Round-trip from | $535 |
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Travelers have found that booking a Saturday departure is the best way to save up to 158% on the cost of booking your flights compared to booking on days of the week where this route is of high demand.
Travelers have found it’s best to book a flight 55 days in advance to save up to 550% compared to booking the same week of travel. As your travel date approaches, the cost of this flight route may potentially increase. While opting to book 55 days out may not be an option for all, there are still additional ways to secure a deal in the near future. You might find a flight from Chicago Midway Airport to Simpson Bay 1-2 weeks in advance for as low as $464, or $841 for flights within the next 24 hours.
Our data shows that September tends to be the cheapest month to fly to Simpson Bay from Chicago Midway Airport. Users have commonly found prices around $743 for the month, but tickets can be as low as $481. Due to multiple factors, prepare for potentially higher prices in July.
Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Chicago Midway Airport to Simpson Bay as you normally would.
Fly from
Fly to
Budget
$299 - $868
Route
Depart
Return
Price
Chicago MidwaySimpson Bay Princess Juliana
MDW - SXM
MDWSXM
Chicago Midway
Thu 6/6
2 stops19h 24m
Simpson Bay Princess Juliana
Fri 6/14
2 stops15h 09m
Chicago MidwaySimpson Bay Princess Juliana
MDW - SXM
MDWSXM
Chicago Midway
Thu 8/1
2 stops22h 37m
Simpson Bay Princess Juliana
Mon 8/5
2 stops30h 06m
Chicago MidwaySimpson Bay Princess Juliana
MDW - SXM
MDWSXM
Chicago Midway
Tue 7/23
1 stop18h 00m
Simpson Bay Princess Juliana
Sat 8/17
2 stops18h 25m
Chicago MidwaySimpson Bay Princess Juliana
MDW - SXM
MDWSXM
Chicago Midway
Mon 8/12
1 stop6h 49m
Simpson Bay Princess Juliana
Sun 8/18
1 stop21h 34m
Chicago MidwaySimpson Bay Princess Juliana
MDW - SXM
MDWSXM
Chicago Midway
Tue 9/10
2 stops18h 50m
Simpson Bay Princess Juliana
Sun 9/15
1 stop21h 39m
Chicago MidwaySimpson Bay Princess Juliana
MDW - SXM
MDWSXM
Chicago Midway
Tue 9/10
1 stop21h 04m
Simpson Bay Princess Juliana
Sun 9/15
1 stop21h 39m
Chicago MidwaySimpson Bay Princess Juliana
MDW - SXM
MDWSXM
Chicago Midway
Sat 6/8
1 stop6h 55m
Simpson Bay Princess Juliana
Sat 6/15
2 stops21h 17m
Chicago MidwaySimpson Bay Princess Juliana
MDW - SXM
MDWSXM
Chicago Midway
Fri 6/7
2 stops30h 40m
Simpson Bay Princess Juliana
Fri 6/14
2 stops15h 09m
Chicago MidwaySimpson Bay Princess Juliana
MDW - SXM
MDWSXM
Chicago Midway
Mon 6/17
3 stops37h 19m
Simpson Bay Princess Juliana
Sun 6/23
3 stops31h 08m
Currently, September is the cheapest month in which you can book a flight from Chicago Midway Airport to Simpson Bay (average of $535). Flying from Chicago Midway Airport to Simpson Bay in July is currently the most expensive (average of $777). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
January
$548
February
$588
March
$656
April
$605
May
$580
June
$660
July
$777
August
$648
September
$535
October
$656
November
$603
December
$633
Overall
Boarding
Comfort
Food
Entertainment
Crew
Reviews
Bad experience with the staff boarding the gate. I couldn’t board with my carry on, personal item and a funny bag. I had to put my passport inside my pockets and put the funny bag inside the personal item. Then after passing the staff pull out everything again.
Overall
Boarding
Comfort
Food
Entertainment
Crew
Reviews
Bad experience with the staff boarding the gate. I couldn’t board with my carry on, personal item and a funny bag. I had to put my passport inside my pockets and put the funny bag inside the personal item. Then after passing the staff pull out everything again.
Overall
Boarding
Comfort
Food
Entertainment
Crew
Reviews
Bad experience with the staff boarding the gate. I couldn’t board with my carry on, personal item and a funny bag. I had to put my passport inside my pockets and put the funny bag inside the personal item. Then after passing the staff pull out everything again.
Cheapflights helps you search for flights from Midway to Simpson Bay via 900+ travel sites so you don’t have to. After performing a flight search, users can also filter their flight selection by filtering for price, number of stops, airlines, and so on.
It’s simple! Cheapflights, which is free to use for everyone, saves millions of users time and money every year by helping them find the cheapest and most suitable flights from Midway to Simpson Bay.
Yes, we can. To see specific flights from Midway to Simpson Bay with no change fees, users can toggle flexible booking options after using the search form above to find flights.
Yes, Cheapflights has a feature called Price Alert, which notifies users when flight prices change. Track prices for your flight to Simpson Bay from Midway today and book when prices fit your budget.