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Cheap flights from Illinois to Simpson Bay from $128

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 6/17. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

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Find the cheapest flights from Illinois to Simpson Bay

Cheap round-trip flights

Enter your travel dates to find the best prices.
Spirit Airlines Logo
7:15 pm - 1:37 pm
ORD
-
SXM
17h 22m
1 stop
Spirit Airlines Logo
2:42 pm - 12:24 am
SXM
-
ORD
10h 42m
1 stop
$277Spirit Airlines
Sat, Apr 18 - Sat, Apr 25
Spirit Airlines Logo
7:15 pm - 1:37 pm
ORD
-
SXM
17h 22m
1 stop
Spirit Airlines Logo
2:42 pm - 12:24 am
SXM
-
ORD
10h 42m
1 stop
$279Spirit Airlines
Sat, Apr 18 - Sat, Apr 25
Spirit Airlines Logo
7:15 pm - 1:37 pm
ORD
-
SXM
17h 22m
1 stop
Spirit Airlines Logo
2:42 pm - 12:24 am
SXM
-
ORD
10h 42m
1 stop
$281Spirit Airlines
Sat, Apr 18 - Sat, Apr 25
Spirit Airlines Logo
7:15 pm - 1:37 pm
ORD
-
SXM
17h 22m
1 stop
Spirit Airlines Logo
2:42 pm - 9:36 am
SXM
-
ORD
19h 54m
1 stop
$301Spirit Airlines
Fri, Apr 24 - Thu, Apr 30
Multiple Airlines Logo
5:05 am - 1:37 pm
ORD
-
SXM
7h 32m
1 stop
Multiple Airlines Logo
4:00 pm - 1:05 pm
SXM
-
ORD
22h 05m
1 stop
$321Multiple Airlines
Sun, Apr 19 - Fri, Apr 24
Multiple Airlines Logo
8:40 am - 2:55 pm
ORD
-
SXM
53h 15m
2 stops
Multiple Airlines Logo
2:42 pm - 12:24 am
SXM
-
ORD
10h 42m
1 stop
$322Multiple Airlines
Sat, Apr 18 - Sat, Apr 25
Air Canada Logo
2:15 pm - 5:00 pm
STL
-
SXM
25h 45m
1 stop
Air Canada Logo
6:00 pm - 12:06 pm
SXM
-
STL
19h 06m
1 stop
$329Air Canada
Fri, Jun 5 - Sat, Jun 13
Air Canada Logo
2:15 pm - 5:00 pm
STL
-
SXM
25h 45m
1 stop
Air Canada Logo
6:00 pm - 12:06 pm
SXM
-
STL
19h 06m
1 stop
$339Air Canada
Wed, Jun 3 - Sat, Jun 6
Southwest Logo
8:55 pm - 1:30 pm
MDW
-
SXM
15h 35m
2 stops
Southwest Logo
2:25 pm - 7:35 am
SXM
-
MDW
18h 10m
2 stops
$520Southwest
Sun, Apr 26 - Tue, Apr 28
Southwest Logo
5:05 am - 2:25 pm
MDW
-
SXM
8h 20m
1 stop
Southwest Logo
2:25 pm - 12:15 am
SXM
-
MDW
10h 50m
1 stop
$570Southwest
Sun, May 3 - Fri, May 29

Air Canada flights from Illinois to Simpson Bay

Our best Air Canada deals on Illinois to Simpson Bay flight tickets
Air Canada
Jun 5
STL2:15 pmLambert-St Louis
25h 45m
1 stop
SXM5:00 pmSimpson Bay Princess Juliana
Jun 13
SXM6:00 pmSimpson Bay Princess Juliana
19h 06m
1 stop
STL12:06 pmLambert-St Louis
$329
Air Canada
Jun 3
STL2:15 pmLambert-St Louis
25h 45m
1 stop
SXM5:00 pmSimpson Bay Princess Juliana
Jun 6
SXM6:00 pmSimpson Bay Princess Juliana
19h 06m
1 stop
STL12:06 pmLambert-St Louis
$339
Air Canada
Jun 3
STL1:05 pmLambert-St Louis
26h 55m
2 stops
SXM5:00 pmSimpson Bay Princess Juliana
Jun 6
SXM6:00 pmSimpson Bay Princess Juliana
19h 06m
1 stop
STL12:06 pmLambert-St Louis
$342

