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Cheap flights from Simpson Bay to Chicago from $211

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 5/28. 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

Find the cheapest flights from Simpson Bay to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Spirit Airlines Logo
2:35 pm - 11:15 pm
SXM
-
ORD
9h 40m
1 stop
Spirit Airlines Logo
5:05 am - 1:30 pm
ORD
-
SXM
7h 25m
1 stop
$411Spirit Airlines
Thu, May 28 - Thu, Jun 4
Multiple Airlines Logo
6:00 pm - 9:00 am
SXM
-
ORD
16h 00m
1 stop
Multiple Airlines Logo
7:07 pm - 1:42 pm
ORD
-
SXM
17h 35m
1 stop
$425Multiple Airlines
Sat, Jun 13 - Sat, Jun 20
Frontier Logo
12:43 pm - 11:19 pm
SXM
-
ORD
11h 36m
1 stop
Frontier Logo
5:25 pm - 11:23 am
ORD
-
SXM
16h 58m
1 stop
$463Frontier
Sat, Jun 20 - Fri, Jun 26
Spirit Airlines Logo
2:35 pm - 11:15 pm
SXM
-
ORD
9h 40m
1 stop
Spirit Airlines Logo
5:10 am - 1:30 pm
ORD
-
SXM
7h 20m
1 stop
$474Spirit Airlines
Thu, Jun 11 - Thu, Jun 18
Multiple Airlines Logo
6:00 pm - 9:00 am
SXM
-
ORD
16h 00m
1 stop
Multiple Airlines Logo
5:10 am - 10:25 am
ORD
-
SXM
28h 15m
3 stops
$488Multiple Airlines
Sat, Jun 13 - Sat, Jun 20
Multiple Airlines Logo
11:30 am - 11:56 pm
SXM
-
ORD
13h 26m
2 stops
Multiple Airlines Logo
5:10 am - 1:30 pm
ORD
-
SXM
7h 20m
1 stop
$500Multiple Airlines
Thu, Jun 11 - Thu, Jun 18
Multiple Airlines Logo
2:35 pm - 7:55 am
SXM
-
ORD
18h 20m
2 stops
Multiple Airlines Logo
5:05 am - 1:30 pm
ORD
-
SXM
7h 25m
1 stop
$507Multiple Airlines
Thu, May 28 - Thu, Jun 4
Spirit Airlines Logo
2:35 pm - 10:14 pm
SXM
-
ORD
32h 39m
3 stops
Spirit Airlines Logo
5:05 am - 1:30 pm
ORD
-
SXM
7h 25m
1 stop
$512Spirit Airlines
Thu, May 28 - Thu, Jun 4
Multiple Airlines Logo
6:00 pm - 9:00 am
SXM
-
ORD
16h 00m
1 stop
Multiple Airlines Logo
6:00 am - 10:00 am
ORD
-
SXM
27h 00m
1 stop
$532Multiple Airlines
Sat, Jun 13 - Sat, Jun 20
Multiple Airlines Logo
6:00 pm - 9:00 am
SXM
-
ORD
16h 00m
1 stop
Multiple Airlines Logo
1:55 pm - 10:00 am
ORD
-
SXM
19h 05m
2 stops
$534Multiple Airlines
Sat, Jun 13 - Sat, Jun 20

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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
May 28
SXM2:35 pmSimpson Bay Princess Juliana
9h 40m
1 stop
ORD11:15 pmChicago O'Hare Intl
Jun 4
ORD5:05 amChicago O'Hare Intl
7h 25m
1 stop
SXM1:30 pmSimpson Bay Princess Juliana
$411
Spirit Airlines
Jun 11
SXM2:35 pmSimpson Bay Princess Juliana
9h 40m
1 stop
ORD11:15 pmChicago O'Hare Intl
Jun 18
ORD5:10 amChicago O'Hare Intl
7h 20m
1 stop
SXM1:30 pmSimpson Bay Princess Juliana
$474
Spirit Airlines
May 28
SXM2:35 pmSimpson Bay Princess Juliana
32h 39m
3 stops
ORD10:14 pmChicago O'Hare Intl
Jun 4
ORD5:05 amChicago O'Hare Intl
7h 25m
1 stop
SXM1:30 pmSimpson Bay Princess Juliana
$512

