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Simpson Bay

$127+ 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 2/7. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SXM
Des 27 — Jan 31
Jum 12/27
Jum 1/3
1 adult, Economy
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The best prices from Chicago to Simpson Bay Princess Juliana are usually found in September or February, booked 54 days in advance, depart on a Wednesday or Tuesday and return on a Tuesday

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 Desember 22, 2024.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$323
(Kiwi.com)

One-way from

$127
(Kiwi.com)

Popular in

December

Cheapest in

September

Average price

$819
Provider with most accurate pricing for Chicago (CHI)-Simpson Bay Princess Juliana flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Simpson Bay Princess Juliana flights.
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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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High demand for flights, 5% potential price rise
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Best time to find cheap flights, 1% potential price drop
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Average for round-trip flights in December 2024
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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 Desember 22, 2024.

This Kiwi.com deal was found by Cheapflights users on 12/21. 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.
Kam 12/262:19 pmORD - SXM
2 stops25h 00mMultiple Airlines
Sen 12/303:25 pmSXM - ORD
1 stop21h 39mMultiple Airlines
Deal found 12/21$742
This American Airlines deal was found by Cheapflights users on 12/22. 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.
Sel 12/315:00 amORD - SXM
1 stop9h 09mAmerican Airlines
Sel 1/215:19 pmSXM - ORD
1 stop9h 08mAmerican Airlines
Deal found 12/22$800
This CheapOair deal was found by Cheapflights users on 12/21. 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.
Jum 12/275:11 pmORD - SXM
1 stop19h 19mSpirit Airlines
Sen 12/303:25 pmSXM - ORD
1 stop26h 41mSpirit Airlines
Deal found 12/21$846
This United Airlines deal was found by Cheapflights users on 12/21. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sen 12/306:08 pmORD - SXM
1 stop17h 43mUnited Airlines
Sel 12/314:55 pmSXM - ORD
1 stop8h 30mUnited Airlines
Deal found 12/21$1,075
This Delta deal was found by Cheapflights users on 12/21. 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.
Sel 12/245:40 amORD - SXM
1 stop7h 31mDelta
Min 12/291:50 pmSXM - ORD
1 stop9h 30mDelta
Deal found 12/21$1,165
This Air Canada deal was found by Cheapflights users on 12/21. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sab 12/213:35 pmORD - SXM
1 stop22h 20mAir Canada
Sen 12/305:15 pmSXM - ORD
1 stop17h 42mAir Canada
Deal found 12/21$1,176
This Delta deal was found by Cheapflights users on 12/21. 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.
Jum 12/275:04 pmMDW - SXM
1 stop19h 16mDelta
Sel 12/311:50 pmSXM - MDW
1 stop10h 16mDelta
Deal found 12/21$1,310

Find flights from Chicago to Simpson Bay within your budget

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 Desember 22, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Jum 1/10

1:44 pm-5:18 pm

1 stop25h 34m

Simpson Bay Princess Juliana

Sab 1/18

6:29 pm-12:51 am

1 stop8h 22m

$323

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sab 1/18

5:11 am-2:30 pm

1 stop7h 19m

Simpson Bay Princess Juliana

Sab 1/25

3:25 pm-11:32 pm

1 stop10h 07m

$384

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sab 5/31

7:25 pm-11:07 am

1 stop14h 42m

Simpson Bay Princess Juliana

Sab 6/14

12:15 pm-11:39 pm

1 stop12h 24m

$538

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Min 3/23

5:45 pm-5:15 pm

2 stops22h 30m

Simpson Bay Princess Juliana

Sen 3/31

6:35 pm-1:31 pm

2 stops19h 56m

$569

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sel 3/25

8:30 pm-3:15 pm

1 stop17h 45m

Simpson Bay Princess Juliana

Min 3/30

3:55 pm-10:47 am

1 stop19h 52m

$596

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Rab 1/22

6:00 am-3:16 pm

1 stop7h 16m

Simpson Bay Princess Juliana

Rab 1/29

1:40 pm-10:20 pm

1 stop10h 40m

$630

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Rab 3/26

5:00 am-1:10 pm

1 stop7h 10m

Simpson Bay Princess Juliana

Rab 4/2

2:26 pm-9:24 pm

1 stop7h 58m

$630

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Jum 5/30

4:21 pm-10:58 am

1 stop17h 37m

Simpson Bay Princess Juliana

Sab 6/14

12:18 pm-11:38 pm

1 stop12h 20m

$654

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Kam 1/9

10:19 am-3:17 pm

2 stops26h 58m

Simpson Bay Princess Juliana

Sen 1/13

4:10 pm-12:46 pm

2 stops22h 36m

$827

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Rab 2/5

1:05 pm-11:55 am

2 stops20h 50m

Simpson Bay Princess Juliana

Rab 2/12

10:00 am-8:45 am

3 stops24h 45m

$870

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/21

Showing 1-10 of 19 results
1
2

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 December.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
AranGrantPrice Accuracy3 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.

Travel insights for flights from Chicago to Simpson Bay

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

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 December 13, 2024.

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 54 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 $690). 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 Desember 22, 2024.

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 45% versus a flight in the morning.

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 Desember 22, 2024.
Get a feel of what it's like to fly with Frontier, American Airlines and Spirit 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
8,594 reviews

Food

7.3

Overall

8.0

Boarding

8.2

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
8,594 reviews
Delta
8.0
Very good
8,594 reviews

Food

7.3

Overall

8.0

Boarding

8.2

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.

JetBlue
7.4
Good
3,265 reviews
Delta
8.0
Very good
8,594 reviews

Food

7.3

Overall

8.0

Boarding

8.2

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
9,028 reviews
Delta
8.0
Very good
8,594 reviews

Food

7.3

Overall

8.0

Boarding

8.2

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
7.3
Good
2,812 reviews
Delta
8.0
Very good
8,594 reviews

Food

7.3

Overall

8.0

Boarding

8.2

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
8,594 reviews

Food

7.3

Overall

8.0

Boarding

8.2

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 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 ($384), JetBlue ($538), and Frontier ($569) offers the cheapest pricing from Chicago to Simpson Bay. Users have found that Spirit Airlines is 45% cheaper than the other options available to this destination.

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

    $127 is the cheapest one-way deal found within the past few days, from Frontier. You may also be able to find cheap deals on Spirit Airlines and Delta, with prices starting from $153 and $312, respectively.

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

    On average you can expect to pay $1,080 for a flight from Chicago to Simpson Bay. The cheapest flight overall is $656 while the most popular route, (Chicago O'Hare Intl - Simpson Bay Princess Juliana) is currently priced at $323.

  • 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 $690). 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

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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 Desember 22, 2024.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$259Average$452FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$553Average$731FlexibilityNo cancel feeOn-time71%
DeltaCheapest$554Average$709FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$633Average$889FlexibilityNo cancel feeOn-time69%
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