MDW - SXM

$240 Find Cheap Flights from Chicago Midway Airport to Simpson Bay - Compare and Save

1 adult
1 adult, Economy, 0 bags

Save 25% or more on flights. Compare deals from all over the web.

Never overpay with our price tracking tools.

Filter searches by price, airline and more to find your best flights.

Everything you should know

Cheapest round-trip
$574
Typical prices: $531-$750
Southwest
Thu 11/29Mon 12/3
MDW - SXM • 1 stop
Cheapest one-way
$240
Typical prices: $229-$355
Southwest
Sat 12/15
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
May
Cheapest • 26% price drop
August
Most popular
Good to know
+1
Good to know
+1
Top layover airports
Orlando (MCO)
Cheapest • Avg $694 (round-trip)
Baltimore/Washington (BWI)
Shortest trip • 7h 42m (one-way)
Insights
Insights
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Simpson Bay!
Flight Deals
Booking Insights
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

Sun, Nov 29 - Thu, Dec 3
Southwest Logo
5:40 am - 3:40 pmMDW  Chicago Midway-SXM Simpson Bay Princess Juliana
8h 00m1 stop Orlando
Southwest Logo
3:15 pm - 12:05 pmSXM  Simpson Bay Princess Juliana-MDW Chicago Midway
22h 50m2 stops Orlando Las Vegas Harry Reid Intl
$574Southwest
Sun, Nov 29 - Thu, Dec 3
Southwest Logo
8:40 pm - 3:40 pmMDW  Chicago Midway-SXM Simpson Bay Princess Juliana
17h 00m2 stops Baltimore/Washington Orlando
Southwest Logo
3:15 pm - 12:05 pmSXM  Simpson Bay Princess Juliana-MDW Chicago Midway
22h 50m2 stops Orlando Las Vegas Harry Reid Intl
$574Southwest
Wed, Feb 3 - Wed, Feb 24
Southwest Logo
5:25 am - 2:15 pmMDW  Chicago Midway-SXM Simpson Bay Princess Juliana
6h 50m1 stop Orlando
Southwest Logo
3:15 pm - 10:50 pmSXM  Simpson Bay Princess Juliana-MDW Chicago Midway
9h 35m1 stop Orlando
$577Southwest
Wed, Feb 3 - Wed, Feb 24
Southwest Logo
5:25 am - 2:15 pmMDW  Chicago Midway-SXM Simpson Bay Princess Juliana
6h 50m1 stop Orlando
Southwest Logo
3:15 pm - 9:45 amSXM  Simpson Bay Princess Juliana-MDW Chicago Midway
20h 30m2 stops Orlando Denver Intl
$581Southwest
Tue, Dec 8 - Tue, Dec 15
Southwest Logo
5:20 am - 2:15 pmMDW  Chicago Midway-SXM Simpson Bay Princess Juliana
6h 55m1 stop Orlando
Southwest Logo
3:15 pm - 12:05 pmSXM  Simpson Bay Princess Juliana-MDW Chicago Midway
22h 50m2 stops Orlando Las Vegas Harry Reid Intl
$601Southwest
Tue, Dec 8 - Tue, Dec 15
Southwest Logo
3:35 pm - 2:15 pmMDW  Chicago Midway-SXM Simpson Bay Princess Juliana
20h 40m2 stops Phoenix Sky Harbor Intl Orlando
Southwest Logo
3:15 pm - 12:05 pmSXM  Simpson Bay Princess Juliana-MDW Chicago Midway
22h 50m2 stops Orlando Las Vegas Harry Reid Intl
$601Southwest
Mon, Dec 21 - Tue, Dec 29
Delta Logo
6:00 am - 2:49 pmMDW  Chicago Midway-SXM Simpson Bay Princess Juliana
6h 49m1 stop Atlanta Hartsfield-Jackson
Delta Logo
1:40 pm - 10:22 pmSXM  Simpson Bay Princess Juliana-MDW Chicago Midway
10h 42m1 stop Atlanta Hartsfield-Jackson
$617Delta
Sun, Dec 13 - Sat, Dec 19
Southwest Logo
5:05 am - 2:15 pmMDW  Chicago Midway-SXM Simpson Bay Princess Juliana
7h 10m1 stop Baltimore/Washington
Southwest Logo
4:40 pm - 11:05 pmSXM  Simpson Bay Princess Juliana-MDW Chicago Midway
8h 25m1 stop Baltimore/Washington
$618Southwest
Sun, Dec 13 - Sat, Dec 19
Southwest Logo
5:05 am - 2:15 pmMDW  Chicago Midway-SXM Simpson Bay Princess Juliana
7h 10m1 stop Baltimore/Washington
Southwest Logo
4:40 pm - 9:55 amSXM  Simpson Bay Princess Juliana-MDW Chicago Midway
19h 15m2 stops Baltimore/Washington Orlando
$623Southwest
Sun, Dec 13 - Sat, Dec 19
Southwest Logo
8:25 pm - 2:15 pmMDW  Chicago Midway-SXM Simpson Bay Princess Juliana
15h 50m2 stops Baltimore/Washington Orlando
Southwest Logo
4:40 pm - 8:20 amSXM  Simpson Bay Princess Juliana-MDW Chicago Midway
17h 40m2 stops Baltimore/Washington Denver Intl
$623Southwest
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 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 typically range from $531 to $750. The lowest price found in the past 5 days was $574, on Southwest.

