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$206+ 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 8/27. Fares are subject to change and may not be available on all flights or dates of travel.
SXM — CHI
Aug 4 — Aug 111
Mon 8/4
Mon 8/11
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 July 30, 2025.

Round-trip from

$354
(Gotogate)

One-way from

$206
(FlightHub)

Good one-way deal

$550 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 July 30, 2025.

This Gotogate deal was found by Cheapflights users on 7/28. 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 8/303:05 pmSXM - ORD
1 stop9h 54mSpirit Airlines
Sat 9/65:05 amORD - SXM
1 stop7h 55mSpirit Airlines
Deal found 7/28$354
This Mytrip deal was found by Cheapflights users on 7/28. 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 8/303:05 pmSXM - ORD
1 stop9h 54mMultiple Airlines
Sat 9/611:48 amORD - SXM
3 stops22h 38mMultiple Airlines
Deal found 7/28$463
This American Airlines deal was found by Cheapflights users on 7/30. 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 10/92:40 pmSXM - ORD
2 stops10h 13mAmerican Airlines
Wed 10/159:12 pmORD - SXM
2 stops15h 25mAmerican Airlines
Deal found 7/30$599
This Delta deal was found by Cheapflights users on 7/28. 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 8/303:21 pmSXM - MDW
1 stop25h 02mDelta
Sat 9/66:00 amMDW - SXM
1 stop6h 56mDelta
Deal found 7/28$828
This Mytrip deal was found by Cheapflights users on 7/28. 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 8/166:10 pmSXM - MDW
3 stops24h 27mMultiple Airlines
Sat 8/231:43 pmMDW - SXM
2 stops22h 32mMultiple Airlines
Deal found 7/28$2,089

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 July 30, 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

Sat 8/30

3:05 pm-11:59 pm

1 stop9h 54m

Chicago O'Hare Intl

Sat 9/6

5:05 am-2:00 pm

1 stop7h 55m

$354

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sat 8/30

3:05 pm-11:59 pm

1 stop9h 54m

Chicago O'Hare Intl

Sat 9/6

11:48 am-11:26 am

3 stops22h 38m

$463

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Thu 10/9

2:40 pm-11:53 pm

2 stops10h 13m

Chicago O'Hare Intl

Wed 10/15

9:12 pm-1:37 pm

2 stops15h 25m

$599

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Sat 8/30

3:21 pm-3:23 pm

1 stop25h 02m

Chicago Midway

Sat 9/6

6:00 am-1:56 pm

1 stop6h 56m

$828

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Sat 8/16

6:10 pm-5:37 pm

3 stops24h 27m

Chicago Midway

Sat 8/23

1:43 pm-1:15 pm

2 stops22h 32m

$2,089

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Wed 8/27

3:05 pm-11:59 pm

1 stop9h 54m

$206

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Fri 8/29

3:05 pm-6:41 pm

2 stops28h 36m

$274

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sun 9/28

2:35 pm-12:21 pm

1 stop22h 46m

$293

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Mon 1/19

5:00 pm-9:13 am

1 stop18h 13m

$369

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Wed 10/1

3:20 pm-10:14 pm

1 stop7h 54m

$370

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/28

Showing 1-10 of 16 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.

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated July 30, 2025.
Peruse reviews from past customers who have flown with Delta, Air Transat, and United Airlines from Simpson Bay to Chicago to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,980 reviews

Boarding

8.2

Crew

8.5

Food

7.3

Overall

8.0

Comfort

7.9

Entertainment

7.9

Reviews

1 / 20
8.0
Excellent

Michael,Jul 2025

AMS - ATL

Overall it was great experience, with the exception of snack food. The food offered in two main meals was just fine but for the mid-flight snack, the only option was a large cookie, too sweet and high sugar content. Snacks at the back of the plane were also mainly sweets. There was one nice baked cheddar option but it quickly ran out.
Delta
8.0
Very good
7,980 reviews
Delta
8.0
Very good
7,980 reviews

Boarding

8.2

Crew

8.5

Food

7.3

Overall

8.0

Comfort

7.9

Entertainment

7.9

Reviews

1 / 20
8.0
Excellent

Michael,Jul 2025

AMS - ATL

Overall it was great experience, with the exception of snack food. The food offered in two main meals was just fine but for the mid-flight snack, the only option was a large cookie, too sweet and high sugar content. Snacks at the back of the plane were also mainly sweets. There was one nice baked cheddar option but it quickly ran out.
Air Transat
7.7
Good
424 reviews
Delta
8.0
Very good
7,980 reviews

Boarding

8.2

Crew

8.5

Food

7.3

Overall

8.0

Comfort

7.9

Entertainment

7.9

Reviews

1 / 20
8.0
Excellent

Michael,Jul 2025

AMS - ATL

Overall it was great experience, with the exception of snack food. The food offered in two main meals was just fine but for the mid-flight snack, the only option was a large cookie, too sweet and high sugar content. Snacks at the back of the plane were also mainly sweets. There was one nice baked cheddar option but it quickly ran out.
United Airlines
7.4
Good
8,896 reviews
Delta
8.0
Very good
7,980 reviews

Boarding

8.2

Crew

8.5

Food

7.3

Overall

8.0

Comfort

7.9

Entertainment

7.9

Reviews

1 / 20
8.0
Excellent

Michael,Jul 2025

AMS - ATL

Overall it was great experience, with the exception of snack food. The food offered in two main meals was just fine but for the mid-flight snack, the only option was a large cookie, too sweet and high sugar content. Snacks at the back of the plane were also mainly sweets. There was one nice baked cheddar option but it quickly ran out.
JetBlue
7.3
Good
2,913 reviews
Delta
8.0
Very good
7,980 reviews

Boarding

8.2

Crew

8.5

Food

7.3

Overall

8.0

Comfort

7.9

Entertainment

7.9

Reviews

1 / 20
8.0
Excellent

Michael,Jul 2025

AMS - ATL

Overall it was great experience, with the exception of snack food. The food offered in two main meals was just fine but for the mid-flight snack, the only option was a large cookie, too sweet and high sugar content. Snacks at the back of the plane were also mainly sweets. There was one nice baked cheddar option but it quickly ran out.
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,980 reviews

Boarding

8.2

Crew

8.5

Food

7.3

Overall

8.0

Comfort

7.9

Entertainment

7.9

Reviews

1 / 20
8.0
Excellent

Michael,Jul 2025

AMS - ATL

Overall it was great experience, with the exception of snack food. The food offered in two main meals was just fine but for the mid-flight snack, the only option was a large cookie, too sweet and high sugar content. Snacks at the back of the plane were also mainly sweets. There was one nice baked cheddar option but it quickly ran out.

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 1 airline. Simpson Bay Princess Juliana is conveniently located just 0.5 mi from Simpson Bay’s city center.

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

    According to our current data, Spirit Airlines ($354), American Airlines ($600), and Delta ($828) offers the cheapest pricing from Simpson Bay to Chicago.

  • 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 Spirit Airlines ($206), JetBlue ($293), and Air Canada ($369).

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

    On average you can expect to pay $735 for a flight from Simpson Bay to Chicago. The cheapest flight overall is $389 while the most popular route, (Simpson Bay Princess Juliana - Chicago O'Hare Intl) is currently priced at $354.

  • 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
Valparaiso
Chesterton

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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

Top airline flying from Simpson Bay to Chicago

Discover the top airline that operate flights from Simpson Bay to Chicago. 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 July 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$554Average$680FlexibilityNo cancel feeOn-time71%

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