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Cheap flights from Simpson Bay to Chicago from $230

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 Chicago 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.
1 adult
1 adult, Economy, 0 bags

Find the cheapest flights from Simpson Bay to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
JetBlue Logo
1:42 pm - 11:44 pm
SXM
-
ORD
11h 02m
1 stop
JetBlue Logo
5:27 pm - 4:22 pm
ORD
-
SXM
21h 55m
1 stop
$453JetBlue
Fri, Jul 10 - Fri, Jul 17
Frontier Logo
12:43 pm - 11:10 pm
SXM
-
ORD
11h 27m
1 stop
Frontier Logo
5:13 pm - 11:30 am
ORD
-
SXM
17h 17m
1 stop
$474Frontier
Sat, Jul 18 - Fri, Jul 24
Frontier Logo
12:43 pm - 11:10 pm
SXM
-
ORD
11h 27m
1 stop
Frontier Logo
5:13 pm - 11:30 am
ORD
-
SXM
17h 17m
1 stop
$477Frontier
Sat, Jul 18 - Fri, Jul 24
JetBlue Logo
1:42 pm - 11:44 pm
SXM
-
ORD
11h 02m
1 stop
JetBlue Logo
5:27 pm - 10:07 am
ORD
-
SXM
15h 40m
1 stop
$479JetBlue
Fri, Jul 10 - Fri, Jul 17
JetBlue Logo
1:42 pm - 11:44 pm
SXM
-
ORD
11h 02m
1 stop
JetBlue Logo
6:00 am - 10:07 am
ORD
-
SXM
27h 07m
1 stop
$498JetBlue
Sat, Jul 11 - Fri, Jul 17
JetBlue Logo
1:42 pm - 11:44 pm
SXM
-
ORD
11h 02m
1 stop
JetBlue Logo
8:10 pm - 4:22 pm
ORD
-
SXM
19h 12m
2 stops
$511JetBlue
Fri, Jul 10 - Fri, Jul 17
JetBlue Logo
1:42 pm - 11:44 pm
SXM
-
ORD
11h 02m
1 stop
JetBlue Logo
8:10 pm - 4:22 pm
ORD
-
SXM
19h 12m
2 stops
$536JetBlue
Sat, Jul 11 - Fri, Jul 17
Frontier Logo
12:43 pm - 11:10 pm
SXM
-
ORD
11h 27m
1 stop
Frontier Logo
7:05 am - 11:30 am
ORD
-
SXM
27h 25m
2 stops
$540Frontier
Sat, Jul 18 - Fri, Jul 24
JetBlue Logo
1:42 pm - 11:44 pm
SXM
-
ORD
11h 02m
1 stop
JetBlue Logo
8:10 pm - 4:22 pm
ORD
-
SXM
19h 12m
2 stops
$548JetBlue
Fri, Jul 10 - Fri, Jul 17
Frontier Logo
12:43 pm - 11:10 pm
SXM
-
ORD
11h 27m
1 stop
Frontier Logo
7:05 am - 11:30 am
ORD
-
SXM
27h 25m
2 stops
$552Frontier
Sat, Jul 18 - Fri, Jul 24

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American Airlines flights from Simpson Bay to Chicago O'Hare Intl Airport

Our best American Airlines deals on Simpson Bay to Chicago O'Hare Intl Airport flight tickets
American Airlines
Jul 29
SXM1:34 pmSimpson Bay Princess Juliana
9h 27m
1 stop
ORD10:01 pmChicago O'Hare Intl
Aug 6
ORD6:59 amChicago O'Hare Intl
7h 40m
1 stop
SXM3:39 pmSimpson Bay Princess Juliana
$657
American Airlines
Jul 18
SXM4:45 pmSimpson Bay Princess Juliana
14h 53m
2 stops
ORD6:38 amChicago O'Hare Intl
Jul 24
ORD8:55 pmChicago O'Hare Intl
13h 38m
2 stops
SXM11:33 amSimpson Bay Princess Juliana
$670
American Airlines
Jul 10
SXM1:34 pmSimpson Bay Princess Juliana
11h 27m
2 stops
ORD12:01 amChicago O'Hare Intl
Jul 17
ORD8:55 pmChicago O'Hare Intl
13h 38m
2 stops
SXM11:33 amSimpson Bay Princess Juliana
$759

JetBlue flights from Simpson Bay to Chicago O'Hare Intl Airport

Our best JetBlue deals on Simpson Bay to Chicago O'Hare Intl Airport flight tickets
JetBlue
Jul 10
SXM1:42 pmSimpson Bay Princess Juliana
11h 02m
1 stop
ORD11:44 pmChicago O'Hare Intl
Jul 17
ORD5:27 pmChicago O'Hare Intl
21h 55m
1 stop
SXM4:22 pmSimpson Bay Princess Juliana
$453
JetBlue
Jul 10
SXM1:42 pmSimpson Bay Princess Juliana
11h 02m
1 stop
ORD11:44 pmChicago O'Hare Intl
Jul 17
ORD5:27 pmChicago O'Hare Intl
15h 40m
1 stop
SXM10:07 amSimpson Bay Princess Juliana
$479
JetBlue
Jul 11
SXM1:42 pmSimpson Bay Princess Juliana
11h 02m
1 stop
ORD11:44 pmChicago O'Hare Intl
Jul 17
ORD6:00 amChicago O'Hare Intl
27h 07m
1 stop
SXM10:07 amSimpson Bay Princess Juliana
$498

momondo Fare Finder

 
Customize your flight search to find flights from Simpson Bay to Chicago O'Hare Intl Airport 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 June 16, 2026.
Use the filters below to find and compare flights from Simpson Bay to Chicago O'Hare Intl Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Fri 7/10

