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

According to our current data, Spirit Airlines ($377), Frontier ($431), and Air Canada ($571) offers the cheapest pricing from Chicago to Simpson Bay. Users have found that Spirit Airlines is 48% 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 American Airlines, with prices starting from $308 and $378, respectively.

What is the cheapest day to fly from Chicago to Simpson Bay?

Travelers seeking maximum savings on their Chicago to Simpson Bay flight should consider departing on Wednesday at noon when fares are most often at their lowest. Saturday mornings flights should be avoided if possible as fares are typically the most expensive at this time.

What are the cheapest flights from Chicago to Simpson Bay?

On average you can expect to pay $1,043 for a flight from Chicago to Simpson Bay. The cheapest flight overall is $757 while the most popular route, (Chicago O'Hare Intl - Simpson Bay Princess Juliana) is currently priced at $337.

What are the most popular airlines that fly from Chicago to Simpson Bay?

Consider American Airlines, Delta or Spirit Airlines when booking your flight. These represent the most popular airlines when flying from Chicago to Simpson Bay.

What is the cheapest day to fly round-trip from Chicago to Simpson Bay?

Departing on a Monday is a good option for securing a great price. You can expect to save up to 44% when planning your travel around this day of the week.

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

Travelers have found it’s best to book a flight 51 days in advance to save up to 78% compared to booking the same week of travel. As your travel date approaches, the cost of this flight route may potentially increase. While opting to book 51 days out may not be an option for all, there are still additional ways to secure a deal in the near future. You might find a flight from Chicago to Simpson Bay 1-2 weeks in advance for as low as $442, or $1,114 for flights within the next 24 hours.

What is the cheapest month to fly from Chicago to Simpson Bay?

Flights from Chicago to Simpson Bay lean towards being more expensive in March. Prices are generally better when you fly from Chicago to Simpson Bay in September, with the cheapest ticket starting at $369.

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.

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.

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.

$139+ Flights from Chicago to Simpson Bay

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Find cheap flights from Chicago to Simpson Bay with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

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Cheapflights Tip: The best prices from Chicago to Simpson Bay Princess Juliana are usually found in September or October, booked 88 days in advance, depart on a Tuesday or Monday and return on a Monday

Cheap flight deals from Chicago to Simpson Bay

Most accurate provider	FlightHub 3 stars
Most trusted provider	FlightHub 3 stars
Round-trip from	$377 (Cheapflightsfares)
One-way from	$139 (Cheapflightsfares)
Popular in	March
Cheapest in	September
Average price	$727
Good round-trip deal	$795 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

Highest demand for flights based on searches. 2% potential increase in price ($17 potential increase over avg. RT price).

Search Deals

Cheapest flight prices on average. 1% potential price decrease ($9 potential savings vs. average RT price).

Search Deals

Average for round-trip flights in April 2025

Search Deals

Price to beat on a round-trip flight from Chicago (CHI) to Simpson Bay Princess Juliana.

Search Deals

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 April 1, 2025.

