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Cheap flights from Simpson Bay to Chicago from $218

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 4/25. 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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0 bags

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Cheap round-trip flights

Enter your travel dates to find the best prices.
Spirit Airlines Logo
2:42 pm - 12:24 am
SXM
-
ORD
10h 42m
1 stop
Spirit Airlines Logo
7:15 pm - 1:37 pm
ORD
-
SXM
17h 22m
1 stop
$376Spirit Airlines
Sat, Apr 18 - Sat, Apr 25
Spirit Airlines Logo
2:42 pm - 12:24 am
SXM
-
ORD
10h 42m
1 stop
Spirit Airlines Logo
7:15 pm - 1:37 pm
ORD
-
SXM
17h 22m
1 stop
$399Spirit Airlines
Sat, Apr 18 - Sat, Apr 25
Multiple Airlines Logo
2:40 pm - 10:53 am
SXM
-
ORD
21h 13m
1 stop
Multiple Airlines Logo
7:15 pm - 1:37 pm
ORD
-
SXM
17h 22m
1 stop
$401Multiple Airlines
Sat, Apr 18 - Sat, Apr 25
Spirit Airlines Logo
2:35 pm - 11:17 pm
SXM
-
ORD
9h 42m
1 stop
Spirit Airlines Logo
5:05 am - 1:30 pm
ORD
-
SXM
7h 25m
1 stop
$407Spirit Airlines
Wed, Apr 1 - Tue, Apr 7
Spirit Airlines Logo
2:42 pm - 12:24 am
SXM
-
ORD
10h 42m
1 stop
Spirit Airlines Logo
7:15 pm - 1:37 pm
ORD
-
SXM
17h 22m
1 stop
$410Spirit Airlines
Sat, Apr 18 - Sat, Apr 25
Spirit Airlines Logo
2:35 pm - 11:17 pm
SXM
-
ORD
9h 42m
1 stop
Spirit Airlines Logo
5:05 am - 1:30 pm
ORD
-
SXM
7h 25m
1 stop
$430Spirit Airlines
Wed, Apr 1 - Wed, Apr 8
Multiple Airlines Logo
4:00 pm - 7:58 am
SXM
-
ORD
16h 58m
2 stops
Multiple Airlines Logo
5:05 am - 1:30 pm
ORD
-
SXM
7h 25m
1 stop
$433Multiple Airlines
Wed, Apr 1 - Tue, Apr 7
Multiple Airlines Logo
4:00 pm - 10:53 am
SXM
-
ORD
19h 53m
2 stops
Multiple Airlines Logo
5:05 am - 1:30 pm
ORD
-
SXM
7h 25m
1 stop
$439Multiple Airlines
Tue, Mar 31 - Tue, Apr 7
Multiple Airlines Logo
4:00 pm - 9:50 am
SXM
-
ORD
18h 50m
1 stop
Multiple Airlines Logo
5:05 am - 1:30 pm
ORD
-
SXM
7h 25m
1 stop
$440Multiple Airlines
Tue, Mar 31 - Tue, Apr 7
Spirit Airlines Logo
2:35 pm - 11:17 pm
SXM
-
ORD
9h 42m
1 stop
Spirit Airlines Logo
6:10 pm - 1:30 pm
ORD
-
SXM
18h 20m
1 stop
$441Spirit Airlines
Wed, Apr 1 - Fri, Apr 10

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
Apr 18
SXM2:42 pmSimpson Bay Princess Juliana
10h 42m
1 stop
ORD12:24 amChicago O'Hare Intl
Apr 25
ORD7:15 pmChicago O'Hare Intl
17h 22m
1 stop
SXM1:37 pmSimpson Bay Princess Juliana
$376
Spirit Airlines
Apr 18
SXM2:42 pmSimpson Bay Princess Juliana
10h 42m
1 stop
ORD12:24 amChicago O'Hare Intl
Apr 25
ORD7:15 pmChicago O'Hare Intl
17h 22m
1 stop
SXM1:37 pmSimpson Bay Princess Juliana
$399
Spirit Airlines
Apr 1
SXM2:35 pmSimpson Bay Princess Juliana
9h 42m
1 stop
ORD11:17 pmChicago O'Hare Intl
Apr 7
ORD5:05 amChicago O'Hare Intl
7h 25m
1 stop
SXM1:30 pmSimpson Bay Princess Juliana
$407