1:42 pm-11:44 pm

1 stop11h 02m

Chicago O'Hare Intl

Fri 7/17

5:27 pm-4:22 pm

1 stop21h 55m

$453

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sat 7/18

12:43 pm-11:10 pm

1 stop11h 27m

Chicago O'Hare Intl

Fri 7/24

5:13 pm-11:30 am

1 stop17h 17m

$474

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sat 7/18

12:43 pm-11:10 pm

1 stop11h 27m

Chicago O'Hare Intl

Fri 7/24

5:13 pm-11:30 am

1 stop17h 17m

$477
Quickest round-trip

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Fri 7/10

1:42 pm-11:44 pm

1 stop11h 02m

Chicago O'Hare Intl

Fri 7/17

5:27 pm-10:07 am

1 stop15h 40m

$479

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sat 7/11

1:42 pm-11:44 pm

1 stop11h 02m

Chicago O'Hare Intl

Fri 7/17

6:00 am-10:07 am

1 stop27h 07m

$498

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Fri 7/10

1:42 pm-11:44 pm

1 stop11h 02m

Chicago O'Hare Intl

Fri 7/17

8:10 pm-4:22 pm

2 stops19h 12m

$511

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sat 7/11

1:42 pm-11:44 pm

1 stop11h 02m

Chicago O'Hare Intl

Fri 7/17

8:10 pm-4:22 pm

2 stops19h 12m

$536

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sat 7/18

12:43 pm-11:10 pm

1 stop11h 27m

Chicago O'Hare Intl

Fri 7/24

7:05 am-11:30 am

2 stops27h 25m

$540

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Fri 7/10

1:42 pm-11:44 pm

1 stop11h 02m

Chicago O'Hare Intl

Fri 7/17

8:10 pm-4:22 pm

2 stops19h 12m

$548

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sat 7/18

12:43 pm-11:10 pm

1 stop11h 27m

Chicago O'Hare Intl

Fri 7/24

7:05 am-11:30 am

2 stops27h 25m

$552

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 Chicago from

How to get the cheapest flight ticket from Simpson Bay to Chicago O'Hare Intl Airport

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 Simpson Bay Princess Juliana to Chicago O'Hare Intl flight route?

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

What cabin class options are available on Simpson Bay to Chicago O'Hare Intl Airport flights?

There are 2 cabin classes available to choose from on Simpson Bay to Chicago O'Hare Intl Airport 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 Chicago O'Hare Intl Airport flights?

You could potentially save up to 30% on your flight if you consider stops on a Simpson Bay to Chicago O'Hare Intl Airport flight.

How have Simpson Bay to Chicago O'Hare Intl Airport flight prices changed over time?

When to book flights from Simpson Bay to Chicago O'Hare Intl Airport

Are you open to changing your travel dates? Check out the ideal times to fly from Simpson Bay to Chicago O'Hare Intl Airport according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Simpson Bay to Chicago O'Hare Intl Airport (SXM to ORD) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Simpson Bay to Chicago O'Hare Intl Airport

Fastest flight time

8h 36m

Direct flights

Sun
The fastest flight from Simpson Bay to Chicago O'Hare Intl Airport takes 8h 36m
Direct flights go from Simpson Bay to Chicago O'Hare Intl Airport on Sunday. There are no airlines offering direct flights.
Search flight deals

Frequently asked questions about flying from Simpson Bay to Chicago O'Hare Intl Airport

  • How far is Simpson Bay Princess Juliana to Chicago O'Hare Intl by plane?

    There are 2203.6 mi between Simpson Bay Princess Juliana and Chicago O'Hare Intl. 8h 36m is a normal flight duration for this route.

  • When did momondo last update prices for flights from Simpson Bay Princess Juliana Airport to Chicago O'Hare Intl Airport?

    Prices for flights from Simpson Bay Princess Juliana Airport to Chicago O'Hare Intl Airport are refreshed on a daily basis.

  • How old do you have to be to fly from Simpson Bay Princess Juliana Airport to Chicago O'Hare Intl Airport?

    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 Chicago O'Hare Intl Airport.

  • What documentation or ID do you need to fly to Chicago O'Hare Intl Airport?

    The travel and health documents you'll need for your trip to Chicago O'Hare Intl Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago O'Hare Intl Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Simpson Bay to Chicago O'Hare Intl Airport?

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
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Why use momondo?

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

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Simpson Bay to Chicago. Millions of users trust and use momondo every year so you are in good hands.

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

Yes. momondo allows you to filter the results for Simpson Bay to Chicago flights to just show those with flexible booking policies.

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

momondo helps you find the best flight between Simpson Bay and Chicago 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 Simpson Bay to Chicago right now. Can momondo alert me if prices change?

Of course. momondo tracks the price of Simpson Bay to Chicago flights. All you need is a valid email address and we will do the rest; it is that quick and easy.

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