HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news

Cheap flights from Midway (MDW) to Simpson Bay (SXM) from $187

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 5/18. 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
May 10 — May 171
From?
To?
Fri 5/10
Fri 5/17
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

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 May 5, 2024.

Round-trip from

$546
From Chicago Midway to Simpson Bay Princess Juliana
Search Deals

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 158% 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 $464, 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 $743 for the month, but tickets can be as low as $481. Due to multiple factors, prepare for potentially higher prices in July.

When is the cheapest time to fly from Chicago Midway Airport to Simpson Bay (MDW - 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 Frontier flights from Midway to Simpson Bay

Explore cheap flight options specifically provided by Frontier for the route between Midway and Simpson Bay. Find affordable fares and compare prices with other airlines to secure the best deal for your journey. Over the last 7 days, Cheapflights users made 2,795,183 searches. Data last updated May 5, 2024.
Consider these cheap Frontier flights we've found departing from Chicago to Simpson Bay. Make sure to check back often as deals are often changing.
Sat 5/189:08 pmMDW - SXM
1 stop16h 59mFrontier
Sat 5/254:14 pmSXM - MDW
1 stop15h 40mFrontier
Deal found 5/4$187
Sat 5/187:53 amMDW - SXM
2 stops30h 14mFrontier
Sat 5/254:14 pmSXM - MDW
1 stop15h 40mFrontier
Deal found 5/4$245
Sun 8/42:54 pmMDW - SXM
2 stops22h 37mFrontier
Sat 8/104:30 pmSXM - MDW
1 stop22h 29mFrontier
Deal found 5/4$377
Sun 8/42:54 pmMDW - SXM
2 stops22h 37mFrontier
Sat 8/104:30 pmSXM - MDW
2 stops29h 19mFrontier
Deal found 5/4$441
Thu 6/62:36 pmMDW - SXM
2 stops25h 39mFrontier
Sat 6/154:20 pmSXM - MDW
1 stop18h 11mFrontier
Deal found 5/4$642
Thu 6/62:36 pmMDW - SXM
2 stops25h 39mFrontier
Sat 6/154:20 pmSXM - MDW
2 stops25h 45mFrontier
Deal found 5/4$723

Cheap Delta flights from Midway to Simpson Bay

Explore cheap flight options specifically provided by Delta for the route between Midway and Simpson Bay. Find affordable fares and compare prices with other airlines to secure the best deal for your journey. Over the last 7 days, Cheapflights users made 2,795,183 searches. Data last updated May 5, 2024.
Have a look at some of the cheapest available Delta flights departing from Chicago and landing in Simpson Bay. Deals are refreshing constantly so come back soon for more options.
Mon 6/36:00 amMDW - SXM
1 stop6h 40mDelta
Mon 6/103:20 pmSXM - MDW
2 stops18h 28mDelta
Deal found 5/4$584
Tue 7/236:00 amMDW - SXM
1 stop6h 49mDelta
Sat 8/173:19 pmSXM - MDW
1 stop18h 53mDelta
Deal found 5/4$585
Sat 10/262:05 pmMDW - SXM
1 stop22h 44mDelta
Fri 11/13:19 pmSXM - MDW
1 stop22h 52mDelta
Deal found 5/4$608
Sat 6/86:00 amMDW - SXM
1 stop6h 55mDelta
Sat 6/153:38 pmSXM - MDW
2 stops21h 17mDelta
Deal found 5/4$609
Thu 9/121:10 pmMDW - SXM
2 stops23h 39mDelta
Mon 9/163:19 pmSXM - MDW
1 stop18h 58mDelta
Deal found 5/4$614
Thu 9/121:05 pmMDW - SXM
1 stop23h 44mDelta
Mon 9/163:19 pmSXM - MDW
1 stop21h 39mDelta
Deal found 5/4$615
Sat 10/2610:11 amMDW - SXM
1 stop26h 38mDelta
Mon 10/283:19 pmSXM - MDW
1 stop26h 57mDelta
Deal found 5/4$634
Sun 10/276:00 amMDW - SXM
1 stop6h 49mDelta
Wed 10/303:19 pmSXM - MDW
2 stops18h 26mDelta
Deal found 5/4$639
Sun 10/276:00 amMDW - SXM
1 stop6h 49mDelta
Wed 10/303:19 pmSXM - MDW
1 stop18h 58mDelta
Deal found 5/4$640

