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Cheap flights from Chicago Midway Airport to Simpson Bay from $677

This is the cheapest round-trip 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 12/5. 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

Delta Logo
6:00 am - 2:35 pmMDW-SXM
6h 35m1 stop
Delta Logo
4:00 pm - 9:44 pmSXM-MDW
7h 44m1 stop
$677Delta
Find Deal
vie., dic. 5 - sáb., dic. 13
Delta Logo
6:00 am - 2:56 pmMDW-SXM
6h 56m1 stop
Delta Logo
1:45 pm - 9:46 pmSXM-MDW
10h 01m1 stop
$767Delta
Find Deal
sáb., ene. 24 - dom., feb. 1
Delta Logo
6:00 am - 2:35 pmMDW-SXM
6h 35m1 stop
Delta Logo
4:00 pm - 9:44 pmSXM-MDW
7h 44m1 stop
$807Delta
Find Deal
sáb., dic. 6 - sáb., dic. 13
Delta Logo
6:00 am - 2:56 pmMDW-SXM
6h 56m1 stop
Delta Logo
1:45 pm - 9:46 pmSXM-MDW
10h 01m1 stop
$852Delta
Find Deal
vie., ene. 23 - sáb., ene. 31
Delta Logo
6:00 am - 2:49 pmMDW-SXM
6h 49m1 stop
Delta Logo
4:00 pm - 9:44 pmSXM-MDW
7h 44m1 stop
$892Delta
Find Deal
mié., nov. 5 - mar., nov. 11
Delta Logo
6:00 am - 2:56 pmMDW-SXM
6h 56m1 stop
Delta Logo
1:45 pm - 9:46 pmSXM-MDW
10h 01m1 stop
$897Delta
Find Deal
sáb., ene. 24 - sáb., ene. 31
Logo
4:15 pm - 12:15 pmMDW-SXM
18h 00m1 stop
Logo
4:20 pm - 10:05 amSXM-MDW
19h 45m1 stop
$1,106
Find Deal
lun., dic. 22 - lun., dic. 29
WestJet Logo
1:48 pm - 3:21 pmMDW-SXM
23h 33m2 stops
WestJet Logo
4:20 pm - 1:09 pmSXM-MDW
22h 49m2 stops
$3,140WestJet
Find Deal
mié., nov. 5 - mar., nov. 11
WestJet Logo
9:15 am - 2:19 pmMDW-SXM
28h 04m2 stops
WestJet Logo
2:10 pm - 9:36 pmSXM-MDW
32h 26m2 stops
$3,165WestJet
Find Deal
mié., sep. 10 - dom., sep. 14
WestJet Logo
2:00 pm - 3:21 pmMDW-SXM
23h 21m2 stops
WestJet Logo
4:20 pm - 1:09 pmSXM-MDW
22h 49m2 stops
$3,212WestJet
Find Deal
sáb., nov. 29 - dom., dic. 7

Delta flights from Chicago Midway Airport to Simpson Bay

Our best Delta deals on Chicago Midway Airport to Simpson Bay flight tickets
Delta
Dec 5
MDW6:00 amChicago Midway
6h 35m
1 stop
SXM2:35 pmSimpson Bay Princess Juliana
Dec 13
SXM4:00 pmSimpson Bay Princess Juliana
7h 44m
1 stop
MDW9:44 pmChicago Midway
$677
Find similar
Delta
Jan 24
MDW6:00 amChicago Midway
6h 56m
1 stop
SXM2:56 pmSimpson Bay Princess Juliana
Feb 1
SXM1:45 pmSimpson Bay Princess Juliana
10h 01m
1 stop
MDW9:46 pmChicago Midway
$767
Find similar
Delta
Dec 6
MDW6:00 amChicago Midway
6h 35m
1 stop
SXM2:35 pmSimpson Bay Princess Juliana
Dec 13
SXM4:00 pmSimpson Bay Princess Juliana
7h 44m
1 stop
MDW9:44 pmChicago Midway
$807
Find similar

