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Cheap flights from Midway (MDW) to Simpson Bay (SXM) from $301

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 9/6. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
MDW — SXM
Jun 15 — Jun 221
From?
To?
Sat 6/15
Sat 6/22
1 adult, Economy
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Cheap flight deals from Midway to Simpson Bay

Discover tips and strategies to find the most affordable flight options for your journey from Midway (MDW) to Simpson Bay (SXM). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated June 10, 2024.

Round-trip from

$522

One-way from

$462
From Chicago Midway to Simpson Bay Princess Juliana
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One-way flight from Chicago Midway to Simpson Bay Princess Juliana
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What is the cheapest day to fly round-trip from Chicago Midway Airport to Simpson Bay?

Travelers have found that booking a Saturday departure is the best way to save up to 135% on the cost of booking your flights compared to booking on days of the week where this route is of high demand.

How far in advance should I book a flight from Chicago Midway Airport to Simpson Bay?

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 $625, or $841 for flights within the next 24 hours.

What is the cheapest month to fly from Chicago Midway Airport to Simpson Bay?

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 $742 for the month, but tickets can be as low as $481. Due to multiple factors, prepare for potentially higher prices in July.

What is the cheapest time of day to fly from MDW to SXM?

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.

Cheap Midway to Simpson Bay flights in June & July 2024

Find cheap flight options from Midway to Simpson Bay specifically for the months of June and July 2024. Explore affordable fares based on user searches. Over the last 7 days, Cheapflights users made 3,080,152 searches. Prices were last updated on June 10, 2024.
Scroll through some of the best deals on flights from Chicago to Simpson Bay in 2024. Check back in a little while for more flight options.
Thu 7/42:36 pmMDW - SXM
2 stops25h 34mFrontier
Mon 7/86:20 pmSXM - MDW
2 stops28h 05mFrontier
Deal found 6/9$962
Tue 7/236:55 pmMDW - SXM
1 stop17h 50mDelta
Sat 8/173:10 pmSXM - MDW
1 stop7h 36mDelta
Deal found 6/10$990
Tue 7/236:00 amMDW - SXM
1 stop6h 45mDelta
Sat 8/173:10 pmSXM - MDW
2 stops18h 28mDelta
Deal found 6/10$994
Sun 7/286:55 pmMDW - SXM
1 stop17h 50mDelta
Sun 8/43:10 pmSXM - MDW
1 stop7h 36mDelta
Deal found 6/9$1,034
Sun 6/306:00 amMDW - SXM
1 stop6h 55mDelta
Wed 7/103:10 pmSXM - MDW
2 stops18h 28mDelta
Deal found 6/9$1,063
Tue 7/236:55 pmMDW - SXM
1 stop17h 50mDelta
Tue 7/303:10 pmSXM - MDW
1 stop19h 28mDelta
Deal found 6/9$1,064
Sat 7/66:00 amMDW - SXM
1 stop6h 55mDelta
Sat 7/133:10 pmSXM - MDW
1 stop7h 36mDelta
Deal found 6/10$1,129
Sat 7/66:00 amMDW - SXM
1 stop6h 55mDelta
Sat 7/133:10 pmSXM - MDW
2 stops18h 28mDelta
Deal found 6/10$1,133
Sun 7/286:55 pmMDW - SXM
1 stop17h 50mDelta
Sun 8/43:10 pmSXM - MDW
2 stops18h 28mDelta
Deal found 6/9$1,148

