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Simpson Bay

$139+ Cheap flights from Chicago (CHI) 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 9/15. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SXM
Aug 23 — Aug 301
Sat 8/23
Sat 8/30
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Simpson Bay Princess Juliana are usually found in August or September, booked 89 days in advance, depart on a Monday or Tuesday and return on a Monday

Cheap flight deals from Chicago to Simpson Bay

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) 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 August 18, 2025.

Round-trip from

$317
(Cheapflightsfares)

One-way from

$139
(Cheapflightsfares)

Popular in

December

Cheapest in

August

Average price

$637

Good round-trip deal

$882 or less
From Chicago (CHI) to Simpson Bay Princess Juliana
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One-way flight from Chicago (CHI) to Simpson Bay Princess Juliana
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Highest demand for flights based on searches. 10% potential increase in price ($81 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($24 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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Price to beat on a round-trip flight from Chicago (CHI) to Simpson Bay Princess Juliana.
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Find flight deals from Chicago to Simpson Bay

Cheapest flights from Chicago to Simpson Bay
Explore the most affordable flight options available from Chicago to Simpson Bay. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 18, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 8/16. 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 9/65:05 amORD - SXM
1 stop7h 55mSpirit Airlines
Sat 9/133:05 pmSXM - ORD
1 stop8h 43mSpirit Airlines
Deal found 8/16$317
This Cheapflightsfares deal was found by Cheapflights users on 8/17. 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 10/185:05 amORD - SXM
1 stop7h 54mSpirit Airlines
Sat 10/253:05 pmSXM - ORD
1 stop9h 40mSpirit Airlines
Deal found 8/17$337
This Cheapflightsfares deal was found by Cheapflights users on 8/16. 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
Mon 9/293:05 pmSXM - ORD
1 stop8h 43mSpirit Airlines
Deal found 8/16$360
This Cheapflightsfares deal was found by Cheapflights users on 8/14. 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 9/125:05 amORD - SXM
1 stop7h 55mSpirit Airlines
Mon 9/153:05 pmSXM - ORD
1 stop8h 43mSpirit Airlines
Deal found 8/14$362
This CheapOair deal was found by Cheapflights users on 8/15. 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.
Mon 9/295:05 amORD - SXM
1 stop7h 55mSpirit Airlines
Mon 10/63:05 pmSXM - ORD
1 stop9h 40mSpirit Airlines
Deal found 8/15$367
This Kiwi.com deal was found by Cheapflights users on 8/14. 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 9/128:49 pmORD - SXM
2 stops16h 11mMultiple Airlines
Mon 9/153:05 pmSXM - ORD
1 stop8h 43mMultiple Airlines
Deal found 8/14$379
This Kiwi.com deal was found by Cheapflights users on 8/15. 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.
Sat 9/139:35 amMDW - SXM
1 stop26h 39mMultiple Airlines
Fri 9/193:05 pmSXM - MDW
2 stops19h 46mMultiple Airlines
Deal found 8/15$501
This Kiwi.com deal was found by Cheapflights users on 8/15. 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.
Sat 9/69:35 amMDW - SXM
1 stop26h 39mMultiple Airlines
Sat 9/133:05 pmSXM - MDW
2 stops19h 13mMultiple Airlines
Deal found 8/15$508
This Delta deal was found by Cheapflights users on 8/15. 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.
Sun 10/196:00 amMDW - SXM
1 stop6h 49mDelta
Sun 10/263:14 pmSXM - MDW
1 stop8h 00mDelta
Deal found 8/15$612
This Delta deal was found by Cheapflights users on 8/16. 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.
Fri 12/56:00 amMDW - SXM
1 stop6h 35mDelta
Sat 12/134:00 pmSXM - MDW
1 stop7h 44mDelta
Deal found 8/16$677
This Delta deal was found by Cheapflights users on 8/16. 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.
Fri 11/286:00 amMDW - SXM
1 stop6h 35mDelta
Sat 12/64:00 pmSXM - MDW
1 stop7h 44mDelta
Deal found 8/16$767
This Delta deal was found by Cheapflights users on 8/17. 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 12/66:00 amMDW - SXM
1 stop6h 35mDelta
Sat 12/134:00 pmSXM - MDW
1 stop7h 44mDelta
Deal found 8/17$807

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago 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 18, 2025.
Use the filters below to find and compare flights from Chicago to Simpson Bay that are best for you.

