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Cheap flights from Simpson Bay to Illinois from $220

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Simpson Bay to Illinois departing on 9/8. 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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Find the cheapest flights from Simpson Bay to Illinois

Cheap round-trip flights

Spirit Airlines Logo
3:05 pm - 10:42 amSXM-ORD
20h 37m2 stops
Spirit Airlines Logo
5:05 am - 2:00 pmORD-SXM
7h 55m1 stop
$373Spirit Airlines
Find Deal
Sat, Sep 20 - Sat, Sep 27
Spirit Airlines Logo
3:05 pm - 11:10 amSXM-ORD
21h 05m2 stops
Spirit Airlines Logo
5:05 am - 2:00 pmORD-SXM
7h 55m1 stop
$391Spirit Airlines
Find Deal
Sat, Aug 30 - Sat, Sep 6
JetBlue Logo
1:29 pm - 7:55 amSXM-ORD
19h 26m1 stop
JetBlue Logo
8:34 am - 1:15 pmORD-SXM
27h 41m1 stop
$461JetBlue
Find Deal
Sat, Aug 30 - Sat, Sep 6
JetBlue Logo
1:29 pm - 7:55 amSXM-ORD
19h 26m1 stop
JetBlue Logo
9:51 am - 1:15 pmORD-SXM
26h 24m2 stops
$480JetBlue
Find Deal
Sat, Aug 30 - Sat, Sep 6
Logo
3:05 pm - 10:42 amSXM-ORD
20h 37m2 stops
Logo
6:44 pm - 7:30 pmORD-SXM
23h 46m3 stops
$488
Find Deal
Sat, Sep 20 - Sat, Sep 27
Logo
3:05 pm - 4:12 pmSXM-ORD
26h 07m3 stops
Logo
6:44 pm - 8:12 amORD-SXM
36h 28m3 stops
$495
Find Deal
Mon, Sep 22 - Mon, Sep 29
American Airlines Logo
2:20 pm - 11:48 pmSXM-ORD
10h 28m2 stops
American Airlines Logo
8:34 pm - 1:19 pmORD-SXM
15h 45m2 stops
$603American Airlines
Find Deal
Sat, Sep 20 - Sat, Sep 27
American Airlines Logo
4:24 pm - 8:53 amSXM-ORD
17h 29m1 stop
American Airlines Logo
7:05 pm - 3:15 pmORD-SXM
19h 10m1 stop
$612American Airlines
Find Deal
Thu, Oct 9 - Wed, Oct 15
United Airlines Logo
5:00 pm - 11:44 pmSXM-ORD
8h 44m1 stop
United Airlines Logo
8:45 am - 3:57 pmORD-SXM
5h 12mnonstop
$893United Airlines
Find Deal
Sun, Dec 28 - Sun, Jan 4
United Airlines Logo
2:20 pm - 6:21 pmSXM-ORD
6h 01mnonstop
United Airlines Logo
8:45 am - 3:57 pmORD-SXM
5h 12mnonstop
$3,455United Airlines
Find Deal
Sun, Dec 28 - Sun, Jan 4

Spirit Airlines flights from Simpson Bay to Illinois

Our best Spirit Airlines deals on Simpson Bay to Illinois flight tickets
Spirit Airlines
Sep 20
SXM3:05 pmSimpson Bay Princess Juliana
20h 37m
2 stops
ORD10:42 amChicago O'Hare Intl
Sep 27
ORD5:05 amChicago O'Hare Intl
7h 55m
1 stop
SXM2:00 pmSimpson Bay Princess Juliana
$373
Find similar
Spirit Airlines
Aug 30
SXM3:05 pmSimpson Bay Princess Juliana
21h 05m
2 stops
ORD11:10 amChicago O'Hare Intl
Sep 6
ORD5:05 amChicago O'Hare Intl
7h 55m
1 stop
SXM2:00 pmSimpson Bay Princess Juliana
$391
Find similar
Spirit Airlines
Sep 22
SXM3:05 pmSimpson Bay Princess Juliana
20h 47m
1 stop
ORD10:52 amChicago O'Hare Intl
Sep 29
ORD5:05 amChicago O'Hare Intl
7h 55m
1 stop
SXM2:00 pmSimpson Bay Princess Juliana
$398
Find similar

American Airlines flights from Simpson Bay to Illinois

Our best American Airlines deals on Simpson Bay to Illinois flight tickets
American Airlines
Sep 20
SXM2:20 pmSimpson Bay Princess Juliana
10h 28m
2 stops
ORD11:48 pmChicago O'Hare Intl
Sep 27
ORD8:34 pmChicago O'Hare Intl
15h 45m
2 stops
SXM1:19 pmSimpson Bay Princess Juliana
$603
Find similar
American Airlines
Oct 9
SXM4:24 pmSimpson Bay Princess Juliana
17h 29m
1 stop
ORD8:53 amChicago O'Hare Intl
Oct 15
ORD7:05 pmChicago O'Hare Intl
19h 10m
1 stop
SXM3:15 pmSimpson Bay Princess Juliana
$612
Find similar
American Airlines
Oct 9
SXM4:24 pmSimpson Bay Princess Juliana
16h 54m
2 stops
ORD8:18 amChicago O'Hare Intl
Oct 15
ORD8:44 pmChicago O'Hare Intl
15h 53m
2 stops
SXM1:37 pmSimpson Bay Princess Juliana
$617
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Simpson Bay to Illinois 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 12, 2025.
Use the filters below to find and compare flights from Simpson Bay to Illinois that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sat 9/20