Cheap Midway to Simpson Bay flights in May & June 2024

Find cheap flight options from Midway to Simpson Bay specifically for the months of May and June 2024. Explore affordable fares based on user searches. Over the last 7 days, Cheapflights users made 2,795,183 searches. Prices were last updated on May 5, 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.
Sat 5/189:08 pmMDW - SXM
1 stop16h 59mFrontier
Sat 5/254:14 pmSXM - MDW
1 stop15h 40mFrontier
Deal found 5/4$187
Sat 5/187:53 amMDW - SXM
2 stops30h 14mFrontier
Sat 5/254:14 pmSXM - MDW
1 stop15h 40mFrontier
Deal found 5/4$245
Mon 6/36:00 amMDW - SXM
1 stop6h 40mDelta
Mon 6/103:20 pmSXM - MDW
2 stops18h 28mDelta
Deal found 5/4$584
Sat 6/86:00 amMDW - SXM
1 stop6h 55mDelta
Sat 6/153:38 pmSXM - MDW
2 stops21h 17mDelta
Deal found 5/4$609
Thu 6/62:36 pmMDW - SXM
2 stops25h 39mFrontier
Sat 6/154:20 pmSXM - MDW
1 stop18h 11mFrontier
Deal found 5/4$642
Thu 6/62:36 pmMDW - SXM
2 stops25h 39mFrontier
Sat 6/154:20 pmSXM - MDW
2 stops25h 45mFrontier
Deal found 5/4$723
Mon 6/36:00 amMDW - SXM
1 stop6h 40mDelta
Mon 6/103:20 pmSXM - MDW
1 stop19h 31mDelta
Deal found 5/4$760
Sat 6/296:00 amMDW - SXM
1 stop6h 55mDelta
Sat 7/63:20 pmSXM - MDW
2 stops18h 29mDelta
Deal found 5/4$933
Thu 5/96:00 amMDW - SXM
1 stop6h 40mDelta
Tue 5/143:10 pmSXM - MDW
1 stop17h 45mDelta
Deal found 5/4$940

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 2,795,183 searches. Data last updated May 5, 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.
Sat 5/189:08 pmMDW - SXM
1 stop16h 59mFrontier
Sat 5/254:14 pmSXM - MDW
1 stop15h 40mFrontier
Deal found 5/4$187
Sat 5/187:53 amMDW - SXM
2 stops30h 14mFrontier
Sat 5/254:14 pmSXM - MDW
1 stop15h 40mFrontier
Deal found 5/4$245
Sun 8/42:54 pmMDW - SXM
2 stops22h 37mFrontier
Sat 8/104:30 pmSXM - MDW
1 stop22h 29mFrontier
Deal found 5/4$377
Sun 8/42:54 pmMDW - SXM
2 stops22h 37mFrontier
Sat 8/104:30 pmSXM - MDW
2 stops29h 19mFrontier
Deal found 5/4$441
Mon 6/36:00 amMDW - SXM
1 stop6h 40mDelta
Mon 6/103:20 pmSXM - MDW
2 stops18h 28mDelta
Deal found 5/4$584
Tue 7/236:00 amMDW - SXM
1 stop6h 49mDelta
Sat 8/173:19 pmSXM - MDW
1 stop18h 53mDelta
Deal found 5/4$585
Sat 10/266:15 pmMDW - SXM
1 stop18h 34mDelta
Wed 10/303:19 pmSXM - MDW
1 stop22h 52mDelta
Deal found 5/4$608
Sat 6/86:00 amMDW - SXM
1 stop6h 55mDelta
Sat 6/153:38 pmSXM - MDW
2 stops21h 17mDelta
Deal found 5/4$609
Thu 9/121:10 pmMDW - SXM
2 stops23h 39mDelta
Mon 9/163:19 pmSXM - MDW
1 stop18h 58mDelta
Deal found 5/4$614

