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

JetBlue, Southwest, and Delta are the most popular carriers operating from Illinois to Simpson Bay Princess Juliana

What airlines fly to Simpson Bay?

American Airlines, United Airlines and JetBlue 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 59% 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.

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 July 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.

$117 Cheap Flights from Illinois to Simpson Bay in 2026

Discover deals from 900+ travel sites with momondo.

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.

6:00 am - 2:00 pm

ORD

SXM

7h 00m

1 stop

3:05 pm - 11:31 pm

SXM

ORD

9h 26m

1 stop

$317JetBlue

Fri, Sep 18 - Fri, Sep 25

5:10 am - 1:25 pm

MDW

SXM

7h 15m

1 stop

3:00 pm - 10:05 pm

SXM

MDW

8h 05m

1 stop

$325Southwest

Mon, Jul 20 - Wed, Jul 29

5:10 am - 1:25 pm

MDW

SXM

7h 15m

1 stop

3:00 pm - 7:10 am

SXM

MDW

17h 10m

2 stops

$330Southwest

Mon, Jul 20 - Wed, Jul 29

6:00 am - 2:00 pm

ORD

SXM

7h 00m

1 stop

3:05 pm - 11:31 pm

SXM

ORD

9h 26m

1 stop

$350JetBlue

Thu, Sep 24 - Sun, Sep 27

6:00 am - 2:00 pm

ORD

SXM

7h 00m

1 stop

1:45 pm - 11:44 pm

SXM

ORD

10h 59m

1 stop

$354JetBlue

Sat, Oct 3 - Sat, Oct 17

6:00 am - 2:00 pm

ORD

SXM

7h 00m

1 stop

6:00 pm - 7:44 am

SXM

ORD

14h 44m

2 stops

$414Multiple Airlines

Mon, Sep 21 - Thu, Oct 1

6:00 am - 2:00 pm

ORD

SXM

7h 00m

1 stop

6:00 pm - 8:12 pm

SXM

ORD

27h 12m

2 stops

$417Multiple Airlines

Sat, Oct 3 - Sat, Oct 17

3:34 pm - 1:22 pm

STL

SXM

20h 48m

2 stops

2:22 pm - 10:20 am

SXM

STL

20h 58m

2 stops

$470American Airlines

Sat, Sep 26 - Wed, Sep 30

5:00 am - 3:39 pm

STL

SXM

9h 39m

1 stop

4:39 pm - 10:52 am

SXM

STL

19h 13m

2 stops

$475American Airlines

Wed, Aug 12 - Wed, Aug 19

8:55 am - 2:45 pm

STL

SXM

28h 50m

1 stop

2:40 pm - 4:26 pm

SXM

STL

26h 46m

2 stops

$552Air Canada

Sat, Oct 24 - Sat, Oct 31

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JetBlue flights from Illinois to Simpson Bay

