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Cheap flights from Simpson Bay to Chicago from $230

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 10/30. 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
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.
Air Canada Logo
6:00 pm - 9:00 am
SXM
-
ORD
16h 00m
1 stop
Air Canada Logo
5:35 pm - 5:00 pm
ORD
-
SXM
22h 25m
1 stop
$398Air Canada
Sat, Sep 12 - Fri, Sep 18
Air Canada Logo
6:00 pm - 9:00 am
SXM
-
ORD
16h 00m
1 stop
Air Canada Logo
8:40 pm - 5:00 pm
ORD
-
SXM
19h 20m
1 stop
$399Air Canada
Sat, Sep 19 - Fri, Sep 25
Air Canada Logo
6:00 pm - 10:15 am
SXM
-
ORD
17h 15m
2 stops
Air Canada Logo
8:40 pm - 5:00 pm
ORD
-
SXM
19h 20m
1 stop
$401Air Canada
Sat, Sep 12 - Fri, Sep 18
Air Canada Logo
6:00 pm - 10:15 am
SXM
-
ORD
17h 15m
2 stops
Air Canada Logo
5:35 pm - 5:00 pm
ORD
-
SXM
22h 25m
1 stop
$402Air Canada
Sat, Sep 19 - Fri, Sep 25
Southwest Logo
1:55 pm - 9:00 pm
SXM
-
MDW
8h 05m
1 stop
Southwest Logo
5:00 am - 2:05 pm
MDW
-
SXM
8h 05m
1 stop
$431Southwest
Sat, Sep 12 - Fri, Sep 18
Air Canada Logo
6:00 pm - 7:44 am
SXM
-
ORD
14h 44m
2 stops
Air Canada Logo
6:21 pm - 5:00 pm
ORD
-
SXM
21h 39m
2 stops
$454Air Canada
Sat, Sep 12 - Fri, Sep 18
Air Canada Logo
6:00 pm - 10:15 am
SXM
-
ORD
17h 15m
2 stops
Air Canada Logo
6:21 pm - 5:00 pm
ORD
-
SXM
21h 39m
2 stops
$463Air Canada
Sat, Sep 19 - Fri, Sep 25
JetBlue Logo
1:42 pm - 2:24 pm
SXM
-
ORD
25h 42m
1 stop
JetBlue Logo
8:20 pm - 11:33 am
ORD
-
SXM
14h 13m
1 stop
$477JetBlue
Fri, Aug 28 - Fri, Sep 4
Air Canada Logo
4:45 pm - 9:23 am
SXM
-
ORD
18h 38m
1 stop
Air Canada Logo
8:45 am - 3:45 pm
ORD
-
SXM
29h 00m
1 stop
$503Air Canada
Wed, Nov 25 - Tue, Dec 1
Air Canada Logo
4:45 pm - 11:07 am
SXM
-
ORD
20h 22m
2 stops
Air Canada Logo
8:50 pm - 3:45 pm
ORD
-
SXM
16h 55m
1 stop
$508Air Canada
Wed, Nov 25 - Tue, Dec 1

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Air Canada flights from Simpson Bay to Chicago

Our best Air Canada deals on Simpson Bay to Chicago flight tickets
Air Canada
Sep 12
SXM6:00 pmSimpson Bay Princess Juliana
16h 00m
1 stop
ORD9:00 amChicago O'Hare Intl
Sep 18
ORD5:35 pmChicago O'Hare Intl
22h 25m
1 stop
SXM5:00 pmSimpson Bay Princess Juliana
$398
Air Canada
Sep 19
SXM6:00 pmSimpson Bay Princess Juliana
16h 00m
1 stop
ORD9:00 amChicago O'Hare Intl
Sep 25
ORD8:40 pmChicago O'Hare Intl
19h 20m
1 stop
SXM5:00 pmSimpson Bay Princess Juliana
$399
Air Canada
Sep 12
SXM6:00 pmSimpson Bay Princess Juliana
17h 15m
2 stops
ORD10:15 amChicago O'Hare Intl
Sep 18
ORD8:40 pmChicago O'Hare Intl
19h 20m
1 stop
SXM5:00 pmSimpson Bay Princess Juliana
$401

