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$199+ 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 11/14. Fares are subject to change and may not be available on all flights or dates of travel.
SXM — CHI
Oct 17 — Oct 241
Fri 10/17
Fri 10/24
1 adult, Economy
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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 September 17, 2025.

Round-trip from

$350
(Priceline)

One-way from

$199
(Cheapflightsfares)

Good one-way deal

$389 or less
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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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 September 17, 2025.

This Mytrip deal was found by Cheapflights users on 9/16. 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 10/203:05 pmSXM - ORD
1 stop9h 40mSpirit Airlines
Fri 10/244:44 pmORD - SXM
3 stops20h 16mSpirit Airlines
Deal found 9/16$440
This JetBlue deal was found by Cheapflights users on 9/15. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/65:44 pmSXM - ORD
1 stop29h 08mJetBlue
Wed 11/126:44 amORD - SXM
1 stop7h 54mJetBlue
Deal found 9/15$460
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/33:05 pmSXM - ORD
1 stop8h 43mMultiple Airlines
Wed 10/86:58 pmORD - SXM
2 stops39h 29mMultiple Airlines
Deal found 9/15$496
This American Airlines deal was found by Cheapflights users on 9/15. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/62:51 pmSXM - ORD
1 stop10h 49mAmerican Airlines
Wed 11/127:00 amORD - SXM
1 stop7h 22mAmerican Airlines
Deal found 9/15$503
This Trip.com deal was found by Cheapflights users on 9/16. 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.
Sun 10/261:20 pmSXM - ORD
Nonstop6h 01mUnited Airlines
Sun 11/28:45 amORD - SXM
Nonstop5h 12mUnited Airlines
Deal found 9/16$512
This Mytrip deal was found by Cheapflights users on 9/15. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/33:05 pmSXM - ORD
1 stop8h 43mSpirit Airlines
Wed 10/86:58 pmORD - SXM
3 stops42h 02mSpirit Airlines
Deal found 9/15$521
This Delta deal was found by Cheapflights users on 9/15. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/64:14 pmSXM - MDW
2 stops18h 26mDelta
Wed 11/126:48 pmMDW - SXM
2 stops18h 07mDelta
Deal found 9/15$600
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/64:20 pmSXM - MDW
1 stop19h 45mMultiple Airlines
Wed 11/124:15 pmMDW - SXM
1 stop21h 06mMultiple Airlines
Deal found 9/15$668
This Delta deal was found by Cheapflights users on 9/16. 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.
Mon 10/203:14 pmSXM - MDW
1 stop8h 00mDelta
Fri 10/246:00 amMDW - SXM
1 stop6h 49mDelta
Deal found 9/16$913
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/263:20 pmSXM - MDW
1 stop19h 45mMultiple Airlines
Sun 11/211:00 amMDW - SXM
2 stops21h 50mMultiple Airlines
Deal found 9/15$944
This Kiwi.com deal was found by Cheapflights users on 9/16. 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 9/2112:25 pmSXM - MDW
2 stops21h 14mMultiple Airlines
Sat 9/279:35 amMDW - SXM
1 stop26h 39mMultiple Airlines
Deal found 9/16$972
This Delta deal was found by Cheapflights users on 9/15. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/263:14 pmSXM - MDW
1 stop8h 00mDelta
Sun 11/25:00 amMDW - SXM
1 stop6h 49mDelta
Deal found 9/15$978

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 September 17, 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

Mon 10/20

3:05 pm-11:45 pm

1 stop9h 40m

Chicago O'Hare Intl

Fri 10/24

4:44 pm-2:00 pm

3 stops20h 16m

$440

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Thu 11/6

5:44 pm-8:52 pm

1 stop29h 08m

Chicago O'Hare Intl

Wed 11/12

6:44 am-4:38 pm

1 stop7h 54m

$460

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Fri 10/3

3:05 pm-10:48 pm

1 stop8h 43m

Chicago O'Hare Intl

Wed 10/8

6:58 pm-11:27 am

2 stops39h 29m

$496

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Thu 11/6

2:51 pm-11:40 pm

1 stop10h 49m

Chicago O'Hare Intl

Wed 11/12

7:00 am-4:22 pm

1 stop7h 22m

$503

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sun 10/26

4:00 pm-9:02 am

1 stop18h 02m

Chicago O'Hare Intl

Sun 11/2

8:45 am-3:57 pm

Nonstop5h 12m

$518

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Fri 10/3

3:05 pm-10:48 pm

1 stop8h 43m

Chicago O'Hare Intl

Wed 10/8

6:58 pm-2:00 pm

3 stops42h 02m

$521

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Thu 11/6

4:14 pm-8:40 am

2 stops18h 26m

Chicago Midway

Wed 11/12

6:48 pm-2:55 pm

2 stops18h 07m

$600

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Fri 3/6

4:26 pm-3:25 pm

2 stops24h 59m

Chicago Midway

Tue 3/10

9:30 am-11:15 am

2 stops24h 45m

$697

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Thu 11/6

4:20 pm-10:05 am

1 stop19h 45m

Chicago Midway

Wed 11/12

11:00 am-3:21 pm

1 stop26h 21m

$698

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sat 12/13

4:30 pm-12:08 am

1 stop9h 38m

$229

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/16

Showing 1-10 of 22 results
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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
No data available for this route at this time. Please check back soon.

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, JetBlue, and American Airlines fly from Simpson Bay to Chicago in about 9h 40m. The time it takes to get you to your destination can typically vary by up to 19h 28m. 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 airlines to fly from Simpson Bay to Chicago one-way?

    The cheapest airlines for a one-way flight from Simpson Bay to Chicago are Frontier ($229), Air Canada ($231), and Spirit Airlines ($268).

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

    On average you can expect to pay $479 for a flight from Simpson Bay to Chicago. The cheapest flight overall is $314 while the most popular route, (Simpson Bay Princess Juliana - Chicago O'Hare Intl) is currently priced at $400.

  • 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.

  • What is the cheapest month to book a flight from Simpson Bay to Chicago?

    Currently, August is the cheapest month in which you can book a flight from Simpson Bay to Chicago (average of $245). Flying from Simpson Bay to Chicago in March is currently the most expensive (average of $321). 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

Traveling to a place near Chicago?

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

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Alternative routes for Simpson Bay to Chicago

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