Latest deals
Insights
When to book
FAQs
Reviews
Price Alerts

Cheap flights from Chicago Midway Airport to Simpson Bay from $349

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 12/29. 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

Discover deals from 900+ travel sites with momondo.

Save money when you book flights with momondo

Big names and deals

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

Find the cheapest flights from Chicago Midway Airport to Simpson Bay

Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
5:31 pm - 12:30 pmMDW-SXM
16h 59m2 stops
Delta Logo
1:55 pm - 10:09 pmSXM-MDW
10h 14m1 stop
$373Delta
Find Deal
Mon, Jan 5 - Wed, Jan 14
Delta Logo
6:00 am - 2:28 pmMDW-SXM
6h 28m1 stop
Delta Logo
3:53 pm - 11:47 pmSXM-MDW
9h 54m1 stop
$375Delta
Find Deal
Mon, Dec 8 - Fri, Dec 12
Delta Logo
6:00 am - 2:55 pmMDW-SXM
6h 55m1 stop
Delta Logo
4:20 pm - 11:40 pmSXM-MDW
9h 20m1 stop
$377Delta
Find Deal
Mon, Nov 10 - Fri, Nov 14
Frontier Logo
6:00 am - 3:20 pmMDW-SXM
7h 20m1 stop
Frontier Logo
4:30 pm - 11:25 pmSXM-MDW
8h 55m1 stop
$489Frontier
Find Deal
Sat, Jan 24 - Sat, Jan 31
Multiple Airlines Logo
7:44 am - 8:30 amMDW-SXM
22h 46m2 stops
Multiple Airlines Logo
4:20 pm - 10:05 amSXM-MDW
19h 45m1 stop
$543Multiple Airlines
Find Deal
Tue, Jan 13 - Sun, Jan 18
Frontier Logo
6:00 am - 3:20 pmMDW-SXM
7h 20m1 stop
Frontier Logo
4:30 pm - 11:25 pmSXM-MDW
8h 55m1 stop
$549Frontier
Find Deal
Sat, Feb 21 - Sat, Feb 28
Delta Logo
5:31 pm - 2:55 pmMDW-SXM
19h 24m1 stop
Delta Logo
1:55 pm - 10:09 pmSXM-MDW
10h 14m1 stop
$574Delta
Find Deal
Mon, Jan 5 - Wed, Jan 14
Multiple Airlines Logo
8:56 pm - 3:10 pmMDW-SXM
16h 14m2 stops
Multiple Airlines Logo
4:20 pm - 10:05 amSXM-MDW
19h 45m1 stop
$592Multiple Airlines
Find Deal
Sun, Mar 1 - Thu, Mar 5
WestJet Logo
1:50 pm - 3:21 pmMDW-SXM
23h 31m2 stops
WestJet Logo
4:20 pm - 6:18 pmSXM-MDW
27h 58m2 stops
$680WestJet
Find Deal
Wed, Dec 10 - Wed, Dec 17
WestJet Logo
9:59 am - 3:21 pmMDW-SXM
27h 22m2 stops
WestJet Logo
4:20 pm - 6:18 pmSXM-MDW
27h 58m3 stops
$738WestJet
Find Deal
Wed, Dec 10 - Wed, Dec 17

Delta flights from Chicago Midway Airport to Simpson Bay

Our best Delta deals on Chicago Midway Airport to Simpson Bay flight tickets
Delta
Jan 5
MDW5:31 pmChicago Midway
16h 59m
2 stops
SXM12:30 pmSimpson Bay Princess Juliana
Jan 14
SXM1:55 pmSimpson Bay Princess Juliana
10h 14m
1 stop
MDW10:09 pmChicago Midway
$373
Find similar
Delta
Dec 8
MDW6:00 amChicago Midway
6h 28m
1 stop
SXM2:28 pmSimpson Bay Princess Juliana
Dec 12
SXM3:53 pmSimpson Bay Princess Juliana
9h 54m
1 stop
MDW11:47 pmChicago Midway
$375
Find similar
Delta
Nov 10
MDW6:00 amChicago Midway
6h 55m
1 stop
SXM2:55 pmSimpson Bay Princess Juliana
Nov 14
SXM4:20 pmSimpson Bay Princess Juliana
9h 20m
1 stop
MDW11:40 pmChicago Midway
$377
Find similar

Frontier flights from Chicago Midway Airport to Simpson Bay

Our best Frontier deals on Chicago Midway Airport to Simpson Bay flight tickets
Frontier
Jan 24
MDW6:00 amChicago Midway
7h 20m
1 stop
SXM3:20 pmSimpson Bay Princess Juliana
Jan 31
SXM4:30 pmSimpson Bay Princess Juliana
8h 55m
1 stop
MDW11:25 pmChicago Midway
$489
Find similar
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
$549
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
$1,127
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 October 27, 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

Mon 1/5

5:31 pm-12:30 pm

2 stops16h 59m

Simpson Bay Princess Juliana

Wed 1/14

1:55 pm-10:09 pm

1 stop10h 14m

$373

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Mon 12/8

6:00 am-2:28 pm

1 stop6h 28m

Simpson Bay Princess Juliana

Fri 12/12

3:53 pm-11:47 pm

1 stop9h 54m

$375

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Mon 11/10

6:00 am-2:55 pm

1 stop6h 55m

Simpson Bay Princess Juliana

Fri 11/14

4:20 pm-11:40 pm

1 stop9h 20m

$377

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Sat 1/24

6:00 am-3:20 pm

1 stop7h 20m

Simpson Bay Princess Juliana

Sat 1/31

4:30 pm-11:25 pm

1 stop8h 55m

$489

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Tue 1/13

7:44 am-8:30 am

2 stops22h 46m

Simpson Bay Princess Juliana

Sun 1/18

4:20 pm-10:05 am

1 stop19h 45m

$543

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

$549

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Mon 1/5

5:31 pm-2:55 pm

1 stop19h 24m

Simpson Bay Princess Juliana

Wed 1/14

1:55 pm-10:09 pm

1 stop10h 14m

$574

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Sun 3/1

8:56 pm-3:10 pm

2 stops16h 14m

Simpson Bay Princess Juliana

Thu 3/5

4:20 pm-10:05 am

1 stop19h 45m

$592

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Wed 12/10

1:50 pm-3:21 pm

2 stops23h 31m

Simpson Bay Princess Juliana

Wed 12/17

4:20 pm-6:18 pm

2 stops27h 58m

$680

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Wed 12/10

9:59 am-3:21 pm

2 stops27h 22m

Simpson Bay Princess Juliana

Wed 12/17

4:20 pm-6:18 pm

3 stops27h 58m

$738

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

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 $891. 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 $873.

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

Direct flights

None
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 28m 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 $622Free CancellationRating
7.9
7,996 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.

An easier way to manage your Simpson Bay trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Wed 11/26
Wed 12/3
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to St. Maarten

Fly your favorite airline to Simpson Bay

Airlines are sorted and displayed according to clicks in the past 7 days on momondo
Delta
American Airlines
United Airlines
Turkish Airlines
Lufthansa
Frontier
British Airways
Qatar Airways
Spirit Airlines
Ryanair
Alaska Airlines
Emirates