MDW - SXM

$189 Find Cheap Flights from Chicago Midway Airport to Simpson Bay - Compare and Save

1 adult
1 adult, Economy, 0 bags

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Everything you should know

Cheapest round-trip
$465
Typical prices: $517-$765
Southwest
Tue 11/27Mon 12/3
MDW - SXM • 1 stop
Cheapest one-way
$189
Typical prices: $241-$355
Southwest
Sun 12/9
MDW - SXM • 1 stop
Nonstop flights
Not available
There are currently no direct flights between Chicago Midway Airport and Simpson Bay. You'll need to take a connecting flight to reach the destination.
Insights
Insights
When to travel
February
Cheapest • 40% price drop
August
Most popular
Good to know
+1
Good to know
+1
Top layover airports
Atlanta Hartsfield-Jackson (ATL)
Cheapest • Avg $714 (round-trip)
Baltimore/Washington (BWI)
Shortest trip • 7h 42m (one-way)
Insights
Insights
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We hope you love your trip to Simpson Bay!
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Flight Deals

Cheap Flights from Midway to Simpson Bay (MDW-SXM)

 
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Midway to Simpson Bay

Fri, Nov 27 - Thu, Dec 3
Southwest Logo
5:05 am - 2:15 pmMDW  Chicago Midway-SXM Simpson Bay Princess Juliana
7h 10m1 stop Baltimore/Washington
Southwest Logo
3:15 pm - 5:40 amSXM  Simpson Bay Princess Juliana-MDW Chicago Midway
16h 25m2 stops Orlando Las Vegas Harry Reid Intl
$465Southwest
Wed, Jan 20 - Wed, Jan 27
Southwest Logo
5:45 am - 2:35 pmMDW  Chicago Midway-SXM Simpson Bay Princess Juliana
6h 50m1 stop Orlando
Southwest Logo
3:35 pm - 10:50 pmSXM  Simpson Bay Princess Juliana-MDW Chicago Midway
9h 15m1 stop Orlando
$467Southwest
Sun, Jan 31 - Thu, Feb 4
Southwest Logo
5:00 am - 2:35 pmMDW  Chicago Midway-SXM Simpson Bay Princess Juliana
7h 35m1 stop Orlando
Southwest Logo
3:35 pm - 10:50 pmSXM  Simpson Bay Princess Juliana-MDW Chicago Midway
9h 15m1 stop Orlando
$467Southwest
Thu, Jan 7 - Thu, Jan 14
Southwest Logo
5:45 am - 2:35 pmMDW  Chicago Midway-SXM Simpson Bay Princess Juliana
6h 50m1 stop Orlando
Southwest Logo
3:35 pm - 10:50 pmSXM  Simpson Bay Princess Juliana-MDW Chicago Midway
9h 15m1 stop Orlando
$467Southwest
Mon, Feb 15 - Thu, Feb 18
Southwest Logo
5:10 am - 3:15 pmMDW  Chicago Midway-SXM Simpson Bay Princess Juliana
8h 05m1 stop Orlando
Southwest Logo
3:35 pm - 10:55 pmSXM  Simpson Bay Princess Juliana-MDW Chicago Midway
9h 20m1 stop Orlando
$467Southwest
Tue, Jan 12 - Wed, Jan 20
Southwest Logo
5:45 am - 2:35 pmMDW  Chicago Midway-SXM Simpson Bay Princess Juliana
6h 50m1 stop Orlando
Southwest Logo
3:35 pm - 5:45 amSXM  Simpson Bay Princess Juliana-MDW Chicago Midway
16h 10m2 stops Orlando Phoenix Sky Harbor Intl
$472Southwest
Thu, Feb 25 - Tue, Mar 2
Southwest Logo
8:20 pm - 3:15 pmMDW  Chicago Midway-SXM Simpson Bay Princess Juliana
16h 55m2 stops Baltimore/Washington 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
$472Southwest
Wed, Jan 27 - Wed, Feb 3
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
$472Southwest
Mon, Feb 15 - Thu, Feb 18
Southwest Logo
8:20 pm - 2:35 pmMDW  Chicago Midway-SXM Simpson Bay Princess Juliana
16h 15m2 stops Baltimore/Washington Orlando
Southwest Logo
3:35 pm - 8:30 amSXM  Simpson Bay Princess Juliana-MDW Chicago Midway
18h 55m2 stops Orlando Baltimore/Washington
$472Southwest
Wed, Jan 20 - Wed, Jan 27
Southwest Logo
7:30 pm - 2:35 pmMDW  Chicago Midway-SXM Simpson Bay Princess Juliana
17h 05m2 stops Las Vegas Harry Reid 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
$472Southwest
Booking Insights

Price, demand and travel trends for Chicago Midway Airport to Simpson Bay flights

Use KAYAK data on prices, travel dates, airlines and seasonal trends to compare options and book flights from Chicago Midway Airport to Simpson Bay with more confidence.

