S$370 Cheap Flights from Chicago to St. Thomas

View S$370 flight on Tue, 10 Mar, 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 S$370 for one-way flights and S$749 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Mon, 2 Mar - Mon, 9 Mar
MDW
Chicago
STT
St. Thomas
S$749 Return, found 16 hours ago
S$749
Return
found 16 hours ago
Select Delta flight, departing Mon, 2 Mar from Chicago to St. Thomas, returning Mon, 9 Mar, priced at S$749 found 16 hours ago
Delta
Mon, 2 Mar - Mon, 9 Mar
MDW
Chicago
STT
St. Thomas
S$846 Return, found 16 hours ago
S$846
Return
found 16 hours ago
Select Delta flight, departing Mon, 2 Mar from Chicago to St. Thomas, returning Mon, 9 Mar, priced at S$846 found 16 hours ago
Delta
Mon, 2 Mar - Mon, 9 Mar
MDW
Chicago
STT
St. Thomas
S$903 Return, found 16 hours ago
S$903
Return
found 16 hours ago
Select Delta flight, departing Mon, 2 Mar from Chicago to St. Thomas, returning Mon, 9 Mar, priced at S$903 found 16 hours ago
Delta
Mon, 2 Mar - Mon, 9 Mar
MDW
Chicago
STT
St. Thomas
S$999 Return, found 16 hours ago
S$999
Return
found 16 hours ago
Select Delta flight, departing Mon, 2 Mar from Chicago to St. Thomas, returning Mon, 9 Mar, priced at S$999 found 16 hours ago
Delta
Tue, 10 Mar - Fri, 13 Mar
MDW
Chicago
STT
St. Thomas
S$1,189 Return, found 16 hours ago
S$1,189
Return
found 16 hours ago
Select Delta flight, departing Tue, 10 Mar from Chicago to St. Thomas, returning Fri, 13 Mar, priced at S$1,189 found 16 hours ago
Delta
Tue, 10 Mar - Fri, 13 Mar
MDW
Chicago
STT
St. Thomas
S$1,361 Return, found 16 hours ago
S$1,361
Return
found 16 hours ago
Select Delta flight, departing Tue, 10 Mar from Chicago to St. Thomas, returning Fri, 13 Mar, priced at S$1,361 found 16 hours ago

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

September is typically the cheapest month to fly

From S$460 - S$1,416 per traveller.

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 S$749. 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.

Travel information

Travel information

Origin airport
Midway Intl.
Destination airport
Cyril E. King
Return price
S$748
Distance
3364 km

Book with confidence

Book with confidence

Perfect flights from Chicago to St. Thomas

Your Journey from Chicago to St. Thomas

Start your unforgettable journey with Expedia. Our broad selection of flights from Chicago to St. Thomas caters to every travel need. Whether you're yearning for a romantic escape, a solo adventure, or a cultural immersion, we've got you covered.
 

Choosing Your Ideal Flight

With Expedia, you have access to a wide range of airlines, including Delta. Our selection of flights from Midway Intl. to Cyril E. King caters to every traveler's requirements, ensuring your journey aligns with your schedule. With options from 8 airlines, you're bound to find the perfect flight.
 

Maximizing Value with Chicago to St. Thomas Flights

Experience the joy of finding cheap flights from Midway Intl. to Cyril E. King that fit your budget. Keep an eye out for our special deals and discounts, and check our flexible one-way fares from S$370 and roundtrip prices from S$749*.
 

Pre-Flight Essentials

Ensure a smooth journey from Chicago to St. Thomas with Expedia. From information about check-in times and in-flight amenities to guidance on baggage policies, we provide all the essentials to prepare you for your flight.
 

Experience the Vibrant St. Thomas

Picture yourself stepping off the plane in St. Thomas and immersing yourself in the unique atmosphere of . From local markets to cultural festivals, each city offers its distinct charm. Make the most of your trip by exploring local attractions and indulging in the local cuisine. With Expedia, explore all this and more, tailored to your budget.
 

Added Convenience on Your Chicago to St. Thomas Flight

Traveling with Expedia is more than just a flight. We offer details about in-flight amenities, baggage policies, and more to ensure a smooth and hassle-free journey. Choose from our variety of airlines and embark on a memorable journey from Chicago to St. Thomas.
 

Beyond the Flight – Exploring St. Thomas

With Expedia, your adventure extends beyond the flight. Explore St. Thomas at your own pace by renting a car or booking a hotel. Discover hidden gems off the beaten path and create unforgettable memories.
 

Book Your Flight from Chicago to St. Thomas with Confidence

Planning your next great adventure is a breeze with Expedia. Our user-friendly platform, unbeatable prices, and round-the-clock customer support make your travel experience seamless and stress-free. Embark on your journey from Chicago to St. Thomas with confidence. Book your travel arrangements with Expedia today.
 
*Note: Prices may vary based on availability and are subject to change.
Perfect flights from Chicago to St. Thomas

Explore a world of travel with Expedia

Explore a world of travel with Expedia

Chicago Airports

Chicago

O'Hare Intl. to St. Thomas
S$659.20
*Available to Expedia members.