Southwest flights from Illinois to Simpson Bay

Our best Southwest deals on Illinois to Simpson Bay flight tickets
Southwest
May 5
STL5:30 amLambert-St Louis
7h 00m
1 stop
SXM1:30 pmSimpson Bay Princess Juliana
May 15
SXM2:25 pmSimpson Bay Princess Juliana
10h 15m
1 stop
STL11:40 pmLambert-St Louis
$515
Southwest
May 5
STL5:40 pmLambert-St Louis
18h 50m
2 stops
SXM1:30 pmSimpson Bay Princess Juliana
May 15
SXM2:25 pmSimpson Bay Princess Juliana
10h 15m
1 stop
STL11:40 pmLambert-St Louis
$520
Southwest
May 25
STL5:00 amLambert-St Louis
7h 30m
1 stop
SXM1:30 pmSimpson Bay Princess Juliana
May 29
SXM2:25 pmSimpson Bay Princess Juliana
10h 15m
1 stop
STL11:40 pmLambert-St Louis
$523

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 April 5, 2026.
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

Cheapest round-trip

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sat 4/18

7:15 pm-1:37 pm

1 stop17h 22m

Simpson Bay Princess Juliana

Sat 4/25

2:42 pm-12:24 am

1 stop10h 42m

$277

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sat 4/18

7:15 pm-1:37 pm

1 stop17h 22m

Simpson Bay Princess Juliana

Sat 4/25

2:42 pm-12:24 am

1 stop10h 42m

$279

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sat 4/18

7:15 pm-1:37 pm

1 stop17h 22m

Simpson Bay Princess Juliana

Sat 4/25

2:42 pm-12:24 am

1 stop10h 42m

$281

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Fri 4/24

7:15 pm-1:37 pm

1 stop17h 22m

Simpson Bay Princess Juliana

Thu 4/30

2:42 pm-9:36 am

1 stop19h 54m

$301

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sun 4/19

5:05 am-1:37 pm

1 stop7h 32m

Simpson Bay Princess Juliana

Fri 4/24

4:00 pm-1:05 pm

1 stop22h 05m

$321

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sat 4/18

8:40 am-2:55 pm

2 stops53h 15m

Simpson Bay Princess Juliana

Sat 4/25

2:42 pm-12:24 am

1 stop10h 42m

$322

St. LouisSimpson Bay

STL - SXM

STLSXM

Lambert-St Louis

Fri 6/5

2:15 pm-5:00 pm

1 stop25h 45m

Simpson Bay Princess Juliana

Sat 6/13

6:00 pm-12:06 pm

1 stop19h 06m

$329

St. LouisSimpson Bay

STL - SXM

STLSXM

Lambert-St Louis

Wed 6/3

2:15 pm-5:00 pm

1 stop25h 45m

Simpson Bay Princess Juliana

Sat 6/6

6:00 pm-12:06 pm

1 stop19h 06m

$339

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Sun 4/26

8:55 pm-1:30 pm

2 stops15h 35m

Simpson Bay Princess Juliana

Tue 4/28

2:25 pm-7:35 am

2 stops18h 10m

$520
Quickest round-trip

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Sun 5/3

5:05 am-2:25 pm

1 stop8h 20m

Simpson Bay Princess Juliana

Fri 5/29

2:25 pm-12:15 am

1 stop10h 50m

$570

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

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 $427. 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 $443.

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 $795. 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 $654 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 $481 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 43% 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

$737

Fastest flight time

5h 12m

Direct flights

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 $737
The fastest flight from Illinois to Simpson Bay takes 5h 12m
Direct flights go from Illinois to Simpson Bay on 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?

  • 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 $231Free CancellationRating
6.3
8,589 reviews
Search Spirit Airlines flights
DeltaPriceFrom $240Free CancellationRating
7.9
8,384 reviews
Search Delta flights
United AirlinesPriceFrom $389Free CancellationRating
7.4
9,546 reviews
Search United Airlines flights
Air CanadaPriceFrom $487Free CancellationRating
7.1
10,894 reviews
Search Air Canada flights
American AirlinesPriceFrom $501Free CancellationRating
7.1
11,561 reviews
Search American Airlines flights
JetBluePriceFrom $568Free CancellationRating
7.2
2,913 reviews
Search JetBlue 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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