What airlines fly to Simpson Bay?

American Airlines, Spirit Airlines and United 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 49% of people opting to fly with this airline when traveling to Simpson Bay. Keep in mind that there are 5 different airlines that fly to Simpson Bay on a routine basis, so you have a few additional options to choose from.

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

Spirit Airlines, Frontier, and American Airlines are the most popular carriers operating from Illinois to Simpson Bay Princess Juliana

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 5 operators available for flights from Illinois to Simpson Bay Princess Juliana Airport as of February 2026.

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.

$72 Cheap Flights from Illinois to Simpson Bay in 2026

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Find the cheapest flights from Illinois to Simpson Bay

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

8:16 pm - 2:15 pm

ORD

SXM

15h 59m

1 stop

3:20 pm - 11:47 pm

SXM

ORD

10h 27m

1 stop

$223Spirit Airlines

Sat, Feb 28 - Sat, Mar 7

8:16 pm - 2:15 pm

ORD

SXM

15h 59m

1 stop

3:20 pm - 11:47 pm

SXM

ORD

10h 27m

1 stop

$237Spirit Airlines

Sat, Feb 28 - Sat, Mar 7

6:00 am - 3:20 pm

MDW

SXM

7h 20m

1 stop

2:35 pm - 10:09 pm

SXM

MDW

8h 34m

1 stop

$343Frontier

Sat, Mar 7 - Sat, Mar 14

4:05 pm - 2:40 pm

STL

SXM

20h 35m

2 stops

4:00 pm - 3:29 pm

SXM

STL

24h 29m

1 stop

$366Air Canada

Wed, Mar 4 - Wed, Mar 11

2:41 pm - 3:20 pm

MDW

SXM

22h 39m

1 stop

2:35 pm - 10:09 pm

SXM

MDW

8h 34m

1 stop

$382Frontier

Fri, Mar 6 - Sat, Mar 14

4:05 pm - 1:35 pm

STL

SXM

20h 30m

2 stops

2:40 pm - 3:24 pm

SXM

STL

25h 44m

2 stops

$420Air Canada

Sat, Mar 28 - Sat, Apr 4

6:54 pm - 1:21 pm

STL

SXM

17h 27m

1 stop

2:26 pm - 10:58 pm

SXM

STL

9h 32m

1 stop

$463American Airlines

Sun, May 17 - Thu, May 21

6:54 pm - 3:22 pm

STL

SXM

19h 28m

2 stops

2:26 pm - 8:33 am

SXM

STL

19h 07m

2 stops

$468American Airlines

Sun, May 17 - Thu, May 21

6:00 am - 2:50 pm

STL

SXM

6h 50m

1 stop

12:55 pm - 11:58 pm

SXM

STL

12h 03m

1 stop

$495Delta

Mon, Mar 2 - Sun, Mar 8

6:00 am - 1:54 pm

MDW

SXM

6h 54m

1 stop

12:55 pm - 10:31 pm

SXM

MDW

10h 36m

1 stop

$585Delta

Tue, Mar 10 - Tue, Mar 17

Spirit Airlines flights from Illinois to Simpson Bay

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

Spirit Airlines

Feb 28

ORD8:16 pmChicago O'Hare Intl

15h 59m

1 stop

SXM2:15 pmSimpson Bay Princess Juliana

Mar 7

SXM3:20 pmSimpson Bay Princess Juliana

10h 27m

1 stop

ORD11:47 pmChicago O'Hare Intl

$223

Spirit Airlines

Feb 28

ORD8:16 pmChicago O'Hare Intl

15h 59m

1 stop

SXM2:15 pmSimpson Bay Princess Juliana

Mar 7

SXM3:20 pmSimpson Bay Princess Juliana

10h 27m

1 stop

ORD11:47 pmChicago O'Hare Intl

$237

Spirit Airlines

Mar 8

ORD8:16 pmChicago O'Hare Intl

15h 59m

1 stop

SXM1:15 pmSimpson Bay Princess Juliana

Mar 11

SXM2:20 pmSimpson Bay Princess Juliana

10h 27m

1 stop

ORD11:47 pmChicago O'Hare Intl

$238

Frontier flights from Illinois to Simpson Bay

Our best Frontier deals on Illinois to Simpson Bay flight tickets

Frontier

Mar 7

MDW6:00 amChicago Midway

7h 20m

1 stop

SXM3:20 pmSimpson Bay Princess Juliana

Mar 14

SXM2:35 pmSimpson Bay Princess Juliana

8h 34m

1 stop

MDW10:09 pmChicago Midway

$343

Frontier

Mar 6

MDW2:41 pmChicago Midway

22h 39m

1 stop

SXM3:20 pmSimpson Bay Princess Juliana

Mar 14

SXM2:35 pmSimpson Bay Princess Juliana

8h 34m

1 stop

MDW10:09 pmChicago Midway

$382

Frontier

Mar 6

MDW9:51 pmChicago Midway

15h 29m

2 stops

SXM3:20 pmSimpson Bay Princess Juliana

Mar 14

SXM2:35 pmSimpson Bay Princess Juliana

8h 34m

1 stop

MDW10:09 pmChicago Midway

$414

Fly from

Fly to

Route

Depart

Return

Price

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sat 2/28

8:16 pm-2:15 pm

1 stop15h 59m

Simpson Bay Princess Juliana

Sat 3/7

3:20 pm-11:47 pm

1 stop10h 27m

$223

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sat 2/28

8:16 pm-2:15 pm

1 stop15h 59m

Simpson Bay Princess Juliana

Sat 3/7

3:20 pm-11:47 pm

1 stop10h 27m

$237

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Sat 3/7

6:00 am-3:20 pm

1 stop7h 20m

Simpson Bay Princess Juliana

Sat 3/14

2:35 pm-10:09 pm

1 stop8h 34m

$343

St. LouisSimpson Bay

STL - SXM

STLSXM

Lambert-St Louis

