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

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

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

September is typically the cheapest month to fly

From £268 - £734 per traveller.

Graph displaying average flight prices per month

Flight from Chicago to St. Thomas route information
Origin airport
Midway Intl.
Destination airport
Cyril E. King
Distance
3364 km

Compare flights from Chicago to St. Thomas easily and book with confidence

For travelling on business or for pleasure, Expedia makes it easy to book your flights from Chicago to St. Thomas. Operating between them flights per day, airlines cover the route. And fly direct, getting you to Cyril E. King in just hours. If you have a preferred carrier, use our advanced search tool to find the right flight from Midway Intl. to Cyril E. King.  

To make things even better, in the advanced search, you can also choose to fly economy, premium economy, business or first class, select your maximum number of stops, and pick your preferred departure and arrival time. You can also opt for refundable and direct flights. 

Grab a great deal on your flight from Midway Intl. (MDW) to Cyril E. King (STT)

The easiest way to view the best deals on flights from Chicago to St. Thomas today is to enter your travel dates and hit search. From here, you can sort your results by price to see the cheapest flights first. Right now, return flights from Midway Intl. to Cyril E. King start at just and range up to .  

To find an even better deal, try  

  • being flexible on your dates – midweek flights can be cheaper
  • looking for other airports near Chicago and St. Thomas
  • booking your flight during , the cheapest month on this route
  • varying your flight times – early morning and late at night are sometimes cheaper 

Why you should book your Chicago to St. Thomas flight with Expedia!

We cater for all flight types, cabin classes and airlines. So whether you’re booking flights from Midway Intl. to Cyril E. King for a budget break or a business trip with a bit of pleasure thrown in, we make it easy to secure the seat that’s right for you.  

Thanks to our supersized inventory that offers great choice all in one place, you know you’ll get a great deal with Expedia. Especially if you bundle your flight together with your hotel, you will unlock amazing savings. For added peace of mind, you can choose flexible bookings or filter to find refundable options, so you won’t pay a fee to change your flight.  

Frequently asked questions

How much is a flight from Midway Intl. Airport (MDW) to Cyril E. King Airport (STT)?
If you're planning on travelling from Midway Intl. Airport (MDW) to STT, round-trip flights start from . This price is based on fares listed within the last 7 days on Expedia for flights departing within the next year, so don't let a good deal slip through your fingers. Book today and save yourself money and time. Prices and availability are subject to change. Additional terms apply.
Do I need to pay a cancellation fee if I cancel my flight from Midway Airport to STT?
Most flights can be cancelled online, but whether or not you incur a fee differs between airlines. If you do have to cancel your escape, follow the easy instructions in the Customer Service Portal.
How do I find cheap flights from Chicago Airport to STT that have flexible change policies?
Many airlines offer the option to reschedule your flight without a change fee. All you pay is the difference between the original flight and the new flight. When you're searching for Chicago Airport to Cyril E. King Airport (STT) flights, you'll see a "no change fees" filter for you to select.
How far is the flight from MDW to Cyril E. King Airport?
Expect to be cruising at altitude for a while, as the flight distance between Chicago Airport and Cyril E. King Airport is 3,400 kilometres. Set up a playlist of your favourite songs before leaving home to stay entertained during the flight.
Which airlines fly direct from Midway Airport to Cyril E. King Airport?
Flying nonstop between Midway Intl. Airport (MDW) and STT isn't possible right now. However, you'll still be able to find a flight to St. Thomas with at least one stop.
Are MDW to Cyril E. King Airport flight tickets cheaper when they're purchased at the last minute?
Last-minute planners can occasionally pick up a bargain, with some super cheap fares from Midway Airport to Cyril E. King Airport popping up a few weeks prior to the departure date. If you'd rather book ahead of time, Expedia compares and updates the best flight deals frequently — as early as a year in advance in some cases. It does depend on the carrier though, as not all airlines issue prices so far in advance.

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Chicago Airports

Chicago

O'Hare Intl. to St. Thomas
£693.90
*Available to Expedia members.