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Cheap flights from Simpson Bay to Chicago from $185

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 12/13. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Cheap round-trip flights

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Delta Logo
4:30 pm - 9:55 amSXM-ORD
19h 25m1 stop
Delta Logo
8:02 pm - 2:55 pmORD-SXM
16h 53m1 stop
$365Delta
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Sat, Nov 22 - Sat, Nov 29
Multiple Airlines Logo
4:30 pm - 10:58 amSXM-ORD
20h 28m1 stop
Multiple Airlines Logo
5:05 am - 3:10 pmORD-SXM
8h 05m1 stop
$381Multiple Airlines
Find Deal
Sat, Jan 17 - Sat, Jan 24
American Airlines Logo
2:03 pm - 11:09 pmSXM-ORD
11h 06m1 stop
American Airlines Logo
9:10 pm - 12:58 pmORD-SXM
13h 48m2 stops
$396American Airlines
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Sat, Jan 17 - Sat, Jan 24
Lufthansa Logo
2:40 pm - 6:40 pmSXM-ORD
6h 00mnonstop
Lufthansa Logo
8:45 am - 3:57 pmORD-SXM
5h 12mnonstop
$409Lufthansa
Find Deal
Sat, Nov 22 - Sat, Nov 29
Spirit Airlines Logo
3:20 pm - 5:11 pmSXM-ORD
27h 51m3 stops
Spirit Airlines Logo
5:00 am - 2:15 pmORD-SXM
7h 15m1 stop
$419Spirit Airlines
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Sat, Nov 22 - Sat, Nov 29
Lufthansa Logo
5:00 pm - 11:43 pmSXM-ORD
8h 43m1 stop
Lufthansa Logo
8:45 am - 3:57 pmORD-SXM
5h 12mnonstop
$420Lufthansa
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Sat, Nov 22 - Sat, Nov 29
Spirit Airlines Logo
3:20 pm - 12:09 amSXM-ORD
10h 49m1 stop
Spirit Airlines Logo
5:00 am - 2:15 pmORD-SXM
7h 15m1 stop
$436Spirit Airlines
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Wed, Dec 17 - Wed, Dec 24
JetBlue Logo
2:30 pm - 5:44 pmSXM-ORD
29h 14m1 stop
JetBlue Logo
2:05 pm - 2:28 pmORD-SXM
22h 23m1 stop
$465JetBlue
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Sun, Jan 11 - Sun, Jan 18
JetBlue Logo
5:36 pm - 5:44 pmSXM-ORD
26h 08m2 stops
JetBlue Logo
8:45 am - 2:28 pmORD-SXM
27h 43m1 stop
$490JetBlue
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Sun, Jan 11 - Sun, Jan 18
American Airlines Logo
2:03 pm - 11:09 pmSXM-ORD
11h 06m1 stop
American Airlines Logo
8:04 am - 3:07 pmORD-SXM
5h 03mnonstop
$609American Airlines
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Sat, Jan 17 - Sat, Jan 24

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
Jan 17
SXM2:03 pmSimpson Bay Princess Juliana
11h 06m
1 stop
ORD11:09 pmChicago O'Hare Intl
Jan 24
ORD9:10 pmChicago O'Hare Intl
13h 48m
2 stops
SXM12:58 pmSimpson Bay Princess Juliana
$396
Find similar
American Airlines
Jan 17
SXM2:03 pmSimpson Bay Princess Juliana
11h 06m
1 stop
ORD11:09 pmChicago O'Hare Intl
Jan 24
ORD8:04 amChicago O'Hare Intl
5h 03m
SXM3:07 pmSimpson Bay Princess Juliana
$609
Find similar
American Airlines
Feb 14
SXM3:00 pmSimpson Bay Princess Juliana
5h 54m
ORD6:54 pmChicago O'Hare Intl
Feb 21
ORD5:26 pmChicago O'Hare Intl
17h 14m
1 stop
SXM12:40 pmSimpson Bay Princess Juliana
$629
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Lufthansa flights from Simpson Bay to Chicago O'Hare Intl Airport