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

Based on deals KAYAK users found in the last 12 months, Sunday is the cheapest day of the week to fly from Chicago Midway Airport to Simpson Bay. It’s 15% cheaper than the average day, while Monday is the most expensive, with prices 70% higher.

Find deals

Key details for Chicago Midway Airport to Simpson Bay flights

Low season

May

Cheapest flight

$240
Beat the crowds with an average 69% drop in travelers.
The most popular month to fly with an average 53% increase in travelers.
One-way 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 answers about this route, including flight times, airports, airlines and booking tips.

  • 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.

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

    A nonstop flight from Chicago Midway Airport to Simpson Bay takes 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.

  • 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 $531 to $750, with an average of $684 over the past 12 months. Anything below $531 counts as a good deal.

  • 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 $574 to $4,131. That means the highest observed fare was about 7x 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 in line with typical prices for this route. Average one-way fares are about $284.

  • 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 averaging $40 for economy cars. Top options include:

    • Right Cars
    • Ace
    • Budget
    • Europcar
    • Alamo

  • 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).

  • 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) - 56% of one-stop connections
    • Orlando (MCO) - 41% of one-stop connections
    • Baltimore/Washington (BWI) - 2% of one-stop connections

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

    Yes. Flexible dates can save you up to 50% on flights from Chicago Midway Airport to Simpson Bay. Sunday is the cheapest departure day at $584 round-trip on average, while Monday is the most expensive at $1,167, a difference of $583.

    Cheaper weekend fares like these are typical of routes dominated by weekday business travel.

  • 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 54m via Atlanta Hartsfield-Jackson (ATL) and 8h 15m 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.

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.
  • If your dates are flexible, aim for a Sunday departure and avoid flying on Monday. On this route, Sunday flights average $584, about $583 less than Monday fares (50% savings) based on the last 12 months.
  • If you can choose when to travel, plan your Chicago Midway Airport to Simpson Bay trip for May. Fares historically average $507 round-trip in that month - typically $508 less than the most expensive month, which is December (based on the last 12 months).
  • If you're arriving late at night and need somewhere to stay, check out these hotels close to Simpson Bay Princess Juliana Airport.

    • Simpson Bay Resort Marina & Spa
    • Hilton Vacation Club Flamingo Beach St. Maarten
    • The Atrium Beach Resort and Spa Sint Maarten, an Ascend Collection Hotel

More options for your flight from Midway to Simpson Bay

Complete your trip to Simpson Bay with a hotel stay or car rental

Car rentals in Simpson Bay
Hotels in Simpson Bay
Vacations in Simpson Bay