Midway to Simpson Bay 2024 flight deals

Discover exclusive flight deals for travel between Midway and Simpson Bay in 2024. Find excellent offers based on user searches. Over the last 7 days, Cheapflights users made 3,080,152 searches. Data last updated June 10, 2024.
Scroll through some of the best deals on flights from Chicago to Simpson Bay in 2024. Check back in a little while for more flight options.
Fri 9/68:13 pmMDW - SXM
2 stops17h 18mFrontier
Sat 9/144:04 pmSXM - MDW
2 stops19h 51mFrontier
Deal found 6/9$301
Fri 8/166:00 amMDW - SXM
1 stop6h 45mDelta
Fri 8/303:10 pmSXM - MDW
1 stop7h 36mDelta
Deal found 6/10$580
Fri 9/66:00 amMDW - SXM
1 stop6h 45mDelta
Fri 9/133:15 pmSXM - MDW
2 stops18h 25mDelta
Deal found 6/9$584
Fri 9/66:00 amMDW - SXM
1 stop6h 45mDelta
Fri 9/133:15 pmSXM - MDW
1 stop19h 33mDelta
Deal found 6/9$585
Fri 9/66:00 amMDW - SXM
1 stop6h 45mDelta
Mon 9/93:15 pmSXM - MDW
2 stops18h 25mDelta
Deal found 6/10$609
Fri 9/66:00 amMDW - SXM
1 stop6h 45mDelta
Mon 9/93:15 pmSXM - MDW
1 stop19h 33mDelta
Deal found 6/10$610
Wed 8/146:00 amMDW - SXM
1 stop6h 45mDelta
Mon 8/193:10 pmSXM - MDW
2 stops18h 28mDelta
Deal found 6/9$814
Sat 9/76:00 amMDW - SXM
1 stop6h 45mDelta
Sat 9/143:15 pmSXM - MDW
2 stops18h 25mDelta
Deal found 6/10$839
Sat 9/76:00 amMDW - SXM
1 stop6h 45mDelta
Sat 9/143:15 pmSXM - MDW
1 stop19h 33mDelta
Deal found 6/10$840

Midway to Simpson Bay flights leaving soon

Find last-minute flight options from Midway to Simpson Bay for spontaneous travel. Discover available flights and compare prices based on user searches. Secure great deals and offers for spontaneous trips with quick booking options. Over the last 7 days, Cheapflights users made 3,080,152 searches. Data last updated June 10, 2024.
Have a look at some of the last-minute flights available departing from Chicago to Simpson Bay. Users should double check the flight they book to ensure it matches the day, time, and destination they're looking for.
Sat 6/156:00 amMDW - SXM
1 stop6h 55mDelta
Wed 6/193:20 pmSXM - MDW
2 stops18h 28mDelta
Deal found 6/9$1,570
Wed 6/196:49 pmMDW - SXM
1 stop18h 06mDelta
Mon 6/243:20 pmSXM - MDW
2 stops18h 28mDelta
Deal found 6/9$1,617
Wed 6/196:00 amMDW - SXM
1 stop6h 55mDelta
Mon 6/243:20 pmSXM - MDW
1 stop19h 31mDelta
Deal found 6/9$1,638
Sat 6/156:00 amMDW - SXM
1 stop6h 55mDelta
Wed 6/193:20 pmSXM - MDW
1 stop21h 35mDelta
Deal found 6/9$1,772
Wed 6/196:49 pmMDW - SXM
1 stop18h 06mDelta
Sun 6/233:20 pmSXM - MDW
2 stops18h 28mDelta
Deal found 6/9$2,244
Wed 6/196:49 pmMDW - SXM
1 stop18h 06mDelta
Sun 6/233:20 pmSXM - MDW
1 stop19h 31mDelta
Deal found 6/9$2,268
Wed 6/193:45 pmMDW - SXM
2 stops20h 27mWestJet
Sun 6/232:10 pmSXM - MDW
2 stops25h 45mWestJet
Deal found 6/9$3,272

One-way flights to Simpson Bay from Midway

Search for one-way flight options from Midway to Simpson Bay. Find affordable one-way fares based on user searches. Compare prices and availability to plan your one-way journey according to your preferred dates and budget. Over the last 7 days, Cheapflights users made 3,080,152 searches. Data last updated June 10, 2024.
Take a look at some of the best available options we've come across on one-way flights from Chicago to Simpson Bay. Users needing a return flight from Chicago to Simpson Bay should utilize the search form above.
Sun 6/306:56 amMDW - SXM
3 stops29h 52mMultiple Airlines
Deal found 6/9$374
Sun 6/306:00 amMDW - SXM
1 stop6h 55mDelta
Deal found 6/9$462
Fri 6/216:00 amMDW - SXM
1 stop6h 55mDelta
Deal found 6/9$586
Sat 6/226:00 amMDW - SXM
1 stop6h 55mDelta
Deal found 6/9$696
Sun 6/308:40 amMDW - SXM
2 stops25h 10mMultiple Airlines
Deal found 6/9$797

Find flights from Midway to Simpson Bay within your budget

Customize your flight search to find flights from Midway 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, Cheapflights users made 3,080,152 searches. Data last updated June 10, 2024.

