$259 Cheap Flights from Chicago (MDW) to St. Thomas (STT)

View $259 flight on Mon, Apr 6, 2026Opens in a new window

Popular airlines from Chicago Midway Airport (MDW) to Cyril E. King Airport (STT)

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Cheap Flights from Chicago to St. Thomas (MDW-STT)

Prices were available within the past 7 days and start at $259 for one-way flights and $509 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Wed, Jan 7 - Tue, Jan 13
MDW
Chicago
STT
St. Thomas
$509 Roundtrip, found 6 hours ago
$509
Roundtrip
found 6 hours ago
Select Delta flight, departing Wed, Jan 7 from Chicago to St. Thomas, returning Tue, Jan 13, priced at $509 found 6 hours ago
Delta
Tue, Jan 20 - Sun, Jan 25
MDW
Chicago
STT
St. Thomas
$514 Roundtrip, found 9 hours ago
$514
Roundtrip
found 9 hours ago
Select Delta flight, departing Tue, Jan 20 from Chicago to St. Thomas, returning Sun, Jan 25, priced at $514 found 9 hours ago
Delta
Mon, Jan 26 - Thu, Jan 29
MDW
Chicago
STT
St. Thomas
$519 Roundtrip, found 9 hours ago
$519
Roundtrip
found 9 hours ago
Select Delta flight, departing Mon, Jan 26 from Chicago to St. Thomas, returning Thu, Jan 29, priced at $519 found 9 hours ago
Delta
Sat, Oct 18 - Tue, Oct 21
MDW
Chicago
STT
St. Thomas
$534 Roundtrip, found 6 days ago
$534
Roundtrip
found 6 days ago
Select Delta flight, departing Sat, Oct 18 from Chicago to St. Thomas, returning Tue, Oct 21, priced at $534 found 6 days ago
Delta
Mon, Jan 26 - Wed, Jan 28
MDW
Chicago
STT
St. Thomas
$569 Roundtrip, found 9 hours ago
$569
Roundtrip
found 9 hours ago
Select Delta flight, departing Mon, Jan 26 from Chicago to St. Thomas, returning Wed, Jan 28, priced at $569 found 9 hours ago
Southwest Airlines
Sun, Mar 8 - Thu, Mar 12
MDW
Chicago
STT
St. Thomas
$579 Roundtrip, found 12 hours ago
$579
Roundtrip
found 12 hours ago
Select Southwest Airlines flight, departing Sun, Mar 8 from Chicago to St. Thomas, returning Thu, Mar 12, priced at $579 found 12 hours ago
Delta
Tue, Jan 6 - Sat, Jan 17
MDW
Chicago
STT
St. Thomas
$584 Roundtrip, found 1 hour ago
$584
Roundtrip
found 1 hour ago
Select Delta flight, departing Tue, Jan 6 from Chicago to St. Thomas, returning Sat, Jan 17, priced at $584 found 1 hour ago
Delta
Thu, Mar 5 - Mon, Mar 9
MDW
Chicago
STT
St. Thomas
$589 Roundtrip, found 3 hours ago
$589
Roundtrip
found 3 hours ago
Select Delta flight, departing Thu, Mar 5 from Chicago to St. Thomas, returning Mon, Mar 9, priced at $589 found 3 hours ago
Southwest Airlines
Sun, Mar 8 - Wed, Mar 11
MDW
Chicago
STT
St. Thomas
$596 Roundtrip, found 13 hours ago
$596
Roundtrip
found 13 hours ago
Select Southwest Airlines flight, departing Sun, Mar 8 from Chicago to St. Thomas, returning Wed, Mar 11, priced at $596 found 13 hours ago
Delta
Sat, Oct 18 - Sat, Oct 25
MDW
Chicago
STT
St. Thomas
$609 Roundtrip, found 6 days ago
$609
Roundtrip
found 6 days ago
Select Delta flight, departing Sat, Oct 18 from Chicago to St. Thomas, returning Sat, Oct 25, priced at $609 found 6 days ago

Find the cheapest month to fly from Chicago (MDW) to St. Thomas (STT)

September is typically the cheapest month to fly

From $359 - $1,104 per traveler.

Frequently asked questions

How much does a flight from Midway Intl. Airport (MDW) to Cyril E. King Airport (STT) cost?
Secure a cheap one-way flight from $259 or cheap return flight from $509 from Midway Intl. Airport (MDW) to Cyril E. King Airport (STT) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to see our cheapest flight offers on this route.
What is the cheapest month to fly from Midway Intl. Airport (MDW) to Cyril E. King Airport (STT)?
January is the cheapest month to fly from MDW to STT. Timing your trip outside of the busy season is often the key to better flight prices.
Which airlines fly direct from Midway Intl. Airport (MDW) to Cyril E. King Airport (STT)?
Although Chicago, IL (MDW-Midway Intl.) has no direct flights to Cyril E. King Airport (STT), other airports have nonstop options. Flying from O'Hare Intl. Airport (ORD) will get you to St. Thomas without any layovers.
What is the cheapest airline that flies from Midway Intl. Airport (MDW) to Cyril E. King Airport (STT)?
To find the cheapest airline that'll fly you from MDW to STT, use Expedia's filter tool. Tailor your search based on your travel style, such as preferred carriers and seat class. You can then sort your results by "Price (lowest to highest)" to list the most affordable options first.
How many flights per day from Midway Intl. Airport (MDW) to Cyril E. King Airport (STT)?
Nonstop flights from Midway Intl. Airport (MDW) to Cyril E. King Airport (STT) aren't available daily, so you'll have to take a flight with a layover. Explore your options with Expedia's filter tool. Enter your travel details and choose either "1 Stop" or "2+ Stops."
What day of the week has the most flights from MDW to STT?
Typically you'll find the greatest selection of flight options on a Friday. Tuesdays are often the quietest.* But this can vary based on the time of year, carrier and other factors.*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 Cyril E. King Airport (STT)?
To land at Cyril E. King Airport (STT) on time, opt for a flight that leaves Midway Intl. Airport (MDW) before 3 PM. The likelihood of cancellations is 22% higher, on average, for departures after this time.**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 Cyril E. King Airport (STT) last-minute?
Booking your flight from MDW to STT just before your journey is generally more expensive. However, if you're flexible with your itinerary, you could land a cheap last-minute fare.
Is it cheaper to book a MDW to STT flight and hotel package?
You'll generally save money by securing a MDW to STT 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 everything in one convenient place. Once you've selected your ideal accommodations and flights, consider other add-ons like activities, tours and car rentals.
Can I cancel or change the date of my flight from Midway Intl. Airport (MDW) to Cyril E. King Airport (STT)?
In most cases, you can reschedule or cancel your MDW to STT flight. However, there may be additional charges, especially if you booked over 24 hours ago. Check your itinerary for the airline's policies and fees on flight changes, or if you need further information, go to our Customer Service portal.

Travel information

Travel information

Origin airport
Midway Intl.
Destination airport
Cyril E. King
Airlines serving
Delta, Southwest Airlines
Roundtrip price
$509
Distance
2102 mi

Book with confidence

Book with confidence

Chicago to St. Thomas Flights

The cheapest times to fly from Chicago to St. Thomas

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 St. Thomas are during the month of January. You can find some of the cheapest flights from Chicago to St. Thomas with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Chicago to St. Thomas

Sunday is one of the best days to book for cheap flights from Chicago to St. Thomas: 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 St. Thomas

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 St. Thomas in 2025. You can also book with separate airlines for your outbound and return journeys, from $259 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 St. Thomas 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 St. Thomas 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 St. Thomas Flights

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