JetBlue flights from Simpson Bay to Chicago

Our best JetBlue deals on Simpson Bay to Chicago flight tickets
JetBlue
Aug 28
SXM1:42 pmSimpson Bay Princess Juliana
25h 42m
1 stop
ORD2:24 pmChicago O'Hare Intl
Sep 4
ORD8:20 pmChicago O'Hare Intl
14h 13m
1 stop
SXM11:33 amSimpson Bay Princess Juliana
$477
JetBlue
Sep 10
SXM3:05 pmSimpson Bay Princess Juliana
9h 03m
1 stop
ORD11:08 pmChicago O'Hare Intl
Sep 17
ORD3:00 pmChicago O'Hare Intl
22h 00m
1 stop
SXM2:00 pmSimpson Bay Princess Juliana
$529
JetBlue
Aug 28
SXM1:42 pmSimpson Bay Princess Juliana
25h 42m
1 stop
ORD2:24 pmChicago O'Hare Intl
Sep 4
ORD8:20 pmChicago O'Hare Intl
16h 22m
2 stops
SXM1:42 pmSimpson Bay Princess Juliana
$536

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 July 31, 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

Sat 9/12

6:00 pm-9:00 am

1 stop16h 00m

Chicago O'Hare Intl

Fri 9/18

5:35 pm-5:00 pm

1 stop22h 25m

$398

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sat 9/19

6:00 pm-9:00 am

1 stop16h 00m

Chicago O'Hare Intl

Fri 9/25

8:40 pm-5:00 pm

1 stop19h 20m

$399

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sat 9/12

6:00 pm-10:15 am

2 stops17h 15m

Chicago O'Hare Intl

Fri 9/18

8:40 pm-5:00 pm

1 stop19h 20m

$401

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sat 9/19

6:00 pm-10:15 am

2 stops17h 15m

Chicago O'Hare Intl

Fri 9/25

5:35 pm-5:00 pm

1 stop22h 25m

$402
Quickest round-trip

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Sat 9/12

1:55 pm-9:00 pm

1 stop8h 05m

Chicago Midway

Fri 9/18

5:00 am-2:05 pm

1 stop8h 05m

$431

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sat 9/12

6:00 pm-7:44 am

2 stops14h 44m

Chicago O'Hare Intl

Fri 9/18

6:21 pm-5:00 pm

2 stops21h 39m

$454

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sat 9/19

6:00 pm-10:15 am

2 stops17h 15m

Chicago O'Hare Intl

Fri 9/25

6:21 pm-5:00 pm

2 stops21h 39m

$463

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Fri 8/28

1:42 pm-2:24 pm

1 stop25h 42m

Chicago O'Hare Intl

Fri 9/4

8:20 pm-11:33 am

1 stop14h 13m

$477

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Wed 11/25

4:45 pm-9:23 am

1 stop18h 38m

Chicago O'Hare Intl

Tue 12/1

8:45 am-3:45 pm

1 stop29h 00m

$503

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Wed 11/25

4:45 pm-11:07 am

2 stops20h 22m

Chicago O'Hare Intl

Tue 12/1

8:50 pm-3:45 pm

1 stop16h 55m

$508

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 is only 1 cabin class 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 3% on your flight if you consider stops on a Simpson Bay to Chicago flight.

How have Simpson Bay to Chicago flight prices changed over time?

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

8h 05m

Direct flights

Mon, Tue and Sun

Airports in Chicago

3 airports
The fastest flight from Simpson Bay to Chicago takes 8h 05m
Direct flights go from Simpson Bay to Chicago on Monday, Tuesday and 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 8h 05m.

  • 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
Portage
Benton Harbor
Lansing
Saint Joseph
Valparaiso
Schererville
Munster
Chesterton
Monticello
Crown Point
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