3:05 pm-10:42 am

2 stops20h 37m

Chicago O'Hare Intl

Sat 9/27

5:05 am-2:00 pm

1 stop7h 55m

$373

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sat 8/30

3:05 pm-11:10 am

2 stops21h 05m

Chicago O'Hare Intl

Sat 9/6

5:05 am-2:00 pm

1 stop7h 55m

$391

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sat 8/30

1:29 pm-7:55 am

1 stop19h 26m

Chicago O'Hare Intl

Sat 9/6

8:34 am-1:15 pm

1 stop27h 41m

$461

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sat 8/30

1:29 pm-7:55 am

1 stop19h 26m

Chicago O'Hare Intl

Sat 9/6

9:51 am-1:15 pm

2 stops26h 24m

$480

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sat 9/20

3:05 pm-10:42 am

2 stops20h 37m

Chicago O'Hare Intl

Sat 9/27

6:44 pm-7:30 pm

3 stops23h 46m

$488

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Mon 9/22

3:05 pm-4:12 pm

3 stops26h 07m

Chicago O'Hare Intl

Mon 9/29

6:44 pm-8:12 am

3 stops36h 28m

$495

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sat 9/20

2:20 pm-11:48 pm

2 stops10h 28m

Chicago O'Hare Intl

Sat 9/27

8:34 pm-1:19 pm

2 stops15h 45m

$603

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Thu 10/9

4:24 pm-8:53 am

1 stop17h 29m

Chicago O'Hare Intl

Wed 10/15

7:05 pm-3:15 pm

1 stop19h 10m

$612

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sun 12/28

5:00 pm-11:44 pm

1 stop8h 44m

Chicago O'Hare Intl

Sun 1/4

8:45 am-3:57 pm

Nonstop5h 12m

$893

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sun 12/28

2:20 pm-6:21 pm

Nonstop6h 01m

Chicago O'Hare Intl

Sun 1/4

8:45 am-3:57 pm

Nonstop5h 12m

$3,455

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 Illinois from

How to get the cheapest flight ticket from Simpson Bay to Illinois

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 day to depart on your flight to Illinois?

The cheapest day to depart from Simpson Bay to Illinois is on a Monday when prices can be found for as low as $372. Flights from Simpson Bay to Illinois on a Sunday will generally be more expensive and average around $773. 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 Illinois?

Our most recent data shows that the best time of day to fly to Illinois is in the afternoon. Flights from Simpson Bay to Illinois during this time can be as low as $614. Flights at noon are often more expensive with an average ticket price of $735.

What is the cheapest Simpson Bay Princess Juliana to Illinois flight route?

Fly from Simpson Bay Princess Juliana to Chicago O'Hare Intl for the best Simpson Bay Princess Juliana - Illinois flight prices

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

There are 3 cabin classes available to choose from on Simpson Bay Princess Juliana to Illinois 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 Simpson Bay to Illinois flights?

You could potentially save up to 33% on your flight if you consider stops on a Simpson Bay to Illinois flight.

Cheap Simpson Bay to Illinois flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Simpson Bay to Illinois

Best Price Found

$220

Fastest flight time

6h 00m

Direct flights

Mon and Sun

Airports in Illinois

2 airports
The best one-way flight to Illinois from Simpson Bay in the past 72 hours is $220. The best round-trip flight deal from Simpson Bay to Illinois found on momondo in the last 72 hours is $373.
The fastest flight from Simpson Bay to Illinois takes 6h 00m
Direct flights go from Simpson Bay to Illinois on Monday and Sunday. Airlines offering direct flights are: United Airlines and American Airlines.
There are 2 airports near Illinois: Chicago O'Hare Intl (ORD), Chicago Midway (MDW)
Search flight deals

  • When did momondo last update prices for flights from Simpson Bay Princess Juliana Airport to Illinois?

    Prices for flights from Simpson Bay Princess Juliana Airport to Illinois are updated daily.

  • How old do you have to be to fly from Simpson Bay Princess Juliana Airport to Illinois?

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Simpson Bay Princess Juliana Airport to Illinois.

  • What documentation or ID do you need to fly to Illinois?

    The necessary travel and health documents for your Illinois trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Simpson Bay to Illinois?

Why use momondo?

Why should I use momondo to find a flight deal from Simpson Bay to Illinois?

Finding the right flight to Illinois from Simpson Bay 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 Illinois quick and easy, saving you time and money.

Can I find flights from Simpson Bay to Illinois with flexible booking policies on momondo?

All flight searches from Simpson Bay to Illinois on momondo can be filtered to show those which offer flexible booking policies.

How can momondo help me find flights from Simpson Bay to Illinois?

momondo provides multiple filters to help you find the best flight to Illinois from Simpson Bay. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

I’m not ready to book a flight from Simpson Bay to Illinois right now. Can momondo alert me if prices change?

If you are simply researching potential flights to Illinois, momondo offers a useful price alert feature which will track prices for flights to Illinois from Simpson Bay and alert you when they change.

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