$742 Cheap Flights from Chicago (MDW) to Gustavia (SBH)

View $742 flight on Tue, Nov 18, 2025Opens in a new window

Popular airlines from Chicago Midway Airport (MDW) to Gustavia (SBH-Gustaf III)

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Cheap Flights from Chicago to Gustavia (MDW-SBH)

Prices were available within the past 7 days and start at $742 for one-way flights and $1,424 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Wed, Jan 21 - Sun, Jan 25
MDW
Chicago
SBH
Gustavia
$1,424 Roundtrip, found 4 days ago
$1,424
Roundtrip
found 4 days ago
Select Delta flight, departing Wed, Jan 21 from Chicago to Gustavia, returning Sun, Jan 25, priced at $1,424 found 4 days ago
Delta
Wed, Jan 21 - Mon, Jan 26
MDW
Chicago
SBH
Gustavia
$1,454 Roundtrip, found 4 days ago
$1,454
Roundtrip
found 4 days ago
Select Delta flight, departing Wed, Jan 21 from Chicago to Gustavia, returning Mon, Jan 26, priced at $1,454 found 4 days ago
Delta
Fri, May 1 - Wed, May 6
MDW
Chicago
SBH
Gustavia
$1,485 Roundtrip, found 2 days ago
$1,485
Roundtrip
found 2 days ago
Select Delta flight, departing Fri, May 1 from Chicago to Gustavia, returning Wed, May 6, priced at $1,485 found 2 days ago
Delta
Wed, Jan 21 - Sun, Jan 25
MDW
Chicago
SBH
Gustavia
$1,494 Roundtrip, found 4 days ago
$1,494
Roundtrip
found 4 days ago
Select Delta flight, departing Wed, Jan 21 from Chicago to Gustavia, returning Sun, Jan 25, priced at $1,494 found 4 days ago
Delta
Tue, Apr 14 - Mon, Apr 20
MDW
Chicago
SBH
Gustavia
$1,555 Roundtrip, found 2 days ago
$1,555
Roundtrip
found 2 days ago
Select Delta flight, departing Tue, Apr 14 from Chicago to Gustavia, returning Mon, Apr 20, priced at $1,555 found 2 days ago
Delta
Fri, May 1 - Wed, May 6
MDW
Chicago
SBH
Gustavia
$1,660 Roundtrip, found 2 days ago
$1,660
Roundtrip
found 2 days ago
Select Delta flight, departing Fri, May 1 from Chicago to Gustavia, returning Wed, May 6, priced at $1,660 found 2 days ago
Delta
Tue, Nov 18 - Mon, Nov 24
MDW
Chicago
SBH
Gustavia
$1,680 Roundtrip, found 2 days ago
$1,680
Roundtrip
found 2 days ago
Select Delta flight, departing Tue, Nov 18 from Chicago to Gustavia, returning Mon, Nov 24, priced at $1,680 found 2 days ago
Delta
Tue, Jul 14 - Mon, Jul 20
MDW
Chicago
SBH
Gustavia
$1,740 Roundtrip, found 2 days ago
$1,740
Roundtrip
found 2 days ago
Select Delta flight, departing Tue, Jul 14 from Chicago to Gustavia, returning Mon, Jul 20, priced at $1,740 found 2 days ago
Delta
Tue, Apr 14 - Mon, Apr 20
MDW
Chicago
SBH
Gustavia
$1,745 Roundtrip, found 2 days ago
$1,745
Roundtrip
found 2 days ago
Select Delta flight, departing Tue, Apr 14 from Chicago to Gustavia, returning Mon, Apr 20, priced at $1,745 found 2 days ago
Delta
Fri, Jun 19 - Wed, Jun 24
MDW
Chicago
SBH
Gustavia
$1,750 Roundtrip, found 6 hours ago
$1,750
Roundtrip
found 6 hours ago
Select Delta flight, departing Fri, Jun 19 from Chicago to Gustavia, returning Wed, Jun 24, priced at $1,750 found 6 hours ago

Alternative airports near Gustavia

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to Princess Juliana Intl. SXM. Cheapest option available. Flights from $707
SXM
Princess Juliana Intl.
Cheapest
Flights from $707

Frequently asked questions

How much does a flight from Midway Intl. Airport (MDW) to Gustaf III Airport (SBH) cost?
Get a cheap one-way flight from $742 or cheap return flight from $1,424 from Midway Intl. Airport (MDW) to Gustaf III Airport (SBH) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to find our cheapest flight offers on this route.
What is the cheapest month to fly from Midway Intl. Airport (MDW) to Gustaf III Airport (SBH)?
January is the least expensive month to fly from MDW to SBH. Avoiding peak travel times is often the key to finding a great deal.
What is the cheapest airline that flies from Midway Intl. Airport (MDW) to Gustaf III Airport (SBH)?
Use the filters on Expedia to compare airlines and find the most affordable carrier that'll take you from MDW to SBH. Then, sort your results by "Price (lowest to highest)" to snag a great deal.
How many flights per day from Midway Intl. Airport (MDW) to Gustaf III Airport (SBH)?
Direct flights from Midway Intl. Airport (MDW) to Gustaf III Airport (SBH) aren't available daily, so you'll need to take a flight with a layover. Explore your options with Expedia's filters. Enter your travel details and choose either "1 Stop" or "2+ Stops."
What day of the week has the most flights from MDW to SBH?
Friday is typically the busiest day for flights, while Tuesday is often the quietest.* Remember that flight schedules can change depending on various factors, including the season and airline.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Midway Intl. Airport (MDW) to Gustaf III Airport (SBH)?
To touch down at Gustaf III Airport (SBH) on time, choose a flight that leaves Midway Intl. Airport (MDW) before 3 PM. The likelihood of cancellations is 22% higher, on average, for departures after this hour.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
Is it cheaper to buy a plane ticket from Midway Intl. Airport (MDW) to Gustaf III Airport (SBH) last-minute?
Booking your plane ticket from MDW to SBH just before your journey is typically more expensive. However, if there's some wiggle room with your departure times and dates, you could land a cheap last-minute fare.
Is it cheaper to book a MDW to SBH flight and hotel package?
You'll typically save money by securing a MDW to SBH flight and hotel package compared to booking separately. In fact, you could save hundreds of dollars by bundling with Expedia. And it's simple to manage it all in one convenient place. Once you've chosen your ideal flights and accommodations, consider adding extras including tours, activities and car rentals.
Can I cancel or change the date of my flight from Midway Intl. Airport (MDW) to Gustaf III Airport (SBH)?
In most instances, you're able to reschedule or cancel your MDW to SBH flight. However, there may be additional charges, especially if you made your booking more than 24 hours ago. Check your itinerary for the airline's fees and rules on flight changes, or if you'd like more details, head to our Customer Service portal.

Travel information

Travel information

Origin airport
Midway Intl.
Destination airport
Gustaf III
Roundtrip price
$1,424
Distance
2208 mi

Book with confidence

Book with confidence

Chicago to Gustavia Flights

The cheapest times to fly from Chicago to Gustavia

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Chicago to Gustavia are during the month of January. You can find some of the cheapest flights from Chicago to Gustavia with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Chicago to Gustavia

Sunday is one of the best days to book for cheap flights from Chicago to Gustavia: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Chicago to Gustavia

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Chicago to Gustavia in 2025. You can also book with separate airlines for your outbound and return journeys, from $742 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Chicago to Gustavia flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Chicago to Gustavia airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Chicago to Gustavia Flights

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*Available to One Key members.