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Simpson Bay

$61+ 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 3/4. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SXM
Mar 5 — Mar 121
Thu 3/5
Thu 3/12
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Simpson Bay Princess Juliana are usually found in January or February, booked 10 days in advance, depart on a Tuesday or Monday and return on a Monday

Cheap 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 February 3, 2026.

This Expedia deal was found by Cheapflights users on 2/2. 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.
Wed 3/48:16 pm
ORD
-
SXM
1 stop15h 59m
Spirit Airlines
Sat 3/73:20 pm
SXM
-
ORD
1 stop10h 27m
Spirit Airlines
Deal found 2/2$213
This Travelocity deal was found by Cheapflights users on 2/1. 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.
Mon 2/238:16 pm
ORD
-
SXM
1 stop15h 59m
Spirit Airlines
Fri 2/273:20 pm
SXM
-
ORD
1 stop10h 27m
Spirit Airlines
Deal found 2/1$215
This Orbitz deal was found by Cheapflights users on 2/2. 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.
Wed 3/48:16 pm
ORD
-
SXM
1 stop15h 59m
Spirit Airlines
Mon 3/92:20 pm
SXM
-
ORD
1 stop10h 27m
Spirit Airlines
Deal found 2/2$222
This Orbitz deal was found by Cheapflights users on 2/1. 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.
Thu 3/58:16 pm
ORD
-
SXM
1 stop15h 59m
Spirit Airlines
Tue 3/102:20 pm
SXM
-
ORD
1 stop10h 27m
Spirit Airlines
Deal found 2/1$230
This Expedia deal was found by Cheapflights users on 2/2. 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.
Sat 2/75:15 am
ORD
-
SXM
1 stop7h 00m
Spirit Airlines
Wed 2/183:20 pm
SXM
-
ORD
1 stop10h 27m
Spirit Airlines
Deal found 2/2$237
This CheapOair deal was found by Cheapflights users on 2/2. 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 2/288:16 pm
ORD
-
SXM
1 stop15h 59m
Spirit Airlines
Sat 3/73:20 pm
SXM
-
ORD
1 stop10h 27m
Spirit Airlines
Deal found 2/2$246
This Expedia deal was found by Cheapflights users on 2/2. 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.
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 2/2$249
This Cheapflightsfares deal was found by Cheapflights users on 2/2. 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.
Mon 2/165:15 am
ORD
-
SXM
1 stop7h 00m
Spirit Airlines
Fri 2/203:20 pm
SXM
-
ORD
1 stop10h 27m
Spirit Airlines
Deal found 2/2$253
This Travelocity deal was found by Cheapflights users on 2/2. 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.
Thu 2/195:15 am
ORD
-
SXM
1 stop7h 00m
Spirit Airlines
Tue 2/243:20 pm
SXM
-
ORD
1 stop10h 27m
Spirit Airlines
Deal found 2/2$265
This CheapOair deal was found by Cheapflights users on 2/3. 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 stop22h 02m
Spirit Airlines
Deal found 2/3$271
This Kiwi.com deal was found by Cheapflights users on 2/1. 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.
Mon 2/235:58 pm
ORD
-
SXM
2 stops18h 17m
Multiple Airlines
Fri 2/273:20 pm
SXM
-
ORD
1 stop10h 04m
Multiple Airlines
Deal found 2/1$282
This Priceline deal was found by Cheapflights users on 2/1. 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 3/76:00 am
MDW
-
SXM
1 stop7h 20m
Frontier
Sat 3/142:35 pm
SXM
-
MDW
1 stop30h 12m
Frontier
Deal found 2/1$401

Find 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 February 3, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$210
(Travelocity)

One-way from

$61
(Kiwi.com)

Popular in

December

Cheapest in

January

Average price

$600

Good round-trip deal

$612 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 Chicago (CHI) to Simpson Bay Princess Juliana
Search Deals
One-way flight from Chicago (CHI) 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 ($10 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2026
Search Deals
Price to beat on a round-trip flight from Chicago (CHI) to Simpson Bay Princess Juliana.
Search Deals

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 February 3, 2026.
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

