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Cheap flights from Illinois to Simpson Bay from $135

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 11/13. 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
1 adult, Economy, 0 bags

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Illinois to Simpson Bay

Cheap round-trip flights

Enter your travel dates to find the best prices.
Air Canada Logo
5:35 pm - 2:45 pmORD  Chicago O'Hare Intl-SXM Simpson Bay Princess Juliana
20h 10m1 stop Toronto Pearson Intl
Air Canada Logo
2:40 pm - 3:52 pmSXM  Simpson Bay Princess Juliana-ORD Chicago O'Hare Intl
26h 12m1 stop Montreal Pierre Elliott Trudeau Intl
$348Air Canada
Sat, Oct 24 - Sat, Oct 31
Air Canada Logo
3:40 pm - 2:45 pmORD  Chicago O'Hare Intl-SXM Simpson Bay Princess Juliana
22h 05m2 stops Montreal Pierre Elliott Trudeau Intl Toronto Pearson Intl
Air Canada Logo
2:40 pm - 3:52 pmSXM  Simpson Bay Princess Juliana-ORD Chicago O'Hare Intl
26h 12m1 stop Montreal Pierre Elliott Trudeau Intl
$351Air Canada
Sat, Oct 24 - Sat, Oct 31
Multiple Airlines Logo
7:25 am - 2:45 pmORD  Chicago O'Hare Intl-SXM Simpson Bay Princess Juliana
29h 20m2 stops Toronto Island Montreal Pierre Elliott Trudeau Intl
Multiple Airlines Logo
2:30 pm - 11:28 pmSXM  Simpson Bay Princess Juliana-ORD Chicago O'Hare Intl
10h 58m1 stop Fort Lauderdale
$406Multiple Airlines
Fri, Nov 27 - Wed, Dec 2
Multiple Airlines Logo
1:55 pm - 2:45 pmORD  Chicago O'Hare Intl-SXM Simpson Bay Princess Juliana
22h 50m1 stop Montreal Pierre Elliott Trudeau Intl
Multiple Airlines Logo
2:30 pm - 11:28 pmSXM  Simpson Bay Princess Juliana-ORD Chicago O'Hare Intl
10h 58m1 stop Fort Lauderdale
$406Multiple Airlines
Fri, Nov 27 - Wed, Dec 2
JetBlue Logo
6:00 am - 2:00 pmORD  Chicago O'Hare Intl-SXM Simpson Bay Princess Juliana
7h 00m1 stop Fort Lauderdale
JetBlue Logo
3:05 pm - 11:08 pmSXM  Simpson Bay Princess Juliana-ORD Chicago O'Hare Intl
9h 03m1 stop Fort Lauderdale
$442JetBlue
Sat, Sep 12 - Sat, Sep 19
JetBlue Logo
6:00 am - 2:00 pmORD  Chicago O'Hare Intl-SXM Simpson Bay Princess Juliana
7h 00m1 stop Fort Lauderdale
JetBlue Logo
3:05 pm - 11:08 pmSXM  Simpson Bay Princess Juliana-ORD Chicago O'Hare Intl
9h 03m1 stop Fort Lauderdale
$442JetBlue
Sun, Sep 13 - Thu, Sep 17
American Airlines Logo
6:09 pm - 2:31 pmSTL  Lambert-St Louis-SXM Simpson Bay Princess Juliana
18h 22m1 stop Miami
American Airlines Logo
2:03 pm - 10:05 pmSXM  Simpson Bay Princess Juliana-STL Lambert-St Louis
10h 02m1 stop Miami
$518American Airlines
Sat, Jan 23 - Fri, Jan 29
American Airlines Logo
4:57 pm - 2:31 pmSTL  Lambert-St Louis-SXM Simpson Bay Princess Juliana
19h 34m2 stops Dallas/Fort Worth Miami
American Airlines Logo
2:03 pm - 11:58 pmSXM  Simpson Bay Princess Juliana-STL Lambert-St Louis
11h 55m2 stops Miami Chicago O'Hare Intl
$523American Airlines
Sat, Jan 23 - Fri, Jan 29
Delta Logo
6:00 am - 1:53 pmSTL  Lambert-St Louis-SXM Simpson Bay Princess Juliana
6h 53m1 stop Atlanta Hartsfield-Jackson
Delta Logo
3:05 pm - 11:54 pmSXM  Simpson Bay Princess Juliana-STL Lambert-St Louis
9h 49m1 stop Atlanta Hartsfield-Jackson
$545Delta
Fri, Oct 2 - Fri, Oct 9
Delta Logo
6:00 am - 2:40 pmSTL  Lambert-St Louis-SXM Simpson Bay Princess Juliana
6h 40m1 stop Atlanta Hartsfield-Jackson
Delta Logo
1:40 pm - 11:39 pmSXM  Simpson Bay Princess Juliana-STL Lambert-St Louis
11h 59m1 stop Atlanta Hartsfield-Jackson
$596Delta
Sun, Jan 10 - Fri, Jan 22