How much is a round-trip flight from Chicago Midway Airport to Simpson Bay?

Round-trip flights from Chicago Midway Airport to Simpson Bay start at $465. Prices are below average for this route right now, with typical round-trip fares ranging from $517 to $765. The lowest price found in the past 5 days was $465 on Southwest.

What's the cheapest day of the week to fly from Chicago Midway Airport to Simpson Bay?

Friday is the cheapest day of the week to fly from Chicago Midway Airport to Simpson Bay, it is 21% cheaper than the average day. Monday is the most expensive day with flight prices 75% higher than average. Based on deals found by KAYAK users in the last 12 months.

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Key details for Chicago Midway Airport to Simpson Bay flights

Low season

May

Cheapest flight

$189
Best time to beat the crowds with an average 24% drop in price.
Flight from Chicago Midway Airport to Simpson Bay

When to book flights from Midway to Simpson Bay

Are your dates flexible? Find out the best times to travel from Midway to Simpson Bay based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price

Your Chicago Midway Airport to Simpson Bay flight questions, answered

Find helpful route details based on KAYAK data, including flight times, airports, airlines and booking questions.

  • Which airports can I use when flying from Chicago Midway Airport to Simpson Bay?

    Flights from Chicago Midway Airport to Simpson Bay usually depart from Chicago Midway (MDW) and arrive at Simpson Bay Princess Juliana (SXM).

  • What cabin classes can I book on flights from Chicago Midway Airport to Simpson Bay?

    Only Economy Class is available on flights from Chicago Midway Airport to Simpson Bay.

  • Which airports do connecting flights from Chicago Midway Airport to Simpson Bay pass through?

    One-stop flights from Chicago Midway Airport to Simpson Bay most commonly connect through:

    • Atlanta Hartsfield-Jackson (ATL) - 65% of one-stop connections
    • Orlando (MCO) - 32% of one-stop connections
    • Baltimore/Washington (BWI) - 3% of one-stop connections

    Atlanta Hartsfield-Jackson (ATL) handles the largest share of one-stop connections on this route.

  • Can I save money by using flexible dates for flights from Chicago Midway Airport to Simpson Bay?

    Yes. Being flexible with your travel dates can save you up to 55% on the Chicago Midway Airport to Simpson Bay route. Friday is the cheapest departure day at $531 round-trip on average, while Monday is the most expensive at $1,167, a difference of $636. KAYAK's flexible dates feature shows options up to 3 days before and after your selected dates, making it easier to compare nearby fares.

  • How long is a flight from Chicago Midway Airport to Simpson Bay?

    A nonstop flight from Chicago Midway Airport to Simpson Bay takes 0h 00m, covering 2,189 miles.

  • Do I need a passport to fly from Chicago Midway Airport to Simpson Bay?

    Yes, a valid passport is required for this international route. Many destinations require at least six months of validity beyond your travel dates. Check your passport expiry well before booking.

  • Have flight prices from Chicago Midway Airport to Simpson Bay changed much recently?

    Yes. Based on fares seen in the past 5 days, round-trip prices on this route showed a wide range, from about $465 to $3,886. That means the highest observed fare was about 8x higher than the lowest one.

  • How are flight prices from Chicago Midway Airport to Simpson Bay looking right now?

    One-way fares from Chicago Midway Airport to Simpson Bay are currently lower than usual. Average one-way flight prices are about $243, which is 16% below the typical average for this route.

  • How much time can I save by choosing a different layover airport from Chicago Midway Airport to Simpson Bay?

    Flying via Baltimore/Washington (BWI) gives the shortest average 1-stop total travel time at 7h 42m, compared with 7h 59m via Atlanta Hartsfield-Jackson (ATL) and 8h 08m via Orlando (MCO).

  • What is the time difference between Chicago Midway Airport and Simpson Bay?

    Simpson Bay is 1 hour ahead of Chicago Midway Airport (Atlantic Time vs Central Time). Plan for the time shift when scheduling connections or first-day activities.

  • What car rental options are available at Simpson Bay Princess Juliana Airport (SXM)?

    Simpson Bay Princess Juliana Airport (SXM) hosts 5 major car rental companies, with daily rates starting from around $2 for economy cars. Top options include:
    • Ace
    • Right Cars
    • Europcar
    • Budget
    • Alamo

  • How much should I expect to pay for a Chicago Midway Airport to Simpson Bay flight?

    Round-trip flights from Chicago Midway Airport to Simpson Bay range from $517 to $765, with an average of $665 over the past 12 months. Anything below $517 counts as a good deal.

Your guide to booking Chicago Midway Airport to Simpson Bay flights

Get tips on when to book, when to fly and what to know before your trip.

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