Fly from

Any airport

Fly to

Any airport

Budget

$301 - $962

Route

Depart

Return

Price

Chicago MidwaySimpson Bay Princess Juliana

MDW - SXM

MDWSXM

Chicago Midway

Fri 9/6

2 stops17h 18m

Simpson Bay Princess Juliana

Sat 9/14

2 stops19h 51m

$301

Chicago MidwaySimpson Bay Princess Juliana

MDW - SXM

MDWSXM

Chicago Midway

Fri 9/6

1 stop6h 45m

Simpson Bay Princess Juliana

Fri 9/13

2 stops18h 25m

$584

Chicago MidwaySimpson Bay Princess Juliana

MDW - SXM

MDWSXM

Chicago Midway

Fri 9/6

1 stop6h 45m

Simpson Bay Princess Juliana

Fri 9/13

1 stop19h 33m

$585

Chicago MidwaySimpson Bay Princess Juliana

MDW - SXM

MDWSXM

Chicago Midway

Fri 9/6

1 stop6h 45m

Simpson Bay Princess Juliana

Mon 9/9

2 stops18h 25m

$609

Chicago MidwaySimpson Bay Princess Juliana

MDW - SXM

MDWSXM

Chicago Midway

Fri 9/6

1 stop6h 45m

Simpson Bay Princess Juliana

Mon 9/9

1 stop19h 33m

$610

Chicago MidwaySimpson Bay Princess Juliana

MDW - SXM

MDWSXM

Chicago Midway

Wed 8/14

1 stop6h 45m

Simpson Bay Princess Juliana

Mon 8/19

2 stops18h 28m

$814

Chicago MidwaySimpson Bay Princess Juliana

MDW - SXM

MDWSXM

Chicago Midway

Fri 8/2

1 stop20h 09m

Simpson Bay Princess Juliana

Sat 8/10

1 stop18h 15m

$903

Chicago MidwaySimpson Bay Princess Juliana

MDW - SXM

MDWSXM

Chicago Midway

Fri 8/2

1 stop20h 09m

Simpson Bay Princess Juliana

Sat 8/10

2 stops28h 39m

$935

Chicago MidwaySimpson Bay Princess Juliana

MDW - SXM

MDWSXM

Chicago Midway

Thu 7/4

2 stops25h 34m

Simpson Bay Princess Juliana

Mon 7/8

2 stops28h 05m

$962

Flights are sorted by cheapest first

Deals found on 6/9

What is the cheapest day to fly from Chicago Midway Airport to Simpson Bay?

Use this chart to determine the cheapest time to fly round-trip from Midway to Simpson Bay. Price data was last updated on June 9, 2024.
Morning
Noon
Afternoon
Evening
All times are departure.
Travelers seeking maximum savings on their Chicago Midway Airport to Simpson Bay flight should consider departing on Sunday mornings when fares are most often at their lowest. Saturday mornings flights should be avoided if possible as fares are typically the most expensive at this time.
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Best time to book a flight from Midway to Simpson Bay

Have a flexible travel schedule? Discover the best time to fly to Simpson Bay from Midway with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Reviews of airlines servicing Simpson Bay

Get insights into the airlines that provide service to Simpson Bay. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Simpson Bay. Reviews last updated June 10, 2024.
Peruse reviews from past customers who have flown with Frontier, Delta and WestJet from Chicago to Simpson Bay to help guide your decision. In addition to providing an overall rating, users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
10,295 reviews

Overall

8.0

Crew

8.6

Entertainment

8.0

Boarding

8.2

Comfort

7.9

Food

7.4

Reviews

1 / 10

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.

Delta
8.0
Very good
10,295 reviews
Delta
8.0
Very good
10,295 reviews

Overall

8.0

Crew

8.6

Entertainment

8.0

Boarding

8.2

Comfort

7.9

Food

7.4

Reviews

1 / 10

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.

WestJet
7.5
Good
2,847 reviews
Delta
8.0
Very good
10,295 reviews

Overall

8.0

Crew

8.6

Entertainment

8.0

Boarding

8.2

Comfort

7.9

Food

7.4

Reviews

1 / 10

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.