Fly from

Chicago

Fly to

Simpson Bay

Route

Depart

Return

Price

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sat 9/6

5:05 am-2:00 pm

1 stop7h 55m

Simpson Bay Princess Juliana

Sat 9/13

3:05 pm-10:48 pm

1 stop8h 43m

$317

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

Fri 9/19

5:05 am-2:00 pm

1 stop7h 55m

Simpson Bay Princess Juliana

Mon 9/29

3:05 pm-10:48 pm

1 stop8h 43m

$360

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Fri 9/12

5:05 am-2:00 pm

1 stop7h 55m

Simpson Bay Princess Juliana

Mon 9/15

3:05 pm-10:48 pm

1 stop8h 43m

$362

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

$362

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sat 9/13

5:05 am-2:00 pm

1 stop7h 55m

Simpson Bay Princess Juliana

Fri 9/19

3:05 pm-10:48 pm

1 stop8h 43m

$362

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Mon 9/29

5:05 am-2:00 pm

1 stop7h 55m

Simpson Bay Princess Juliana

Mon 10/6

3:05 pm-11:45 pm

1 stop9h 40m

$367

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Fri 9/12

8:49 pm-2:00 pm

2 stops16h 11m

Simpson Bay Princess Juliana

Mon 9/15

3:05 pm-10:48 pm

1 stop8h 43m

$379

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Sat 9/13

9:35 am-1:14 pm

1 stop26h 39m

Simpson Bay Princess Juliana

Fri 9/19

3:05 pm-9:51 am

2 stops19h 46m

$501

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Sat 9/6

9:35 am-1:14 pm

1 stop26h 39m

Simpson Bay Princess Juliana

Sat 9/13

3:05 pm-9:18 am

2 stops19h 13m

$508

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/16

Showing 1-10 of 25 results
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Best time to book a flight from Chicago to Simpson Bay

Have a flexible travel schedule? Discover the best time to fly to Simpson Bay from Chicago 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 Chicago to Simpson Bay

How far ahead should I book a flight from Chicago to Simpson Bay?

Use this chart to determine the optimal time to book a round-trip flight from Chicago to Simpson Bay. Price data was last updated on August 8, 2025.

The price you pay for your flight from Chicago to Simpson Bay may vary depending on when you book. For the best chance of a lower fare, look to book 88 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

What is the cheapest month to book a flight from Chicago to Simpson Bay?

Currently, September is the cheapest month in which you can book a flight from Chicago to Simpson Bay (average of $459). Flying from Chicago 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 CHI to SXM?

Find hourly flight availability from Chicago 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 18, 2025.

When flying from Chicago to Simpson Bay, the time of day you fly usually plays a role in the price. Save by searching for a flight at noon, which can drop the price by up to 54% versus a flight in the morning.

How much does it cost to fly round-trip from Chicago to Simpson Bay?

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 August 18, 2025.
See what other customers who have flown with Delta, United Airlines, and American Airlines from Chicago to Simpson Bay have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,981 reviews

Food

7.3

Crew

8.5

Entertainment

7.9

Boarding

8.2

Overall

8.0

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Delta
8.0
Very good
7,981 reviews
Delta
8.0
Very good
7,981 reviews

Food

7.3

Crew

8.5

Entertainment

7.9

Boarding

8.2

Overall

8.0

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
United Airlines
7.4
Good
8,925 reviews
Delta
8.0
Very good
7,981 reviews

Food

7.3

Crew

8.5

Entertainment

7.9

Boarding

8.2

Overall

8.0

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,981 reviews

Food

7.3

Crew

8.5

Entertainment

7.9

Boarding

8.2

Overall

8.0

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Spirit Airlines
6.3
Okay
8,038 reviews
Delta
8.0
Very good
7,981 reviews

Food

7.3

Crew

8.5

Entertainment

7.9

Boarding

8.2

Overall

8.0

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

Related info for your journey

Find useful and relevant information for your journey from Chicago 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 Chicago?

    Most people fly into Simpson Bay Princess Juliana (SXM) if they book a flight to Simpson Bay from Chicago. On average, Princess Juliana has 0 inbound flights from Chicago per day from 4 airlines. Simpson Bay Princess Juliana is conveniently located just 0.5 mi from Simpson Bay’s city center.

  • What are the cheapest airlines flying from Chicago to Simpson Bay round-trip?

    According to our current data, Spirit Airlines ($333), Delta ($564), and American Airlines ($614) offers the cheapest pricing from Chicago to Simpson Bay. Users have found that Spirit Airlines is 54% cheaper than the other options available to this destination.

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

    $139 is the cheapest one-way deal found within the past few days, from Spirit Airlines. You may also be able to find cheap deals on Delta and WestJet, with prices starting from $799 and $1,571, respectively.

  • What are the cheapest flights from Chicago to Simpson Bay?

    On average you can expect to pay $625 for a flight from Chicago to Simpson Bay. The cheapest flight overall is $313 while the most popular route, (Chicago O'Hare Intl - Simpson Bay Princess Juliana) is currently priced at $317.

  • Can I find deals for flights from Chicago to Simpson Bay that include hotel bookings?

    Yes. In addition to deals on Chicago to Simpson Bay flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Simpson Bay?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Simpson Bay.

  • Can I find deals for business class flights from Chicago to Simpson Bay?

    Yes. Cheapflights offers flight deals from Chicago 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 Chicago to Simpson Bay?

    Currently, September is the cheapest month in which you can book a flight from Chicago to Simpson Bay (average of $459). Flying from Chicago 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

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Alternative routes for Chicago to Simpson Bay

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Simpson Bay flights
St. Louis to Simpson Bay flights
Midway to Simpson Bay flights

Top 4 airlines flying from Chicago to Simpson Bay

Discover the top 4 airlines that operate flights from Chicago 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 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$333Average$401FlexibilityNo cancel feeOn-time65%
DeltaCheapest$564Average$721FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$614Average$713FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$654Average$911FlexibilityNo cancel feeOn-time69%

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