$106 Cheap Flights from Chicago (ORD) to St. Thomas (STT)

View $106 flight on Mon, Nov 3, 2025Opens in a new window

Popular airlines from Chicago O'Hare Intl. Airport (ORD) to Cyril E. King Airport (STT)

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

Prices were available within the past 7 days and start at $106 for one-way flights and $261 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Spirit Airlines
Thu, Oct 30 - Mon, Nov 3
ORD
Chicago
STT
St. Thomas
$261 Roundtrip, just found
$261
Roundtrip
just found
Select Spirit Airlines flight, departing Thu, Oct 30 from Chicago to St. Thomas, returning Mon, Nov 3, priced at $261 just found
Spirit Airlines
Mon, Aug 11 - Fri, Aug 15
ORD
Chicago
STT
St. Thomas
$263 Roundtrip, just found
$263
Roundtrip
just found
Select Spirit Airlines flight, departing Mon, Aug 11 from Chicago to St. Thomas, returning Fri, Aug 15, priced at $263 just found
Spirit Airlines
Tue, Aug 26 - Sat, Aug 30
ORD
Chicago
STT
St. Thomas
$266 Roundtrip, found 8 hours ago
$266
Roundtrip
found 8 hours ago
Select Spirit Airlines flight, departing Tue, Aug 26 from Chicago to St. Thomas, returning Sat, Aug 30, priced at $266 found 8 hours ago
Spirit Airlines
Wed, Aug 6 - Sat, Aug 16
ORD
Chicago
STT
St. Thomas
$269 Roundtrip, found 19 hours ago
$269
Roundtrip
found 19 hours ago
Select Spirit Airlines flight, departing Wed, Aug 6 from Chicago to St. Thomas, returning Sat, Aug 16, priced at $269 found 19 hours ago
Spirit Airlines
Tue, Aug 26 - Sat, Aug 30
ORD
Chicago
STT
St. Thomas
$271 Roundtrip, found 8 hours ago
$271
Roundtrip
found 8 hours ago
Select Spirit Airlines flight, departing Tue, Aug 26 from Chicago to St. Thomas, returning Sat, Aug 30, priced at $271 found 8 hours ago
Spirit Airlines
Mon, Aug 18 - Mon, Aug 25
ORD
Chicago
STT
St. Thomas
$275 Roundtrip, just found
$275
Roundtrip
just found
Select Spirit Airlines flight, departing Mon, Aug 18 from Chicago to St. Thomas, returning Mon, Aug 25, priced at $275 just found
Frontier Airlines
Fri, Aug 1 - Fri, Aug 8
ORD
Chicago
STT
St. Thomas
$408 Roundtrip, found 1 hour ago
$408
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Fri, Aug 1 from Chicago to St. Thomas, returning Fri, Aug 8, priced at $408 found 1 hour ago
JetBlue Airways
Fri, Oct 31 - Sat, Nov 15
ORD
Chicago
STT
St. Thomas
$419 Roundtrip, found 7 hours ago
$419
Roundtrip
found 7 hours ago
Select JetBlue Airways flight, departing Fri, Oct 31 from Chicago to St. Thomas, returning Sat, Nov 15, priced at $419 found 7 hours ago
American Airlines
Wed, Mar 18 - Wed, Mar 25
ORD
Chicago
STT
St. Thomas
$500 Roundtrip, found 1 hour ago
$500
Roundtrip
found 1 hour ago
Select American Airlines flight, departing Wed, Mar 18 from Chicago to St. Thomas, returning Wed, Mar 25, priced at $500 found 1 hour ago
Delta
Wed, Mar 18 - Wed, Mar 25
ORD
Chicago
STT
St. Thomas
$509 Roundtrip, found 1 hour ago
$509
Roundtrip
found 1 hour ago
Select Delta flight, departing Wed, Mar 18 from Chicago to St. Thomas, returning Wed, Mar 25, priced at $509 found 1 hour ago

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

May is typically the cheapest month to fly

From $206 - $561 per traveler.

Graph displaying average flight prices per month

Alternative airports near St. Thomas

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

Select flight to Terrance B. Lettsome Intl. EIS. Flights from $949
EIS
Terrance B. Lettsome Intl.
Flights from $949
Select flight to Benjamin Rivera Noriega CPX. Flights from $698
CPX
Benjamin Rivera Noriega
Flights from $698
Flights from Chicago (ORD) to St. Thomas (STT)
Origin airport
O'Hare Intl.
Destination airport
Cyril E. King
Airlines serving
American Airlines, Delta, Frontier Airlines, JetBlue Airways, Spirit Airlines, United
Roundtrip price
$260
Distance
2117 mi

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 October. 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 $106 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.

