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$160+ 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 3/7. Fares are subject to change and may not be available on all flights or dates of travel.
SXM — CHI
Mar 14 — Mar 211
Sat 3/14
Sat 3/21
1 adult, Economy
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Cheap 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 February 12, 2026.

This Cheapflightsfares deal was found by Cheapflights users on 2/9. 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.
Thu 5/72:11 pm
SXM
-
ORD
1 stop10h 30m
Spirit Airlines
Mon 5/115:15 am
ORD
-
SXM
1 stop7h 01m
Spirit Airlines
Deal found 2/9$339
This Priceline deal was found by Cheapflights users on 2/9. 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 4/232:11 pm
SXM
-
ORD
1 stop10h 30m
Spirit Airlines
Sun 5/35:15 am
ORD
-
SXM
1 stop7h 01m
Spirit Airlines
Deal found 2/9$340
This Trip.com deal was found by Cheapflights users on 2/9. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/262:20 pm
SXM
-
ORD
1 stop9h 57m
Spirit Airlines
Thu 4/25:05 am
ORD
-
SXM
1 stop7h 25m
Spirit Airlines
Deal found 2/9$431
This Mytrip deal was found by Cheapflights users on 2/11. 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.
Thu 5/72:35 pm
SXM
-
ORD
1 stop10h 39m
Spirit Airlines
Thu 5/145:05 am
ORD
-
SXM
1 stop7h 25m
Spirit Airlines
Deal found 2/11$450
This Kiwi.com deal was found by Cheapflights users on 2/9. 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.
Thu 3/262:20 pm
SXM
-
ORD
2 stops21h 32m
Multiple Airlines
Thu 4/25:05 am
ORD
-
SXM
1 stop7h 25m
Multiple Airlines
Deal found 2/9$464
This Mytrip deal was found by Cheapflights users on 2/9. 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.
Thu 3/262:40 pm
SXM
-
ORD
2 stops29h 12m
Air Canada
Thu 4/26:40 pm
ORD
-
SXM
2 stops41h 55m
Air Canada
Deal found 2/9$490
This Mytrip deal was found by Cheapflights users on 2/11. 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.
Thu 5/72:55 pm
SXM
-
ORD
2 stops18h 03m
Multiple Airlines
Thu 5/145:05 am
ORD
-
SXM
1 stop7h 25m
Multiple Airlines
Deal found 2/11$511
This Mytrip deal was found by Cheapflights users on 2/9. 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.
Thu 4/232:11 pm
SXM
-
ORD
1 stop10h 30m
Multiple Airlines
Sun 5/38:45 am
ORD
-
SXM
2 stops28h 05m
Multiple Airlines
Deal found 2/9$524
This Kiwi.com deal was found by Cheapflights users on 2/11. 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 3/152:20 pm
SXM
-
ORD
1 stop21h 57m
Spirit Airlines
Sun 3/226:01 pm
ORD
-
SXM
2 stops18h 14m
Spirit Airlines
Deal found 2/11$539
This Southwest deal was found by Cheapflights users on 2/9. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/232:35 pm
SXM
-
MDW
1 stop10h 05m
Southwest
Sun 5/35:05 am
MDW
-
SXM
1 stop8h 20m
Southwest
Deal found 2/9$546
This Vliegwinkel deal was found by Cheapflights users on 2/11. 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 Vliegwinkel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/152:40 pm
SXM
-
ORD
1 stop21h 38m
Air Canada
Sun 3/228:00 am
ORD
-
SXM
1 stop30h 00m
Air Canada
Deal found 2/11$596
This Air Canada deal was found by Cheapflights users on 2/10. 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.
Sat 2/145:00 pm
SXM
-
ORD
1 stop18h 13m
Air Canada
Sat 2/2112:50 pm
ORD
-
SXM
1 stop23h 50m
Air Canada
Deal found 2/10$606

Find 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 February 12, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$339
(Cheapflightsfares)

One-way from

$160
(Super.com)

Good one-way deal

$577 or less
Provider with most accurate pricing for Simpson Bay Princess Juliana-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Simpson Bay Princess Juliana-Chicago (CHI) flights.
Search Deals
From Simpson Bay Princess Juliana to Chicago (CHI)
Search Deals
One-way flight from Simpson Bay Princess Juliana to Chicago (CHI)
Search Deals
Price to beat on a one-way flight from Simpson Bay Princess Juliana to Chicago (CHI).
Search Deals

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 February 12, 2026.
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

Thu 5/7

2:11 pm-11:41 pm

1 stop10h 30m

Chicago O'Hare Intl

Mon 5/11

5:15 am-1:16 pm

1 stop7h 01m

$339

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Thu 4/23

2:11 pm-11:41 pm

1 stop10h 30m

Chicago O'Hare Intl

Sun 5/3

5:15 am-1:16 pm

1 stop7h 01m

$340

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Thu 3/26

2:20 pm-11:17 pm

1 stop9h 57m

Chicago O'Hare Intl

Thu 4/2

5:05 am-1:30 pm

1 stop7h 25m

$431

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Thu 5/7

2:35 pm-12:14 am

1 stop10h 39m

Chicago O'Hare Intl

Thu 5/14

5:05 am-1:30 pm

1 stop7h 25m

$450

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Thu 3/26

2:20 pm-10:52 am

2 stops21h 32m

Chicago O'Hare Intl

Thu 4/2

5:05 am-1:30 pm

1 stop7h 25m

$464

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Thu 3/26

2:40 pm-6:52 pm

2 stops29h 12m

Chicago O'Hare Intl

Thu 4/2

6:40 pm-1:35 pm

2 stops41h 55m

$490

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Thu 5/7

2:55 pm-7:58 am

2 stops18h 03m

Chicago O'Hare Intl

Thu 5/14

5:05 am-1:30 pm

1 stop7h 25m

$511

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Thu 4/23

2:11 pm-11:41 pm

1 stop10h 30m

Chicago O'Hare Intl

Sun 5/3

8:45 am-1:50 pm

2 stops28h 05m

$524

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sun 3/15

2:20 pm-11:17 am

1 stop21h 57m

Chicago O'Hare Intl

Sun 3/22

6:01 pm-1:15 pm

2 stops18h 14m

$539

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Thu 4/23

2:35 pm-11:40 pm

1 stop10h 05m

Chicago Midway

Sun 5/3

5:05 am-2:25 pm

1 stop8h 20m

$546

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/10

Showing 1-10 of 29 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 February.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*3 stars
ExpediaPrice Accuracy1 starTrust 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 FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Simpson Bay-Chicago flight deals on Cheapflights vs. FlightHub >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 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 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 February 12, 2026.

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, Southwest, and Delta fly from Simpson Bay to Chicago in about 10h 05m. The time it takes to get you to your destination can typically vary by up to 31m. The distance between Simpson Bay and Chicago is about 2189 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 $582 for a flight from Simpson Bay to Chicago. The cheapest flight overall is $288 while the most popular route, (Simpson Bay Princess Juliana - Chicago O'Hare Intl) is currently priced at $311.

  • 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
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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Alternative routes for Simpson Bay to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
Simpson Bay to O'Hare Intl flights
Simpson Bay to Midway flights

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