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$359+ 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 5/13. Fares are subject to change and may not be available on all flights or dates of travel.
SXM — ORD
Apr 29 — May 61
Tue 4/29
Tue 5/6
1 adult, Economy
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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 April 24, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$443
(Frontier)

One-way from

$359
(Kiwi.com)

Good one-way deal

$554 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 Illinois
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One-way flight from Simpson Bay Princess Juliana to Illinois
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Price to beat on a one-way flight from Simpson Bay Princess Juliana to Illinois.
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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 April 24, 2025.

This Frontier deal was found by Cheapflights users on 4/23. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/712:33 pmSXM - ORD
1 stop12h 33mFrontier
Sat 6/145:01 amORD - SXM
2 stops11h 15mFrontier
Deal found 4/23$443
This Booking.com deal was found by Cheapflights users on 4/23. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/712:33 pmSXM - ORD
1 stop12h 33mMultiple Airlines
Sat 6/145:05 amORD - SXM
1 stop7h 55mMultiple Airlines
Deal found 4/23$474
This Mytrip deal was found by Cheapflights users on 4/23. 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 6/73:05 pmSXM - ORD
2 stops19h 19mSpirit Airlines
Sat 6/149:28 pmORD - SXM
3 stops39h 32mSpirit Airlines
Deal found 4/23$553
This JetBlue deal was found by Cheapflights users on 4/23. 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.
Tue 8/2612:15 pmSXM - ORD
1 stop12h 10mJetBlue
Sat 8/306:00 amORD - SXM
1 stop7h 41mJetBlue
Deal found 4/23$575
This American Airlines deal was found by Cheapflights users on 4/23. 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 10/94:10 pmSXM - ORD
1 stop8h 47mAmerican Airlines
Wed 10/156:00 amORD - SXM
1 stop8h 10mAmerican Airlines
Deal found 4/23$618
This WestJet deal was found by Cheapflights users on 4/23. 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 WestJet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/92:10 pmSXM - ORD
2 stops27h 33mWestJet
Wed 10/151:16 pmORD - SXM
2 stops23h 03mWestJet
Deal found 4/23$1,335
This United Airlines deal was found by Cheapflights users on 4/23. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/911:55 amSXM - ORD
3 stops31h 55mUnited Airlines
Wed 10/152:20 pmORD - SXM
2 stops20h 00mUnited Airlines
Deal found 4/23$8,127

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 April 24, 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 6/7

12:33 pm-12:06 am

1 stop12h 33m

Chicago O'Hare Intl

Sat 6/14

5:01 am-5:16 pm

2 stops11h 15m

$443

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sat 6/7

12:33 pm-12:06 am

1 stop12h 33m

Chicago O'Hare Intl

Sat 6/14

5:05 am-2:00 pm

1 stop7h 55m

$474

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sat 6/7

3:05 pm-9:24 am

2 stops19h 19m

Chicago O'Hare Intl

Sat 6/14

9:28 pm-2:00 pm

3 stops39h 32m

$553

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Tue 8/26

12:15 pm-11:25 pm

1 stop12h 10m

Chicago O'Hare Intl

Sat 8/30

6:00 am-2:41 pm

1 stop7h 41m

$575

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Thu 10/9

4:10 pm-11:57 pm

1 stop8h 47m

Chicago O'Hare Intl

Wed 10/15

6:00 am-3:10 pm

1 stop8h 10m

$618

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Thu 10/9

2:10 pm-4:43 pm

2 stops27h 33m

Chicago O'Hare Intl

Wed 10/15

1:16 pm-1:19 pm

2 stops23h 03m

$1,335

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Thu 10/9

11:55 am-6:50 pm

3 stops31h 55m

Chicago O'Hare Intl

Wed 10/15

2:20 pm-11:20 am

2 stops20h 00m

$8,127

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Tue 5/13

6:45 pm-5:41 pm

3 stops23h 56m

$359

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Tue 5/13

12:40 pm-9:54 pm

1 stop10h 14m

$433

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Tue 5/13

2:24 pm-12:11 am

2 stops10h 47m

$484

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/24

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

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

Find hourly flight availability from Simpson Bay to Illinois. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated April 24, 2025.

