HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Simpson Bay

$139+ 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 9/20. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — SXM
Aug 27 — Sep 31
Wed 8/27
Wed 9/3
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Illinois to Simpson Bay with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 August 22, 2025.

Round-trip from

$337
(Cheapflightsfares)

One-way from

$139
(Cheapflightsfares)

Popular in

December

Cheapest in

August

Average price

$637

Good round-trip deal

$797 or less

Good one-way deal

$353 or less
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. 10% potential increase in price ($81 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($24 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in August 2025
Search Deals
Price to beat on a round-trip flight from Illinois to Simpson Bay Princess Juliana.
Search Deals
Price to beat on a one-way flight from Illinois to Simpson Bay Princess Juliana.
Search Deals

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 August 22, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 8/20. 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 10/115:05 amORD - SXM
1 stop7h 54mSpirit Airlines
Sat 10/183:05 pmSXM - ORD
1 stop9h 40mSpirit Airlines
Deal found 8/20$337
This Cheapflightsfares deal was found by Cheapflights users on 8/20. 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.
Sun 10/57:29 pmORD - SXM
1 stop17h 30mSpirit Airlines
Sat 10/253:05 pmSXM - ORD
1 stop9h 40mSpirit Airlines
Deal found 8/20$350
This FlightHub deal was found by Cheapflights users on 8/21. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/115:05 amORD - SXM
1 stop7h 54mSpirit Airlines
Fri 10/173:05 pmSXM - ORD
1 stop9h 40mSpirit Airlines
Deal found 8/21$356
This Cheapflightsfares deal was found by Cheapflights users on 8/21. 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 11/85:05 amORD - SXM
1 stop8h 05mSpirit Airlines
Sat 11/154:28 pmSXM - ORD
1 stop9h 14mSpirit Airlines
Deal found 8/21$362
This Cheapflightsfares deal was found by Cheapflights users on 8/21. 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.
Fri 9/195:05 amORD - SXM
1 stop7h 55mSpirit Airlines
Fri 9/263:05 pmSXM - ORD
1 stop8h 43mSpirit Airlines
Deal found 8/21$367
This Cheapflightsfares deal was found by Cheapflights users on 8/20. 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.
Tue 11/115:59 pmORD - SXM
1 stop19h 11mSpirit Airlines
Sat 11/154:28 pmSXM - ORD
1 stop9h 14mSpirit Airlines
Deal found 8/20$369
This FlightHub deal was found by Cheapflights users on 8/20. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/167:29 pmORD - SXM
1 stop17h 30mSpirit Airlines
Mon 10/203:05 pmSXM - ORD
1 stop9h 40mSpirit Airlines
Deal found 8/20$371
This Priceline deal was found by Cheapflights users on 8/20. 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 10/45:05 amORD - SXM
1 stop7h 55mSpirit Airlines
Sat 10/113:05 pmSXM - ORD
1 stop9h 40mSpirit Airlines
Deal found 8/20$402
This Priceline deal was found by Cheapflights users on 8/21. 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.
Mon 10/65:05 amORD - SXM
1 stop7h 54mSpirit Airlines
Mon 10/133:05 pmSXM - ORD
1 stop9h 40mSpirit Airlines
Deal found 8/21$407
This Mytrip deal was found by Cheapflights users on 8/19. 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 9/205:05 amORD - SXM
1 stop7h 55mSpirit Airlines
Sat 9/273:05 pmSXM - ORD
2 stops21h 05mSpirit Airlines
Deal found 8/19$411
This Kiwi.com deal was found by Cheapflights users on 8/21. 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 11/912:20 pmSTL - SXM
1 stop24h 50mMultiple Airlines
Fri 11/144:28 pmSXM - STL
2 stops43h 44mMultiple Airlines
Deal found 8/21$465
This Delta deal was found by Cheapflights users on 8/21. 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 9/176:01 amSTL - SXM
1 stop6h 49mDelta
Sun 9/213:20 pmSXM - STL
1 stop9h 04mDelta
Deal found 8/21$497

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 August 22, 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