Our best Lufthansa deals on Simpson Bay to Chicago O'Hare Intl Airport flight tickets
Lufthansa
Nov 22
SXM2:40 pmSimpson Bay Princess Juliana
6h 00m
ORD6:40 pmChicago O'Hare Intl
Nov 29
ORD8:45 amChicago O'Hare Intl
5h 12m
SXM3:57 pmSimpson Bay Princess Juliana
$409
Find similar
Lufthansa
Nov 22
SXM5:00 pmSimpson Bay Princess Juliana
8h 43m
1 stop
ORD11:43 pmChicago O'Hare Intl
Nov 29
ORD8:45 amChicago O'Hare Intl
5h 12m
SXM3:57 pmSimpson Bay Princess Juliana
$420
Find similar

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 November 2, 2025.
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

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sat 11/22

4:30 pm-9:55 am

1 stop19h 25m

Chicago O'Hare Intl

Sat 11/29

8:02 pm-2:55 pm

1 stop16h 53m

$365

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sat 1/17

4:30 pm-10:58 am

1 stop20h 28m

Chicago O'Hare Intl

Sat 1/24

5:05 am-3:10 pm

1 stop8h 05m

$381

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sat 1/17

2:03 pm-11:09 pm

1 stop11h 06m

Chicago O'Hare Intl

Sat 1/24

9:10 pm-12:58 pm

2 stops13h 48m

$396

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sat 11/22

2:40 pm-6:40 pm

Nonstop6h 00m

Chicago O'Hare Intl

Sat 11/29

8:45 am-3:57 pm

Nonstop5h 12m

$409

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sat 11/22

3:20 pm-5:11 pm

3 stops27h 51m

Chicago O'Hare Intl

Sat 11/29

5:00 am-2:15 pm

1 stop7h 15m

$419

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sat 11/22

5:00 pm-11:43 pm

1 stop8h 43m

Chicago O'Hare Intl

Sat 11/29

8:45 am-3:57 pm

Nonstop5h 12m

$420

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Wed 12/17

3:20 pm-12:09 am

1 stop10h 49m

Chicago O'Hare Intl

Wed 12/24

5:00 am-2:15 pm

1 stop7h 15m

$436

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sun 1/11

2:30 pm-5:44 pm

1 stop29h 14m

Chicago O'Hare Intl

Sun 1/18

2:05 pm-2:28 pm

1 stop22h 23m

$465

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sun 1/11

5:36 pm-5:44 pm

2 stops26h 08m

Chicago O'Hare Intl

Sun 1/18

8:45 am-2:28 pm

1 stop27h 43m

$490

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sat 1/17

2:03 pm-11:09 pm

1 stop11h 06m

Chicago O'Hare Intl

Sat 1/24

8:04 am-3:07 pm

Nonstop5h 03m

$609

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 day to depart on your flight to Chicago O'Hare Intl Airport?

The cheapest day to depart on your flight to Chicago O'Hare Intl Airport is on a Monday when prices can be found for as low as $372. This is often the case because there is less demand to fly during this day of the week. On the other hand, Sunday is the most expensive day to depart from Simpson Bay because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $773.

What is the cheapest time of day to depart on your flight to Chicago O'Hare Intl Airport?

Flying to Chicago O'Hare Intl Airport from Simpson Bay at noon is the least expensive time of day to depart. momondo users have found prices as low as $452 when looking at flights departing at noon. Try not to purchase tickets in the afternoon because they tend to be around $754. Of course, these prices can vary depending on the time of year and what airport you fly to.

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 Princess Juliana to Chicago O'Hare Intl flights?

There are 3 cabin classes available to choose from on Simpson Bay Princess Juliana to Chicago O'Hare Intl 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 3% 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

5h 39m

Direct flights

Mon and Sun
The fastest flight from Simpson Bay to Chicago O'Hare Intl Airport takes 5h 39m
Direct flights go from Simpson Bay to Chicago O'Hare Intl Airport on Monday and Sunday. There are no airlines offering direct flights.
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  • 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. 5h 39m 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
Lake Geneva
South Haven
Schaumburg
Rockford
Merrillville
Gurnee
Naperville
Rosemont
Kenosha
New Buffalo
Joliet
Oak Brook
Orland Park
Racine
Hammond
Tinley Park
Janesville
Aurora
Elgin
Benton Harbor

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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