What is the cheapest airline that flies from Illinois to Simpson Bay Princess Juliana?

Spirit Airlines, JetBlue, and Air Canada are the most popular carriers operating from Illinois to Simpson Bay Princess Juliana

What airlines fly to Simpson Bay?

American Airlines, United Airlines and Spirit Airlines are the top three most popular airlines that fly to Simpson Bay from Illinois according to our data. American Airlines is the first choice among our users, with 52% of people opting to fly with this airline when traveling to Simpson Bay. Keep in mind that there are 4 different airlines that fly to Simpson Bay on a routine basis, so you have a few additional options to choose from.

When did momondo last update prices for flights from Illinois to Simpson Bay Princess Juliana Airport?

Prices for flights from Illinois to Simpson Bay Princess Juliana Airport are updated daily.

How many operators does momondo search for flights from Illinois to Simpson Bay Princess Juliana Airport?

There are 4 operators available for flights from Illinois to Simpson Bay Princess Juliana Airport as of October 2025.

How old do you have to be to fly from Illinois to Simpson Bay Princess Juliana Airport?

The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Illinois to Simpson Bay Princess Juliana Airport.

What documentation or ID do you need to fly to Simpson Bay Princess Juliana Airport?

The required travel and health documents for your Simpson Bay Princess Juliana Airport trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Simpson Bay Princess Juliana Airport. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

$133 Cheap Flights from Illinois to Simpson Bay in 2025/26

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Cheap round-trip flights

Enter your travel dates to find the best prices.