Fri 4/187:47 pmORD - SXM

1 stop17h 13mSpirit Airlines

Sat 5/33:05 pmSXM - ORD

1 stop10h 53mSpirit Airlines

Deal found 4/1

$377

Fri 5/305:14 pmORD - SXM

1 stop17h 10mMultiple Airlines

Mon 6/23:05 pmSXM - ORD

1 stop10h 00mMultiple Airlines

Deal found 3/30

$428

Fri 5/309:12 pmMDW - SXM

1 stop13h 12mFrontier

Sat 6/1412:36 pmSXM - MDW

1 stop8h 41mFrontier

Deal found 4/1

$431

Fri 5/235:14 pmORD - SXM

1 stop17h 10mFrontier

Sat 5/3112:34 pmSXM - ORD

1 stop20h 44mFrontier

Deal found 3/30

$447

Tue 5/135:00 amORD - SXM

1 stop7h 15mAmerican Airlines

Tue 5/202:05 pmSXM - ORD

1 stop8h 38mAmerican Airlines

Deal found 3/30

$621

Fri 7/45:45 amORD - SXM

1 stop7h 15mDelta

Wed 7/93:10 pmSXM - ORD

1 stop9h 45mDelta

Deal found 3/31

$647

Fri 4/48:25 pmORD - SXM

2 stops41h 25mAir Canada

Sun 4/133:55 pmSXM - ORD

2 stops27h 59mAir Canada

Deal found 4/1

$674

Tue 7/19:31 pmORD - SXM

1 stop13h 58mUnited Airlines

Wed 7/91:35 pmSXM - ORD

1 stop11h 02mUnited Airlines

Deal found 3/31

$722

Sat 4/266:04 amMDW - SXM

1 stop7h 01mDelta

Sat 5/31:46 pmSXM - MDW

1 stop9h 36mDelta

Deal found 3/31

$752

Thu 4/2410:20 amMDW - SXM

2 stops26h 56mWestJet

Tue 4/292:20 pmSXM - MDW

2 stops27h 59mWestJet

Deal found 3/31

$1,519

Best flights from Chicago to Simpson Bay
Discover carefully curated flight deals from Chicago to Simpson Bay that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated April 1, 2025.

Fri 4/187:47 pmORD - SXM

1 stop17h 13mSpirit Airlines

Sat 5/33:05 pmSXM - ORD

1 stop10h 53mSpirit Airlines

Deal found 4/1

$377

Sat 5/175:05 amORD - SXM

1 stop7h 55mMultiple Airlines

Sat 5/2412:34 pmSXM - ORD

1 stop20h 48mMultiple Airlines

Deal found 4/1

$403

Fri 5/309:12 pmMDW - SXM

1 stop13h 12mFrontier

Sat 6/1412:36 pmSXM - MDW

1 stop8h 41mFrontier

Deal found 4/1

$431

Fri 4/118:25 pmORD - SXM

1 stop18h 20mAir Canada

Mon 4/144:15 pmSXM - ORD

1 stop17h 40mAir Canada

Deal found 4/1

$571

Tue 5/135:30 amORD - SXM

1 stop7h 24mDelta

Thu 5/223:19 pmSXM - ORD

1 stop9h 39mDelta

Deal found 4/1

$622

Sat 5/37:17 pmORD - SXM

1 stop16h 57mAmerican Airlines

Wed 5/73:24 pmSXM - ORD

2 stops16h 02mAmerican Airlines

Deal found 4/1

$627

Tue 7/81:07 amORD - SXM

1 stop9h 17mCopa Airlines

Sun 7/1312:23 pmSXM - ORD

1 stop12h 57mCopa Airlines

Deal found 4/1

$783

Wed 5/216:00 amORD - SXM

1 stop7h 43mUnited Airlines

Fri 5/301:35 pmSXM - ORD

1 stop9h 37mUnited Airlines

Deal found 4/1

$805

Sat 6/141:40 pmORD - SXM

2 stops22h 35mWestJet

Sun 6/222:10 pmSXM - ORD

2 stops51h 34mWestJet

Deal found 4/1

$848

Thu 7/35:10 amORD - SXM

2 stops53h 18mFrontier

Mon 7/76:26 pmSXM - ORD

2 stops30h 02mFrontier

Deal found 4/1

$499

Sat 4/266:04 amMDW - SXM

1 stop7h 01mDelta

Sat 5/31:46 pmSXM - MDW

1 stop9h 36mDelta

Deal found 3/31

$752

Thu 4/2410:20 amMDW - SXM

2 stops26h 56mWestJet

Tue 4/292:20 pmSXM - MDW

2 stops27h 59mWestJet

Deal found 3/31

$1,519

Last-minute flights from Chicago to Simpson Bay
Discover last-minute flight deals from Chicago to Simpson Bay. Data last updated April 1, 2025 and is based on user searches.

