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Cheap flights from Chicago Midway Airport to Simpson Bay from $100

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago Midway Airport to Simpson Bay departing on 2/21. 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 Chicago Midway Airport to Simpson Bay

Cheap round-trip flights

Enter your travel dates to find the best prices.
Frontier Logo
6:00 am - 3:20 pm
MDW
-
SXM
7h 20m1 stop
Frontier Logo
4:30 pm - 11:25 pm
SXM
-
MDW
8h 55m1 stop
$287Frontier
Sat, Feb 21 - Sat, Feb 28
Frontier Logo
6:00 am - 3:20 pm
MDW
-
SXM
7h 20m1 stop
Frontier Logo
4:30 pm - 11:25 pm
SXM
-
MDW
8h 55m1 stop
$308Frontier
Sat, Feb 14 - Sat, Feb 28
Frontier Logo
6:00 am - 3:20 pm
MDW
-
SXM
7h 20m1 stop
Frontier Logo
4:30 pm - 11:25 pm
SXM
-
MDW
8h 55m1 stop
$359Frontier
Sat, Feb 14 - Sat, Feb 28
Delta Logo
6:00 am - 2:55 pm
MDW
-
SXM
6h 55m1 stop
Delta Logo
1:55 pm - 10:22 pm
SXM
-
MDW
10h 27m1 stop
$501Delta
Sun, Feb 1 - Fri, Feb 6
Delta Logo
5:31 pm - 12:30 pm
MDW
-
SXM
16h 59m2 stops
Delta Logo
1:55 pm - 10:07 pm
SXM
-
MDW
10h 12m1 stop
$506Delta
Wed, Jan 7 - Wed, Jan 14
Multiple Airlines Logo
5:10 pm - 2:10 pm
MDW
-
SXM
19h 00m2 stops
Multiple Airlines Logo
4:20 pm - 10:10 am
SXM
-
MDW
19h 50m1 stop
$553Multiple Airlines
Wed, Jan 7 - Wed, Jan 14
Delta Logo
6:00 am - 2:55 pm
MDW
-
SXM
6h 55m1 stop
Delta Logo
1:55 pm - 10:22 pm
SXM
-
MDW
10h 27m1 stop
$581Delta
Sun, Jan 25 - Fri, Jan 30
Delta Logo
6:00 am - 2:50 pm
MDW
-
SXM
6h 50m1 stop
Delta Logo
1:55 pm - 10:07 pm
SXM
-
MDW
10h 12m1 stop
$584Delta
Wed, Dec 31 - Fri, Jan 9
Delta Logo
6:00 am - 2:50 pm
MDW
-
SXM
6h 50m1 stop
Delta Logo
1:38 pm - 10:42 pm
SXM
-
MDW
11h 04m1 stop
$614Delta
Fri, Feb 27 - Fri, Mar 6
Delta Logo
6:00 am - 2:50 pm
MDW
-
SXM
6h 50m1 stop
Delta Logo
1:38 pm - 10:44 pm
SXM
-
MDW
11h 06m1 stop
$661Delta
Tue, Feb 17 - Tue, Feb 24

Frontier flights from Chicago Midway Airport to Simpson Bay

Our best Frontier deals on Chicago Midway Airport to Simpson Bay flight tickets
Frontier
Feb 21
MDW6:00 amChicago Midway
7h 20m
1 stop
SXM3:20 pmSimpson Bay Princess Juliana
Feb 28
SXM4:30 pmSimpson Bay Princess Juliana
8h 55m
1 stop
MDW11:25 pmChicago Midway
$287
Find similar
Frontier
Feb 14
MDW6:00 amChicago Midway
7h 20m
1 stop
SXM3:20 pmSimpson Bay Princess Juliana
Feb 28
SXM4:30 pmSimpson Bay Princess Juliana
8h 55m
1 stop
MDW11:25 pmChicago Midway
$308
Find similar
Frontier
Apr 4
MDW6:00 amChicago Midway
7h 40m
1 stop
SXM2:40 pmSimpson Bay Princess Juliana
Apr 11
SXM3:40 pmSimpson Bay Princess Juliana
9h 02m
1 stop
MDW11:42 pmChicago Midway
$457
Find similar