5:05 am - 3:10 pmORD-SXM

8h 05m1 stop

4:28 pm - 11:42 pmSXM-ORD

9h 14m1 stop

$343Spirit Airlines

Find Deal

Wed, Jan 28 - Fri, Feb 6

5:05 am - 3:10 pmORD-SXM

8h 05m1 stop

4:28 pm - 11:42 pmSXM-ORD

9h 14m1 stop

$361Spirit Airlines

Find Deal

Sat, Jan 31 - Sat, Feb 7

5:00 am - 4:22 pmORD-SXM

9h 22m1 stop

5:24 pm - 12:37 amSXM-ORD

9h 13m1 stop

$375American Airlines

Find Deal

Tue, Nov 18 - Tue, Nov 25

7:07 pm - 2:19 pmORD-SXM

17h 12m1 stop

5:24 pm - 12:37 amSXM-ORD

9h 13m1 stop

$377American Airlines

Find Deal

Sat, Nov 8 - Wed, Nov 12

4:01 pm - 2:10 pmORD-SXM

44h 09m2 stops

3:15 pm - 1:57 pmSXM-ORD

24h 42m1 stop

$393Multiple Airlines

Find Deal

Wed, Dec 3 - Wed, Dec 10

8:45 am - 2:15 pmORD-SXM

27h 30m1 stop

3:20 pm - 11:37 amSXM-ORD

22h 17m2 stops

$399Multiple Airlines

Find Deal

Thu, Nov 27 - Mon, Dec 1

6:00 am - 2:55 pmMDW-SXM

6h 55m1 stop

4:20 pm - 11:40 pmSXM-MDW

9h 20m1 stop

$433Delta

Find Deal

Sun, Nov 9 - Wed, Nov 12

6:45 am - 4:38 pmORD-SXM

7h 53m1 stop

3:22 pm - 10:21 pmSXM-ORD

8h 59m1 stop

$453JetBlue

Find Deal

Mon, Nov 17 - Sat, Nov 22

6:45 am - 4:38 pmORD-SXM

7h 53m1 stop

2:28 pm - 10:21 pmSXM-ORD

9h 53m1 stop

$459JetBlue

Find Deal

Wed, Nov 19 - Sat, Nov 22

6:00 am - 2:56 pmMDW-SXM

6h 56m1 stop

1:45 pm - 9:46 pmSXM-MDW

10h 01m1 stop

$587Delta

Find Deal

Wed, Jan 28 - Fri, Feb 6

Spirit Airlines flights from Illinois to Simpson Bay

Our best Spirit Airlines deals on Illinois to Simpson Bay flight tickets

Spirit Airlines

Jan 28

ORD5:05 amChicago O'Hare Intl

8h 05m

1 stop

SXM3:10 pmSimpson Bay Princess Juliana

Feb 6

SXM4:28 pmSimpson Bay Princess Juliana

9h 14m

1 stop

ORD11:42 pmChicago O'Hare Intl

$343

Find similar

Spirit Airlines

Jan 31

ORD5:05 amChicago O'Hare Intl

8h 05m

1 stop

SXM3:10 pmSimpson Bay Princess Juliana

Feb 7

SXM4:28 pmSimpson Bay Princess Juliana

9h 14m

1 stop

ORD11:42 pmChicago O'Hare Intl

$361

Find similar

Spirit Airlines

Feb 9

ORD5:05 amChicago O'Hare Intl

8h 05m

1 stop

SXM3:10 pmSimpson Bay Princess Juliana

Feb 18

SXM4:28 pmSimpson Bay Princess Juliana

9h 14m

1 stop

ORD11:42 pmChicago O'Hare Intl

$385

Find similar

American Airlines flights from Illinois to Simpson Bay

Our best American Airlines deals on Illinois to Simpson Bay flight tickets

American Airlines

Nov 18

ORD5:00 amChicago O'Hare Intl

9h 22m

1 stop

SXM4:22 pmSimpson Bay Princess Juliana

Nov 25

SXM5:24 pmSimpson Bay Princess Juliana

9h 13m

1 stop

ORD12:37 amChicago O'Hare Intl

$375

Find similar

American Airlines

Nov 8

ORD7:07 pmChicago O'Hare Intl

17h 12m

1 stop

SXM2:19 pmSimpson Bay Princess Juliana

Nov 12

SXM5:24 pmSimpson Bay Princess Juliana

9h 13m

1 stop

ORD12:37 amChicago O'Hare Intl

$377

Find similar

American Airlines

Dec 4

ORD6:35 pmChicago O'Hare Intl

17h 17m

1 stop

SXM1:52 pmSimpson Bay Princess Juliana

Dec 11

SXM5:25 pmSimpson Bay Princess Juliana

20h 41m

1 stop

ORD12:06 pmChicago O'Hare Intl

$378

Find similar

Fly from

Fly to

Route

Depart

Return

Price

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Wed 1/28

5:05 am-3:10 pm

1 stop8h 05m

Simpson Bay Princess Juliana

Fri 2/6

4:28 pm-11:42 pm

1 stop9h 14m

$343

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sat 1/31

5:05 am-3:10 pm

1 stop8h 05m

Simpson Bay Princess Juliana

Sat 2/7

4:28 pm-11:42 pm

1 stop9h 14m

$361

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Tue 11/18

5:00 am-4:22 pm

1 stop9h 22m

Simpson Bay Princess Juliana

Tue 11/25

5:24 pm-12:37 am

1 stop9h 13m

$375

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sat 11/8

7:07 pm-2:19 pm

1 stop17h 12m

Simpson Bay Princess Juliana

Wed 11/12

5:24 pm-12:37 am

1 stop9h 13m

$377

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Wed 12/3

4:01 pm-2:10 pm

2 stops44h 09m

Simpson Bay Princess Juliana

Wed 12/10

3:15 pm-1:57 pm

1 stop24h 42m

$393

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Thu 11/27

8:45 am-2:15 pm

1 stop27h 30m

Simpson Bay Princess Juliana

Mon 12/1

3:20 pm-11:37 am

2 stops22h 17m

$399

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Sun 11/9

6:00 am-2:55 pm

1 stop6h 55m

Simpson Bay Princess Juliana

Wed 11/12

4:20 pm-11:40 pm

1 stop9h 20m

$433

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Mon 11/17

6:45 am-4:38 pm

1 stop7h 53m

Simpson Bay Princess Juliana

Sat 11/22

3:22 pm-10:21 pm

1 stop8h 59m

$453

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Wed 11/19

6:45 am-4:38 pm

1 stop7h 53m

Simpson Bay Princess Juliana

Sat 11/22

2:28 pm-10:21 pm

1 stop9h 53m

$459

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Wed 1/28

6:00 am-2:56 pm

1 stop6h 56m

Simpson Bay Princess Juliana

Fri 2/6

1:45 pm-9:46 pm

1 stop10h 01m

$587

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

How to get the cheapest flight ticket from Illinois to Simpson Bay

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

Prices

Airlines

What is the cheapest month to fly to Simpson Bay?