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 2,795,183 searches. Data last updated May 5, 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.
Thu 5/96:00 amMDW - SXM
1 stop6h 40mDelta
Tue 5/143:10 pmSXM - MDW
1 stop17h 45mDelta
Deal found 5/4$940
Thu 5/96:00 amMDW - SXM
1 stop6h 40mDelta
Tue 5/143:10 pmSXM - MDW
2 stops18h 56mDelta
Deal found 5/4$1,054
Tue 5/146:00 amMDW - SXM
1 stop6h 40mDelta
Sat 5/182:20 pmSXM - MDW
1 stop8h 41mDelta
Deal found 5/4$1,189
Tue 5/141:21 pmMDW - SXM
2 stops47h 19mDelta
Sat 5/182:20 pmSXM - MDW
1 stop8h 41mDelta
Deal found 5/4$1,212
Tue 5/149:46 amMDW - SXM
3 stops33h 39mMultiple Airlines
Mon 5/2010:10 amSXM - MDW
3 stops24h 37mMultiple Airlines
Deal found 5/3$1,326

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 2,795,183 searches. Data last updated May 5, 2024.

Fly from

Any airport

Fly to

Any airport

Budget

$187 - $1,326

Route

Depart

Return

Price

Chicago MidwaySimpson Bay Princess Juliana

MDW - SXM

MDWSXM

Chicago Midway

Sat 5/18

1 stop16h 59m

Simpson Bay Princess Juliana

Sat 5/25

1 stop15h 40m

$187

Chicago MidwaySimpson Bay Princess Juliana

MDW - SXM

MDWSXM

Chicago Midway

Sat 5/18

2 stops30h 14m

Simpson Bay Princess Juliana

Sat 5/25

1 stop15h 40m

$245

Chicago MidwaySimpson Bay Princess Juliana

MDW - SXM

MDWSXM

Chicago Midway

Sun 8/4

2 stops22h 37m

Simpson Bay Princess Juliana

Sat 8/10

1 stop22h 29m

$377

Chicago MidwaySimpson Bay Princess Juliana

MDW - SXM

MDWSXM

Chicago Midway

Sun 8/4

2 stops22h 37m

Simpson Bay Princess Juliana

Sat 8/10

2 stops29h 19m

$441

Chicago MidwaySimpson Bay Princess Juliana

MDW - SXM

MDWSXM

Chicago Midway

Mon 6/3

1 stop6h 40m

Simpson Bay Princess Juliana

Mon 6/10

2 stops18h 28m

$584

Chicago MidwaySimpson Bay Princess Juliana

MDW - SXM

MDWSXM

Chicago Midway

Tue 7/23

1 stop6h 49m

Simpson Bay Princess Juliana

Sat 8/17

1 stop18h 53m

$585

Chicago MidwaySimpson Bay Princess Juliana

MDW - SXM

MDWSXM

Chicago Midway

Sat 10/26

1 stop22h 44m

Simpson Bay Princess Juliana

Fri 11/1

1 stop22h 52m

$608

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

$609

Chicago MidwaySimpson Bay Princess Juliana

MDW - SXM

MDWSXM

Chicago Midway

Tue 5/14

3 stops33h 39m

Simpson Bay Princess Juliana

Mon 5/20

3 stops24h 37m

$1,326

Flights are sorted by cheapest first

Deals found on 5/4

When is the cheapest time 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 April 28, 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.
Search Deals

Average price of flights to Simpson Bay by month

Plan your trip from Midway to Simpson Bay by taking into account the cheapest months to travel. The average price of a one-way flight from Midway to Simpson Bay is currently $0 while a round-trip flight costs $551. Price data was last updated on April 28, 2024.

