$292 Cheap Flights from St. Thomas (STT) to Chicago (MDW)

View $292 flight on Sat, Jan 17, 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 $292 for one-way flights and $509 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Thu, Jan 22 - Tue, Jan 27
STT
St. Thomas
MDW
Chicago
$509 Roundtrip, found 4 hours ago
$509
Roundtrip
found 4 hours ago
Select Delta flight, departing Thu, Jan 22 from St. Thomas to Chicago, returning Tue, Jan 27, priced at $509 found 4 hours ago
Delta
Tue, Jan 13 - Fri, Jan 23
STT
St. Thomas
MDW
Chicago
$514 Roundtrip, found 1 day ago
$514
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Jan 13 from St. Thomas to Chicago, returning Fri, Jan 23, priced at $514 found 1 day ago
Delta
Sat, Aug 30 - Mon, Sep 15
STT
St. Thomas
MDW
Chicago
$534 Roundtrip, found 5 days ago
$534
Roundtrip
found 5 days ago
Select Delta flight, departing Sat, Aug 30 from St. Thomas to Chicago, returning Mon, Sep 15, priced at $534 found 5 days ago
Delta
Thu, Sep 25 - Mon, Sep 29
STT
St. Thomas
MDW
Chicago
$554 Roundtrip, found 1 day ago
$554
Roundtrip
found 1 day ago
Select Delta flight, departing Thu, Sep 25 from St. Thomas to Chicago, returning Mon, Sep 29, priced at $554 found 1 day ago
Delta
Mon, Oct 6 - Tue, Oct 21
STT
St. Thomas
MDW
Chicago
$559 Roundtrip, found 2 days ago
$559
Roundtrip
found 2 days ago
Select Delta flight, departing Mon, Oct 6 from St. Thomas to Chicago, returning Tue, Oct 21, priced at $559 found 2 days ago
Delta
Sun, Jan 11 - Mon, Jan 19
STT
St. Thomas
MDW
Chicago
$569 Roundtrip, found 1 day ago
$569
Roundtrip
found 1 day ago
Select Delta flight, departing Sun, Jan 11 from St. Thomas to Chicago, returning Mon, Jan 19, priced at $569 found 1 day ago
Delta
Sun, Jan 11 - Fri, Jan 23
STT
St. Thomas
MDW
Chicago
$574 Roundtrip, found 1 day ago
$574
Roundtrip
found 1 day ago
Select Delta flight, departing Sun, Jan 11 from St. Thomas to Chicago, returning Fri, Jan 23, priced at $574 found 1 day ago
Delta
Wed, Sep 17 - Sat, Sep 27
STT
St. Thomas
MDW
Chicago
$579 Roundtrip, found 5 days ago
$579
Roundtrip
found 5 days ago
Select Delta flight, departing Wed, Sep 17 from St. Thomas to Chicago, returning Sat, Sep 27, priced at $579 found 5 days ago
Delta
Thu, Sep 25 - Sat, Sep 27
STT
St. Thomas
MDW
Chicago
$584 Roundtrip, found 1 day ago
$584
Roundtrip
found 1 day ago
Select Delta flight, departing Thu, Sep 25 from St. Thomas to Chicago, returning Sat, Sep 27, priced at $584 found 1 day ago
Southwest Airlines
Thu, Feb 5 - Tue, Feb 10
STT
St. Thomas
MDW
Chicago
$992 Roundtrip, found 3 days ago
$992
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Thu, Feb 5 from St. Thomas to Chicago, returning Tue, Feb 10, priced at $992 found 3 days ago

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 $453
ORD
O'Hare Intl.
Cheapest
Average driving time to city center23 min
Flights from $453
Flights from St. Thomas (STT) to Chicago (MDW)
Origin airport
Cyril E. King
Destination airport
Midway Intl.
Airlines serving
Delta
Roundtrip price
$509
Distance
2102 mi

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 January. 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 2025. You can also book with separate airlines for your outbound and return journeys, from $292 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.

 

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 $292 or cheap return flight from $509 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 January, 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.

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*Available to One Key members.