In general, August is the cheapest month to fly from Illinois to Simpson Bay. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $585. If you aren’t able to travel to Simpson Bay during the month of August, then flying in September is also cheap. Prices for this month can be found on momondo for an average of $612.

What is the cheapest day to depart on your flight to Simpson Bay?

Our data shows that Tuesday is the least expensive day to fly to Simpson Bay. Tickets to fly out on this day can be as low as $644. Flights from Illinois to Simpson Bay on a Saturday will generally be more expensive and average around $910. Keep in mind that these prices on both days could fluctuate depending on the season and the demand.

What is the cheapest time of day to depart on your flight to Simpson Bay?

According to our data, the cheapest time of day to fly to Simpson Bay is at noon. momondo users have found flights departing from Illinois to Simpson Bay at noon for as low as $417. Keep in mind that these prices may fluctuate based on what airline you choose and the time of year you plan to travel. In contrast, the most expensive time of day to depart to Simpson Bay is in the morning when prices are around $882.

What is the cheapest Illinois to Simpson Bay Princess Juliana flight route?

Fly from Chicago O'Hare Intl to Simpson Bay Princess Juliana for the best Illinois - Simpson Bay Princess Juliana flight prices

How far in advance should I book a flight to Simpson Bay?

You are more likely to see cheaper flights to Simpson Bay from Illinois when booking weeks ahead of your departure date. In general, you can expect to find flights to Simpson Bay for around $700 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Simpson Bay from Illinois for as low as $522 on momondo.

What cabin class options are available on Illinois to Simpson Bay Princess Juliana flights?

There are 2 cabin classes available to choose from on Illinois to Simpson Bay Princess Juliana flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Illinois to Simpson Bay flights?

You could potentially save up to 5% on your flight if you consider stops on a Illinois to Simpson Bay flight.

Cheap Illinois to Simpson Bay flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Illinois to Simpson Bay

Best Price Found	$553
Fastest flight time	4h 45m
Direct flights	Mon and Sun
Airports in Simpson Bay	1 airport

The best flight deal from Illinois to Simpson Bay found on momondo in the last 72 hours is $553

The fastest flight from Illinois to Simpson Bay takes 4h 45m

Direct flights go from Illinois to Simpson Bay on Monday and Sunday. There are no airlines offering direct flights.

There is 1 airport near Simpson Bay: Simpson Bay Princess Juliana (SXM)

Search flight deals

When did momondo last update prices for flights from Illinois to Simpson Bay Princess Juliana Airport?
Prices for flights from Illinois to Simpson Bay Princess Juliana Airport are updated daily.
How many operators does momondo search for flights from Illinois to Simpson Bay Princess Juliana Airport?
There are 4 operators available for flights from Illinois to Simpson Bay Princess Juliana Airport as of October 2025.
How old do you have to be to fly from Illinois to Simpson Bay Princess Juliana Airport?
The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Illinois to Simpson Bay Princess Juliana Airport.
What documentation or ID do you need to fly to Simpson Bay Princess Juliana Airport?
The required travel and health documents for your Simpson Bay Princess Juliana Airport trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Simpson Bay Princess Juliana Airport. We recommend that you seek guidance from your airline or a reliable third party such as IATA.
What is the most popular plane model from Illinois to Simpson Bay?
momondo data reveals that the most frequently booked plane model on the route from Illinois to Simpson Bay is Boeing 737 MAX 8, representing 39.33% of all bookings. The subsequent popular models are Airbus A319 at 34.83% and Boeing 737-700 at 25.84%.

