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Cheap flights from Illinois to Simpson Bay from $108

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 9/3. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

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Find the cheapest flights from Illinois to Simpson Bay

Cheap round-trip flights

Spirit Airlines Logo
5:05 am - 2:00 pmORD-SXM
7h 55m1 stop
Spirit Airlines Logo
3:05 pm - 11:59 pmSXM-ORD
9h 54m1 stop
$311Spirit Airlines
Find Deal
Sat, Aug 30 - Wed, Sep 3
Spirit Airlines Logo
5:05 am - 2:00 pmORD-SXM
7h 55m1 stop
Spirit Airlines Logo
3:05 pm - 10:48 pmSXM-ORD
8h 43m1 stop
$320Spirit Airlines
Find Deal
Sat, Aug 30 - Sat, Sep 6
Spirit Airlines Logo
5:05 am - 2:00 pmORD-SXM
7h 55m1 stop
Spirit Airlines Logo
3:05 pm - 10:48 pmSXM-ORD
8h 43m1 stop
$337Spirit Airlines
Find Deal
Mon, Sep 8 - Mon, Sep 15
Logo
10:27 am - 8:12 amORD-SXM
20h 45m2 stops
Logo
3:05 pm - 10:48 pmSXM-ORD
8h 43m1 stop
$355
Find Deal
Tue, Sep 2 - Sat, Sep 6
Logo
10:27 am - 8:12 amORD-SXM
20h 45m2 stops
Logo
3:05 pm - 10:48 pmSXM-ORD
8h 43m1 stop
$404
Find Deal
Tue, Sep 16 - Sat, Sep 27
Air Canada Logo
8:15 pm - 2:40 pmORD-SXM
16h 25m2 stops
Air Canada Logo
3:40 pm - 9:13 amSXM-ORD
19h 33m2 stops
$476Air Canada
Find Deal
Wed, Nov 26 - Thu, Dec 4
JetBlue Logo
7:00 am - 4:29 pmORD-SXM
7h 29m1 stop
JetBlue Logo
6:00 pm - 10:28 amSXM-ORD
18h 28m1 stop
$477JetBlue
Find Deal
Sun, Dec 7 - Sat, Dec 13
Air Canada Logo
8:15 pm - 2:40 pmORD-SXM
16h 25m2 stops
Air Canada Logo
3:40 pm - 2:55 pmSXM-ORD
25h 15m1 stop
$482Air Canada
Find Deal
Wed, Nov 26 - Thu, Dec 4
Delta Logo
6:01 am - 1:50 pmSTL-SXM
6h 49m1 stop
Delta Logo
3:20 pm - 11:24 pmSXM-STL
9h 04m1 stop
$497Delta
Find Deal
Sat, Sep 13 - Sun, Oct 5
Delta Logo
6:00 am - 2:55 pmMDW-SXM
6h 55m1 stop
Delta Logo
1:45 pm - 9:46 pmSXM-MDW
10h 01m1 stop
$587Delta
Find Deal
Tue, Dec 30 - Thu, Jan 8

American Airlines flights from Illinois to Simpson Bay

Our best American Airlines deals on Illinois to Simpson Bay flight tickets
American Airlines
Sep 19
STL6:00 pmLambert-St Louis
18h 19m
2 stops
SXM1:19 pmSimpson Bay Princess Juliana
Sep 26
SXM2:20 pmSimpson Bay Princess Juliana
10h 39m
1 stop
STL11:59 pmLambert-St Louis
$502
Find similar
American Airlines
Sep 13
STL9:56 amLambert-St Louis
26h 23m
2 stops
SXM1:19 pmSimpson Bay Princess Juliana
Sep 21
SXM2:20 pmSimpson Bay Princess Juliana
19h 56m
2 stops
STL9:16 amLambert-St Louis
$507
Find similar
American Airlines
Sep 26
STL8:23 amLambert-St Louis
28h 17m
1 stop
SXM1:40 pmSimpson Bay Princess Juliana
Sep 30
SXM2:20 pmSimpson Bay Princess Juliana
23h 31m
2 stops
STL12:51 pmLambert-St Louis
$510
Find similar