Wed 3/4

4:05 pm-2:40 pm

2 stops20h 35m

Simpson Bay Princess Juliana

Wed 3/11

4:00 pm-3:29 pm

1 stop24h 29m

$366

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Fri 3/6

2:41 pm-3:20 pm

1 stop22h 39m

Simpson Bay Princess Juliana

Sat 3/14

2:35 pm-10:09 pm

1 stop8h 34m

$382

St. LouisSimpson Bay

STL - SXM

STLSXM

Lambert-St Louis

Sat 3/28

4:05 pm-1:35 pm

2 stops20h 30m

Simpson Bay Princess Juliana

Sat 4/4

2:40 pm-3:24 pm

2 stops25h 44m

$420

St. LouisSimpson Bay

STL - SXM

STLSXM

Lambert-St Louis

Sun 5/17

6:54 pm-1:21 pm

1 stop17h 27m

Simpson Bay Princess Juliana

Thu 5/21

2:26 pm-10:58 pm

1 stop9h 32m

$463

St. LouisSimpson Bay

STL - SXM

STLSXM

Lambert-St Louis

Sun 5/17

6:54 pm-3:22 pm

2 stops19h 28m

Simpson Bay Princess Juliana

Thu 5/21

2:26 pm-8:33 am

2 stops19h 07m

$468

St. LouisSimpson Bay

STL - SXM

STLSXM

Lambert-St Louis

Mon 3/2

6:00 am-2:50 pm

1 stop6h 50m

Simpson Bay Princess Juliana

Sun 3/8

12:55 pm-11:58 pm

1 stop12h 03m

$495

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Tue 3/10

6:00 am-1:54 pm

1 stop6h 54m

Simpson Bay Princess Juliana

Tue 3/17

12:55 pm-10:31 pm

1 stop10h 36m

$585

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, January 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 $584. If you aren’t able to travel to Simpson Bay during the month of January, then flying in February is also cheap. Prices for this month can be found on momondo for an average of $607.

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

Our data shows that Sunday is the least expensive day to fly to Simpson Bay. Tickets to fly out on this day can be as low as $659. Flights from Illinois to Simpson Bay on a Saturday will generally be more expensive and average around $794. Keep in mind that these prices on both days could fluctuate depending on the season and the demand.

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 $636 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 $458 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 63% 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	$612
Fastest flight time	5h 12m
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 $612

The fastest flight from Illinois to Simpson Bay takes 5h 12m

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

There is 1 airport in Simpson Bay. From Illinois there are direct flights to 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 5 operators available for flights from Illinois to Simpson Bay Princess Juliana Airport as of February 2026.
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 57.55% of all bookings. The subsequent popular models are Airbus A319 at 24.53%, Boeing 737-700 at 5.66%, and Airbus A320-100/200 at 5.66%.

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 $231	Free Cancellation	Rating 6.3 8,451 reviews	Search Spirit Airlines flights
Delta	PriceFrom $290	Free Cancellation	Rating 7.9 8,198 reviews	Search Delta flights
United Airlines	PriceFrom $410	Free Cancellation	Rating 7.4 9,287 reviews	Search United Airlines flights
American Airlines	PriceFrom $501	Free Cancellation	Rating 7.2 11,283 reviews	Search American Airlines flights
JetBlue	PriceFrom $568	Free Cancellation	Rating 7.2 2,897 reviews	Search JetBlue 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

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Cheap flights from Illinois to Simpson Bay from $72

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 2/28. 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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Spirit Airlines flights from Illinois to Simpson Bay

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See travel insights to Simpson Bay from

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

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 Illinois to Simpson Bay Princess Juliana flight route?

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?

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

What is the cheapest airline that flies 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

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

Cabin classes currently available on flights to Simpson Bay

List of cabin classes available on flights landing in Simpson Bay. Availability may vary depending on flight origin and airline.

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