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Cheap flights from Illinois to Simpson Bay from $70

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 1/17. 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
8:43 pm - 2:10 pm
ORD
-
SXM
15h 27m1 stop
Spirit Airlines Logo
3:15 pm - 11:46 pm
SXM
-
ORD
10h 31m1 stop
$211Spirit Airlines
Thu, Jan 15 - Thu, Jan 22
Spirit Airlines Logo
5:15 am - 2:10 pm
ORD
-
SXM
6h 55m1 stop
Spirit Airlines Logo
3:15 pm - 11:46 pm
SXM
-
ORD
10h 31m1 stop
$212Spirit Airlines
Sat, Jan 10 - Sat, Jan 17
Spirit Airlines Logo
5:15 am - 2:10 pm
ORD
-
SXM
6h 55m1 stop
Spirit Airlines Logo
3:15 pm - 11:46 pm
SXM
-
ORD
10h 31m1 stop
$223Spirit Airlines
Sat, Jan 10 - Sat, Jan 17
Air Canada Logo
4:05 pm - 4:00 pm
STL
-
SXM
21h 55m1 stop
Air Canada Logo
5:00 pm - 3:29 pm
SXM
-
STL
24h 29m1 stop
$400Air Canada
Sun, Jan 4 - Mon, Jan 12
Air Canada Logo
4:05 pm - 4:00 pm
STL
-
SXM
21h 55m1 stop
Air Canada Logo
4:00 pm - 3:29 pm
SXM
-
STL
24h 29m1 stop
$425Air Canada
Tue, Mar 3 - Fri, Mar 13
Delta Logo
6:00 am - 2:55 pm
STL
-
SXM
6h 55m1 stop
Delta Logo
1:55 pm - 11:37 pm
SXM
-
STL
11h 42m1 stop
$465Delta
Wed, Jan 14 - Thu, Jan 22
American Airlines Logo
5:04 pm - 1:45 pm
STL
-
SXM
18h 41m2 stops
American Airlines Logo
5:33 pm - 11:59 pm
SXM
-
STL
8h 26m1 stop
$470American Airlines
Tue, Jan 13 - Fri, Jan 23
American Airlines Logo
6:02 pm - 12:58 pm
STL
-
SXM
16h 56m1 stop
American Airlines Logo
1:41 pm - 10:05 pm
SXM
-
STL
10h 24m1 stop
$495American Airlines
Sun, Feb 1 - Sat, Feb 14
Delta Logo
6:00 am - 2:55 pm
MDW
-
SXM
6h 55m1 stop
Delta Logo
1:55 pm - 10:22 pm
SXM
-
MDW
10h 27m1 stop
$501Delta
Mon, Jan 19 - Fri, Jan 23
KLM Logo
6:45 am - 4:03 pm
MDW
-
SXM
7h 18m1 stop
KLM Logo
3:42 pm - 9:08 am
SXM
-
MDW
19h 26m1 stop
$568KLM
Sat, Jan 10 - Sat, Jan 17

Spirit Airlines flights from Illinois to Simpson Bay

Our best Spirit Airlines deals on Illinois to Simpson Bay flight tickets
Spirit Airlines
Jan 15
ORD8:43 pmChicago O'Hare Intl
15h 27m
1 stop
SXM2:10 pmSimpson Bay Princess Juliana
Jan 22
SXM3:15 pmSimpson Bay Princess Juliana
10h 31m
1 stop
ORD11:46 pmChicago O'Hare Intl
$211
Find similar
Spirit Airlines
Jan 10
ORD5:15 amChicago O'Hare Intl
6h 55m
1 stop
SXM2:10 pmSimpson Bay Princess Juliana
Jan 17
SXM3:15 pmSimpson Bay Princess Juliana
10h 31m
1 stop
ORD11:46 pmChicago O'Hare Intl
$212
Find similar
Spirit Airlines
Jan 10
ORD5:15 amChicago O'Hare Intl
6h 55m
1 stop
SXM2:10 pmSimpson Bay Princess Juliana
Jan 17
SXM3:15 pmSimpson Bay Princess Juliana
10h 31m
1 stop
ORD11:46 pmChicago O'Hare Intl
$223
Find similar