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 2
SXM4:45 pmSimpson Bay Princess Juliana
14h 45m
2 stops
ORD6:30 amChicago O'Hare Intl
Jul 7
ORD5:10 amChicago O'Hare Intl
9h 32m
2 stops
SXM3:42 pmSimpson Bay Princess Juliana
$670
American Airlines
Jun 10
SXM4:43 pmSimpson Bay Princess Juliana
15h 14m
2 stops
ORD6:57 amChicago O'Hare Intl
Jun 17
ORD5:10 amChicago O'Hare Intl
9h 32m
2 stops
SXM3:42 pmSimpson Bay Princess Juliana
$675
American Airlines
May 28
SXM2:53 pmSimpson Bay Princess Juliana
10h 06m
1 stop
ORD11:59 pmChicago O'Hare Intl
Jun 4
ORD9:26 pmChicago O'Hare Intl
14h 14m
1 stop
SXM12:40 pmSimpson Bay Princess Juliana
$727

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 May 1, 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

Thu 5/28

2:35 pm-11:15 pm

1 stop9h 40m

Chicago O'Hare Intl

Thu 6/4

5:05 am-1:30 pm

1 stop7h 25m

$411

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sat 6/13

6:00 pm-9:00 am

1 stop16h 00m

Chicago O'Hare Intl

Sat 6/20

7:07 pm-1:42 pm

1 stop17h 35m

$425

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sat 6/20

12:43 pm-11:19 pm

1 stop11h 36m

Chicago O'Hare Intl

Fri 6/26

5:25 pm-11:23 am

1 stop16h 58m

$463
Quickest round-trip

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Thu 6/11

2:35 pm-11:15 pm

1 stop9h 40m

Chicago O'Hare Intl

Thu 6/18

5:10 am-1:30 pm

1 stop7h 20m

$474

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sat 6/13

6:00 pm-9:00 am

1 stop16h 00m

Chicago O'Hare Intl

Sat 6/20

5:10 am-10:25 am

3 stops28h 15m

$488

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Thu 6/11

11:30 am-11:56 pm

2 stops13h 26m

Chicago O'Hare Intl

Thu 6/18

5:10 am-1:30 pm

1 stop7h 20m

$500

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Thu 5/28

2:35 pm-7:55 am

2 stops18h 20m

Chicago O'Hare Intl

Thu 6/4

5:05 am-1:30 pm

1 stop7h 25m

$507

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Thu 5/28

2:35 pm-10:14 pm

3 stops32h 39m

Chicago O'Hare Intl

Thu 6/4

5:05 am-1:30 pm

1 stop7h 25m

$512

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sat 6/13

6:00 pm-9:00 am

1 stop16h 00m

Chicago O'Hare Intl

Sat 6/20

6:00 am-10:00 am

1 stop27h 00m

$532

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sat 6/13

6:00 pm-9:00 am

1 stop16h 00m

Chicago O'Hare Intl

Sat 6/20

1:55 pm-10:00 am

2 stops19h 05m

$534

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

Can stopping save me money on Simpson Bay to Chicago O'Hare Intl Airport flights?

You could potentially save up to 54% 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

9h 40m

Direct flights

Mon
The fastest flight from Simpson Bay to Chicago O'Hare Intl Airport takes 9h 40m
Direct flights go from Simpson Bay to Chicago O'Hare Intl Airport on Monday. 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. 9h 40m 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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Rosemont
Naperville
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Orland Park
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Aurora
Janesville
Racine
Hammond
Tinley Park
Elgin
Evanston

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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