Cheap Flights from Chicago (MDW) to St. Thomas (SPB)

Popular airlines from Chicago Midway Airport (MDW) to St. Thomas (SPB-St. Thomas Seaplane Base)

Alternative airports near St. Thomas

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

Select flight to Cyril E. King STT. Cheapest option available. Flights from $840
STT
Cyril E. King
Cheapest
Flights from $840

Frequently asked questions

How much does a flight from Midway Intl. Airport (MDW) to St. Thomas Seaplane Base Airport (SPB) cost?
Snag a cheap one-way flight or cheap return flight from Midway Intl. Airport (MDW) to St. Thomas Seaplane Base Airport (SPB) 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 St. Thomas Seaplane Base Airport (SPB)?
Traveling in is a good way to save, as it's the cheapest month for flights between MDW and SPB. You'll usually find the lowest fares during off-peak months.
What is the cheapest airline that flies from Midway Intl. Airport (MDW) to St. Thomas Seaplane Base Airport (SPB)?
Use the filter tool on Expedia to compare different airlines and find the most affordable carrier that'll take you from MDW to SPB. 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 St. Thomas Seaplane Base Airport (SPB)?
Direct flights from Midway Intl. Airport (MDW) to St. Thomas Seaplane Base Airport (SPB) aren't available daily, so you'll need to take a flight with a layover. Explore your options with our filter tool. Enter your travel dates and choose either "1 Stop" or "2+ Stops."
What day of the week has the most flights from MDW to SPB?
You'll generally find Tuesday the quietest day for flights, while Fridays are often the busiest.* However this can vary from season to season and during public holidays or peak travel times.*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 St. Thomas Seaplane Base Airport (SPB)?
Opt for a flight from Midway Intl. Airport (MDW) to St. Thomas Seaplane Base Airport (SPB) that leaves before 3 PM to reduce the risk of cancellations. Departures after this hour are on average 22% more likely to be canceled.**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 St. Thomas Seaplane Base Airport (SPB) last-minute?
Booking your flight from MDW to SPB just before your getaway is generally more expensive. But if you're flexible with your departure times and dates, you could grab a cheap last-minute fare.
Is it cheaper to book a MDW to SPB flight and hotel package?
You'll typically save money by securing a MDW to SPB flight and hotel package compared to booking separately. In fact, you could save hundreds of dollars by bundling with Expedia. And it's easy to manage it all in one convenient place. Once you've selected your preferred accommodations and flights, consider adding extras like activities, car rentals and tours.
Can I cancel or change the date of my flight from Midway Intl. Airport (MDW) to St. Thomas Seaplane Base Airport (SPB)?
It's generally possible to cancel or reschedule your MDW to SPB flight. However, if the booking was made more than 24 hours ago, additional charges may apply. Check your airline's policies in your itinerary to see what changes are possible and if any costs are involved. You'll also find further details on our Customer Service portal.

Travel information

Origin airport
Midway Intl.
Destination airport
St. Thomas Seaplane Base
Distance
2103 mi

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 . 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 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
*Available to One Key members.