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Cheap flights from Simpson Bay to Chicago from $206

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 8/30. 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 Simpson Bay to Chicago

Cheap round-trip flights

Spirit Airlines Logo
3:05 pm - 10:48 pmSXM-ORD
8h 43m1 stop
Spirit Airlines Logo
5:05 am - 2:00 pmORD-SXM
7h 55m1 stop
$336Spirit Airlines
Find Deal
Mon, Sep 22 - Mon, Sep 29
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
$399Spirit Airlines
Find Deal
Sat, Sep 6 - Sat, Sep 13
Spirit Airlines Logo
3:05 pm - 4:18 pmSXM-ORD
26h 13m3 stops
Spirit Airlines Logo
5:05 am - 2:00 pmORD-SXM
7h 55m1 stop
$413Spirit Airlines
Find Deal
Sat, Sep 6 - Sat, Sep 13
Spirit Airlines Logo
3:05 pm - 10:18 amSXM-ORD
20h 13m2 stops
Spirit Airlines Logo
5:05 am - 2:00 pmORD-SXM
7h 55m1 stop
$456Spirit Airlines
Find Deal
Mon, Sep 22 - Mon, Sep 29
Logo
3:05 pm - 4:18 pmSXM-ORD
26h 13m3 stops
Logo
4:35 pm - 11:26 amORD-SXM
17h 51m2 stops
$480
Find Deal
Sat, Sep 6 - Sat, Sep 13
Logo
3:05 pm - 4:18 pmSXM-ORD
26h 13m3 stops
Logo
11:57 am - 11:26 amORD-SXM
22h 29m3 stops
$500
Find Deal
Sat, Sep 6 - Sat, Sep 13
American Airlines Logo
2:40 pm - 11:53 pmSXM-ORD
10h 13m2 stops
American Airlines Logo
9:12 pm - 1:37 pmORD-SXM
15h 25m2 stops
$599American Airlines
Find Deal
Thu, Oct 9 - Wed, Oct 15
American Airlines Logo
4:24 pm - 11:58 pmSXM-ORD
8h 34m1 stop
American Airlines Logo
9:12 pm - 1:37 pmORD-SXM
15h 25m2 stops
$600American Airlines
Find Deal
Thu, Oct 9 - Wed, Oct 15
American Airlines Logo
4:24 pm - 11:58 pmSXM-ORD
8h 34m1 stop
American Airlines Logo
1:51 pm - 1:37 pmORD-SXM
22h 46m1 stop
$608American Airlines
Find Deal
Thu, Oct 9 - Wed, Oct 15
American Airlines Logo
4:24 pm - 11:58 pmSXM-ORD
8h 34m1 stop
American Airlines Logo
1:51 pm - 1:37 pmORD-SXM
22h 46m1 stop
$609American Airlines
Find Deal
Thu, Oct 9 - Wed, Oct 15

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
Oct 9
SXM2:40 pmSimpson Bay Princess Juliana
10h 13m
2 stops
ORD11:53 pmChicago O'Hare Intl
Oct 15
ORD9:12 pmChicago O'Hare Intl
15h 25m
2 stops
SXM1:37 pmSimpson Bay Princess Juliana
$599
Find similar
American Airlines
Oct 9
SXM4:24 pmSimpson Bay Princess Juliana
8h 34m
1 stop
ORD11:58 pmChicago O'Hare Intl
Oct 15
ORD9:12 pmChicago O'Hare Intl
15h 25m
2 stops
SXM1:37 pmSimpson Bay Princess Juliana
$600
Find similar
American Airlines
Oct 9
SXM4:24 pmSimpson Bay Princess Juliana
8h 34m
1 stop
ORD11:58 pmChicago O'Hare Intl
Oct 15
ORD1:51 pmChicago O'Hare Intl
22h 46m
1 stop
SXM1:37 pmSimpson Bay Princess Juliana
$608
Find similar