 

Frequently asked questions

How much does a flight from O'Hare Intl. Airport (ORD) to Cyril E. King Airport (STT) cost?
Score cheap return tickets from O'Hare Intl. Airport (ORD) to Cyril E. King Airport (STT) starting from $762. Reserve your seat and get ready for takeoff. This information is based on the cheapest price found on Expedia for this return journey departing within the next three months. This airfare is for a United flight leaving ORD on August 2 2025 and touching down at STT. The price was last updated on July 11 2025 and has not changed since.
What is the cheapest month to fly from ORD to STT?
The cheapest flights from ORD to STT are usually during off-peak season, when demand is lower. To save money, avoid flying during public holidays, school breaks and major local events.
Which airlines fly direct from O'Hare Intl. Airport (ORD) to Cyril E. King Airport (STT)?
If you're departing from O'Hare Intl. Airport (ORD), you can board a nonstop flight to Cyril E. King Airport (STT) with United Airlines.
What is the cheapest airline that flies from ORD to STT?
Journey from ORD to STT with United. This carrier currently offers the cheapest one-way fare on this route, starting at $283. This fare is based on the lowest price found on Expedia departing within the next three months. The flight takes off from ORD on August 16 2025. Prices were last updated on July 11 2025 and have not changed since.
How many flights per day from O'Hare Intl. Airport (ORD) to Cyril E. King Airport (STT)?
On average, you can take your pick of 4 direct flights flying from O'Hare Intl. Airport (ORD) to Cyril E. King Airport (STT) weekly. If you can't find one that fits your schedule, consider booking a flight that has a layover. Customize your search results on Expedia to include one or more stops and opt for the next best alternative.
What are the most popular departure times for flights from O'Hare Intl. Airport (ORD) to Cyril E. King Airport (STT)?
More travelers fly between ORD and STT at 8 AM than at any other time. Prefer a quieter experience? Travel outside of rush hours and you could save on your fare as well.
What day of the week has the most flights from ORD to STT?
Saturday has the most flights from O'Hare Intl. Airport (ORD) to Cyril E. King Airport (STT). Consider traveling on this day and you'll have a greater chance of finding a departure that fits your plans.
What is the earliest flight from O'Hare Intl. Airport (ORD) to Cyril E. King Airport (STT)?
The first flight of the day taking off from O'Hare Intl. Airport (ORD) is at around 8:35AM UTC-6. Hop on this flight and you'll land at Cyril E. King Airport (STT) at approximately 3:20PM UTC-4. The entire trip takes 4h 45m.
How long does it take to fly from O'Hare Intl. Airport (ORD) to Cyril E. King Airport (STT)?
Flights from ORD to STT have an average travel time of 4 hours and 49 minutes. The distance between the two is 2,100 mi.
What airline has the least delays from ORD to STT?
United Airlines has the best performance for on-time direct flights from O'Hare Intl. Airport (ORD) to Cyril E. King Airport (STT), with an on-time rating of 83%. Use the Expedia App to view your flight status before you take off and get notified of any trip changes.
What is the best time to fly from O'Hare Intl. Airport (ORD) to Cyril E. King Airport (STT)?
To land at Cyril E. King Airport (STT) on schedule, book a flight that leaves O'Hare Intl. Airport (ORD) before 3 PM. The likelihood of cancellations is 22% higher, on average, for departures after this hour.**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 St. Thomas from O'Hare Intl. Airport (ORD)?
Explore your flight options from O'Hare Intl. Airport (ORD) to Cyril E. King Airport (STT). This is the only St. Thomas airport you can land at if you're taking a direct flight.
Is it cheaper to buy a plane ticket from O'Hare Intl. Airport (ORD) to Cyril E. King Airport (STT) last-minute?
Last-minute fares from ORD to STT are typically more expensive. To lock in the best rates, start looking for flights early. That said, if you can play around with your travel dates, you may find a cheap ticket right before your journey.
Is it cheaper to book an ORD to STT flight and hotel package?
Securing an ORD to STT flight and hotel package is generally cheaper than booking separately. With Expedia, you can enjoy the ease of organizing your travels all in one place. Select from our extensive range of stays and then add activities, flights and car rentals to your booking. Bundle everything together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from O'Hare Intl. Airport (ORD) to Cyril E. King Airport (STT)?
Typically, you can cancel or reschedule your ORD to STT flight. However, there may be additional fees, especially if you booked over 24 hours ago. Check your itinerary for the airline's fees and rules on flight changes, or if you need more details, head to our Customer Service portal.

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