Fri 4/48:25 pmORD - SXM

2 stops41h 25mAir Canada

Sun 4/133:55 pmSXM - ORD

1 stop19h 52mAir Canada

Deal found 4/1

$674

Mon 4/75:10 amORD - SXM

1 stop7h 50mSpirit Airlines

Wed 4/303:05 pmSXM - ORD

1 stop10h 15mSpirit Airlines

Deal found 3/31

$440

Mon 4/72:53 pmORD - SXM

2 stops19h 27mMultiple Airlines

Wed 4/303:05 pmSXM - ORD

1 stop10h 15mMultiple Airlines

Deal found 3/31

$460

Mon 4/76:00 amMDW - SXM

1 stop6h 59mDelta

Wed 4/301:46 pmSXM - MDW

1 stop9h 36mDelta

Deal found 3/31

$792

Wed 4/95:00 amORD - SXM

1 stop7h 14mAmerican Airlines

Tue 4/153:18 pmSXM - ORD

1 stop9h 36mAmerican Airlines

Deal found 4/1

$842

Wed 4/91:15 pmMDW - SXM

2 stops48h 01mWestJet

Tue 4/153:10 pmSXM - MDW

2 stops42h 57mWestJet

Deal found 3/31

$3,427

Fri 4/187:47 pmORD - SXM

1 stop17h 13mSpirit Airlines

Sat 5/33:05 pmSXM - ORD

1 stop10h 53mSpirit Airlines

Deal found 4/1

$377

Sat 4/1910:37 amORD - SXM

Nonstop5h 12mBrussels Airlines

Sat 4/261:25 pmSXM - ORD

Nonstop5h 43mBrussels Airlines

Deal found 3/31

$965

Thu 4/2410:20 amMDW - SXM

2 stops26h 56mWestJet

Tue 4/292:20 pmSXM - MDW

2 stops27h 59mWestJet

Deal found 3/31

$1,519

Sat 4/266:04 amMDW - SXM

1 stop7h 01mDelta

Sat 5/31:46 pmSXM - MDW

1 stop9h 36mDelta

Deal found 3/31

$752

Sat 4/2610:37 amORD - SXM

Nonstop5h 12mUnited Airlines

Sat 5/31:35 pmSXM - ORD

1 stop11h 09mUnited Airlines

Deal found 4/1

$933

Tue 5/135:00 amORD - SXM

1 stop7h 15mAmerican Airlines

Tue 5/202:05 pmSXM - ORD

1 stop8h 38mAmerican Airlines

Deal found 3/30

$621

One-way flights from Chicago to Simpson Bay
Search for one-way flight options from Chicago to Simpson Bay. Find affordable one-way fares based on user searches. Data last updated April 1, 2025.

Fri 4/255:36 amORD - SXM

1 stop7h 24mSpirit Airlines

Deal found 3/31

$139

Sat 4/1911:45 amORD - SXM

2 stops22h 35mMultiple Airlines

Deal found 3/31

$233

Mon 5/125:30 amORD - SXM

1 stop7h 24mDelta

Deal found 4/1

$308

Thu 5/156:00 amMDW - SXM

1 stop6h 54mDelta

Deal found 3/31

$333

Fri 5/165:00 amORD - SXM

1 stop7h 15mAmerican Airlines

Deal found 4/1

$378

Sat 4/1210:37 amORD - SXM

Nonstop5h 12mUnited Airlines

Deal found 4/1

$463

Cheapflights Fare Finder

Use the filters below to find and compare flights from Chicago to Simpson Bay that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Fri 4/18

7:47 pm-2:00 pm

1 stop17h 13m

Simpson Bay Princess Juliana

Sat 5/3

3:05 pm-12:58 am

1 stop10h 53m

$377

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Fri 5/30

5:14 pm-11:24 am

1 stop17h 10m

Simpson Bay Princess Juliana

Mon 6/2

3:05 pm-12:05 am

1 stop10h 00m

$428

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Fri 5/30

9:12 pm-11:24 am

1 stop13h 12m

Simpson Bay Princess Juliana

Sat 6/14

12:36 pm-8:17 pm

1 stop8h 41m

$431

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Fri 5/23

5:14 pm-11:24 am

1 stop17h 10m

Simpson Bay Princess Juliana

Sat 5/31

12:34 pm-8:18 am

1 stop20h 44m

$447

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Tue 5/13

5:00 am-1:15 pm

1 stop7h 15m

Simpson Bay Princess Juliana

Tue 5/20

2:05 pm-9:43 pm

1 stop8h 38m

$621

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Thu 5/15

5:30 am-1:54 pm

1 stop7h 24m

Simpson Bay Princess Juliana

Tue 5/20

3:19 pm-11:58 pm

1 stop9h 39m

$647

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Fri 4/4

8:25 pm-2:50 pm

2 stops41h 25m

Simpson Bay Princess Juliana

Sun 4/13

3:55 pm-10:47 am

1 stop19h 52m

$674

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Sat 4/26

6:04 am-2:05 pm

1 stop7h 01m

Simpson Bay Princess Juliana

Sat 5/3

1:46 pm-10:22 pm

1 stop9h 36m

$752

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sat 4/26

10:37 am-4:49 pm

Nonstop5h 12m

Simpson Bay Princess Juliana

Sat 5/3

1:35 pm-11:44 pm

1 stop11h 09m

$933

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sat 4/19

10:37 am-4:49 pm

Nonstop5h 12m

Simpson Bay Princess Juliana

Sat 4/26

1:25 pm-6:08 pm

Nonstop5h 43m

$965

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/31

Showing 1-10 of 16 results

Compare providers for flights from Chicago to Simpson Bay

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 April.

