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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 12/15. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SXM
Oct 17 — Oct 241
Fri 10/17
Fri 10/24
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 88 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 September 17, 2025.

Round-trip from

$337
(Cheapflightsfares)

One-way from

$139
(Cheapflightsfares)

Popular in

December

Cheapest in

August

Average price

$612

Good round-trip deal

$642 or less

Good one-way deal

$368 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. 8% potential increase in price ($72 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($23 potential savings vs. average RT price).
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Average for round-trip flights in September 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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Price to beat on a one-way 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 September 17, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 9/15. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/15:05 amORD - SXM
1 stop7h 55mSpirit Airlines
Wed 11/54:28 pmSXM - ORD
1 stop9h 14mSpirit Airlines
Deal found 9/15$337
This Cheapflightsfares deal was found by Cheapflights users on 9/16. 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 10/185:05 amORD - SXM
1 stop7h 55mSpirit Airlines
Sat 10/253:05 pmSXM - ORD
1 stop9h 40mSpirit Airlines
Deal found 9/16$342
This Cheapflightsfares deal was found by Cheapflights users on 9/17. 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.
Fri 10/317:43 pmORD - SXM
1 stop17h 17mSpirit Airlines
Mon 11/34:05 pmSXM - ORD
1 stop10h 58mSpirit Airlines
Deal found 9/17$345
This Priceline deal was found by Cheapflights users on 9/17. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/275:05 amORD - SXM
1 stop7h 55mSpirit Airlines
Fri 10/313:05 pmSXM - ORD
1 stop10h 58mSpirit Airlines
Deal found 9/17$350
This Priceline deal was found by Cheapflights users on 9/17. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/15:05 amORD - SXM
1 stop7h 55mSpirit Airlines
Sat 11/84:28 pmSXM - ORD
1 stop9h 14mSpirit Airlines
Deal found 9/17$351
This Orbitz deal was found by Cheapflights users on 9/17. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/296:05 pmORD - SXM
2 stops43h 55mMultiple Airlines
Sat 12/64:28 pmSXM - ORD
1 stop9h 14mMultiple Airlines
Deal found 9/17$369
This Expedia deal was found by Cheapflights users on 9/15. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/42:00 pmORD - SXM
1 stop24h 00mMultiple Airlines
Wed 12/104:28 pmSXM - ORD
1 stop9h 14mMultiple Airlines
Deal found 9/15$373
This Orbitz deal was found by Cheapflights users on 9/16. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/85:05 amORD - SXM
1 stop8h 05mMultiple Airlines
Fri 11/145:00 pmSXM - ORD
2 stops41h 01mMultiple Airlines
Deal found 9/16$384
This Kiwi.com deal was found by Cheapflights users on 9/15. 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.
Sun 10/267:43 pmORD - SXM
1 stop17h 17mSpirit Airlines
Sat 11/13:05 pmSXM - ORD
1 stop21h 45mSpirit Airlines
Deal found 9/15$398
This Mytrip deal was found by Cheapflights users on 9/16. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/279:20 amMDW - SXM
2 stops28h 01mWestJet
Fri 10/313:20 pmSXM - MDW
2 stops22h 48mWestJet
Deal found 9/16$639
This Delta deal was found by Cheapflights users on 9/15. 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.
Wed 11/196:00 amMDW - SXM
1 stop6h 55mDelta
Sun 11/234:20 pmSXM - MDW
1 stop9h 12mDelta
Deal found 9/15$757
This Delta deal was found by Cheapflights users on 9/15. 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.
Sat 11/16:00 amMDW - SXM
1 stop6h 49mDelta
Wed 11/54:14 pmSXM - MDW
1 stop8h 00mDelta
Deal found 9/15$762

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 September 17, 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 11/1

5:05 am-2:00 pm

1 stop7h 55m

Simpson Bay Princess Juliana

Wed 11/5

4:28 pm-11:42 pm

1 stop9h 14m

$337

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Fri 10/3

5:05 am-2:00 pm

1 stop7h 55m

Simpson Bay Princess Juliana

Fri 10/10

3:05 pm-11:45 pm

1 stop9h 40m

$342

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

$342

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

Fri 11/14

4:28 pm-11:42 pm

1 stop9h 14m

$346

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sat 10/18

5:05 am-2:00 pm

1 stop7h 55m

Simpson Bay Princess Juliana

Sat 10/25

3:05 pm-11:45 pm

1 stop9h 40m

$367

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

Fri 11/14

5:00 pm-8:01 am

2 stops41h 01m

$384

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Mon 10/27

5:05 am-2:00 pm

1 stop7h 55m

Simpson Bay Princess Juliana

Fri 10/31

4:00 pm-11:18 am

2 stops20h 18m

$405

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Thu 10/23

7:43 pm-2:00 pm

1 stop17h 17m

Simpson Bay Princess Juliana

Sun 10/26

12:25 pm-9:22 am

2 stops21h 57m

$407

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Thu 12/11

6:28 pm-4:00 pm

1 stop19h 32m

Simpson Bay Princess Juliana

Mon 12/15

5:00 pm-12:51 pm

2 stops21h 51m

$443

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Thu 11/6

5:59 pm-3:10 pm

1 stop19h 11m

Simpson Bay Princess Juliana

Thu 11/13

12:25 pm-12:30 pm

2 stops26h 05m

$446

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/16

Showing 1-10 of 35 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 September 12, 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 $652). 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 September 17, 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 53% 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 September 17, 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
7,961 reviews

Boarding

8.2

Overall

8.0

Comfort

7.9

Crew

8.5

Entertainment

7.9

Food

7.3

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
7,961 reviews
Delta
8.0
Very good
7,961 reviews

Boarding

8.2

Overall

8.0

Comfort

7.9

Crew

8.5

Entertainment

7.9

Food

7.3

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
8,926 reviews
Delta
8.0
Very good
7,961 reviews

Boarding

8.2

Overall

8.0

Comfort

7.9

Crew

8.5

Entertainment

7.9

Food

7.3

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
7,961 reviews

Boarding

8.2

Overall

8.0

Comfort

7.9

Crew

8.5

Entertainment

7.9

Food

7.3

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
8,023 reviews
Delta
8.0
Very good
7,961 reviews

Boarding

8.2

Overall

8.0

Comfort

7.9

Crew

8.5

Entertainment

7.9

Food

7.3

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.

  • How long is the flight from Chicago to Simpson Bay?

    Departing from Chicago to Simpson Bay will take you 6h 55m. The distance between Chicago and Simpson Bay is about 2189 mi. Both multi-stop and nonstop flights can be found to your destination and back.

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

    According to our current data, Spirit Airlines ($316), Delta ($318), and American Airlines ($619) offers the cheapest pricing from Chicago to Simpson Bay. Users have found that Spirit Airlines is 56% cheaper than the other options available to this destination.

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

    $141 is the cheapest one-way deal found within the past few days, from Air Canada. You may also be able to find cheap deals on Spirit Airlines and Frontier, with prices starting from $160 and $219, respectively.

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

    On average you can expect to pay $597 for a flight from Chicago to Simpson Bay. The cheapest flight overall is $288 while the most popular route, (Chicago O'Hare Intl - Simpson Bay Princess Juliana) is currently priced at $337.

  • 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 $652). 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
Midway to Simpson Bay flights
St. Louis 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 September 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$316Average$400FlexibilityNo cancel feeOn-time65%
DeltaCheapest$318Average$721FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$619Average$713FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$647Average$908FlexibilityNo cancel feeOn-time69%

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