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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 3/2. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — SXM
Jan 26 — Feb 21
Sun 1/26
Sun 2/2
1 adult, Economy
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Cheap flight deals from Illinois to Simpson Bay

Discover tips and strategies to find the most affordable flight options for your journey from Illinois (USIL) to Simpson Bay (SXM). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated January 21, 2025.

Round-trip from

$401
(Mytrip)

One-way from

$139
(Kiwi.com)

Good round-trip deal

$861 or less

Good one-way deal

$353 or less
From Illinois to Simpson Bay Princess Juliana
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One-way flight from Illinois to Simpson Bay Princess Juliana
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Price to beat on a round-trip flight from Illinois to Simpson Bay Princess Juliana.
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Price to beat on a one-way flight from Illinois to Simpson Bay Princess Juliana.
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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 January 21, 2025.

This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/55:10 amORD - SXM
1 stop7h 18mSpirit Airlines
Wed 3/122:33 pmSXM - ORD
2 stops18h 11mSpirit Airlines
Deal found 1/20$401
This Kiwi.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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/27:13 pmORD - SXM
2 stops19h 56mMultiple Airlines
Thu 3/611:55 amSXM - ORD
1 stop9h 56mMultiple Airlines
Deal found 1/21$409
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.
Thu 3/205:17 pmSTL - SXM
1 stop19h 11mSpirit Airlines
Wed 3/262:33 pmSXM - STL
1 stop26h 49mSpirit Airlines
Deal found 1/21$493
This Priceline 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/108:00 amMDW - SXM
2 stops32h 05mFrontier
Mon 4/146:15 pmSXM - MDW
2 stops26h 30mFrontier
Deal found 1/20$507
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/211:05 pmMDW - SXM
1 stop21h 10mMultiple Airlines
Mon 2/246:31 pmSXM - MDW
2 stops22h 42mMultiple Airlines
Deal found 1/19$569
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.
Thu 3/205:17 pmSTL - SXM
1 stop19h 11mMultiple Airlines
Sun 3/233:55 pmSXM - STL
2 stops48h 11mMultiple Airlines
Deal found 1/21$582
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/46:00 amSTL - SXM
1 stop7h 16mDelta
Tue 3/111:40 pmSXM - STL
1 stop10h 51mDelta
Deal found 1/21$587
This Travelocity 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/236:39 pmORD - SXM
1 stop19h 36mAir Canada
Mon 3/314:15 pmSXM - ORD
1 stop28h 20mAir Canada
Deal found 1/20$591
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.
Tue 3/46:00 pmSTL - SXM
2 stops17h 55mAmerican Airlines
Tue 3/112:10 pmSXM - STL
1 stop10h 46mAmerican Airlines
Deal found 1/21$592
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/306:01 pmORD - SXM
2 stops15h 57mFrontier
Sat 6/1412:18 pmSXM - ORD
1 stop12h 20mFrontier
Deal found 1/20$621
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/56:00 amMDW - SXM
1 stop7h 16mDelta
Wed 3/121:40 pmSXM - MDW
1 stop9h 43mDelta
Deal found 1/19$641
This Air Canada 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/273:50 pmSTL - SXM
1 stop22h 25mAir Canada
Sun 3/303:55 pmSXM - STL
2 stops24h 04mAir Canada
Deal found 1/19$654

Find flights from Illinois to Simpson Bay within your budget

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, 2025.

