sat 11/29

8:45 am-3:57 pm

Nonstop5h 12m

$410

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sat 11/22

3:20 pm-9:01 am

2 stops19h 41m

Chicago O'Hare Intl

Sat 11/29

5:00 am-2:15 pm

1 stop7h 15m

$418

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Mon 12/15

3:20 pm-8:09 pm

3 stops30h 49m

Chicago O'Hare Intl

Mon 12/22

5:00 am-2:15 pm

1 stop7h 15m

$442

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sat 11/22

4:30 pm-9:55 am

1 stop19h 25m

Chicago O'Hare Intl

Sat 11/29

8:02 pm-2:55 pm

1 stop16h 53m

$454

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Mon 12/15

5:00 pm-9:13 am

1 stop18h 13m

Chicago O'Hare Intl

Mon 12/22

5:00 am-2:15 pm

1 stop7h 15m

$454

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Mon 12/1

3:20 pm-12:56 pm

3 stops23h 36m

Chicago O'Hare Intl

Sun 12/7

4:38 pm-2:15 pm

2 stops19h 37m

$461

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/29

Showing 1-10 of 36 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

What is the cheapest time of day to fly from SXM to IL?

Find hourly flight availability from Simpson Bay to Illinois. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated October 30, 2025.

When flying from Simpson Bay to Illinois, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

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 American Airlines and Delta fly from Simpson Bay to Illinois in about 8h 35m. The time it takes to get you to your destination can typically vary by up to 16h 24m. Simpson Bay and Illinois are separated by a distance of 2204 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

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

    While on average a flight from Simpson Bay to Illinois is generally $559, our data shows the cheapest flight currently is $423. When looking at the most popular route, (Simpson Bay Princess Juliana - Chicago O'Hare Intl), you can expect to pay $370 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.

See more FAQs

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