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Cheap flights from Simpson Bay to Chicago from $229

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 7/9. 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
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
$472JetBlue
Fri, Jul 17 - 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
$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 - 4:22 pm
ORD
-
SXM
21h 55m
1 stop
$491JetBlue
Fri, Jul 17 - Fri, Jul 24
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
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
Southwest Logo
2:25 pm - 9:25 pm
SXM
-
MDW
8h 00m
1 stop
Southwest Logo
8:50 pm - 3:05 pm
MDW
-
SXM
17h 15m
2 stops
$542Southwest
Fri, Jul 17 - Fri, Jul 24
Southwest Logo
2:25 pm - 7:15 am
SXM
-
MDW
17h 50m
2 stops
Southwest Logo
8:50 pm - 3:05 pm
MDW
-
SXM
17h 15m
2 stops
$570Southwest
Fri, Jul 17 - Fri, Jul 24
Southwest Logo
2:25 pm - 12:45 am
SXM
-
MDW
11h 20m
1 stop
Southwest Logo
8:50 pm - 3:05 pm
MDW
-
SXM
17h 15m
2 stops
$613Southwest
Fri, Jul 10 - Fri, Jul 17

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JetBlue flights from Simpson Bay to Chicago

Our best JetBlue deals on Simpson Bay to Chicago 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 17
SXM1:42 pmSimpson Bay Princess Juliana
11h 02m
1 stop
ORD11:44 pmChicago O'Hare Intl
Jul 24
ORD5:27 pmChicago O'Hare Intl
21h 55m
1 stop
SXM4:22 pmSimpson Bay Princess Juliana
$472
JetBlue
Jul 17
SXM1:42 pmSimpson Bay Princess Juliana
11h 02m
1 stop
ORD11:44 pmChicago O'Hare Intl
Jul 24
ORD5:27 pmChicago O'Hare Intl
21h 55m
1 stop
SXM4:22 pmSimpson Bay Princess Juliana
$491

United Airlines flights from Simpson Bay to Chicago

Our best United Airlines deals on Simpson Bay to Chicago flight tickets
United Airlines
Jul 17
SXM3:50 pmSimpson Bay Princess Juliana
16h 56m
1 stop
ORD7:46 amChicago O'Hare Intl
Jul 24
ORD9:40 pmChicago O'Hare Intl
13h 53m
1 stop
SXM12:33 pmSimpson Bay Princess Juliana
$665
United Airlines
Jul 2
SXM3:50 pmSimpson Bay Princess Juliana
18h 46m
1 stop
ORD9:36 amChicago O'Hare Intl
Jul 7
ORD9:30 pmChicago O'Hare Intl
16h 13m
1 stop
SXM2:43 pmSimpson Bay Princess Juliana
$755

momondo Fare Finder

 
Customize your flight search to find flights from Simpson Bay to Chicago 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 14, 2026.
Use the filters below to find and compare flights from Simpson Bay to Chicago 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

Fri 7/17

1:42 pm-11:44 pm

1 stop11h 02m

Chicago O'Hare Intl

Fri 7/24

5:27 pm-4:22 pm

1 stop21h 55m

$472

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

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Fri 7/17

1:42 pm-11:44 pm

1 stop11h 02m

Chicago O'Hare Intl

Fri 7/24

5:27 pm-4:22 pm

1 stop21h 55m

$491

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

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
Quickest round-trip

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Fri 7/17

2:25 pm-9:25 pm

1 stop8h 00m

Chicago Midway

Fri 7/24

8:50 pm-3:05 pm

2 stops17h 15m

$542

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Fri 7/17

2:25 pm-7:15 am

2 stops17h 50m

Chicago Midway

Fri 7/24

8:50 pm-3:05 pm

2 stops17h 15m

$570

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Fri 7/10

2:25 pm-12:45 am

1 stop11h 20m

Chicago Midway

Fri 7/17

8:50 pm-3:05 pm

2 stops17h 15m

$613

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

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 flight route?

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

What cabin class options are available on Simpson Bay to Chicago flights?

There are 2 cabin classes available to choose from on Simpson Bay to Chicago 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 flights?

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

When to book flights from Simpson Bay to Chicago

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

Cheap Simpson Bay to Chicago (SXM to CHI) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Simpson Bay to Chicago

Fastest flight time

6h 01m

Direct flights

Sun

Airports in Chicago

3 airports
The fastest flight from Simpson Bay to Chicago takes 6h 01m
Direct flights go from Simpson Bay to Chicago on Sunday. There are no airlines offering direct flights.
There are 3 airports in Chicago. From Simpson Bay there are direct flights to Chicago O'Hare Intl (ORD).
Search flight deals

Frequently asked questions about flying from Simpson Bay to Chicago

  • How far is Simpson Bay Princess Juliana to Chicago by plane?

    Chicago is 2188.1 mi away from Simpson Bay Princess Juliana. By plane, this route typically takes 6h 01m.

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

    Prices for flights from Simpson Bay Princess Juliana Airport to Chicago were last updated today.

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

    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.

  • What documentation or ID do you need to fly to Chicago?

    The necessary travel and health documents for your Chicago trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Simpson Bay to Chicago?

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Portage
Saint Joseph
Lansing
Valparaiso
Schererville
Munster
Crown Point
Chesterton
Monticello
Porter
Griffith
Saint John

Why use momondo?

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

It is quick and easy to find Simpson Bay to Chicago flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Chicago that suits you.

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

momondo does allow users to show only those flights to Chicago from Simpson Bay which offer a flexible booking policy as well as other useful filters and features.

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

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Simpson Bay to Chicago.

I’m not ready to book a flight from Simpson Bay to Chicago right now. Can momondo alert me if prices change?

If you are simply researching potential flights to Chicago, momondo offers a useful price alert feature which will track prices for flights to Chicago from Simpson Bay and alert you when they change.

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Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago
Chicago Midway Airport
Chicago O'Hare Intl Airport
Chicago Greater Rockford Airport