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Fly to

Any airport

Route

Depart

Return

Price

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Wed 3/5

5:10 am-2:28 pm

1 stop7h 18m

Simpson Bay Princess Juliana

Wed 3/12

2:33 pm-7:44 am

2 stops18h 11m

$401

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sun 3/2

7:13 pm-5:09 pm

2 stops19h 56m

Simpson Bay Princess Juliana

Thu 3/6

11:55 am-7:51 pm

1 stop9h 56m

$409

St. LouisSimpson Bay

STL - SXM

STLSXM

Lambert-St Louis

Thu 3/20

5:17 pm-1:28 pm

1 stop19h 11m

Simpson Bay Princess Juliana

Wed 3/26

2:33 pm-4:22 pm

1 stop26h 49m

$493

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Thu 4/10

8:00 am-5:05 pm

2 stops32h 05m

Simpson Bay Princess Juliana

Mon 4/14

6:15 pm-7:45 pm

2 stops26h 30m

$507

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Fri 2/21

1:05 pm-12:15 pm

1 stop21h 10m

Simpson Bay Princess Juliana

Mon 2/24

6:31 pm-3:13 pm

2 stops22h 42m

$569

St. LouisSimpson Bay

STL - SXM

STLSXM

Lambert-St Louis

Thu 3/20

5:17 pm-1:28 pm

1 stop19h 11m

Simpson Bay Princess Juliana

Sun 3/23

3:55 pm-3:06 pm

2 stops48h 11m

$582

St. LouisSimpson Bay

STL - SXM

STLSXM

Lambert-St Louis

Tue 3/4

6:00 am-3:16 pm

1 stop7h 16m

Simpson Bay Princess Juliana

Tue 3/11

1:40 pm-11:31 pm

1 stop10h 51m

$587

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sun 3/23

6:39 pm-3:15 pm

1 stop19h 36m

Simpson Bay Princess Juliana

Mon 3/31

4:15 pm-7:35 pm

1 stop28h 20m

$591

St. LouisSimpson Bay

STL - SXM

STLSXM

Lambert-St Louis

Tue 3/4

6:00 pm-1:55 pm

2 stops17h 55m

Simpson Bay Princess Juliana

Tue 3/11

2:10 pm-11:56 pm

1 stop10h 46m

$592

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Fri 5/30

6:01 pm-10:58 am

2 stops15h 57m

Simpson Bay Princess Juliana

Sat 6/14

12:18 pm-11:38 pm

1 stop12h 20m

$621

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/19

Showing 1-10 of 31 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.

Travel insights for flights from Illinois to Simpson Bay

Get recent, data-driven insights about flights from Illinois to Simpson Bay including ideal travel times, pricing trends, and more.

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 July is currently the most expensive (average of $684). 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, 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.

Reviews of airlines servicing Simpson Bay

Get insights into the airlines that provide service to Simpson Bay. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Simpson Bay. Reviews last updated January 21, 2025.
Read reviews from past customers who have flown Delta, Spirit Airlines and Frontier from Illinois to Simpson Bay. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
8,521 reviews

Food

7.3

Boarding

8.2

Overall

8.0

Crew

8.6

Entertainment

7.9

Comfort

8.0

Reviews

1 / 10

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

Delta
8.0
Very good
8,521 reviews
Delta
8.0
Very good
8,521 reviews

Food

7.3

Boarding

8.2

Overall

8.0

Crew

8.6

Entertainment

7.9

Comfort

8.0

Reviews

1 / 10

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

KLM
7.8
Good
1,341 reviews
Delta
8.0
Very good
8,521 reviews

Food

7.3

Boarding

8.2

Overall

8.0

Crew

8.6

Entertainment

7.9

Comfort

8.0

Reviews

1 / 10

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

United Airlines
7.4
Good
8,985 reviews
Delta
8.0
Very good
8,521 reviews

Food

7.3

Boarding

8.2

Overall

8.0

Crew

8.6

Entertainment

7.9

Comfort

8.0

Reviews

1 / 10

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
8,521 reviews

Food

7.3

Boarding

8.2

Overall

8.0

Crew

8.6

Entertainment

7.9

Comfort

8.0

Reviews

1 / 10

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

WestJet
7.2
Good
2,829 reviews
Delta
8.0
Very good
8,521 reviews

Food

7.3

Boarding

8.2

Overall

8.0

Crew

8.6

Entertainment

7.9

Comfort

8.0

Reviews

1 / 10

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

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.

  • What are the cheapest airlines to fly from Illinois to Simpson Bay one-way?

    The cheapest airline one-way is Spirit Airlines, with whom users have recently found tickets for as low as $151. However, be on the lookout for offers from Air Canada and Frontier, as they are both options that can get you from Illinois to Simpson Bay for a low price.

  • 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 $308. While the most popular route (Chicago O'Hare Intl - Simpson Bay Princess Juliana) can be booked for $336 on average our data indicates $703 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 July is currently the most expensive (average of $684). 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.

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Alternative routes for Illinois to Simpson Bay

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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 January 21, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$271Average$450FlexibilityNo cancel feeOn-time65%
DeltaCheapest$425Average$722FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$579Average$728FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$644Average$875FlexibilityNo cancel feeOn-time69%
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