$214 Cheap Flights from St. Thomas (STT) to Chicago (MDW)

View $214 flight on Thu, Feb 19, 2026Opens in a new window

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

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

Prices were available within the past 7 days and start at $214 for one-way flights and $423 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Thu, Feb 19 - Mon, Feb 23
STT
St. Thomas
MDW
Chicago
$423 Roundtrip, just found
$423
Roundtrip
just found
Select Delta flight, departing Thu, Feb 19 from St. Thomas to Chicago, returning Mon, Feb 23, priced at $423 just found
Southwest Airlines
Thu, Feb 26 - Mon, Mar 2
STT
St. Thomas
MDW
Chicago
$471 Roundtrip, found 1 day ago
$471
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Thu, Feb 26 from St. Thomas to Chicago, returning Mon, Mar 2, priced at $471 found 1 day ago
Delta
Fri, Feb 13 - Sun, Feb 15
STT
St. Thomas
MDW
Chicago
$496 Roundtrip, found 1 hour ago
$496
Roundtrip
found 1 hour ago
Select Delta flight, departing Fri, Feb 13 from St. Thomas to Chicago, returning Sun, Feb 15, priced at $496 found 1 hour ago
Delta
Fri, Feb 20 - Thu, Mar 12
STT
St. Thomas
MDW
Chicago
$501 Roundtrip, found 3 days ago
$501
Roundtrip
found 3 days ago
Select Delta flight, departing Fri, Feb 20 from St. Thomas to Chicago, returning Thu, Mar 12, priced at $501 found 3 days ago
Southwest Airlines
Fri, Feb 13 - Mon, Feb 16
STT
St. Thomas
MDW
Chicago
$509 Roundtrip, found 1 day ago
$509
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Fri, Feb 13 from St. Thomas to Chicago, returning Mon, Feb 16, priced at $509 found 1 day ago
Southwest Airlines
Thu, Feb 12 - Wed, Feb 25
STT
St. Thomas
MDW
Chicago
$519 Roundtrip, found 3 days ago
$519
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Thu, Feb 12 from St. Thomas to Chicago, returning Wed, Feb 25, priced at $519 found 3 days ago
Southwest Airlines
Fri, Feb 13 - Mon, Feb 16
STT
St. Thomas
MDW
Chicago
$529 Roundtrip, found 1 day ago
$529
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Fri, Feb 13 from St. Thomas to Chicago, returning Mon, Feb 16, priced at $529 found 1 day ago
Delta
Thu, Jan 22 - Thu, Jan 29
STT
St. Thomas
MDW
Chicago
$534 Roundtrip, found 6 days ago
$534
Roundtrip
found 6 days ago
Select Delta flight, departing Thu, Jan 22 from St. Thomas to Chicago, returning Thu, Jan 29, priced at $534 found 6 days ago
Southwest Airlines
Thu, Feb 12 - Tue, Feb 17
STT
St. Thomas
MDW
Chicago
$539 Roundtrip, found 3 days ago
$539
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Thu, Feb 12 from St. Thomas to Chicago, returning Tue, Feb 17, priced at $539 found 3 days ago
Delta
Thu, Feb 19 - Mon, Feb 23
STT
St. Thomas
MDW
Chicago
$543 Roundtrip, just found
$543
Roundtrip
just found
Select Delta flight, departing Thu, Feb 19 from St. Thomas to Chicago, returning Mon, Feb 23, priced at $543 just found

Alternative airports near Chicago

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

Select flight to O'Hare Intl. ORD. Cheapest option available. Average driving time to city center is 23 minutes. Flights from $378
ORD
O'Hare Intl.
Cheapest
Average driving time to city center23 min
Flights from $378

Frequently asked questions

How much does a flight from Cyril E. King Airport (STT) to Midway Intl. Airport (MDW) cost?
Grab a cheap one-way flight from $214 or cheap return flight from $423 from Cyril E. King Airport (STT) to Midway Intl. Airport (MDW) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to see our cheapest flight deals on this route.
What is the cheapest month to fly from Cyril E. King Airport (STT) to Midway Intl. Airport (MDW)?
The cheapest month to fly from STT to MDW is February, when there's less demand. Off-peak months are typically when airlines offer lower prices between these airports.
What is the cheapest airline that flies from Cyril E. King Airport (STT) to Midway Intl. Airport (MDW)?
Use the filters on Expedia to compare different airlines and find the most affordable carrier that'll take you from STT to MDW. Then, sort your results by "Price (lowest to highest)" to score a great deal.
How many flights per day from Cyril E. King Airport (STT) to Midway Intl. Airport (MDW)?
You'll need to take a flight with a layover when traveling from Cyril E. King Airport (STT) to Midway Intl. Airport (MDW). Direct flights don't operate daily on this route. However, just filter your search to include one or more stops to find the best option for your trip.
What day of the week has the most flights from STT to MDW?
You'll typically find Tuesday the quietest day for flights, while Fridays tend to be the busiest.* However this can change from season to season and during peak travel times or public holidays.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Cyril E. King Airport (STT) to Midway Intl. Airport (MDW)?
To avoid potential delays on the Cyril E. King Airport (STT) to Midway Intl. Airport (MDW) route, travel before 3 PM. Later departures have a 22% higher chance of cancellation.**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.
What airports do you fly into for Chicago from Cyril E. King Airport (STT)?
O'Hare Intl. Airport (ORD) is the only airport in Chicago with direct flights from Cyril E. King Airport (STT). Check out your options and find affordable fares on Expedia.
Is it cheaper to buy a plane ticket from Cyril E. King Airport (STT) to Midway Intl. Airport (MDW) last-minute?
Last-minute bookings from STT to MDW are generally more expensive. To lock in the cheapest rates, start looking for flights early. That being said, if you're flexible with your travel plans, you may score a cheap fare just before your departure.
Is it cheaper to book a STT to MDW flight and hotel package?
You'll typically save money by booking a STT to MDW 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 place. After choosing your ideal accommodations and flights, you can add extras such as car rentals, tours and activities.
Can I cancel or change the date of my flight from Cyril E. King Airport (STT) to Midway Intl. Airport (MDW)?
If you booked your STT to MDW flight within the last 24 hours, you may be able to modify or cancel it without any fees. Depending on the airline and the type of ticket you purchased, additional charges may apply for changes beyond this timeframe. Airline policies and contact information can be found in your itinerary or confirmation email. Or, visit our Customer Service portal for more details.

Travel information

Origin airport
Cyril E. King
Destination airport
Midway Intl.
Airlines serving
Delta, Southwest Airlines
Roundtrip price
$423
Distance
2102 mi

Book with confidence

St. Thomas to Chicago Flights

The cheapest times to fly from St. Thomas to Chicago

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

 

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

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

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 St. Thomas to Chicago in 2026. You can also book with separate airlines for your outbound and return journeys, from $214 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 St. Thomas to Chicago 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 St. Thomas to Chicago 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.

 

St. Thomas to Chicago Flights

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