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Cheap flights from Chicago Midway Airport to Simpson Bay from $242

1 adult
1 adult, Economy, 0 bags

Find the cheapest flights from Chicago Midway Airport to Simpson Bay

Cheap round-trip flights

Enter your travel dates to find the best prices.
Southwest Logo
4:00 pm - 1:30 pmMDW  Chicago Midway-SXM Simpson Bay Princess Juliana
19h 30m2 stops Nashville Intl Baltimore/Washington
Southwest Logo
3:20 pm - 12:05 pmSXM  Simpson Bay Princess Juliana-MDW Chicago Midway
22h 45m2 stops Orlando Las Vegas Harry Reid Intl
$472Southwest
Fri, Nov 27 - Thu, Dec 3
Southwest Logo
8:25 pm - 3:40 pmMDW  Chicago Midway-SXM Simpson Bay Princess Juliana
17h 15m2 stops Baltimore/Washington Orlando
Southwest Logo
4:40 pm - 11:05 pmSXM  Simpson Bay Princess Juliana-MDW Chicago Midway
8h 25m1 stop Baltimore/Washington
$472Southwest
Sun, Nov 1 - Thu, Nov 5
Southwest Logo
5:05 am - 2:15 pmMDW  Chicago Midway-SXM Simpson Bay Princess Juliana
7h 10m1 stop Baltimore/Washington
Southwest Logo
3:20 pm - 5:40 amSXM  Simpson Bay Princess Juliana-MDW Chicago Midway
16h 20m2 stops Orlando Las Vegas Harry Reid Intl
$472Southwest
Fri, Nov 27 - Thu, Dec 3
Southwest Logo
8:25 pm - 3:40 pmMDW  Chicago Midway-SXM Simpson Bay Princess Juliana
17h 15m2 stops Baltimore/Washington Orlando
Southwest Logo
3:20 pm - 1:05 amSXM  Simpson Bay Princess Juliana-MDW Chicago Midway
11h 45m2 stops Orlando Houston Hobby
$472Southwest
Sun, Nov 1 - Thu, Nov 5
Southwest Logo
7:55 pm - 2:35 pmMDW  Chicago Midway-SXM Simpson Bay Princess Juliana
16h 40m2 stops Phoenix Sky Harbor Intl Orlando
Southwest Logo
3:35 pm - 10:50 pmSXM  Simpson Bay Princess Juliana-MDW Chicago Midway
9h 15m1 stop Orlando
$496Southwest
Thu, Feb 4 - Tue, Feb 9
Southwest Logo
7:55 pm - 2:35 pmMDW  Chicago Midway-SXM Simpson Bay Princess Juliana
16h 40m2 stops Phoenix Sky Harbor Intl Orlando
Southwest Logo
3:35 pm - 5:40 amSXM  Simpson Bay Princess Juliana-MDW Chicago Midway
16h 05m2 stops Orlando Las Vegas Harry Reid Intl
$496Southwest
Thu, Feb 4 - Tue, Feb 9
Southwest Logo
5:10 am - 3:40 pmMDW  Chicago Midway-SXM Simpson Bay Princess Juliana
8h 30m1 stop Orlando
Southwest Logo
3:20 pm - 10:55 pmSXM  Simpson Bay Princess Juliana-MDW Chicago Midway
9h 35m1 stop Orlando
$520Southwest
Sun, Nov 1 - Thu, Nov 5
Southwest Logo
5:00 am - 2:05 pmMDW  Chicago Midway-SXM Simpson Bay Princess Juliana
8h 05m1 stop Orlando
Southwest Logo
3:05 pm - 10:45 pmSXM  Simpson Bay Princess Juliana-MDW Chicago Midway
8h 40m1 stop Orlando
$520Southwest
Fri, Sep 25 - Mon, Sep 28
Southwest Logo
5:00 am - 2:05 pmMDW  Chicago Midway-SXM Simpson Bay Princess Juliana
8h 05m1 stop Orlando
Southwest Logo
2:45 pm - 7:25 amSXM  Simpson Bay Princess Juliana-MDW Chicago Midway
17h 40m2 stops Orlando Baltimore/Washington
$525Southwest
Mon, Oct 19 - Sat, Oct 24
Southwest Logo
5:20 am - 2:20 pmMDW  Chicago Midway-SXM Simpson Bay Princess Juliana
7h 00m1 stop Orlando
Southwest Logo
3:20 pm - 5:40 amSXM  Simpson Bay Princess Juliana-MDW Chicago Midway
16h 20m2 stops Orlando Las Vegas Harry Reid Intl
$525Southwest
Wed, Dec 2 - Mon, Dec 7