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

Rainfall in Illinois by month

Plan your trip to Illinois by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Illinois ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Illinois when rainfall is around 1.7 in.

Temperature in Illinois by month

Plan your trip to Illinois by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Illinois, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 April 24, 2025.
United Airlines
7.4
Good
8,685 reviews

Comfort

7.3

Crew

8.1

Overall

7.4

Entertainment

7.1

Boarding

7.7

Food

6.6

Reviews

1 / 20
4.0
Okay

Thomas,Apr 2025

TPE - SFO

The boarding experience was okay. The dietary food choices were limited, the midway snacks were hard and dry. The seat was uncomfortable - stiff seat cushion, seat back kept springing back to the upright position, narrow seat width. Love the app and the ability to track my luggage. Flight crew was efficient.
United Airlines
7.4
Good
8,685 reviews
United Airlines
7.4
Good
8,685 reviews

Comfort

7.3

Crew

8.1

Overall

7.4

Entertainment

7.1

Boarding

7.7

Food

6.6

Reviews

1 / 20
4.0
Okay

Thomas,Apr 2025

TPE - SFO

The boarding experience was okay. The dietary food choices were limited, the midway snacks were hard and dry. The seat was uncomfortable - stiff seat cushion, seat back kept springing back to the upright position, narrow seat width. Love the app and the ability to track my luggage. Flight crew was efficient.
JetBlue
7.3
Good
2,924 reviews
United Airlines
7.4
Good
8,685 reviews

Comfort

7.3

Crew

8.1

Overall

7.4

Entertainment

7.1

Boarding

7.7

Food

6.6

Reviews

1 / 20
4.0
Okay

Thomas,Apr 2025

TPE - SFO

The boarding experience was okay. The dietary food choices were limited, the midway snacks were hard and dry. The seat was uncomfortable - stiff seat cushion, seat back kept springing back to the upright position, narrow seat width. Love the app and the ability to track my luggage. Flight crew was efficient.
American Airlines
7.2
Good
10,000 reviews
United Airlines
7.4
Good
8,685 reviews

Comfort

7.3

Crew

8.1

Overall

7.4

Entertainment

7.1

Boarding

7.7

Food

6.6

Reviews

1 / 20
4.0
Okay

Thomas,Apr 2025

TPE - SFO

The boarding experience was okay. The dietary food choices were limited, the midway snacks were hard and dry. The seat was uncomfortable - stiff seat cushion, seat back kept springing back to the upright position, narrow seat width. Love the app and the ability to track my luggage. Flight crew was efficient.
WestJet
7.2
Good
2,816 reviews
United Airlines
7.4
Good
8,685 reviews

Comfort

7.3

Crew

8.1

Overall

7.4

Entertainment

7.1

Boarding

7.7

Food

6.6

Reviews

1 / 20
4.0
Okay

Thomas,Apr 2025

TPE - SFO

The boarding experience was okay. The dietary food choices were limited, the midway snacks were hard and dry. The seat was uncomfortable - stiff seat cushion, seat back kept springing back to the upright position, narrow seat width. Love the app and the ability to track my luggage. Flight crew was efficient.
Spirit Airlines
6.3
Okay
7,940 reviews
United Airlines
7.4
Good
8,685 reviews

Comfort

7.3

Crew

8.1

Overall

7.4

Entertainment

7.1

Boarding

7.7

Food

6.6

Reviews

1 / 20
4.0
Okay

Thomas,Apr 2025

TPE - SFO

The boarding experience was okay. The dietary food choices were limited, the midway snacks were hard and dry. The seat was uncomfortable - stiff seat cushion, seat back kept springing back to the upright position, narrow seat width. Love the app and the ability to track my luggage. Flight crew was efficient.

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 flights from Simpson Bay to Illinois?

    While on average a flight from Simpson Bay to Illinois is generally $610, our data shows the cheapest flight currently is $538. When looking at the most popular route, (Simpson Bay Princess Juliana - Chicago O'Hare Intl), you can expect to pay $333 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

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Alternative routes for Simpson Bay to Illinois

See prices for flight routes from nearby airports that may be better suited for you.
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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 April 24, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$554Average$755FlexibilityNo cancel feeOn-time71%

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