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Air Canada flights from Illinois to Simpson Bay

Our best Air Canada deals on Illinois to Simpson Bay flight tickets
Air Canada
Oct 24
ORD5:35 pmChicago O'Hare Intl
20h 10m
1 stop
SXM2:45 pmSimpson Bay Princess Juliana
Oct 31
SXM2:40 pmSimpson Bay Princess Juliana
26h 12m
1 stop
ORD3:52 pmChicago O'Hare Intl
$348
Air Canada
Oct 24
ORD3:40 pmChicago O'Hare Intl
22h 05m
2 stops
SXM2:45 pmSimpson Bay Princess Juliana
Oct 31
SXM2:40 pmSimpson Bay Princess Juliana
26h 12m
1 stop
ORD3:52 pmChicago O'Hare Intl
$351
Air Canada
Oct 16
ORD9:50 amChicago O'Hare Intl
30h 10m
1 stop
SXM5:00 pmSimpson Bay Princess Juliana
Oct 22
SXM6:00 pmSimpson Bay Princess Juliana
16h 00m
1 stop
ORD9:00 amChicago O'Hare Intl
$353

Southwest flights from Illinois to Simpson Bay

Our best Southwest deals on Illinois to Simpson Bay flight tickets
Southwest
Nov 1
MDW8:25 pmChicago Midway
17h 15m
2 stops
SXM3:40 pmSimpson Bay Princess Juliana
Nov 5
SXM3:20 pmSimpson Bay Princess Juliana
11h 45m
2 stops
MDW1:05 amChicago Midway
$472
Southwest
Nov 27
MDW5:05 amChicago Midway
7h 10m
1 stop
SXM2:15 pmSimpson Bay Princess Juliana
Dec 3
SXM3:20 pmSimpson Bay Princess Juliana
16h 20m
2 stops
MDW5:40 amChicago Midway
$489
Southwest
Nov 1
MDW5:10 amChicago Midway
8h 30m
1 stop
SXM3:40 pmSimpson Bay Princess Juliana
Nov 5
SXM3:20 pmSimpson Bay Princess Juliana
9h 35m
1 stop
MDW10:55 pmChicago Midway
$520

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 18, 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 Chicago O'Hare Intl - SXM Simpson Bay Princess Juliana