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WestJet flights from Chicago Midway Airport to Simpson Bay

Our best WestJet deals on Chicago Midway Airport to Simpson Bay flight tickets
WestJet
Aug 26
MDW9:24 amChicago Midway
27h 46m
2 stops
SXM2:10 pmSimpson Bay Princess Juliana
Aug 31
SXM3:20 pmSimpson Bay Princess Juliana
26h 39m
2 stops
MDW4:59 pmChicago Midway
$4,475
WestJet
Aug 26
MDW6:42 pmChicago Midway
18h 28m
2 stops
SXM2:10 pmSimpson Bay Princess Juliana
Aug 31
SXM3:20 pmSimpson Bay Princess Juliana
26h 39m
2 stops
MDW4:59 pmChicago Midway
$4,499
WestJet
Aug 26
MDW9:24 amChicago Midway
27h 46m
2 stops
SXM2:10 pmSimpson Bay Princess Juliana
Aug 31
SXM3:20 pmSimpson Bay Princess Juliana
26h 39m
2 stops
MDW4:59 pmChicago Midway
$4,788

Delta flights from Chicago Midway Airport to Simpson Bay

Our best Delta deals on Chicago Midway Airport to Simpson Bay flight tickets
Delta
Nov 16
MDW6:00 amChicago Midway
6h 45m
1 stop
SXM2:45 pmSimpson Bay Princess Juliana
Nov 24
SXM4:10 pmSimpson Bay Princess Juliana
8h 46m
1 stop
MDW10:56 pmChicago Midway
$665
Delta
Nov 16
MDW6:00 amChicago Midway
6h 45m
1 stop
SXM2:45 pmSimpson Bay Princess Juliana
Nov 24
SXM4:10 pmSimpson Bay Princess Juliana
19h 32m
2 stops
MDW9:42 amChicago Midway
$670
Delta
Sep 30
MDW6:05 amChicago Midway
6h 48m
1 stop
SXM1:53 pmSimpson Bay Princess Juliana
Oct 5
SXM3:18 pmSimpson Bay Princess Juliana
8h 26m
1 stop
MDW10:44 pmChicago Midway
$675

momondo Fare Finder

 
Use the filters below to find and compare flights from Chicago Midway Airport to Simpson Bay that are best for you.

