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Simpson Bay

$165+ 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 7/30. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SXM
Jun 21 — Jun 281
Sat 6/21
Sat 6/28
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Simpson Bay Princess Juliana are usually found in September or October, booked 89 days in advance, depart on a Tuesday or Monday 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 June 16, 2025.

Round-trip from

$366
(Booking.com)

One-way from

$165
(Flightnetwork)

Popular in

March

Cheapest in

September

Average price

$755

Good round-trip deal

$622 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. 5% potential increase in price ($39 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($11 potential savings vs. average RT price).
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Average for round-trip flights in June 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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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 June 16, 2025.

This Booking.com deal was found by Cheapflights users on 6/13. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/65:05 amORD - SXM
1 stop8h 19mMultiple Airlines
Sat 9/131:58 pmSXM - ORD
1 stop23h 59mMultiple Airlines
Deal found 6/13$366
This Cheapflightsfares deal was found by Cheapflights users on 6/14. 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 8/165:05 amORD - SXM
1 stop8h 22mSpirit Airlines
Sat 8/233:27 pmSXM - ORD
1 stop9h 32mSpirit Airlines
Deal found 6/14$377
This Frontier deal was found by Cheapflights users on 6/14. 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 6/209:12 pmMDW - SXM
1 stop13h 14mFrontier
Sat 6/2812:36 pmSXM - MDW
1 stop8h 41mFrontier
Deal found 6/14$391
This Air Canada deal was found by Cheapflights users on 6/15. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/57:20 amORD - SXM
1 stop28h 35mAir Canada
Fri 12/125:15 pmSXM - ORD
2 stops23h 30mAir Canada
Deal found 6/15$503
This American Airlines deal was found by Cheapflights users on 6/14. 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.
Tue 7/2910:05 pmORD - SXM
2 stops14h 44mAmerican Airlines
Tue 8/52:50 pmSXM - ORD
2 stops11h 09mAmerican Airlines
Deal found 6/14$576
This Kiwi.com deal was found by Cheapflights users on 6/14. 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.
Wed 6/255:50 pmMDW - SXM
1 stop18h 25mMultiple Airlines
Sun 6/292:10 pmSXM - MDW
1 stop19h 35mMultiple Airlines
Deal found 6/14$595
This Delta deal was found by Cheapflights users on 6/14. 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 11/156:00 amMDW - SXM
1 stop6h 35mDelta
Sat 11/224:00 pmSXM - MDW
1 stop7h 44mDelta
Deal found 6/14$727
This WestJet deal was found by Cheapflights users on 6/14. 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 WestJet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/247:21 pmMDW - SXM
2 stops40h 54mWestJet
Thu 7/33:10 pmSXM - MDW
2 stops31h 35mWestJet
Deal found 6/14$3,201

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 June 16, 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 9/6

5:05 am-2:24 pm

1 stop8h 19m

Simpson Bay Princess Juliana

Sat 9/13

1:58 pm-12:57 pm

1 stop23h 59m

$366

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sat 8/16

5:05 am-2:27 pm

1 stop8h 22m

Simpson Bay Princess Juliana

Sat 8/23

3:27 pm-11:59 pm

1 stop9h 32m

$377

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Fri 6/20

9:12 pm-11:26 am

1 stop13h 14m

Simpson Bay Princess Juliana

Sat 6/28

12:36 pm-8:17 pm

1 stop8h 41m

$391

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Fri 12/5

7:20 am-1:55 pm

1 stop28h 35m

Simpson Bay Princess Juliana

Fri 12/12

5:15 pm-2:45 pm

2 stops23h 30m

$503

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Tue 7/29

10:05 pm-1:49 pm

2 stops14h 44m

Simpson Bay Princess Juliana

Tue 8/5

2:50 pm-12:59 am

2 stops11h 09m

$576

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Wed 6/25

5:50 pm-1:15 pm

1 stop18h 25m

Simpson Bay Princess Juliana

Sun 6/29

2:10 pm-8:45 am

1 stop19h 35m

$595

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Wed 8/13

6:04 am-1:56 pm

1 stop6h 52m

Simpson Bay Princess Juliana

Wed 8/20

3:21 pm-8:35 am

2 stops18h 14m

$792

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Tue 6/24

7:21 pm-1:15 pm

2 stops40h 54m

Simpson Bay Princess Juliana

Thu 7/3

3:10 pm-9:45 pm

2 stops31h 35m

$3,201

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Wed 7/30

5:05 am-2:00 pm

1 stop7h 55m

$165

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Tue 7/29

1:07 am-11:24 am

1 stop9h 17m

$290

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/15

Showing 1-10 of 14 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 June 13, 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 $657). 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 June 16, 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 56% 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 June 16, 2025.
Get a feel of what it's like to fly with Delta, Copa Airlines and American 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
7,963 reviews

Boarding

8.2

Comfort

7.9

Overall

8.0

Entertainment

7.9

Crew

8.5

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
7,963 reviews
Delta
8.0
Very good
7,963 reviews

Boarding

8.2

Comfort

7.9

Overall

8.0

Entertainment

7.9

Crew

8.5

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!
Copa Airlines
7.5
Good
1,452 reviews
Delta
8.0
Very good
7,963 reviews

Boarding

8.2

Comfort

7.9

Overall

8.0

Entertainment

7.9

Crew

8.5

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
7,963 reviews

Boarding

8.2

Comfort

7.9

Overall

8.0

Entertainment

7.9

Crew

8.5

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!
WestJet
7.2
Good
2,873 reviews
Delta
8.0
Very good
7,963 reviews

Boarding

8.2

Comfort

7.9

Overall

8.0

Entertainment

7.9

Crew

8.5

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!
Air Canada
7.1
Good
9,553 reviews
Delta
8.0
Very good
7,963 reviews

Boarding

8.2

Comfort

7.9

Overall

8.0

Entertainment

7.9

Crew

8.5

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.

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

    According to our current data, Spirit Airlines ($377), Frontier ($391), and Air Canada ($503) offers the cheapest pricing from Chicago to Simpson Bay. Users have found that Spirit Airlines is 47% cheaper than the other options available to this destination.

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

    $165 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 Copa Airlines and Delta, with prices starting from $290 and $293, respectively.

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

    On average you can expect to pay $752 for a flight from Chicago to Simpson Bay. The cheapest flight overall is $607 while the most popular route, (Chicago O'Hare Intl - Simpson Bay Princess Juliana) is currently priced at $366.

  • 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 $657). 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
St. Louis to Simpson Bay flights
Midway 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 June 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$335Average$400FlexibilityNo cancel feeOn-time65%
DeltaCheapest$554Average$721FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$614Average$709FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$654Average$912FlexibilityNo cancel feeOn-time69%

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