HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Illinois

$206+ Cheap flights from Simpson Bay (SXM) to Illinois

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 — ORD
Aug 4 — Aug 111
Mon 8/4
Mon 8/11
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Simpson Bay to Illinois with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap flight deals from Simpson Bay to Illinois

Keep the following information in mind while searching for Simpson Bay to Illinois flight deals. Data was last updated July 30, 2025.

Round-trip from

$336
(Flightnetwork)

One-way from

$206
(FlightHub)

Good one-way deal

$550 or less
From Simpson Bay Princess Juliana to Illinois
Search Deals
One-way flight from Simpson Bay Princess Juliana to Illinois
Search Deals
Price to beat on a one-way flight from Simpson Bay Princess Juliana to Illinois.
Search Deals

Find flight deals from Simpson Bay to Illinois

Cheapest flights from Simpson Bay to Illinois
Explore the most affordable flight options available from Simpson Bay to Illinois. 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 Illinois 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 Illinois that are best for you.

Fly from

Simpson Bay

Fly to

Illinois

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
1
2

Best time to book a flight from Simpson Bay to Illinois

Have a flexible travel schedule? Discover the best time to fly to Illinois 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 Illinois
No data available for this route at this time. Please check back soon.

Reviews of airlines servicing Illinois

Get insights into the airlines that provide service to Illinois. 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 Illinois. Reviews last updated July 30, 2025.
Peruse reviews from past customers who have flown with Delta, United Airlines, and JetBlue from Simpson Bay to Illinois 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.
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.
Air Canada
7.1
Good
9,837 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 Illinois. 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 Illinois?

    Located just 0.5 mi from the city center, Simpson Bay Princess Juliana (SXM) is the airport most travelers will use when flying to Illinois from Simpson Bay.

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

    For one-way options, check prices for Spirit Airlines. According to our data, you can fly for as low as $206. Users have also found prices from $293 and $369 on JetBlue and Air Canada, respectively.

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

    While on average a flight from Simpson Bay to Illinois is generally $735, our data shows the cheapest flight currently is $389. When looking at the most popular route, (Simpson Bay Princess Juliana - Chicago O'Hare Intl), you can expect to pay $354 for that flight.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Simpson Bay to Illinois 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 Illinois?

    Currently, August is the cheapest month in which you can book a flight from Simpson Bay to Illinois (average of $245). Flying from Simpson Bay to Illinois 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Simpson Bay to Illinois

See prices for flight routes from nearby airports that may be better suited for you.
Simpson Bay to John F Kennedy Intl flights
Simpson Bay to Newark flights
Simpson Bay to Miami flights
Simpson Bay to LaGuardia flights
Simpson Bay to Fort Lauderdale flights
Simpson Bay to Atlanta flights
Simpson Bay to West Palm Beach flights
Simpson Bay to Orlando flights
Simpson Bay to Los Angeles flights
Simpson Bay to Las Vegas flights
Simpson Bay to Rochester flights
Simpson Bay to O'Hare Intl flights
Simpson Bay to Dulles Intl flights
Simpson Bay to Philadelphia flights
Simpson Bay to Tampa flights
Simpson Bay to Boston flights
Simpson Bay to Charlotte flights
Simpson Bay to Baltimore flights
Simpson Bay to Dallas/Fort Worth flights
Simpson Bay to Midway flights
Simpson Bay to San Francisco flights
Simpson Bay to Reagan-National flights
Simpson Bay to Raleigh flights
Simpson Bay to Denver flights
Simpson Bay to Asheville flights
Simpson Bay to New Orleans flights
Simpson Bay to Sacramento flights
Simpson Bay to Salt Lake City flights
Simpson Bay to San Diego flights
Simpson Bay to Austin flights
Simpson Bay to Detroit flights
Simpson Bay to Sky Harbor Intl flights
Simpson Bay to Madison flights
Simpson Bay to Baton Rouge flights
Simpson Bay to Fort Wayne flights

Top airline flying from Simpson Bay to Illinois

Discover the top airline that operate flights from Simpson Bay to Illinois. 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%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.