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Price

Cheapest round-trip

ChicagoSimpson Bay

MDW Chicago Midway - SXM Simpson Bay Princess Juliana

MDWSXM

Chicago Midway

Fri 11/27

4:00 pm-1:30 pm

2 stops19h 30m

Simpson Bay Princess Juliana

Thu 12/3

3:20 pm-12:05 pm

2 stops22h 45m

$472

ChicagoSimpson Bay

MDW Chicago Midway - SXM Simpson Bay Princess Juliana

MDWSXM

Chicago Midway

Sun 11/1

8:25 pm-3:40 pm

2 stops17h 15m

Simpson Bay Princess Juliana

Thu 11/5

4:40 pm-11:05 pm

1 stop8h 25m

$472

ChicagoSimpson Bay

MDW Chicago Midway - SXM Simpson Bay Princess Juliana

MDWSXM

Chicago Midway

Fri 11/27

5:05 am-2:15 pm

1 stop7h 10m

Simpson Bay Princess Juliana

Thu 12/3

3:20 pm-5:40 am

2 stops16h 20m

$472

ChicagoSimpson Bay

MDW Chicago Midway - SXM Simpson Bay Princess Juliana

MDWSXM

Chicago Midway

Sun 11/1

8:25 pm-3:40 pm

2 stops17h 15m

Simpson Bay Princess Juliana

Thu 11/5

3:20 pm-1:05 am

2 stops11h 45m

$472

ChicagoSimpson Bay

MDW Chicago Midway - SXM Simpson Bay Princess Juliana

MDWSXM

Chicago Midway

Thu 2/4

7:55 pm-2:35 pm

2 stops16h 40m

Simpson Bay Princess Juliana

Tue 2/9

3:35 pm-10:50 pm

1 stop9h 15m

$496

ChicagoSimpson Bay

MDW Chicago Midway - SXM Simpson Bay Princess Juliana

MDWSXM

Chicago Midway

Thu 2/4

7:55 pm-2:35 pm

2 stops16h 40m

Simpson Bay Princess Juliana

Tue 2/9

3:35 pm-5:40 am

2 stops16h 05m

$496

ChicagoSimpson Bay

MDW Chicago Midway - SXM Simpson Bay Princess Juliana

MDWSXM

Chicago Midway

Sun 11/1

5:10 am-3:40 pm

1 stop8h 30m

Simpson Bay Princess Juliana

Thu 11/5

3:20 pm-10:55 pm

1 stop9h 35m

$520
Quickest round-trip

ChicagoSimpson Bay

MDW Chicago Midway - SXM Simpson Bay Princess Juliana

MDWSXM

Chicago Midway

Fri 9/25

5:00 am-2:05 pm

1 stop8h 05m

Simpson Bay Princess Juliana

Mon 9/28

3:05 pm-10:45 pm

1 stop8h 40m

$520

ChicagoSimpson Bay

MDW Chicago Midway - SXM Simpson Bay Princess Juliana

MDWSXM

Chicago Midway

Mon 10/19

5:00 am-2:05 pm

1 stop8h 05m

Simpson Bay Princess Juliana

Sat 10/24

2:45 pm-7:25 am

2 stops17h 40m

$525

ChicagoSimpson Bay

MDW Chicago Midway - SXM Simpson Bay Princess Juliana

MDWSXM

Chicago Midway

Wed 12/2

5:20 am-2:20 pm

1 stop7h 00m

Simpson Bay Princess Juliana

Mon 12/7

3:20 pm-5:40 am

2 stops16h 20m

$525

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 Simpson Bay from

How to get the cheapest flight ticket from Chicago Midway Airport to Simpson Bay

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 Simpson Bay?

Our data shows that Sunday is the least expensive day to fly to Simpson Bay. Tickets to fly out on this day can be as low as $597. Flights from Chicago Midway Airport to Simpson Bay on a Saturday will generally be more expensive and average around $788. Keep in mind that these prices on both days could fluctuate depending on the season and the demand.

Can stopping save me money on Chicago Midway Airport to Simpson Bay flights?

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

When to book flights from Chicago Midway Airport to Simpson Bay

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

Cheap Chicago Midway Airport to Simpson Bay (MDW to SXM) flight deals and tips

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

Best Price Found

$242

Fastest flight time

6h 36m

Direct flights

None
The best one-way flight to Simpson Bay from Chicago Midway Airport in the past 72 hours is $242. The best round-trip flight deal from Chicago Midway Airport to Simpson Bay found on momondo in the last 72 hours is $472.
The fastest flight from Chicago Midway Airport to Simpson Bay takes 6h 36m
There are no direct flights from Chicago Midway Airport to Simpson Bay. There are no popular flight routes from Chicago Midway Airport to Simpson Bay.
Search flight deals

Frequently asked questions about flying from Chicago Midway Airport to Simpson Bay

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

    Simpson Bay Princess Juliana is 2188.7 mi away from Chicago Midway. Typically, this will take 6h 36m by plane in normal conditions.

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

    Prices for flights from Chicago Midway Airport to Simpson Bay Princess Juliana Airport are refreshed on a daily basis.

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

  • What documentation or ID do you need to fly to Simpson Bay Princess Juliana Airport?

    The necessary travel and health documents for your Simpson Bay Princess Juliana Airport 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.

Traveling to a place near Simpson Bay?

Book flights to Simpson Bay if you plan to visit one of these locations
Philipsburg

Why use momondo?

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

It is quick and easy to find Chicago to Simpson Bay 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 Simpson Bay that suits you.

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

Yes. All flights to Simpson Bay from Chicago on momondo can be compared and filtered by various policies on offer, including flexible booking.

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

Once all potential Chicago to Simpson Bay flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

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

If you are not ready to book a flight from Chicago to Simpson Bay now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Simpson Bay and let you know when they change.

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Cabin classes currently available on flights to Simpson Bay

First Class to Simpson Bay
Business Class to Simpson Bayfrom $1,733