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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.
1 adult
0 bags

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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
2:42 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
Southwest Logo
2:25 pm - 7:35 am
SXM
-
MDW
18h 10m
2 stops
Southwest Logo
6:00 am - 1:30 pm
MDW
-
SXM
6h 30m
1 stop
$568Southwest
Tue, Apr 28 - Tue, May 5
Delta Logo
1:35 pm - 10:28 pm
SXM
-
MDW
9h 53m
1 stop
Delta Logo
6:00 am - 2:05 pm
MDW
-
SXM
7h 05m
1 stop
$676Delta
Tue, Apr 28 - Tue, May 5
Delta Logo
1:35 pm - 10:28 pm
SXM
-
MDW
9h 53m
1 stop
Delta Logo
6:00 am - 2:05 pm
MDW
-
SXM
7h 05m
1 stop
$791Delta
Sat, Apr 18 - Sat, Apr 25

Spirit Airlines flights from Simpson Bay to Chicago

Our best Spirit Airlines deals on Simpson Bay to Chicago 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

Our best Air Canada deals on Simpson Bay to Chicago 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 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 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

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

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 - MDW

SXMMDW

Simpson Bay Princess Juliana

Tue 4/28

2:25 pm-7:35 am

2 stops18h 10m

Chicago Midway

Tue 5/5

6:00 am-1:30 pm

1 stop6h 30m

$568
Quickest round-trip

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Tue 4/28

1:35 pm-10:28 pm

1 stop9h 53m

Chicago Midway

Tue 5/5

6:00 am-2:05 pm

1 stop7h 05m

$676

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Sat 4/18

1:35 pm-10:28 pm

1 stop9h 53m

Chicago Midway

Sat 4/25

6:00 am-2:05 pm

1 stop7h 05m

$791

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 day to depart on your flight to Chicago?

The cheapest day to depart on your flight to Chicago 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. When flying out on a Saturday, the most expensive travel day of the week, you can expect to see flight prices from Simpson Bay to Chicago for around $610.

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 Princess Juliana to Chicago flights?

There are 3 cabin classes available to choose from on Simpson Bay Princess Juliana 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 53% 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

5h 46m

Direct flights

Sun

Airports in Chicago

3 airports
The fastest flight from Simpson Bay to Chicago takes 5h 46m
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

  • 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 5h 46m.

  • 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
Saint Joseph
Portage
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