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$197+ Cheap flights from Simpson Bay (SXM) to Chicago (CHI)

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 12/24. Fares are subject to change and may not be available on all flights or dates of travel.
SXM — CHI
Dec 4 — Dec 111
Thu 12/4
Thu 12/11
1 adult, Economy
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Find flight deals from Simpson Bay to Chicago

Cheapest flights from Simpson Bay to Chicago
Explore the most affordable flight options available from Simpson Bay to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 4, 2025.

This Kiwi.com deal was found by Cheapflights users on 11/2. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/213:20 pmSXM - ORD
1 stop9h 53mMultiple Airlines
Sun 11/2311:48 amORD - SXM
1 stop24h 27mMultiple Airlines
Deal found 11/2$374
This Mytrip deal was found by Cheapflights users on 11/2. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/223:20 pmSXM - ORD
2 stops19h 41mSpirit Airlines
Sat 11/295:00 amORD - SXM
1 stop7h 15mSpirit Airlines
Deal found 11/2$397
This Mytrip deal was found by Cheapflights users on 11/2. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/213:20 pmSXM - ORD
1 stop9h 53mSpirit Airlines
Sun 11/233:53 pmORD - SXM
2 stops20h 22mSpirit Airlines
Deal found 11/2$416
This Priceline deal was found by Cheapflights users on 11/1. 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.
Wed 12/173:20 pmSXM - ORD
1 stop10h 49mSpirit Airlines
Wed 12/245:00 amORD - SXM
1 stop7h 15mSpirit Airlines
Deal found 11/1$436
This Gotogate deal was found by Cheapflights users on 11/2. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/223:40 pmSXM - ORD
1 stop21h 38mMultiple Airlines
Sat 11/295:00 amORD - SXM
1 stop7h 15mMultiple Airlines
Deal found 11/2$488
This Mytrip deal was found by Cheapflights users on 11/1. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/173:20 pmSXM - ORD
1 stop10h 49mMultiple Airlines
Wed 12/249:34 amORD - SXM
2 stops22h 51mMultiple Airlines
Deal found 11/1$516
This Mytrip deal was found by Cheapflights users on 11/1. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/171:05 pmSXM - MDW
2 stops23h 00mMultiple Airlines
Wed 12/2411:00 amMDW - SXM
2 stops22h 55mMultiple Airlines
Deal found 11/1$839
This Delta deal was found by Cheapflights users on 11/1. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/173:53 pmSXM - MDW
1 stop9h 54mDelta
Wed 12/246:00 amMDW - SXM
1 stop6h 50mDelta
Deal found 11/1$1,008
This Mytrip deal was found by Cheapflights users on 11/2. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/223:40 pmSXM - MDW
3 stops28h 38mMultiple Airlines
Sat 11/291:47 pmMDW - SXM
2 stops23h 34mMultiple Airlines
Deal found 11/2$1,023
This Delta deal was found by Cheapflights users on 11/2. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/223:30 pmSXM - MDW
1 stop10h 10mDelta
Sat 11/295:34 pmMDW - SXM
1 stop19h 21mDelta
Deal found 11/2$1,083
This Delta deal was found by Cheapflights users on 11/2. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/214:20 pmSXM - MDW
1 stop9h 20mDelta
Sun 11/236:00 amMDW - SXM
1 stop6h 55mDelta
Deal found 11/2$1,204
This Delta deal was found by Cheapflights users on 11/3. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/181:45 pmSXM - MDW
1 stop12h 02mDelta
Thu 12/256:00 amMDW - SXM
1 stop6h 50mDelta
Deal found 11/3$1,244

Cheap flight deals from Simpson Bay to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Simpson Bay (SXM) to Chicago (CHI). 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 November 4, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$374
(Kiwi.com)

One-way from

$197
(Cheapflightsfares)

Good one-way deal

$389 or less
Provider with most accurate pricing for Simpson Bay Princess Juliana-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Simpson Bay Princess Juliana-Chicago (CHI) flights.
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From Simpson Bay Princess Juliana to Chicago (CHI)
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One-way flight from Simpson Bay Princess Juliana to Chicago (CHI)
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Price to beat on a one-way flight from Simpson Bay Princess Juliana to Chicago (CHI).
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Cheapflights Fare Finder

 
Customize your flight search to find flights from Simpson Bay to Chicago 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 November 4, 2025.
Use the filters below to find and compare flights from Simpson Bay to Chicago that are best for you.

