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Cheap flights from Chicago Midway Airport to Simpson Bay from $308

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 5/12. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Find the cheapest flights from Chicago Midway Airport to Simpson Bay

Cheap round-trip flights

These are some of the best round-trip flight deals from Chicago Midway Airport to Simpson Bay that have been recently found on momondo from popular airlines, departing in the coming months.
9:12 pm - 10:58 amMDW-SXM
12h 46m1 stop
12:18 pm - 11:55 pmSXM-MDW
12h 37m2 stops
$480Frontier
Find Deal
Fri, May 30 - Sat, Jun 14
9:12 pm - 10:58 amMDW-SXM
12h 46m1 stop
12:18 pm - 7:59 pmSXM-MDW
8h 41m1 stop
$527Frontier
Find Deal
Fri, May 30 - Sat, Jun 14
6:00 am - 1:59 pmMDW-SXM
6h 59m1 stop
1:46 pm - 10:22 pmSXM-MDW
9h 36m1 stop
$622Delta
Find Deal
Wed, Apr 9 - Wed, Apr 30
9:12 pm - 3:50 pmMDW-SXM
17h 38m2 stops
12:18 pm - 7:59 pmSXM-MDW
8h 41m1 stop
$636Frontier
Find Deal
Sun, Jun 15 - Sat, Jun 21
6:00 am - 1:59 pmMDW-SXM
6h 59m1 stop
1:46 pm - 10:22 pmSXM-MDW
9h 36m1 stop
$647Delta
Find Deal
Thu, Apr 10 - Thu, Apr 17
6:00 am - 1:59 pmMDW-SXM
6h 59m1 stop
1:46 pm - 10:22 pmSXM-MDW
9h 36m1 stop
$672Delta
Find Deal
Thu, Apr 10 - Mon, Apr 14
12:55 pm - 2:16 pmMDW-SXM
24h 21m1 stop
12:25 pm - 10:20 amSXM-MDW
22h 55m1 stop
Sat, Apr 19 - Sat, Apr 26
12:00 pm - 1:15 pmMDW-SXM
24h 15m2 stops
6:10 pm - 4:24 pmSXM-MDW
23h 14m2 stops
$1,023
Find Deal
Sat, Jul 12 - Sat, Jul 19
2:00 pm - 1:19 pmMDW-SXM
22h 19m2 stops
2:10 pm - 6:03 pmSXM-MDW
28h 53m2 stops
$3,092WestJet
Find Deal
Wed, Jun 18 - Sun, Jun 22
12:48 pm - 1:15 pmMDW-SXM
23h 27m2 stops
2:10 pm - 6:03 pmSXM-MDW
28h 53m2 stops
$3,152WestJet
Find Deal
Wed, Jun 4 - Sun, Jun 8

Delta flights from Chicago Midway Airport to Simpson Bay

Our best Delta deals on Chicago Midway Airport to Simpson Bay flight tickets
Delta
Apr 9
MDW6:00 amChicago Midway
6h 59m
1 stop
SXM1:59 pmSimpson Bay Princess Juliana
Apr 30
SXM1:46 pmSimpson Bay Princess Juliana
9h 36m
1 stop
MDW10:22 pmChicago Midway
Delta
Apr 10
MDW6:00 amChicago Midway
6h 59m
1 stop
SXM1:59 pmSimpson Bay Princess Juliana
Apr 17
SXM1:46 pmSimpson Bay Princess Juliana
9h 36m
1 stop
MDW10:22 pmChicago Midway
Delta
Apr 10
MDW6:00 amChicago Midway
6h 59m
1 stop
SXM1:59 pmSimpson Bay Princess Juliana
Apr 14
SXM1:46 pmSimpson Bay Princess Juliana
9h 36m
1 stop
MDW10:22 pmChicago Midway

Frontier flights from Chicago Midway Airport to Simpson Bay

Our best Frontier deals on Chicago Midway Airport to Simpson Bay flight tickets
Frontier
May 30
MDW9:12 pmChicago Midway
12h 46m
1 stop
SXM10:58 amSimpson Bay Princess Juliana
Jun 14
SXM12:18 pmSimpson Bay Princess Juliana
12h 37m
2 stops
MDW11:55 pmChicago Midway
Frontier
May 30
MDW9:12 pmChicago Midway
12h 46m
1 stop
SXM10:58 amSimpson Bay Princess Juliana
Jun 14
SXM12:18 pmSimpson Bay Princess Juliana
8h 41m
1 stop
MDW7:59 pmChicago Midway
Frontier
Jun 15
MDW9:12 pmChicago Midway
17h 38m
2 stops
SXM3:50 pmSimpson Bay Princess Juliana
Jun 21
SXM12:18 pmSimpson Bay Princess Juliana
8h 41m
1 stop
MDW7:59 pmChicago Midway

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 $919. 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 $907.

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

$308

Fastest flight time

6h 49m

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 $308. The best round-trip flight deal from Chicago Midway Airport to Simpson Bay found on momondo in the last 72 hours is $480.
The fastest flight from Chicago Midway Airport to Simpson Bay takes 6h 49m
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)

  • 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 49m 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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