ORDSXM

Chicago O'Hare Intl

Sat 10/24

5:35 pm-2:45 pm

1 stop20h 10m

Simpson Bay Princess Juliana

Sat 10/31

2:40 pm-3:52 pm

1 stop26h 12m

$348

ChicagoSimpson Bay

ORD Chicago O'Hare Intl - SXM Simpson Bay Princess Juliana

ORDSXM

Chicago O'Hare Intl

Sat 10/24

3:40 pm-2:45 pm

2 stops22h 05m

Simpson Bay Princess Juliana

Sat 10/31

2:40 pm-3:52 pm

1 stop26h 12m

$351

ChicagoSimpson Bay

ORD Chicago O'Hare Intl - SXM Simpson Bay Princess Juliana

ORDSXM

Chicago O'Hare Intl

Fri 11/27

7:25 am-2:45 pm

2 stops29h 20m

Simpson Bay Princess Juliana

Wed 12/2

2:30 pm-11:28 pm

1 stop10h 58m

$406

ChicagoSimpson Bay

ORD Chicago O'Hare Intl - SXM Simpson Bay Princess Juliana

ORDSXM

Chicago O'Hare Intl

Fri 11/27

1:55 pm-2:45 pm

1 stop22h 50m

Simpson Bay Princess Juliana

Wed 12/2

2:30 pm-11:28 pm

1 stop10h 58m

$406
Quickest round-trip

ChicagoSimpson Bay

ORD Chicago O'Hare Intl - SXM Simpson Bay Princess Juliana

ORDSXM

Chicago O'Hare Intl

Sat 9/12

6:00 am-2:00 pm

1 stop7h 00m

Simpson Bay Princess Juliana

Sat 9/19

3:05 pm-11:08 pm

1 stop9h 03m

$442

ChicagoSimpson Bay

ORD Chicago O'Hare Intl - SXM Simpson Bay Princess Juliana

ORDSXM

Chicago O'Hare Intl

Sun 9/13

6:00 am-2:00 pm

1 stop7h 00m

Simpson Bay Princess Juliana

Thu 9/17

3:05 pm-11:08 pm

1 stop9h 03m

$442

St. LouisSimpson Bay

STL Lambert-St Louis - SXM Simpson Bay Princess Juliana

STLSXM

Lambert-St Louis

Sat 1/23

6:09 pm-2:31 pm

1 stop18h 22m

Simpson Bay Princess Juliana

Fri 1/29

2:03 pm-10:05 pm

1 stop10h 02m

$518

St. LouisSimpson Bay

STL Lambert-St Louis - SXM Simpson Bay Princess Juliana

STLSXM

Lambert-St Louis

Sat 1/23

4:57 pm-2:31 pm

2 stops19h 34m

Simpson Bay Princess Juliana

Fri 1/29

2:03 pm-11:58 pm

2 stops11h 55m

$523

St. LouisSimpson Bay

STL Lambert-St Louis - SXM Simpson Bay Princess Juliana

STLSXM

Lambert-St Louis

Fri 10/2

6:00 am-1:53 pm

1 stop6h 53m

Simpson Bay Princess Juliana

Fri 10/9

3:05 pm-11:54 pm

1 stop9h 49m

$545

St. LouisSimpson Bay

STL Lambert-St Louis - SXM Simpson Bay Princess Juliana

STLSXM

Lambert-St Louis

Sun 1/10

6:00 am-2:40 pm

1 stop6h 40m

Simpson Bay Princess Juliana

Fri 1/22

1:40 pm-11:39 pm

1 stop11h 59m

$596

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 $478. If you aren’t able to travel to Simpson Bay during the month of September, then flying in February is also cheap. Prices for this month can be found on momondo for an average of $501.

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 $597. Flights from Illinois to Simpson Bay on a Saturday will generally be more expensive and average around $788. 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 $667 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 $505 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 37% 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

$135

Fastest flight time

5h 12m

Direct flights

Every day

Airports in Simpson Bay

1 airport
The best one-way flight to Simpson Bay from Illinois in the past 72 hours is $135. The best round-trip flight deal from Illinois to Simpson Bay found on momondo in the last 72 hours is $348.
The fastest flight from Illinois to Simpson Bay takes 5h 12m
Direct flights go from Illinois to Simpson Bay every day.
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
DeltaPriceFrom $240Free CancellationRating
7.8
8,503 reviews
Search Delta flights
JetBluePriceFrom $389Free CancellationRating
7.1
3,033 reviews
Search JetBlue flights
United AirlinesPriceFrom $389Free CancellationRating
7.4
10,105 reviews
Search United Airlines flights
Air CanadaPriceFrom $487Free CancellationRating
7.1
11,493 reviews
Search Air Canada flights
American AirlinesPriceFrom $501Free CancellationRating
7.1
11,954 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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