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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 3/2. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SXM
Jan 26 — Feb 21
Sun 1/26
Sun 2/2
1 adult, Economy
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The best prices from Chicago to Simpson Bay Princess Juliana are usually found in February or September, booked 54 days in advance, depart on a Tuesday or Monday 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 January 21, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$401
(Mytrip)

One-way from

$139
(Kiwi.com)

Popular in

July

Cheapest in

February

Average price

$694

Good round-trip deal

$861 or less

Good one-way deal

$353 or less
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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Highest demand for flights based on searches. 6% potential increase in price ($50 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($9 potential savings vs. average RT price).
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Average for round-trip flights in January 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 January 21, 2025.

This Mytrip deal was found by Cheapflights users on 1/20. 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.
Wed 3/55:10 amORD - SXM
1 stop7h 18mSpirit Airlines
Wed 3/122:33 pmSXM - ORD
2 stops18h 11mSpirit Airlines
Deal found 1/20$401
This Kiwi.com deal was found by Cheapflights users on 1/21. 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.
Sun 3/27:13 pmORD - SXM
2 stops19h 56mMultiple Airlines
Thu 3/611:55 amSXM - ORD
1 stop9h 56mMultiple Airlines
Deal found 1/21$409
This Priceline deal was found by Cheapflights users on 1/20. 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.
Thu 4/108:00 amMDW - SXM
2 stops32h 05mFrontier
Mon 4/146:15 pmSXM - MDW
2 stops26h 30mFrontier
Deal found 1/20$507
This Kiwi.com deal was found by Cheapflights users on 1/19. 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 2/211:05 pmMDW - SXM
1 stop21h 10mMultiple Airlines
Mon 2/246:31 pmSXM - MDW
2 stops22h 42mMultiple Airlines
Deal found 1/19$569
This Travelocity deal was found by Cheapflights users on 1/20. 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.
Sun 3/236:39 pmORD - SXM
1 stop19h 36mAir Canada
Mon 3/314:15 pmSXM - ORD
1 stop28h 20mAir Canada
Deal found 1/20$591
This Frontier deal was found by Cheapflights users on 1/20. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/306:01 pmORD - SXM
2 stops15h 57mFrontier
Sat 6/1412:18 pmSXM - ORD
1 stop12h 20mFrontier
Deal found 1/20$621
This Delta deal was found by Cheapflights users on 1/19. 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 3/56:00 amMDW - SXM
1 stop7h 16mDelta
Wed 3/121:40 pmSXM - MDW
1 stop9h 43mDelta
Deal found 1/19$641
This Kissandfly.com deal was found by Cheapflights users on 1/20. 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 Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/66:00 amMDW - SXM
1 stop7h 16mKLM
Thu 3/131:40 pmSXM - MDW
2 stops23h 56mKLM
Deal found 1/20$1,047
This Mytrip deal was found by Cheapflights users on 1/20. 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 2/31:26 pmMDW - SXM
2 stops23h 50mWestJet
Tue 2/114:10 pmSXM - MDW
2 stops22h 32mWestJet
Deal found 1/20$1,188

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 January 21, 2025.

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Fly to

Any airport

Route

Depart

Return

Price

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Wed 3/5

5:10 am-2:28 pm

1 stop7h 18m

Simpson Bay Princess Juliana

Wed 3/12

2:33 pm-7:44 am

2 stops18h 11m

$401

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sun 3/2

7:13 pm-5:09 pm

2 stops19h 56m

Simpson Bay Princess Juliana

Thu 3/6

11:55 am-7:51 pm

1 stop9h 56m

$409

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Thu 4/10

8:00 am-5:05 pm

2 stops32h 05m

Simpson Bay Princess Juliana

Mon 4/14

6:15 pm-7:45 pm

2 stops26h 30m

$507

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Fri 2/21

1:05 pm-12:15 pm

1 stop21h 10m

Simpson Bay Princess Juliana

Mon 2/24

6:31 pm-3:13 pm

2 stops22h 42m

$569

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sun 3/23

6:39 pm-3:15 pm

1 stop19h 36m

Simpson Bay Princess Juliana

Mon 3/31

4:15 pm-7:35 pm

1 stop28h 20m

$591

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Fri 5/30

6:01 pm-10:58 am

2 stops15h 57m

Simpson Bay Princess Juliana

Sat 6/14

12:18 pm-11:38 pm

1 stop12h 20m

$621

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Wed 3/5

6:00 am-3:16 pm

1 stop7h 16m

Simpson Bay Princess Juliana

Wed 3/12

1:40 pm-10:23 pm

1 stop9h 43m

$641

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Thu 3/6

6:00 am-3:16 pm

1 stop7h 16m

Simpson Bay Princess Juliana

Thu 3/13

1:40 pm-12:36 pm

2 stops23h 56m

$1,047

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Mon 2/3

1:26 pm-3:16 pm

2 stops23h 50m

Simpson Bay Princess Juliana

Tue 2/11

4:10 pm-12:42 pm

2 stops22h 32m

$1,188

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sun 3/2

2:29 pm-5:09 pm

2 stops24h 40m

$139

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/19

Showing 1-10 of 17 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 January.
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*3 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 January 17, 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 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 July is currently the most expensive (average of $684). 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 January 21, 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 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 January 21, 2025.
Get a feel of what it's like to fly with Spirit Airlines, Air Canada and Delta 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
8,521 reviews

Crew

8.6

Entertainment

7.9

Overall

8.0

Boarding

8.2

Food

7.3

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
8,521 reviews
Delta
8.0
Very good
8,521 reviews

Crew

8.6

Entertainment

7.9

Overall

8.0

Boarding

8.2

Food

7.3

Comfort

8.0

Reviews

1 / 10

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

KLM
7.8
Good
1,341 reviews
Delta
8.0
Very good
8,521 reviews

Crew

8.6

Entertainment

7.9

Overall

8.0

Boarding

8.2

Food

7.3

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
8,984 reviews
Delta
8.0
Very good
8,521 reviews

Crew

8.6

Entertainment

7.9

Overall

8.0

Boarding

8.2

Food

7.3

Comfort

8.0

Reviews

1 / 10

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

WestJet
7.2
Good
2,829 reviews
Delta
8.0
Very good
8,521 reviews

Crew

8.6

Entertainment

7.9

Overall

8.0

Boarding

8.2

Food

7.3

Comfort

8.0

Reviews

1 / 10

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

Air Canada
7.0
Good
8,633 reviews
Delta
8.0
Very good
8,521 reviews

Crew

8.6

Entertainment

7.9

Overall

8.0

Boarding

8.2

Food

7.3

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 ($401), Frontier ($507), and Air Canada ($591) offers the cheapest pricing from Chicago to Simpson Bay. Users have found that Spirit Airlines is 43% cheaper than the other options available to this destination.

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

    $151 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 Air Canada and United Airlines, with prices starting from $253 and $338, respectively.

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

    On average you can expect to pay $703 for a flight from Chicago to Simpson Bay. The cheapest flight overall is $308 while the most popular route, (Chicago O'Hare Intl - Simpson Bay Princess Juliana) is currently priced at $336.

  • 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 $684). 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.

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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 January 21, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$282Average$445FlexibilityNo cancel feeOn-time65%
DeltaCheapest$554Average$761FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$579Average$731FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$644Average$877FlexibilityNo cancel feeOn-time69%
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