Wed 3/4

6:04 pm-2:40 pm

2 stops18h 36m

Simpson Bay Princess Juliana

Wed 3/11

2:20 pm-11:47 pm

1 stop10h 27m

$298

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Thu 2/26

5:15 am-2:15 pm

1 stop7h 00m

Simpson Bay Princess Juliana

Mon 3/2

3:20 pm-11:47 pm

1 stop10h 27m

$306

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Wed 2/18

12:44 pm-2:15 pm

2 stops23h 31m

Simpson Bay Princess Juliana

Wed 2/25

3:20 pm-11:47 pm

1 stop10h 27m

$315

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Wed 4/15

1:35 pm-1:16 pm

2 stops22h 41m

Simpson Bay Princess Juliana

Mon 4/20

2:11 pm-11:27 am

1 stop22h 16m

$350

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Fri 2/20

8:59 am-2:15 pm

2 stops27h 16m

Simpson Bay Princess Juliana

Tue 2/24

3:20 pm-7:11 pm

1 stop29h 51m

$351

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Wed 3/25

7:15 am-1:40 pm

1 stop29h 25m

Simpson Bay Princess Juliana

Fri 4/3

4:00 pm-1:05 pm

1 stop22h 05m

$385

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sat 2/28

9:18 am-2:15 pm

3 stops26h 57m

Simpson Bay Princess Juliana

Sat 3/7

3:20 pm-11:47 pm

1 stop10h 27m

$385

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sat 3/7

6:51 pm-10:25 am

2 stops13h 34m

Simpson Bay Princess Juliana

Sat 3/14

2:20 pm-11:17 pm

1 stop9h 57m

$386

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sun 3/15

5:05 am-1:15 pm

1 stop7h 10m

Simpson Bay Princess Juliana

Sun 3/22

2:20 pm-5:15 pm

1 stop27h 55m

$392

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Wed 3/25

5:05 am-1:15 pm

1 stop7h 10m

Simpson Bay Princess Juliana

Wed 4/1

2:35 pm-11:17 pm

1 stop9h 42m

$399

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/2

Showing 1-10 of 34 results
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Compare providers for flights from Chicago to Simpson Bay

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Chicago to Simpson Bay in February.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
AranGrantPrice Accuracy2 starsTrust Score*2 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Chicago-Simpson Bay flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago-Simpson Bay flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago-Simpson Bay flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago-Simpson Bay flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago-Simpson Bay flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

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 January 30, 2026.

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 9 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, February is the cheapest month in which you can book a flight from Chicago to Simpson Bay (average of $231). Flying from Chicago 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 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 February 3, 2026.

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

How often are flights from Chicago to Simpson Bay delayed?

About 32% of weekly flights between Chicago and Simpson Bay have experienced delays in the past year, with the average delay time being 97 minutes.

What is the most punctual flight time for Chicago to Simpson Bay flights?

Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving in the morning tend to experience delays more often.

What day of the week experiences the fewest flight delays on this route?

Saturday tends to have the lowest number of delays on this route, whereas Sunday has historically faced a higher average of delays compared to other days of the week.

Which airline has the best punctuality record on Chicago to Simpson Bay flights?

Over the last year, American Airlines have had the lowest number of delays on this route, with just 20% of flights being delayed.

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 February 3, 2026.
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
7.9
Good
8,138 reviews

Entertainment

7.8

Boarding

8.1

Crew

8.5

Overall

7.9

Comfort

7.9

Food

7.2

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Delta
7.9
Good
8,138 reviews
Delta
7.9
Good
8,138 reviews

Entertainment

7.8

Boarding

8.1

Crew

8.5

Overall

7.9

Comfort

7.9

Food

7.2

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
United Airlines
7.4
Good
9,236 reviews
Delta
7.9
Good
8,138 reviews

Entertainment

7.8

Boarding

8.1

Crew

8.5

Overall

7.9

Comfort

7.9

Food

7.2

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
American Airlines
7.2
Good
11,218 reviews
Delta
7.9
Good
8,138 reviews

Entertainment

7.8

Boarding

8.1

Crew

8.5

Overall

7.9

Comfort

7.9

Food

7.2

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Spirit Airlines
6.3
Okay
8,407 reviews
Delta
7.9
Good
8,138 reviews

Entertainment

7.8

Boarding

8.1

Crew

8.5

Overall

7.9

Comfort

7.9

Food

7.2

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.

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 5 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 50m. 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 ($258), Delta ($290), and United Airlines ($410) offers the cheapest pricing from Chicago to Simpson Bay. Users have found that Spirit Airlines is 62% cheaper than the other options available to this destination.

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

    On average you can expect to pay $726 for a flight from Chicago to Simpson Bay. The cheapest flight overall is $554 while the most popular route, (Chicago O'Hare Intl - Simpson Bay Princess Juliana) is currently priced at $213.

  • 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, February is the cheapest month in which you can book a flight from Chicago to Simpson Bay (average of $231). Flying from Chicago 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 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 5 airlines flying from Chicago to Simpson Bay

Discover the top 5 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 February 3, 2026.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$258Average$396FlexibilityNo cancel feeOn-time65%
DeltaCheapest$290Average$522FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$410Average$756FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$501Average$682FlexibilityNo cancel feeOn-time71%
JetBlueCheapest$568Average$731FlexibilityNo cancel feeOn-time62%

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