WestJet flights from Chicago Midway Airport to Simpson Bay

Our best WestJet deals on Chicago Midway Airport to Simpson Bay flight tickets
WestJet
Nov 5
MDW1:48 pmChicago Midway
23h 33m
2 stops
SXM3:21 pmSimpson Bay Princess Juliana
Nov 11
SXM4:20 pmSimpson Bay Princess Juliana
22h 49m
2 stops
MDW1:09 pmChicago Midway
$3,140
Find similar
WestJet
Sep 10
MDW9:15 amChicago Midway
28h 04m
2 stops
SXM2:19 pmSimpson Bay Princess Juliana
Sep 14
SXM2:10 pmSimpson Bay Princess Juliana
32h 26m
2 stops
MDW9:36 pmChicago Midway
$3,165
Find similar
WestJet
Nov 29
MDW2:00 pmChicago Midway
23h 21m
2 stops
SXM3:21 pmSimpson Bay Princess Juliana
Dec 7
SXM4:20 pmSimpson Bay Princess Juliana
22h 49m
2 stops
MDW1:09 pmChicago Midway
$3,212
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 agosto 18, 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

vie. 12/5

6:00 am-2:35 pm

1 stop6h 35m

Simpson Bay Princess Juliana

sáb. 12/13

4:00 pm-9:44 pm

1 stop7h 44m

$677

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

sáb. 1/24

6:00 am-2:56 pm

1 stop6h 56m

Simpson Bay Princess Juliana

dom. 2/1

1:45 pm-9:46 pm

1 stop10h 01m

$767

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

sáb. 12/6

6:00 am-2:35 pm

1 stop6h 35m

Simpson Bay Princess Juliana

sáb. 12/13

4:00 pm-9:44 pm

1 stop7h 44m

$807

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

vie. 1/23

6:00 am-2:56 pm

1 stop6h 56m

Simpson Bay Princess Juliana

sáb. 1/31

1:45 pm-9:46 pm

1 stop10h 01m

$852

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

mié. 11/5

6:00 am-2:49 pm

1 stop6h 49m

Simpson Bay Princess Juliana

mar. 11/11

4:00 pm-9:44 pm

1 stop7h 44m

$892

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

sáb. 1/24

6:00 am-2:56 pm

1 stop6h 56m

Simpson Bay Princess Juliana

sáb. 1/31

1:45 pm-9:46 pm

1 stop10h 01m

$897

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

lun. 12/22

4:15 pm-12:15 pm

1 stop18h 00m

Simpson Bay Princess Juliana

lun. 12/29

4:20 pm-10:05 am

1 stop19h 45m

$1,106

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

mié. 11/5

1:48 pm-3:21 pm

2 stops23h 33m

Simpson Bay Princess Juliana

mar. 11/11

4:20 pm-1:09 pm

2 stops22h 49m

$3,140

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

mié. 9/10

9:15 am-2:19 pm

2 stops28h 04m

Simpson Bay Princess Juliana

dom. 9/14

2:10 pm-9:36 pm

2 stops32h 26m

$3,165

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

sáb. 11/29

2:00 pm-3:21 pm

2 stops23h 21m

Simpson Bay Princess Juliana

dom. 12/7

4:20 pm-1:09 pm

2 stops22h 49m

$3,212

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 12 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 $906. 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 $886.

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

$799

Fastest flight time

6h 35m

Direct flights

None

Airports in Simpson Bay

1 airport
The best one-way flight to Simpson Bay from Chicago Midway Airport in the past 72 hours is $799. The best round-trip flight deal from Chicago Midway Airport to Simpson Bay found on momondo in the last 72 hours is $677.
The fastest flight from Chicago Midway Airport to Simpson Bay takes 6h 35m
There are no direct flights from Chicago Midway Airport to Simpson Bay. Popular non-direct route for this connection is Chicago Midway Airport - Simpson Bay Princess Juliana Airport.
There is 1 airport near Simpson Bay: Simpson Bay Princess Juliana (SXM)
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 35m 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
8.0
7,981 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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