Frontier
6.2
Okay
3,969 reviews
Delta
8.0
Very good
10,295 reviews

Overall

8.0

Crew

8.6

Entertainment

8.0

Boarding

8.2

Comfort

7.9

Food

7.4

Reviews

1 / 10

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.

Related info for your journey

Find useful and relevant information for your journey from Midway to Simpson Bay. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to Simpson Bay from Chicago Midway?

    Located just 0.5 mi from the city center, Simpson Bay Princess Juliana is the airport most travelers will use when flying to Simpson Bay from Chicago Midway. Booking flights from Chicago Midway to Princess Juliana (SXM) should be relatively easy as there are 0 daily inbound flights from Chicago Midway from 1 airline.

  • Can I find flights from Chicago Midway Airport to Simpson Bay for under $400 on Cheapflights?

    Yes, there are multiple flights from Chicago Midway Airport to Simpson Bay for under $400. The cheapest flight booked recently is on Frontier for just $301, but on average you can expect to pay $827.

  • Are there last-minute flights available from Chicago Midway Airport to Simpson Bay for under $1,600?

    There are currently 7+ open flights from Chicago Midway Airport to Simpson Bay within the next 7 days for less than $1,600.

  • What are the cheapest airlines flying from Chicago Midway Airport to Simpson Bay round-trip?

    Our cheapest airline available from Chicago Midway Airport to Simpson Bay is Frontier. Our recent data shows that you can find tickets from as low as $301 on this airline. An additional option worth looking into is Delta, starting at $584.

  • What does MDW to SXM mean?

    MDW stands for Chicago Midway Airport, while SXM stands for Simpson Bay Princess Juliana Airport. These codes are often called IATA codes, a set of identifiers established by IATA (International Air Transport Association) that is widely used by airlines and the aviation industry.

  • Can I find deals for flights from Midway to Simpson Bay that include extra baggage allowance?

    The amount of baggage you can bring on your Midway to Simpson Bay flight depends on the airline and the type of fare you've chosen. After entering your flight details, you'll be able to view the specific baggage policies for each deal in the search results. Keep in mind that certain deals may offer additional baggage allowance.

  • Can I find deals on flights from Midway to Simpson Bay with specific airlines?

    Yes, Cheapflights allows you to browse and filter Midway to Simpson Bay flight deals by airline. After entering your origin and destination, use the available filters to view flights offered by airlines.

  • Can I find deals for flights from Midway to Simpson Bay that include hotel bookings?

    Yes. In addition to deals on Midway to Simpson Bay flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Midway to Simpson Bay?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Midway to Simpson Bay.

  • Can I find deals for business class flights from Midway to Simpson Bay?

    Yes. Cheapflights offers flight deals from Midway to Simpson Bay by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • Can I find deals for flights from Midway to Simpson Bay that allow pets onboard?

    Many airlines flying from Midway to Simpson Bay offer the option to travel with pets. After selecting a flight deal, you can find more information about the airline's pet policy on their official website or by contacting the airline directly. Please note that additional fees and restrictions may apply.

  • Can I find deals on last-minute flights from Midway to Simpson Bay?

    Yes, you can often find last-minute deals on Midway to Simpson Bay flights on Cheapflights. However, these deals can vary and may not always be available. We recommend checking back frequently or signing up for price alerts for the most up-to-date deals.

  • How recently were the Chicago Midway Airport to Simpson Bay flight deals updated?

    The Chicago Midway Airport to Simpson Bay flight deals you see on this page were last updated on 6/10.

  • What is the cheapest month to book a flight from Chicago Midway Airport to Simpson Bay?

    Currently, September is the cheapest month in which you can book a flight from Chicago Midway Airport to Simpson Bay (average of $522). Flying from Chicago Midway Airport to Simpson Bay in July is currently the most expensive (average of $726). 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.

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Alternative routes for Midway to Simpson Bay
See prices for flight routes from nearby airports that may be better suited for you.

O'Hare Intl to Simpson Bay flights

Top airline flying from Midway to Simpson Bay

Discover the top airline that operate flights from Midway to Simpson Bay. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 3,080,152 searches. Data last updated June 10, 2024.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$473Average$946FlexibilityNo cancel feeOn-timeN/A
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Search flights from Midway to Simpson Bay by cabin class

Find flights from Midway to Simpson Bay, based on your preferred cabin class, be it economy, premium economy, business, or first class.
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