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$143+ 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 2/5. Fares are subject to change and may not be available on all flights or dates of travel.
SXM — ORD
Feb 28 — Mar 71
Sat 2/28
Sat 3/7
1 adult, Economy
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Cheap 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 January 29, 2026.

This Cheapflightsfares deal was found by Cheapflights users on 1/27. 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 2/143:20 pm
SXM
-
ORD
1 stop10h 27m
Spirit Airlines
Sat 2/215:15 am
ORD
-
SXM
1 stop7h 00m
Spirit Airlines
Deal found 1/27$266
This Expedia deal was found by Cheapflights users on 1/28. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/73:20 pm
SXM
-
ORD
1 stop10h 27m
Multiple Airlines
Thu 2/196:04 pm
ORD
-
SXM
2 stops19h 56m
Multiple Airlines
Deal found 1/28$309
This Cheapflightsfares deal was found by Cheapflights users on 1/28. 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.
Thu 5/72:11 pm
SXM
-
ORD
1 stop10h 30m
Spirit Airlines
Mon 5/115:15 am
ORD
-
SXM
1 stop7h 01m
Spirit Airlines
Deal found 1/28$339
This Spirit deal was found by Cheapflights users on 1/29. 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 Spirit is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/162:11 pm
SXM
-
ORD
1 stop10h 30m
Spirit Airlines
Tue 4/215:15 am
ORD
-
SXM
1 stop7h 01m
Spirit Airlines
Deal found 1/29$340
This Kiwi.com deal was found by Cheapflights users on 1/28. 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 2/23:20 pm
SXM
-
ORD
1 stop31h 43m
Multiple Airlines
Thu 2/193:40 pm
ORD
-
SXM
1 stop20h 35m
Multiple Airlines
Deal found 1/28$341
This Cheapflightsfares deal was found by Cheapflights users on 1/27. 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.
Thu 5/72:11 pm
SXM
-
ORD
1 stop10h 30m
Spirit Airlines
Sun 5/105:15 am
ORD
-
SXM
1 stop7h 01m
Spirit Airlines
Deal found 1/27$350
This Kiwi.com deal was found by Cheapflights users on 1/29. 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.
Wed 4/152:11 pm
SXM
-
ORD
1 stop10h 30m
Spirit Airlines
Tue 4/215:15 am
ORD
-
SXM
1 stop7h 01m
Spirit Airlines
Deal found 1/29$379
This Kiwi.com deal was found by Cheapflights users on 1/28. 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 5/712:25 pm
SXM
-
ORD
2 stops12h 34m
Multiple Airlines
Mon 5/115:15 am
ORD
-
SXM
1 stop7h 01m
Multiple Airlines
Deal found 1/28$384
This Delta deal was found by Cheapflights users on 1/29. 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.
Wed 4/151:35 pm
SXM
-
MDW
1 stop9h 53m
Delta
Mon 4/206:00 am
MDW
-
SXM
1 stop7h 05m
Delta
Deal found 1/29$562
This Delta deal was found by Cheapflights users on 1/29. 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.
Wed 4/151:35 pm
SXM
-
MDW
1 stop9h 53m
Delta
Sun 4/196:00 am
MDW
-
SXM
1 stop7h 05m
Delta
Deal found 1/29$571
This Delta deal was found by Cheapflights users on 1/27. 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 2/145:25 pm
SXM
-
MDW
2 stops17h 29m
Delta
Sat 2/216:00 am
MDW
-
SXM
1 stop8h 00m
Delta
Deal found 1/27$578
This Delta deal was found by Cheapflights users on 1/29. 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.
Sat 4/181:35 pm
SXM
-
MDW
1 stop9h 53m
Delta
Mon 4/206:00 am
MDW
-
SXM
1 stop7h 05m
Delta
Deal found 1/29$601

Find 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 January 29, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$266
(Cheapflightsfares)

One-way from

$143
(Super.com)

Good one-way deal

$582 or less
Provider with most accurate pricing for Simpson Bay Princess Juliana-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Simpson Bay Princess Juliana-Chicago (CHI) flights.
Search Deals
From Simpson Bay Princess Juliana to Illinois
Search Deals
One-way flight from Simpson Bay Princess Juliana to Illinois
Search Deals
Price to beat on a one-way flight from Simpson Bay Princess Juliana to Illinois.
Search Deals

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 January 29, 2026.
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 2/14

3:20 pm-11:47 pm

1 stop10h 27m

Chicago O'Hare Intl

Sat 2/21

5:15 am-2:15 pm

1 stop7h 00m

$266

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Thu 4/16

2:11 pm-11:41 pm

1 stop10h 30m

Chicago O'Hare Intl

Tue 4/21

5:15 am-1:16 pm

1 stop7h 01m

$340

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Thu 5/7

2:11 pm-11:41 pm

1 stop10h 30m

Chicago O'Hare Intl

Sun 5/10

5:15 am-1:16 pm

1 stop7h 01m

$350

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Thu 5/7

12:25 pm-11:59 pm

2 stops12h 34m

Chicago O'Hare Intl

Mon 5/11

5:15 am-1:16 pm

1 stop7h 01m

$384

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Thu 5/7

2:11 pm-11:41 pm

1 stop10h 30m

Chicago O'Hare Intl

Mon 5/11

5:32 pm-1:16 pm

1 stop18h 44m

$396

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sat 2/14

2:28 pm-11:21 pm

1 stop10h 53m

Chicago O'Hare Intl

Sat 2/21

12:50 pm-2:40 pm

1 stop23h 50m

$417

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Fri 3/13

4:00 pm-11:18 am

2 stops20h 18m

Chicago O'Hare Intl

Sat 3/21

8:40 pm-1:40 pm

2 stops16h 00m

$418

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sat 3/14

2:14 pm-11:17 pm

1 stop10h 03m

Chicago O'Hare Intl

Sat 3/21

6:16 pm-1:08 pm

2 stops17h 52m

$429

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Mon 4/13

4:00 pm-5:45 pm

1 stop26h 45m

Chicago O'Hare Intl

Sun 4/19

4:15 pm-2:50 pm

1 stop21h 35m

$455

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Thu 4/16

1:35 pm-10:28 pm

1 stop9h 53m

Chicago Midway

Tue 4/21

6:00 am-2:05 pm

1 stop7h 05m

$562

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/27

Showing 1-10 of 38 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 January 29, 2026.

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 Spirit Airlines and Delta fly from Simpson Bay to Illinois in about 9h 53m. The time it takes to get you to your destination can typically vary by up to 34m. 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 flights from Simpson Bay to Illinois?

    While on average a flight from Simpson Bay to Illinois is generally $592, our data shows the cheapest flight currently is $360. When looking at the most popular route, (Simpson Bay Princess Juliana - Chicago O'Hare Intl), you can expect to pay $266 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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Alternative routes for Simpson Bay to Illinois

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