$86 Cheap Flights from Chicago (ORD) to St. Thomas (STT)

View $86 flight on Sat, Oct 18, 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 $86 for one-way flights and $214 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Spirit Airlines
Tue, Oct 7 - Sat, Oct 11
ORD
Chicago
STT
St. Thomas
$214 Roundtrip, found 7 hours ago
$214
Roundtrip
found 7 hours ago
Select Spirit Airlines flight, departing Tue, Oct 7 from Chicago to St. Thomas, returning Sat, Oct 11, priced at $214 found 7 hours ago
Spirit Airlines
Sat, Oct 18 - Sat, Oct 25
ORD
Chicago
STT
St. Thomas
$215 Roundtrip, just found
$215
Roundtrip
just found
Select Spirit Airlines flight, departing Sat, Oct 18 from Chicago to St. Thomas, returning Sat, Oct 25, priced at $215 just found
Spirit Airlines
Mon, Oct 6 - Sat, Oct 11
ORD
Chicago
STT
St. Thomas
$229 Roundtrip, found 4 hours ago
$229
Roundtrip
found 4 hours ago
Select Spirit Airlines flight, departing Mon, Oct 6 from Chicago to St. Thomas, returning Sat, Oct 11, priced at $229 found 4 hours ago
Spirit Airlines
Sun, Oct 5 - Sat, Oct 11
ORD
Chicago
STT
St. Thomas
$233 Roundtrip, found 2 hours ago
$233
Roundtrip
found 2 hours ago
Select Spirit Airlines flight, departing Sun, Oct 5 from Chicago to St. Thomas, returning Sat, Oct 11, priced at $233 found 2 hours ago
Spirit Airlines
Sat, Oct 18 - Sat, Oct 25
ORD
Chicago
STT
St. Thomas
$236 Roundtrip, just found
$236
Roundtrip
just found
Select Spirit Airlines flight, departing Sat, Oct 18 from Chicago to St. Thomas, returning Sat, Oct 25, priced at $236 just found
Spirit Airlines
Sat, Oct 11 - Thu, Oct 16
ORD
Chicago
STT
St. Thomas
$237 Roundtrip, found 4 hours ago
$237
Roundtrip
found 4 hours ago
Select Spirit Airlines flight, departing Sat, Oct 11 from Chicago to St. Thomas, returning Thu, Oct 16, priced at $237 found 4 hours ago
JetBlue Airways
Wed, Oct 29 - Sat, Nov 15
ORD
Chicago
STT
St. Thomas
$409 Roundtrip, found 1 day ago
$409
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Wed, Oct 29 from Chicago to St. Thomas, returning Sat, Nov 15, priced at $409 found 1 day ago
American Airlines
Mon, Jan 5 - Mon, Jan 12
ORD
Chicago
STT
St. Thomas
$505 Roundtrip, found 1 hour ago
$505
Roundtrip
found 1 hour ago
Select American Airlines flight, departing Mon, Jan 5 from Chicago to St. Thomas, returning Mon, Jan 12, priced at $505 found 1 hour ago
United
Sun, Nov 30 - Sun, Dec 7
ORD
Chicago
STT
St. Thomas
$505 Roundtrip, just found
$505
Roundtrip
just found
Select United flight, departing Sun, Nov 30 from Chicago to St. Thomas, returning Sun, Dec 7, priced at $505 just found
Delta
Mon, Feb 23 - Thu, Mar 5
ORD
Chicago
STT
St. Thomas
$509 Roundtrip, just found
$509
Roundtrip
just found
Select Delta flight, departing Mon, Feb 23 from Chicago to St. Thomas, returning Thu, Mar 5, priced at $509 just found

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

May is typically the cheapest month to fly

From $208 - $624 per traveler.
Flights from Chicago (ORD) to St. Thomas (STT)
Origin airport
O'Hare Intl.
Destination airport
Cyril E. King
Airlines serving
American Airlines, Delta, JetBlue Airways, Southwest Airlines, Spirit Airlines, United
Roundtrip price
$213
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 $86 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?
Get a cheap one-way flight from $86 or cheap return flight from $214 from O'Hare Intl. Airport (ORD) to Cyril E. King Airport (STT) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to find our cheapest flight deals on this route.
What is the cheapest month to fly from O'Hare Intl. Airport (ORD) to Cyril E. King Airport (STT)?
October is the cheapest month to fly from ORD to STT. Traveling outside of peak seasons is often the key to finding better fares.
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 O'Hare Intl. Airport (ORD) to Cyril E. King Airport (STT)?
The cheapest airline to offer flights between O'Hare Intl. Airport (ORD) and Cyril E. King Airport (STT) will vary based on when you plan to fly. American Airlines and United Airlines are just some of the choices offering well-priced fares. Use Expedia's search tool to compare airlines in one place and find the right ORD to STT flight for your budget.
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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