Currently, September is the cheapest month in which you can book a flight from Chicago Midway Airport to Simpson Bay (average of $546). Flying from Chicago Midway Airport to Simpson Bay in July is currently the most expensive (average of $788). 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

$589

March

$656

April

$600

May

$584

June

$665

July

$788

August

$648

September

$546

October

$661

November

$603

December

$637

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 May 5, 2024.
Peruse reviews from past customers who have flown with Frontier and Delta 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
8.1
Very good
10,838 reviews
Check prices

Overall

8.1

Crew

8.6

Comfort

7.9

Entertainment

8.0

Food

7.4

Boarding

8.2

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
8.1
Very good
10,838 reviews
Delta
8.1
Very good
10,838 reviews
Check prices

Overall

8.1

Crew

8.6

Comfort

7.9

Entertainment

8.0

Food

7.4

Boarding

8.2

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
6.3
Okay
4,098 reviews
Delta
8.1
Very good
10,838 reviews
Check prices

Overall

8.1

Crew

8.6

Comfort

7.9

Entertainment

8.0

Food

7.4

Boarding

8.2

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 $200 on Cheapflights?

    Yes, there are multiple flights from Chicago Midway Airport to Simpson Bay for under $200. The cheapest flight booked recently is on Frontier for just $187, but on average you can expect to pay $587.

  • Are there last-minute flights available from Chicago Midway Airport to Simpson Bay for under $1,000?

    There are currently 5+ open flights from Chicago Midway Airport to Simpson Bay within the next 7 days for less than $1,000.

  • 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 $187 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 5/4.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

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 2,795,183 searches. Data last updated May 5, 2024.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$473Average$946FlexibilityNo cancel feeOn-timeN/A
Search Delta flights
USA to Nairobi flights
Tampa to Las Vegas flights
New York to Dublin flights
Chicago to Indianapolis flights
Denver to Miami flights
Los Angeles to Nashville flights
Los Angeles to Cabo San Lucas flights
Indianapolis to Las Vegas flights
Miami to Buenos Aires flights
New York to Los Angeles flights
USA to Hyderabad flights
Chicago Midway Airport to Sydney flights

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.
First Class
Business Class
Prem Econ Class
Economy Class

Book a flight to one of these trending destinations

User searches for flights to these destinations increased 20% or more in the past 90 days compared to other destinations
Flights to Saint Peter Jersey
Flights to Kirkwall Arpt
Flights to Skiathos
Flights to Naxos
Flights to Ningbo Lishe Intl
Flights to Edremit/Korfez
Flights to Bourgas
Flights to Bodø
Flights to Pellston Emmet County
Flights to Cornwall Newquay
Flights to Ordu/Giresun
Flights to Batumi
Flights to Mason City
Flights to Biarritz Parme
Flights to Zakynthos Dionsios Salomos
Flights to Cortez Montezuma County
Flights to Clermont-Ferrand Aulnat
Flights to Nevsehir
Flights to Hyannis Barnstable
Flights to Girona Costa Brava
Flights to Kagoshima
Flights to Perugia Sant Egidio
Flights to Oran Es Senia
Flights to Chios

Fly with Cheapflights

Find the best flight deals on Cheapflights, where travelers can enjoy low prices and a wide availability of flights to their desired destinations.

How does Cheapflights help users find flights from Midway to Simpson Bay?

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.

Why should you use Cheapflights to find cheap flight tickets from Midway to Simpson Bay?

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.

Can Cheapflights find flights from Midway to Simpson Bay with no change fees?

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.

Can Cheapflights notify me if prices for flights from Midway to Simpson Bay become cheaper?

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.

100% Free
Cheapflights is completely free to use, so you can start saving the moment you arrive.
Book with Flexibility
Our users can plan ahead with confidence and find flights with no change fees
Travel Smart
Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.
View all available airlines