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

Our best Spirit Airlines deals on Simpson Bay to Chicago O'Hare Intl Airport flight tickets
Spirit Airlines
Sep 22
SXM3:05 pmSimpson Bay Princess Juliana
8h 43m
1 stop
ORD10:48 pmChicago O'Hare Intl
Sep 29
ORD5:05 amChicago O'Hare Intl
7h 55m
1 stop
SXM2:00 pmSimpson Bay Princess Juliana
$336
Find similar
Spirit Airlines
Sep 6
SXM3:05 pmSimpson Bay Princess Juliana
20h 37m
2 stops
ORD10:42 amChicago O'Hare Intl
Sep 13
ORD5:05 amChicago O'Hare Intl
7h 55m
1 stop
SXM2:00 pmSimpson Bay Princess Juliana
$399
Find similar
Spirit Airlines
Sep 6
SXM3:05 pmSimpson Bay Princess Juliana
26h 13m
3 stops
ORD4:18 pmChicago O'Hare Intl
Sep 13
ORD5:05 amChicago O'Hare Intl
7h 55m
1 stop
SXM2:00 pmSimpson Bay Princess Juliana
$413
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 July 31, 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

Mon 9/22

3:05 pm-10:48 pm

1 stop8h 43m

Chicago O'Hare Intl

Mon 9/29

5:05 am-2:00 pm

1 stop7h 55m

$336

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sat 9/6

3:05 pm-10:42 am

2 stops20h 37m

Chicago O'Hare Intl

Sat 9/13

5:05 am-2:00 pm

1 stop7h 55m

$399

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sat 9/6

3:05 pm-4:18 pm

3 stops26h 13m

Chicago O'Hare Intl

Sat 9/13

5:05 am-2:00 pm

1 stop7h 55m

$413

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Mon 9/22

3:05 pm-10:18 am

2 stops20h 13m

Chicago O'Hare Intl

Mon 9/29

5:05 am-2:00 pm

1 stop7h 55m

$456

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sat 9/6

3:05 pm-4:18 pm

3 stops26h 13m

Chicago O'Hare Intl

Sat 9/13

4:35 pm-11:26 am

2 stops17h 51m

$480

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sat 9/6

3:05 pm-4:18 pm

3 stops26h 13m

Chicago O'Hare Intl

Sat 9/13

11:57 am-11:26 am

3 stops22h 29m

$500

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Thu 10/9

2:40 pm-11:53 pm

2 stops10h 13m

Chicago O'Hare Intl

Wed 10/15

9:12 pm-1:37 pm

2 stops15h 25m

$599

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Thu 10/9

4:24 pm-11:58 pm

1 stop8h 34m

Chicago O'Hare Intl

Wed 10/15

9:12 pm-1:37 pm

2 stops15h 25m

$600

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Thu 10/9

4:24 pm-11:58 pm

1 stop8h 34m

Chicago O'Hare Intl

Wed 10/15

1:51 pm-1:37 pm

1 stop22h 46m

$608

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Thu 10/9

4:24 pm-11:58 pm

1 stop8h 34m

Chicago O'Hare Intl

Wed 10/15

1:51 pm-1:37 pm

1 stop22h 46m

$609

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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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 $735 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?

As of July 2025, prices for Simpson Bay to Chicago O'Hare Intl Airport flights are approximately 26% cheaper when compared to flights at the same time last year.

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

Best Price Found

$206

Fastest flight time

6h 01m

Direct flights

Mon and Sun
The best one-way flight to Chicago O'Hare Intl Airport from Simpson Bay in the past 72 hours is $206. The best round-trip flight deal from Simpson Bay to Chicago O'Hare Intl Airport found on momondo in the last 72 hours is $336.
The fastest flight from Simpson Bay to Chicago O'Hare Intl Airport takes 6h 01m
Direct flights go from Simpson Bay to Chicago O'Hare Intl Airport on Monday and Sunday. Airlines offering direct flights are: United Airlines and British Airways.
Search flight deals

  • 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 34m 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 many operators does momondo search for flights from Simpson Bay Princess Juliana Airport to Chicago O'Hare Intl Airport?

  • 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?

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

Best airlines flying from Simpson Bay to Chicago O'Hare Intl Airport

Compare and see reviews for airlines that fly from Simpson Bay to Chicago O'Hare Intl Airport with momondo
Airline
Rating
Free Cancellation
Price
American AirlinesPriceFrom $554Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights

Traveling to a place near Chicago?

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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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