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Simpson Bay

$75+ 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 2/25. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — SXM
Feb 20 — Feb 271
Fri 2/20
Fri 2/27
1 adult, Economy
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Cheap 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 January 21, 2026.

This FlightHub deal was found by Cheapflights users on 1/21. 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.
Mon 2/95:15 am
ORD
-
SXM
1 stop7h 00m
Spirit Airlines
Wed 2/183:20 pm
SXM
-
ORD
1 stop10h 27m
Spirit Airlines
Deal found 1/21$219
This CheapOair deal was found by Cheapflights users on 1/21. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/185:15 am
ORD
-
SXM
1 stop7h 00m
Spirit Airlines
Wed 2/253:20 pm
SXM
-
ORD
1 stop10h 27m
Spirit Airlines
Deal found 1/21$227
This CheapOair deal was found by Cheapflights users on 1/20. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/75:15 am
ORD
-
SXM
1 stop7h 00m
Spirit Airlines
Sat 2/143:20 pm
SXM
-
ORD
1 stop10h 27m
Spirit Airlines
Deal found 1/20$235
This Priceline deal was found by Cheapflights users on 1/21. 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 2/238:16 pm
ORD
-
SXM
1 stop15h 59m
Multiple Airlines
Sat 2/283:20 pm
SXM
-
ORD
1 stop9h 19m
Multiple Airlines
Deal found 1/21$250
This FlightHub deal was found by Cheapflights users on 1/20. 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 2/195:15 am
ORD
-
SXM
1 stop7h 00m
Spirit Airlines
Wed 2/253:20 pm
SXM
-
ORD
1 stop10h 27m
Spirit Airlines
Deal found 1/20$259
This Mytrip deal was found by Cheapflights users on 1/19. 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 4/115:30 am
ORD
-
SXM
1 stop7h 50m
Multiple Airlines
Wed 4/152:11 pm
SXM
-
ORD
1 stop10h 30m
Multiple Airlines
Deal found 1/19$269
This Kiwi.com deal was found by Cheapflights users on 1/20. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/125:32 pm
ORD
-
SXM
1 stop18h 44m
Spirit Airlines
Wed 5/202:11 pm
SXM
-
ORD
1 stop10h 30m
Spirit Airlines
Deal found 1/20$271
This Air Canada deal was found by Cheapflights users on 1/20. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/34:05 pm
STL
-
SXM
1 stop21h 55m
Air Canada
Fri 3/134:00 pm
SXM
-
STL
1 stop24h 29m
Air Canada
Deal found 1/20$371
This American Airlines deal was found by Cheapflights users on 1/20. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/16:13 am
STL
-
SXM
1 stop7h 47m
American Airlines
Fri 3/63:17 pm
SXM
-
STL
1 stop10h 39m
American Airlines
Deal found 1/20$465
This American Airlines deal was found by Cheapflights users on 1/21. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/185:15 am
STL
-
SXM
1 stop7h 06m
American Airlines
Mon 3/234:01 pm
SXM
-
STL
1 stop21h 43m
American Airlines
Deal found 1/21$474
This American Airlines deal was found by Cheapflights users on 1/21. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/23:33 pm
STL
-
SXM
2 stops18h 56m
American Airlines
Sun 3/82:17 pm
SXM
-
STL
2 stops19h 18m
American Airlines
Deal found 1/21$475
This Booking.com deal was found by Cheapflights users on 1/21. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/46:00 am
MDW
-
SXM
1 stop7h 20m
Frontier
Sat 4/113:25 pm
SXM
-
MDW
1 stop29h 42m
Frontier
Deal found 1/21$482

Find 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 January 21, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

Expedia
3 stars

Round-trip from

$219
(FlightHub)

One-way from

$75
(Super.com)

Popular in

December

Cheapest in

January

Average price

$586

Good round-trip deal

$677 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
High demand for flights, 0% potential price rise
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($11 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
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 January 21, 2026.
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

Sun 2/8

5:15 am-2:15 pm

1 stop7h 00m

Simpson Bay Princess Juliana

Sun 2/15

3:20 pm-11:47 pm

1 stop10h 27m

$279

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sat 2/7

4:38 pm-2:15 pm

2 stops19h 37m

Simpson Bay Princess Juliana

Sat 2/14

3:20 pm-11:47 pm

1 stop10h 27m

$283

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Wed 4/15

5:15 am-1:16 pm

1 stop7h 01m

Simpson Bay Princess Juliana

Wed 4/22

2:11 pm-11:41 pm

1 stop10h 30m

$330

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Thu 3/5

8:16 pm-2:15 pm

1 stop15h 59m

Simpson Bay Princess Juliana

Fri 3/13

2:14 pm-11:17 pm

1 stop10h 03m

$342

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sun 2/8

11:55 am-2:15 pm

2 stops24h 20m

Simpson Bay Princess Juliana

Sun 2/15

3:20 pm-11:47 pm

1 stop10h 27m

$351

St. LouisSimpson Bay

STL - SXM

STLSXM

Lambert-St Louis

Tue 3/3

4:05 pm-4:00 pm

1 stop21h 55m

Simpson Bay Princess Juliana

Fri 3/13

4:00 pm-3:29 pm

1 stop24h 29m

$371

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sat 4/18

5:32 pm-1:16 pm

1 stop18h 44m

Simpson Bay Princess Juliana

Sat 4/25

2:11 pm-11:41 pm

1 stop10h 30m

$378

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Fri 2/27

8:16 pm-2:15 pm

1 stop15h 59m

Simpson Bay Princess Juliana

Wed 3/4

3:20 pm-7:54 am

2 stops18h 34m

$394

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Thu 4/9

6:21 pm-2:50 pm

2 stops19h 29m

Simpson Bay Princess Juliana

Mon 4/13

2:14 pm-11:17 pm

1 stop10h 03m

$400

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Fri 4/17

5:15 am-1:16 pm

1 stop7h 01m

Simpson Bay Princess Juliana

Sat 4/25

2:11 pm-11:41 pm

1 stop10h 30m

$401

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/21

Showing 1-10 of 47 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, February is the cheapest month in which you can book a flight from Illinois to Simpson Bay (average of $231). 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 January 21, 2026.

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, Air Canada, and American Airlines can get you from Illinois to Simpson Bay in just under 7h. Your travel time can differ by up to 14h 55m. Airlines will cover a distance of 2204 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 $546. While the most popular route (Chicago O'Hare Intl - Simpson Bay Princess Juliana) can be booked for $222 on average, our data indicates $779 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, February is the cheapest month in which you can book a flight from Illinois to Simpson Bay (average of $231). 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 January 21, 2026.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$280Average$399FlexibilityNo cancel feeOn-time65%
DeltaCheapest$290Average$612FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$410Average$763FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$501Average$691FlexibilityNo cancel feeOn-time71%
JetBlueCheapest$535Average$731FlexibilityNo cancel feeOn-time62%

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