Air Canada flights from Simpson Bay to Chicago O'Hare Intl Airport

Our best Air Canada deals on Simpson Bay to Chicago O'Hare Intl Airport flight tickets
Air Canada
Apr 3
SXM4:00 pmSimpson Bay Princess Juliana
18h 10m
1 stop
ORD9:10 amChicago O'Hare Intl
Apr 9
ORD2:00 pmChicago O'Hare Intl
23h 55m
1 stop
SXM2:55 pmSimpson Bay Princess Juliana
$452
Air Canada
Mar 31
SXM4:00 pmSimpson Bay Princess Juliana
18h 10m
1 stop
ORD9:10 amChicago O'Hare Intl
Apr 9
ORD4:15 pmChicago O'Hare Intl
21h 40m
1 stop
SXM2:55 pmSimpson Bay Princess Juliana
$470
Air Canada
Apr 1
SXM4:00 pmSimpson Bay Princess Juliana
16h 58m
2 stops
ORD7:58 amChicago O'Hare Intl
Apr 9
ORD1:55 pmChicago O'Hare Intl
24h 00m
2 stops
SXM2:55 pmSimpson Bay Princess Juliana
$472

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 March 15, 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

Sat 4/18

2:42 pm-12:24 am

1 stop10h 42m

Chicago O'Hare Intl

Sat 4/25

7:15 pm-1:37 pm

1 stop17h 22m

$376

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sat 4/18

2:42 pm-12:24 am

1 stop10h 42m

Chicago O'Hare Intl

Sat 4/25

7:15 pm-1:37 pm

1 stop17h 22m

$399

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sat 4/18

2:40 pm-10:53 am

1 stop21h 13m

Chicago O'Hare Intl

Sat 4/25

7:15 pm-1:37 pm

1 stop17h 22m

$401
Quickest round-trip

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Wed 4/1

2:35 pm-11:17 pm

1 stop9h 42m

Chicago O'Hare Intl

Tue 4/7

5:05 am-1:30 pm

1 stop7h 25m

$407

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sat 4/18

2:42 pm-12:24 am

1 stop10h 42m

Chicago O'Hare Intl

Sat 4/25

7:15 pm-1:37 pm

1 stop17h 22m

$410

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Wed 4/1

2:35 pm-11:17 pm

1 stop9h 42m

Chicago O'Hare Intl

Wed 4/8

5:05 am-1:30 pm

1 stop7h 25m

$430

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Wed 4/1

4:00 pm-7:58 am

2 stops16h 58m

Chicago O'Hare Intl

Tue 4/7

5:05 am-1:30 pm

1 stop7h 25m

$433

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Tue 3/31

4:00 pm-10:53 am

2 stops19h 53m

Chicago O'Hare Intl

Tue 4/7

5:05 am-1:30 pm

1 stop7h 25m

$439

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Tue 3/31

4:00 pm-9:50 am

1 stop18h 50m

Chicago O'Hare Intl

Tue 4/7

5:05 am-1:30 pm

1 stop7h 25m

$440

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Wed 4/1

2:35 pm-11:17 pm

1 stop9h 42m

Chicago O'Hare Intl

Fri 4/10

6:10 pm-1:30 pm

1 stop18h 20m

$441

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, Saturday 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 $610.

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 53% 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 46m

Direct flights

Sun
The fastest flight from Simpson Bay to Chicago O'Hare Intl Airport takes 5h 46m
Direct flights go from Simpson Bay to Chicago O'Hare Intl Airport on Sunday. There are no airlines offering direct flights.
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. 5h 46m 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
Schaumburg
South Haven
Rockford
Merrillville
Gurnee
Rosemont
Naperville
New Buffalo
Orland Park
Kenosha
Oak Brook
Joliet
Racine
Janesville
Hammond
Aurora
Tinley Park
Elgin
South Holland

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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