Sat 10/11

5:05 am-1:59 pm

1 stop7h 54m

Simpson Bay Princess Juliana

Sat 10/18

3:05 pm-11:45 pm

1 stop9h 40m

$337

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sat 9/20

5:05 am-2:00 pm

1 stop7h 55m

Simpson Bay Princess Juliana

Sat 9/27

3:05 pm-10:48 pm

1 stop8h 43m

$337

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sat 9/27

5:05 am-2:00 pm

1 stop7h 55m

Simpson Bay Princess Juliana

Sat 10/4

3:05 pm-10:48 pm

1 stop8h 43m

$337

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sat 10/18

5:05 am-1:59 pm

1 stop7h 54m

Simpson Bay Princess Juliana

Sat 10/25

3:05 pm-11:45 pm

1 stop9h 40m

$337

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sun 10/5

7:29 pm-1:59 pm

1 stop17h 30m

Simpson Bay Princess Juliana

Sat 10/25

3:05 pm-11:45 pm

1 stop9h 40m

$350

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sat 10/11

5:05 am-1:59 pm

1 stop7h 54m

Simpson Bay Princess Juliana

Fri 10/17

3:05 pm-11:45 pm

1 stop9h 40m

$356

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sat 11/8

5:05 am-3:10 pm

1 stop8h 05m

Simpson Bay Princess Juliana

Sat 11/15

4:28 pm-11:42 pm

1 stop9h 14m

$362

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Fri 9/19

5:05 am-2:00 pm

1 stop7h 55m

Simpson Bay Princess Juliana

Fri 9/26

3:05 pm-10:48 pm

1 stop8h 43m

$367

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Tue 11/11

5:59 pm-3:10 pm

1 stop19h 11m

Simpson Bay Princess Juliana

Sat 11/15

4:28 pm-11:42 pm

1 stop9h 14m

$369

St. LouisSimpson Bay

STL - SXM

STLSXM

Lambert-St Louis

Sun 11/9

12:20 pm-3:10 pm

1 stop24h 50m

Simpson Bay Princess Juliana

Fri 11/14

4:28 pm-10:12 am

2 stops43h 44m

$465

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/21

Showing 1-10 of 45 results
1
2
3
...
5

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 $459). Flying from Illinois to Simpson Bay in March is currently the most expensive (average of $654). 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 August 22, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Illinois to Simpson Bay as you normally would.

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?

    Spirit Airlines and Delta can get you from Illinois to Simpson Bay in just under 6h 45m. Your travel time can differ by up to 1h 09m. Airlines will cover a distance of 2172 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, Lambert-St Louis - Simpson Bay Princess Juliana or Chicago Midway - 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 $313. While the most popular route (Chicago O'Hare Intl - Simpson Bay Princess Juliana) can be booked for $337 on average our data indicates $625 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 $459). Flying from Illinois to Simpson Bay in March is currently the most expensive (average of $654). 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Illinois to Simpson Bay

See prices for flight routes from nearby airports that may be better suited for you.
Newark to Simpson Bay flights
John F Kennedy Intl to Simpson Bay flights
LaGuardia to Simpson Bay flights
Boston to Simpson Bay flights
Atlanta to Simpson Bay flights
Dulles Intl to Simpson Bay flights
Reagan-National to Simpson Bay flights
Miami to Simpson Bay flights
Baltimore to Simpson Bay flights
Philadelphia to Simpson Bay flights
O'Hare Intl to Simpson Bay flights
Fort Lauderdale to Simpson Bay flights
Dallas/Fort Worth to Simpson Bay flights
Charlotte to Simpson Bay flights
Los Angeles to Simpson Bay flights
Orlando to Simpson Bay flights
Hobby to Simpson Bay flights
Tampa to Simpson Bay flights
San Francisco to Simpson Bay flights
Providence to Simpson Bay flights
Denver to Simpson Bay flights
Detroit to Simpson Bay flights
St. Louis to Simpson Bay flights
Minneapolis to Simpson Bay flights
Columbus to Simpson Bay flights
Indianapolis to Simpson Bay flights
Raleigh to Simpson Bay flights
Cincinnati to Simpson Bay flights
Syracuse to Simpson Bay flights
George Bush Intcntl to Simpson Bay flights
Richmond to Simpson Bay flights
Sky Harbor Intl to Simpson Bay flights
Seattle to Simpson Bay flights
Hartford to Simpson Bay flights
Midway to Simpson Bay flights
Austin to Simpson Bay flights
Cleveland to Simpson Bay flights
Omaha to Simpson Bay flights
Albany to Simpson Bay flights
Love Field to Simpson Bay flights
White Plains to Simpson Bay flights
Kansas City to Simpson Bay flights
Ontario to Simpson Bay flights
Pittsburgh to Simpson Bay flights
Jackson to Simpson Bay flights
Grand Rapids to Simpson Bay flights
Lexington to Simpson Bay flights
Memphis to Simpson Bay flights
West Palm Beach to Simpson Bay flights
Rochester to Simpson Bay flights

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 August 22, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$316Average$400FlexibilityNo cancel feeOn-time65%
DeltaCheapest$564Average$721FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$589Average$758FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$654Average$894FlexibilityNo cancel feeOn-time69%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.