Delta flights from Chicago Midway Airport to Simpson Bay

Our best Delta deals on Chicago Midway Airport to Simpson Bay flight tickets
Delta
Feb 1
MDW6:00 amChicago Midway
6h 55m
1 stop
SXM2:55 pmSimpson Bay Princess Juliana
Feb 6
SXM1:55 pmSimpson Bay Princess Juliana
10h 27m
1 stop
MDW10:22 pmChicago Midway
$501
Find similar
Delta
Dec 22
MDW9:29 amChicago Midway
27h 21m
2 stops
SXM2:50 pmSimpson Bay Princess Juliana
Dec 31
SXM1:45 pmSimpson Bay Princess Juliana
10h 37m
1 stop
MDW10:22 pmChicago Midway
$506
Find similar
Delta
Dec 14
MDW6:00 amChicago Midway
6h 28m
1 stop
SXM2:28 pmSimpson Bay Princess Juliana
Dec 20
SXM5:22 pmSimpson Bay Princess Juliana
17h 43m
1 stop
MDW9:05 amChicago Midway
$524
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Chicago Midway Airport to Simpson Bay 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 December 11, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to Simpson Bay that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Sat 2/21

6:00 am-3:20 pm

1 stop7h 20m

Simpson Bay Princess Juliana

Sat 2/28

4:30 pm-11:25 pm

1 stop8h 55m

$287

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Sat 2/14

6:00 am-3:20 pm

1 stop7h 20m

Simpson Bay Princess Juliana

Sat 2/28

4:30 pm-11:25 pm

1 stop8h 55m

$308

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Sat 2/14

6:00 am-3:20 pm

1 stop7h 20m

Simpson Bay Princess Juliana

Sat 2/28

4:30 pm-11:25 pm

1 stop8h 55m

$359

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Sun 2/1

6:00 am-2:55 pm

1 stop6h 55m

Simpson Bay Princess Juliana

Fri 2/6

1:55 pm-10:22 pm

1 stop10h 27m

$501

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Wed 1/7

5:31 pm-12:30 pm

2 stops16h 59m

Simpson Bay Princess Juliana

Wed 1/14

1:55 pm-10:07 pm

1 stop10h 12m

$506

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Wed 1/7

5:10 pm-2:10 pm

2 stops19h 00m

Simpson Bay Princess Juliana

Wed 1/14

4:20 pm-10:10 am

1 stop19h 50m

$553

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Sun 1/25

6:00 am-2:55 pm

1 stop6h 55m

Simpson Bay Princess Juliana

Fri 1/30

1:55 pm-10:22 pm

1 stop10h 27m

$581

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Wed 12/31

6:00 am-2:50 pm

1 stop6h 50m

Simpson Bay Princess Juliana

Fri 1/9

1:55 pm-10:07 pm

1 stop10h 12m

$584

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Fri 2/27

6:00 am-2:50 pm

1 stop6h 50m

Simpson Bay Princess Juliana

Fri 3/6

1:38 pm-10:42 pm

1 stop11h 04m

$614

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Tue 2/17

6:00 am-2:50 pm

1 stop6h 50m

Simpson Bay Princess Juliana

Tue 2/24

1:38 pm-10:44 pm

1 stop11h 06m

$661

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 Tuesday is the least expensive day to fly to Simpson Bay. Tickets to fly out on this day can be as low as $644. Flights from Chicago Midway Airport to Simpson Bay on a Saturday will generally be more expensive and average around $881. Keep in mind that these prices on both days could fluctuate depending on the season and the demand.

What is the cheapest time of day to depart on your flight to Simpson Bay?

According to our data, the cheapest time of day to fly to Simpson Bay is at noon. momondo users have found flights departing from Chicago Midway Airport to Simpson Bay at noon for as low as $417. Keep in mind that these prices may fluctuate based on what airline you choose and the time of year you plan to travel. In contrast, the most expensive time of day to depart to Simpson Bay is in the morning when prices are around $827.

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

Fastest flight time

6h 50m

Direct flights

None
The fastest flight from Chicago Midway Airport to Simpson Bay takes 6h 50m
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

  • 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 50m 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 many operators does momondo search for flights from Chicago Midway Airport to Simpson Bay Princess Juliana Airport?

  • 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.

  • What is the most popular airline from Chicago Midway Airport to Simpson Bay?

Best airlines flying from Chicago Midway Airport to Simpson Bay

Compare and see reviews for airlines that fly from Chicago Midway Airport to Simpson Bay with momondo
Airline
Rating
Free Cancellation
Price
DeltaPriceFrom $512Free CancellationRating
7.9
8,007 reviews
Search Delta flights

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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Delta