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Simpson Bay

$91+ 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
dic. 26 — ene. 21
vie. 12/26
vie. 1/2
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 noviembre 26, 2025.

This Super.com deal was found by Cheapflights users on 11/24. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 12/155:00 amORD - SXM
1 stop7h 15mSpirit Airlines
lun. 12/223:20 pmSXM - ORD
1 stop11h 10mSpirit Airlines
Deal found 11/24$273
This Kiwi.com deal was found by Cheapflights users on 11/26. 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.
dom. 12/143:20 pmORD - SXM
1 stop20h 55mMultiple Airlines
sáb. 12/203:20 pmSXM - ORD
1 stop11h 10mMultiple Airlines
Deal found 11/26$303
This Super.com deal was found by Cheapflights users on 11/24. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 12/85:00 amORD - SXM
1 stop7h 15mSpirit Airlines
vie. 12/123:20 pmSXM - ORD
1 stop10h 49mSpirit Airlines
Deal found 11/24$312
This Mytrip deal was found by Cheapflights users on 11/26. 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.
dom. 12/141:52 pmORD - SXM
2 stops22h 23mSpirit Airlines
sáb. 12/203:20 pmSXM - ORD
1 stop11h 10mSpirit Airlines
Deal found 11/26$330
This Priceline deal was found by Cheapflights users on 11/23. 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.
mié. 12/105:00 amORD - SXM
1 stop7h 15mMultiple Airlines
mar. 12/163:40 pmSXM - ORD
1 stop25h 15mMultiple Airlines
Deal found 11/23$338
This Kiwi.com deal was found by Cheapflights users on 11/24. 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.
dom. 12/73:20 pmORD - SXM
1 stop20h 55mMultiple Airlines
sáb. 12/133:20 pmSXM - ORD
1 stop10h 49mMultiple Airlines
Deal found 11/24$339
This Kiwi.com deal was found by Cheapflights users on 11/25. 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.
jue. 12/186:00 amORD - SXM
2 stops30h 15mMultiple Airlines
lun. 12/223:20 pmSXM - ORD
1 stop11h 10mMultiple Airlines
Deal found 11/25$343
This Mytrip deal was found by Cheapflights users on 11/24. 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.
dom. 12/712:09 pmORD - SXM
3 stops24h 06mSpirit Airlines
sáb. 12/133:20 pmSXM - ORD
1 stop10h 49mSpirit Airlines
Deal found 11/24$357
This Priceline deal was found by Cheapflights users on 11/24. 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.
lun. 12/85:00 amORD - SXM
1 stop7h 15mMultiple Airlines
vie. 12/125:00 pmSXM - ORD
2 stops20h 18mMultiple Airlines
Deal found 11/24$361
This Air Canada deal was found by Cheapflights users on 11/25. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 12/154:05 pmSTL - SXM
1 stop21h 55mAir Canada
mié. 12/245:00 pmSXM - STL
1 stop24h 29mAir Canada
Deal found 11/25$371
This Kiwi.com deal was found by Cheapflights users on 11/25. 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.
lun. 12/153:30 pmSTL - SXM
2 stops44h 45mMultiple Airlines
mié. 12/243:20 pmSXM - STL
1 stop21h 36mMultiple Airlines
Deal found 11/25$374
This Air Canada deal was found by Cheapflights users on 11/25. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 12/154:05 pmSTL - SXM
1 stop21h 55mAir Canada
jue. 12/253:40 pmSXM - STL
2 stops25h 49mAir Canada
Deal found 11/25$381

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 noviembre 26, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$257
(Super.com)

One-way from

$91
(Super.com)

Popular in

April

Cheapest in

August

Average price

$706

Good round-trip deal

$420 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. 5% potential increase in price ($39 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($8 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 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 noviembre 26, 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

MDW - SXM

MDWSXM

Chicago Midway

sáb. 2/21

6:00 am-3:20 pm

1 stop7h 20m

Simpson Bay Princess Juliana

sáb. 2/28

4:30 pm-11:25 pm

1 stop8h 55m

$287

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

dom. 1/25

8:22 pm-2:14 pm

1 stop15h 52m

Simpson Bay Princess Juliana

jue. 1/29

3:09 pm-11:46 pm

1 stop10h 37m

$299

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

sáb. 2/7

1:55 pm-2:40 pm

2 stops22h 45m

Simpson Bay Princess Juliana

sáb. 2/14

4:30 pm-11:35 pm

1 stop9h 05m

$347

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

dom. 1/25

6:00 am-2:55 pm

1 stop6h 55m

Simpson Bay Princess Juliana

jue. 1/29

1:55 pm-10:22 pm

1 stop10h 27m

$355

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

sáb. 1/24

10:07 am-2:14 pm

2 stops26h 07m

Simpson Bay Princess Juliana

sáb. 1/31

3:09 pm-11:46 pm

1 stop10h 37m

$358

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

dom. 1/25

1:58 pm-2:55 pm

2 stops22h 57m

Simpson Bay Princess Juliana

jue. 1/29

4:20 pm-9:49 am

1 stop19h 29m

$360

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

dom. 12/7

1:52 pm-2:15 pm

2 stops22h 23m

Simpson Bay Princess Juliana

sáb. 12/13

3:20 pm-12:09 am

1 stop10h 49m

$363

St. LouisSimpson Bay

STL - SXM

STLSXM

Lambert-St Louis

lun. 12/15

4:05 pm-4:00 pm

1 stop21h 55m

Simpson Bay Princess Juliana

mié. 12/24

5:00 pm-3:29 pm

1 stop24h 29m

$371

St. LouisSimpson Bay

STL - SXM

STLSXM

Lambert-St Louis

lun. 12/15

4:05 pm-4:00 pm

1 stop21h 55m

Simpson Bay Princess Juliana

mié. 12/24

3:20 pm-10:56 am

1 stop21h 36m

$371

St. LouisSimpson Bay

STL - SXM

STLSXM

Lambert-St Louis

lun. 12/15

4:05 pm-4:00 pm

1 stop21h 55m

Simpson Bay Princess Juliana

jue. 12/25

3:40 pm-3:29 pm

2 stops25h 49m

$381

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/25

Showing 1-10 of 44 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 noviembre 26, 2025.

It’s optimal to fly from Illinois to Simpson Bay at noon. By choosing this option you can save up to 27% on the cost of your flight, compared to a flight in the afternoon.

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?

    Frontier, Spirit Airlines, and Delta can get you from Illinois to Simpson Bay in just under 6h 55m. Your travel time can differ by up to 8h 57m. Airlines will cover a distance of 2189 mi. This flight may include one or multiple stops.

  • 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 $366. While the most popular route (Chicago O'Hare Intl - Simpson Bay Princess Juliana) can be booked for $259 on average, our data indicates $617 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

See prices for flight routes from nearby airports that may be better suited for you.
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Top 5 airlines flying from Illinois to Simpson Bay

Discover the top 5 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 noviembre 26, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$315Average$399FlexibilityNo cancel feeOn-time65%
DeltaCheapest$318Average$705FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$420Average$878FlexibilityNo cancel feeOn-time69%
JetBlueCheapest$535Average$711FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$550Average$702FlexibilityNo cancel feeOn-time71%

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