Provider	Price Accuracy	Trust Score*
Expedia	Price Accuracy1 star	Trust Score*3 stars
FlightHub	Price Accuracy3 stars	Trust Score*3 stars
eDreams	Price Accuracy3 stars	Trust Score*3 stars
AranGrant	Price Accuracy3 stars	Trust Score*1 star

*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?

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 July is currently the most expensive (average of $675). 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?

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 55% versus a flight in the morning.

Reviews of airlines servicing Simpson Bay

Get a feel of what it's like to fly with Delta, Copa Airlines and United Airlines from Chicago to Simpson Bay by reading reviews from past customers. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.

Delta

8.0

Very good

7,899 reviews

Reviews

1 / 20

10.0

Excellent

Aaron,Oct 2024

LAX - LHR

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

Delta

8.0

Very good

7,899 reviews

Delta

8.0

Very good

7,899 reviews

Reviews

1 / 20

10.0

Excellent

Aaron,Oct 2024

LAX - LHR

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

Copa Airlines

7.6

Good

1,400 reviews

Delta

8.0

Very good

7,899 reviews

Reviews

1 / 20

10.0

Excellent

Aaron,Oct 2024

LAX - LHR

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

United Airlines

7.4

Good

8,615 reviews

Delta

8.0

Very good

7,899 reviews

Reviews

1 / 20

10.0

Excellent

Aaron,Oct 2024

LAX - LHR

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

7,899 reviews

Reviews

1 / 20

10.0

Excellent

Aaron,Oct 2024

LAX - LHR

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

WestJet

7.2

Good

2,789 reviews

Delta

8.0

Very good

7,899 reviews

Reviews

1 / 20

10.0

Excellent

Aaron,Oct 2024

LAX - LHR

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

Related info for your journey

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 ($377), Frontier ($431), and Air Canada ($571) offers the cheapest pricing from Chicago to Simpson Bay. Users have found that Spirit Airlines is 48% 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 American Airlines, with prices starting from $308 and $378, respectively.
What are the cheapest flights from Chicago to Simpson Bay?
On average you can expect to pay $1,043 for a flight from Chicago to Simpson Bay. The cheapest flight overall is $757 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 July is currently the most expensive (average of $675). 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

Browse thousands of different options on Cheapflights for your next trip

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Top 4 airlines flying from Chicago to Simpson Bay

Airline	Cheapest	Average	Flexibility	On-time
Spirit Airlines	Cheapest$325	Average$401	FlexibilityNo cancel fee	On-time65%
Delta	Cheapest$554	Average$799	FlexibilityNo cancel fee	On-timeN/A
American Airlines	Cheapest$603	Average$725	FlexibilityNo cancel fee	On-time71%
United Airlines	Cheapest$610	Average$896	FlexibilityNo cancel fee	On-time69%

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$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 4/25. Fares are subject to change and may not be available on all flights or dates of travel.

Find cheap flights from Chicago to Simpson Bay with Cheapflights

1. Tell us where you want to go

2. Select your favorite providers

3. Compare prices and book

Cheapflights Tip: The best prices from Chicago to Simpson Bay Princess Juliana are usually found in September or October, booked 88 days in advance, depart on a Tuesday or Monday and return on a Monday

Cheap flight deals from Chicago to Simpson Bay

Most accurate provider

Most trusted provider

Round-trip from

One-way from

Popular in

Cheapest in

Average price

Good round-trip deal

Find flight deals from Chicago to Simpson Bay

Cheapest flights from Chicago to Simpson BayExplore 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 April 1, 2025.

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 April 1, 2025.

Cheapflights Fare Finder

Use the filters below to find and compare flights from Chicago to Simpson Bay that are best for you.

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 April.

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.

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 March 28, 2025.

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

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 April 1, 2025.

Reviews of airlines servicing Simpson Bay

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?

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

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

What are the cheapest flights from Chicago to Simpson Bay?

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

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

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

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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Chicago to Simpson Bay

See prices for flight routes from nearby airports that may be better suited for you.

Top 4 airlines flying from Chicago to Simpson Bay

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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 April 1, 2025.