Spirit Airlines flights from Illinois to Simpson Bay

Our best Spirit Airlines deals on Illinois to Simpson Bay flight tickets
Spirit Airlines
Aug 30
ORD5:05 amChicago O'Hare Intl
7h 55m
1 stop
SXM2:00 pmSimpson Bay Princess Juliana
Sep 3
SXM3:05 pmSimpson Bay Princess Juliana
9h 54m
1 stop
ORD11:59 pmChicago O'Hare Intl
$311
Find similar
Spirit Airlines
Aug 30
ORD5:05 amChicago O'Hare Intl
7h 55m
1 stop
SXM2:00 pmSimpson Bay Princess Juliana
Sep 6
SXM3:05 pmSimpson Bay Princess Juliana
8h 43m
1 stop
ORD10:48 pmChicago O'Hare Intl
$320
Find similar
Spirit Airlines
Sep 8
ORD5:05 amChicago O'Hare Intl
7h 55m
1 stop
SXM2:00 pmSimpson Bay Princess Juliana
Sep 15
SXM3:05 pmSimpson Bay Princess Juliana
8h 43m
1 stop
ORD10:48 pmChicago O'Hare Intl
$337
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Illinois to Simpson Bay 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, momondo users made 832,500 searches. Data last updated August 6, 2025.
Use the filters below to find and compare flights from Illinois to Simpson Bay that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sat 8/30

5:05 am-2:00 pm

1 stop7h 55m

Simpson Bay Princess Juliana

Wed 9/3

3:05 pm-11:59 pm

1 stop9h 54m

$311

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sat 8/30

5:05 am-2:00 pm

1 stop7h 55m

Simpson Bay Princess Juliana

Sat 9/6

3:05 pm-10:48 pm

1 stop8h 43m

$320

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Mon 9/8

5:05 am-2:00 pm

1 stop7h 55m

Simpson Bay Princess Juliana

Mon 9/15

3:05 pm-10:48 pm

1 stop8h 43m

$337

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Tue 9/2

10:27 am-8:12 am

2 stops20h 45m

Simpson Bay Princess Juliana

Sat 9/6

3:05 pm-10:48 pm

1 stop8h 43m

$355

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Tue 9/16

10:27 am-8:12 am

2 stops20h 45m

Simpson Bay Princess Juliana

Sat 9/27

3:05 pm-10:48 pm

1 stop8h 43m

$404

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Wed 11/26

8:15 pm-2:40 pm

2 stops16h 25m

Simpson Bay Princess Juliana

Thu 12/4

3:40 pm-9:13 am

2 stops19h 33m

$476

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sun 12/7

7:00 am-4:29 pm

1 stop7h 29m

Simpson Bay Princess Juliana

Sat 12/13

6:00 pm-10:28 am

1 stop18h 28m

$477

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Wed 11/26

8:15 pm-2:40 pm

2 stops16h 25m

Simpson Bay Princess Juliana

Thu 12/4

3:40 pm-2:55 pm

1 stop25h 15m

$482

St. LouisSimpson Bay

STL - SXM

STLSXM

Lambert-St Louis

Sat 9/13

6:01 am-1:50 pm

1 stop6h 49m

Simpson Bay Princess Juliana

Sun 10/5

3:20 pm-11:24 pm

1 stop9h 04m

$497

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Tue 12/30

6:00 am-2:55 pm

1 stop6h 55m

Simpson Bay Princess Juliana

Thu 1/8

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
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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?

In general, September 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 $612. If you aren’t able to travel to Simpson Bay during the month of September, then flying in August is also cheap. Prices for this month can be found on momondo for an average of $637.

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 $905. 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 $892.

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 $736 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 $549 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.

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

$108

Fastest flight time

4h 45m

Direct flights

Mon and Sun

Airports in Simpson Bay

1 airport
The best one-way flight to Simpson Bay from Illinois in the past 72 hours is $108. The best round-trip flight deal from Illinois to Simpson Bay found on momondo in the last 72 hours is $311.
The fastest flight from Illinois to Simpson Bay takes 4h 45m
Direct flights go from Illinois to Simpson Bay on Monday and Sunday. Airlines offering direct flights are: United Airlines and American Airlines.
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?

  • 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?

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 AirlinesPriceFrom $335Free CancellationRating
6.3
8,051 reviews
Search Spirit Airlines flights
DeltaPriceFrom $425Free CancellationRating
8.0
7,985 reviews
Search Delta flights
American AirlinesPriceFrom $579Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
United AirlinesPriceFrom $654Free CancellationRating
7.4
8,916 reviews
Search United Airlines flights

Traveling to a place near Simpson Bay?

Book flights to Simpson Bay if you plan to visit one of these locations
Philipsburg

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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