Best airlines flying from Illinois to Simpson Bay

Compare and see reviews for airlines that fly from Illinois to Simpson Bay with momondo

Airline	Rating	Free Cancellation	Price
Spirit Airlines	PriceFrom $316	Free Cancellation	Rating 6.3 8,095 reviews	Search Spirit Airlines flights
Delta	PriceFrom $329	Free Cancellation	Rating 7.9 7,978 reviews	Search Delta flights
United Airlines	PriceFrom $597	Free Cancellation	Rating 7.4 8,991 reviews	Search United Airlines flights
American Airlines	PriceFrom $601	Free Cancellation	Rating 7.2 11,024 reviews	Search American Airlines flights

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Why use momondo?

Why should I use momondo to find a flight deal from Illinois to Simpson Bay?

Finding the right flight to Simpson Bay from Illinois is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Simpson Bay quick and easy, saving you time and money.

Can I find flights from Illinois to Simpson Bay with flexible booking policies on momondo?

Yes. momondo allows you to filter the results for Illinois to Simpson Bay flights to just show those with flexible booking policies.

How can momondo help me find flights from Illinois to Simpson Bay?

momondo helps you find the best flight between Illinois and Simpson Bay by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

I’m not ready to book a flight from Illinois to Simpson Bay right now. Can momondo alert me if prices change?

If you are not ready to book a flight from Illinois to Simpson Bay now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Simpson Bay and let you know when they change.

An easier way to manage your Simpson Bay trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

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Cheap flights from Illinois to Simpson Bay from $133

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Illinois to Simpson Bay departing on 12/17. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

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Big names and deals

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Filter for what you want

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Find the cheapest flights from Illinois to Simpson Bay

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Spirit Airlines flights from Illinois to Simpson Bay

Our best Spirit Airlines deals on Illinois to Simpson Bay flight tickets

American Airlines flights from Illinois to Simpson Bay

Our best American Airlines deals on Illinois to Simpson Bay flight tickets

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See travel insights to Simpson Bay from

How to get the cheapest flight ticket from Illinois to Simpson Bay

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest month to fly to Simpson Bay?

What is the cheapest day to depart on your flight to Simpson Bay?

What is the cheapest time of day to depart on your flight to Simpson Bay?

What is the cheapest Illinois to Simpson Bay Princess Juliana flight route?

Fly from Chicago O'Hare Intl to Simpson Bay Princess Juliana for the best Illinois - Simpson Bay Princess Juliana flight prices

How far in advance should I book a flight to Simpson Bay?

What cabin class options are available on Illinois to Simpson Bay Princess Juliana flights?

There are 2 cabin classes available to choose from on Illinois to Simpson Bay Princess Juliana flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Illinois to Simpson Bay flights?

You could potentially save up to 5% on your flight if you consider stops on a Illinois to Simpson Bay flight.

What is the cheapest airline that flies from Illinois to Simpson Bay Princess Juliana?

Spirit Airlines, JetBlue, and Air Canada are the most popular carriers operating from Illinois to Simpson Bay Princess Juliana

What airlines fly to Simpson Bay?

Cheap Illinois to Simpson Bay flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Illinois to Simpson Bay

Best Price Found

Fastest flight time

Direct flights

Airports in Simpson Bay

When did momondo last update prices for flights from Illinois to Simpson Bay Princess Juliana Airport?

How many operators does momondo search for flights from Illinois to Simpson Bay Princess Juliana Airport?

How old do you have to be to fly from Illinois to Simpson Bay Princess Juliana Airport?

What documentation or ID do you need to fly to Simpson Bay Princess Juliana Airport?

What is the most popular plane model from Illinois to Simpson Bay?

Best airlines flying from Illinois to Simpson Bay

Compare and see reviews for airlines that fly from Illinois to Simpson Bay with momondo

Traveling to a place near Simpson Bay?

Why use momondo?

Why should I use momondo to find a flight deal from Illinois to Simpson Bay?

Can I find flights from Illinois to Simpson Bay with flexible booking policies on momondo?

How can momondo help me find flights from Illinois to Simpson Bay?

I’m not ready to book a flight from Illinois to Simpson Bay right now. Can momondo alert me if prices change?

An easier way to manage your Simpson Bay trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

Find better results for your trip to St. Maarten

Fly your favorite airline to Simpson Bay

Airlines are sorted and displayed according to clicks in the past 7 days on momondo