Our best JetBlue deals on Illinois to Simpson Bay flight tickets

JetBlue

Sep 18

ORD6:00 amChicago O'Hare Intl

7h 00m

1 stop

SXM2:00 pmSimpson Bay Princess Juliana

Sep 25

SXM3:05 pmSimpson Bay Princess Juliana

9h 26m

1 stop

ORD11:31 pmChicago O'Hare Intl

$317

JetBlue

Sep 24

ORD6:00 amChicago O'Hare Intl

7h 00m

1 stop

SXM2:00 pmSimpson Bay Princess Juliana

Sep 27

SXM3:05 pmSimpson Bay Princess Juliana

9h 26m

1 stop

ORD11:31 pmChicago O'Hare Intl

$350

JetBlue

Oct 3

ORD6:00 amChicago O'Hare Intl

7h 00m

1 stop

SXM2:00 pmSimpson Bay Princess Juliana

Oct 17

SXM1:45 pmSimpson Bay Princess Juliana

10h 59m

1 stop

ORD11:44 pmChicago O'Hare Intl

$354

American Airlines flights from Illinois to Simpson Bay

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

American Airlines

Sep 26

STL3:34 pmLambert-St Louis

20h 48m

2 stops

SXM1:22 pmSimpson Bay Princess Juliana

Sep 30

SXM2:22 pmSimpson Bay Princess Juliana

20h 58m

2 stops

STL10:20 amLambert-St Louis

$470

American Airlines

Aug 12

STL5:00 amLambert-St Louis

9h 39m

1 stop

SXM3:39 pmSimpson Bay Princess Juliana

Aug 19

SXM4:39 pmSimpson Bay Princess Juliana

19h 13m

2 stops

STL10:52 amLambert-St Louis

$475

American Airlines

Sep 26

STL5:10 pmLambert-St Louis

19h 12m

1 stop

SXM1:22 pmSimpson Bay Princess Juliana

Sep 30

SXM2:22 pmSimpson Bay Princess Juliana

8h 27m

1 stop

STL9:49 pmLambert-St Louis

$476

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Fri 9/18

6:00 am-2:00 pm

1 stop7h 00m

Simpson Bay Princess Juliana

Fri 9/25

3:05 pm-11:31 pm

1 stop9h 26m

$317

Quickest round-trip

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Mon 7/20

5:10 am-1:25 pm

1 stop7h 15m

Simpson Bay Princess Juliana

Wed 7/29

3:00 pm-10:05 pm

1 stop8h 05m

$325

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Mon 7/20

5:10 am-1:25 pm

1 stop7h 15m

Simpson Bay Princess Juliana

Wed 7/29

3:00 pm-7:10 am

2 stops17h 10m

$330

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Thu 9/24

6:00 am-2:00 pm

1 stop7h 00m

Simpson Bay Princess Juliana

Sun 9/27

3:05 pm-11:31 pm

1 stop9h 26m

$350

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sat 10/3

6:00 am-2:00 pm

1 stop7h 00m

Simpson Bay Princess Juliana

Sat 10/17

1:45 pm-11:44 pm

1 stop10h 59m

$354

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Mon 9/21

6:00 am-2:00 pm

1 stop7h 00m

Simpson Bay Princess Juliana

Thu 10/1

6:00 pm-7:44 am

2 stops14h 44m

$414

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sat 10/3

6:00 am-2:00 pm

1 stop7h 00m

Simpson Bay Princess Juliana

Sat 10/17

6:00 pm-8:12 pm

2 stops27h 12m

$417

St. LouisSimpson Bay

STL - SXM

STLSXM

Lambert-St Louis

Sat 9/26

3:34 pm-1:22 pm

2 stops20h 48m

Simpson Bay Princess Juliana

Wed 9/30

2:22 pm-10:20 am

2 stops20h 58m

$470

St. LouisSimpson Bay

STL - SXM

STLSXM

Lambert-St Louis

Wed 8/12

5:00 am-3:39 pm

1 stop9h 39m

Simpson Bay Princess Juliana

Wed 8/19

4:39 pm-10:52 am

2 stops19h 13m

$475

St. LouisSimpson Bay

STL - SXM

STLSXM

Lambert-St Louis

Sat 10/24

8:55 am-2:45 pm

1 stop28h 50m

Simpson Bay Princess Juliana

Sat 10/31

2:40 pm-4:26 pm

2 stops26h 46m

$552

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, February 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 $74. If you aren’t able to travel to Simpson Bay during the month of February, then flying in December is also cheap. Prices for this month can be found on momondo for an average of $240.

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 $617. Flights from Illinois to Simpson Bay on a Saturday will generally be more expensive and average around $813. 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 from Illinois 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 $655 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 $531 on momondo.

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

There are 4 cabin classes available to choose from on Illinois to Simpson Bay 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 61% 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	$805
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 $805

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

Frequently asked questions about flying from Illinois to Simpson Bay

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 July 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 44.44% of all bookings. The subsequent popular models are Airbus A319 at 19.44%, Boeing 737-700 at 16.67%, and Airbus A318/A319/A320/A321 at 5.56%.

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
Delta	PriceFrom $240	Free Cancellation	Rating 7.8 8,452 reviews	Search Delta flights
JetBlue	PriceFrom $389	Free Cancellation	Rating 7.1 3,008 reviews	Search JetBlue flights
United Airlines	PriceFrom $410	Free Cancellation	Rating 7.4 9,926 reviews	Search United Airlines flights
Air Canada	PriceFrom $487	Free Cancellation	Rating 7.1 11,287 reviews	Search Air Canada flights
American Airlines	PriceFrom $500	Free Cancellation	Rating 7.1 11,768 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.

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Cheap flights from Illinois to Simpson Bay from $117

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 9/27. 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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JetBlue flights from Illinois to Simpson Bay

Our best JetBlue 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

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 from Illinois to Simpson Bay?

What cabin class options are available on Illinois to Simpson Bay 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

Frequently asked questions about flying 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?

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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