Air Canada flights from Illinois to Simpson Bay

Our best Air Canada deals on Illinois to Simpson Bay flight tickets
Air Canada
Jan 4
STL4:05 pmLambert-St Louis
21h 55m
1 stop
SXM4:00 pmSimpson Bay Princess Juliana
Jan 12
SXM5:00 pmSimpson Bay Princess Juliana
24h 29m
1 stop
STL3:29 pmLambert-St Louis
$400
Find similar
Air Canada
Mar 3
STL4:05 pmLambert-St Louis
21h 55m
1 stop
SXM4:00 pmSimpson Bay Princess Juliana
Mar 13
SXM4:00 pmSimpson Bay Princess Juliana
24h 29m
1 stop
STL3:29 pmLambert-St Louis
$425
Find similar
Air Canada
Jan 25
STL4:05 pmLambert-St Louis
21h 55m
1 stop
SXM4:00 pmSimpson Bay Princess Juliana
Jan 29
SXM3:40 pmSimpson Bay Princess Juliana
25h 49m
2 stops
STL3:29 pmLambert-St Louis
$453
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 December 21, 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

Thu 1/15

8:43 pm-2:10 pm

1 stop15h 27m

Simpson Bay Princess Juliana

Thu 1/22

3:15 pm-11:46 pm

1 stop10h 31m

$211

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sat 1/10

5:15 am-2:10 pm

1 stop6h 55m

Simpson Bay Princess Juliana

Sat 1/17

3:15 pm-11:46 pm

1 stop10h 31m

$212

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sat 1/10

5:15 am-2:10 pm

1 stop6h 55m

Simpson Bay Princess Juliana

Sat 1/17

3:15 pm-11:46 pm

1 stop10h 31m

$223

St. LouisSimpson Bay

STL - SXM

STLSXM

Lambert-St Louis

Sun 1/4

4:05 pm-4:00 pm

1 stop21h 55m

Simpson Bay Princess Juliana

Mon 1/12

5:00 pm-3:29 pm

1 stop24h 29m

$400

St. LouisSimpson Bay

STL - SXM

STLSXM

Lambert-St Louis

Tue 3/3

4:05 pm-4:00 pm

1 stop21h 55m

Simpson Bay Princess Juliana

Fri 3/13

4:00 pm-3:29 pm

1 stop24h 29m

$425

St. LouisSimpson Bay

STL - SXM

STLSXM

Lambert-St Louis

Wed 1/14

6:00 am-2:55 pm

1 stop6h 55m

Simpson Bay Princess Juliana

Thu 1/22

1:55 pm-11:37 pm

1 stop11h 42m

$465

St. LouisSimpson Bay

STL - SXM

STLSXM

Lambert-St Louis

Tue 1/13

5:04 pm-1:45 pm

2 stops18h 41m

Simpson Bay Princess Juliana

Fri 1/23

5:33 pm-11:59 pm

1 stop8h 26m

$470

St. LouisSimpson Bay

STL - SXM

STLSXM

Lambert-St Louis

Sun 2/1

6:02 pm-12:58 pm

1 stop16h 56m

Simpson Bay Princess Juliana

Sat 2/14

1:41 pm-10:05 pm

1 stop10h 24m

$495

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Mon 1/19

6:00 am-2:55 pm

1 stop6h 55m

Simpson Bay Princess Juliana

Fri 1/23

1:55 pm-10:22 pm

1 stop10h 27m

$501

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Sat 1/10

6:45 am-4:03 pm

1 stop7h 18m

Simpson Bay Princess Juliana

Sat 1/17

3:42 pm-9:08 am

1 stop19h 26m

$568

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, 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 $881. 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 $805.

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 $683 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 $507 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 14% 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

$313

Fastest flight time

5h 03m

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 $313. The best round-trip flight deal from Illinois to Simpson Bay found on momondo in the last 72 hours is $556.
The fastest flight from Illinois to Simpson Bay takes 5h 03m
Direct flights go from Illinois to Simpson Bay on Monday and Sunday. The only airline offering direct flights is United Airlines.
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?

  • 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
DeltaPriceFrom $292Free CancellationRating
7.9
8,021 reviews
Search Delta flights
Spirit AirlinesPriceFrom $312Free CancellationRating
6.3
8,194 reviews
Search Spirit Airlines flights
United AirlinesPriceFrom $410Free CancellationRating
7.4
9,100 reviews
Search United Airlines flights
JetBluePriceFrom $535Free CancellationRating
7.2
2,896 reviews
Search JetBlue flights
American AirlinesPriceFrom $536Free CancellationRating
7.2
11,050 reviews
Search American 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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Airlines are sorted and displayed according to clicks in the past 7 days on momondo
American Airlines
United Airlines
Spirit Airlines
Delta
JetBlue