Fly from

Simpson Bay

Fly to

Chicago

Route

Depart

Return

Price

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Fri 11/21

3:20 pm-11:13 pm

1 stop9h 53m

Chicago O'Hare Intl

Sun 11/23

11:48 am-2:15 pm

1 stop24h 27m

$374

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sat 11/22

3:20 pm-9:01 am

2 stops19h 41m

Chicago O'Hare Intl

Sat 11/29

5:00 am-2:15 pm

1 stop7h 15m

$397

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Fri 11/21

3:20 pm-7:43 am

2 stops18h 23m

Chicago O'Hare Intl

Sun 11/23

3:53 pm-2:15 pm

2 stops20h 22m

$424

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Wed 12/17

3:20 pm-12:09 am

1 stop10h 49m

Chicago O'Hare Intl

Wed 12/24

5:00 am-2:15 pm

1 stop7h 15m

$436

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sat 11/22

3:40 pm-11:18 am

1 stop21h 38m

Chicago O'Hare Intl

Sat 11/29

5:00 am-2:15 pm

1 stop7h 15m

$488

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sat 2/14

2:52 pm-11:13 pm

1 stop10h 21m

Chicago O'Hare Intl

Sat 2/21

6:25 pm-1:50 pm

1 stop17h 25m

$509

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Fri 3/6

4:26 pm-3:23 pm

2 stops24h 57m

Chicago Midway

Tue 3/10

1:00 pm-11:15 am

2 stops21h 15m

$632

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Wed 12/17

1:05 pm-10:05 am

2 stops23h 00m

Chicago Midway

Wed 12/24

11:00 am-11:55 am

2 stops22h 55m

$839

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Wed 12/17

3:53 pm-11:47 pm

1 stop9h 54m

Chicago Midway

Wed 12/24

6:00 am-2:50 pm

1 stop6h 50m

$1,008

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Mon 2/2

4:28 pm-11:42 pm

1 stop9h 14m

$201

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/3

Showing 1-10 of 24 results
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Compare providers for flights from Simpson Bay to Chicago

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 Simpson Bay to Chicago in November.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*1 star
ExpediaPrice Accuracy2 starsTrust Score*3 stars
eDreamsPrice 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 Simpson Bay-Chicago flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Simpson Bay-Chicago flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Simpson Bay-Chicago flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Simpson Bay-Chicago flights, Cheapflights users trust eDreams the most. eDreams 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 Simpson Bay-Chicago 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 Simpson Bay to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Simpson Bay 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 Simpson Bay to Chicago

What is the cheapest time of day to fly from SXM to CHI?

Find hourly flight availability from Simpson Bay to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated November 4, 2025.

When flying from Simpson Bay to Chicago, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Related info for your journey

Find useful and relevant information for your journey from Simpson Bay to Chicago. 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 from for flights from Simpson Bay to Chicago?

    Most people fly from Simpson Bay Princess Juliana (SXM) if they book a flight from Simpson Bay to Chicago. On average, Princess Juliana has 0 outbound flights to Chicago per day from 0 airlines. Simpson Bay Princess Juliana is conveniently located just 0.5 mi from Simpson Bay’s city center.

  • How long is the flight from Simpson Bay to Chicago?

    Airlines like Spirit Airlines and Delta fly from Simpson Bay to Chicago in about 19h 41m. The time it takes to get you to your destination can typically vary by up to 5h 16m. The distance between Simpson Bay and Chicago is about 2204 mi. Both multi-stop and nonstop flights can be found to your destination and back.

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

    On average you can expect to pay $515 for a flight from Simpson Bay to Chicago. The cheapest flight overall is $381 while the most popular route, (Simpson Bay Princess Juliana - Chicago O'Hare Intl) is currently priced at $374.

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

    Yes. In addition to deals on Simpson Bay to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

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

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Simpson Bay to Chicago.

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

    Yes. Cheapflights offers flight deals from Simpson Bay to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

See more FAQs

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Porter
Benton Harbor

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Alternative routes for Simpson Bay to Chicago

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