$113 Cheap Flights from St. Thomas (STT) to Chicago (ORD)

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Cheap flights from St. Thomas (STT) to Chicago (ORD)

Prices were available within the past 7 days and start at $113 for one-way flights and $237 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Spirit Airlines
Wed, Oct 23 - Tue, Nov 19
STT
St. Thomas
ORD
Chicago
$237 Roundtrip, found 4 days ago
$237
Roundtrip
found 4 days ago
Select Spirit Airlines flight, departing Wed, Oct 23 from St. Thomas to Chicago, returning Tue, Nov 19, priced at $237 found 4 days ago
Spirit Airlines
Tue, Oct 22 - Tue, Nov 19
STT
St. Thomas
ORD
Chicago
$254 Roundtrip, found 4 days ago
$254
Roundtrip
found 4 days ago
Select Spirit Airlines flight, departing Tue, Oct 22 from St. Thomas to Chicago, returning Tue, Nov 19, priced at $254 found 4 days ago
Spirit Airlines
Wed, Oct 23 - Mon, Nov 18
STT
St. Thomas
ORD
Chicago
$255 Roundtrip, found 4 days ago
$255
Roundtrip
found 4 days ago
Select Spirit Airlines flight, departing Wed, Oct 23 from St. Thomas to Chicago, returning Mon, Nov 18, priced at $255 found 4 days ago
Spirit Airlines
Mon, Oct 21 - Tue, Nov 19
STT
St. Thomas
ORD
Chicago
$274 Roundtrip, found 4 days ago
$274
Roundtrip
found 4 days ago
Select Spirit Airlines flight, departing Mon, Oct 21 from St. Thomas to Chicago, returning Tue, Nov 19, priced at $274 found 4 days ago
Spirit Airlines
Wed, Oct 23 - Sun, Nov 17
STT
St. Thomas
ORD
Chicago
$274 Roundtrip, found 4 days ago
$274
Roundtrip
found 4 days ago
Select Spirit Airlines flight, departing Wed, Oct 23 from St. Thomas to Chicago, returning Sun, Nov 17, priced at $274 found 4 days ago
Spirit Airlines
Sat, Oct 5 - Sat, Oct 12
STT
St. Thomas
ORD
Chicago
$279 Roundtrip, found 5 days ago
$279
Roundtrip
found 5 days ago
Select Spirit Airlines flight, departing Sat, Oct 5 from St. Thomas to Chicago, returning Sat, Oct 12, priced at $279 found 5 days ago
Spirit Airlines
Sat, Oct 5 - Tue, Oct 8
STT
St. Thomas
ORD
Chicago
$285 Roundtrip, found 5 days ago
$285
Roundtrip
found 5 days ago
Select Spirit Airlines flight, departing Sat, Oct 5 from St. Thomas to Chicago, returning Tue, Oct 8, priced at $285 found 5 days ago
Spirit Airlines
Wed, Oct 23 - Sat, Nov 16
STT
St. Thomas
ORD
Chicago
$290 Roundtrip, found 4 days ago
$290
Roundtrip
found 4 days ago
Select Spirit Airlines flight, departing Wed, Oct 23 from St. Thomas to Chicago, returning Sat, Nov 16, priced at $290 found 4 days ago
Spirit Airlines
Thu, Oct 24 - Sun, Nov 17
STT
St. Thomas
ORD
Chicago
$293 Roundtrip, found 4 days ago
$293
Roundtrip
found 4 days ago
Select Spirit Airlines flight, departing Thu, Oct 24 from St. Thomas to Chicago, returning Sun, Nov 17, priced at $293 found 4 days ago
Spirit Airlines
Tue, Oct 22 - Sun, Nov 17
STT
St. Thomas
ORD
Chicago
$294 Roundtrip, found 4 days ago
$294
Roundtrip
found 4 days ago
Select Spirit Airlines flight, departing Tue, Oct 22 from St. Thomas to Chicago, returning Sun, Nov 17, priced at $294 found 4 days ago
Flight from St. Thomas to Chicago (STT - ORD) route information
Origin airport
Cyril E. King
Destination airport
O'Hare Intl.
Airlines serving
American Airlines, Delta, JetBlue Airways, Spirit Airlines, United
Roundtrip price
$236
Distance
2117 mi

St. Thomas to Chicago Flights

The cheapest times to fly from St. Thomas to Chicago

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 St. Thomas to Chicago are during the month of October. You can find some of the cheapest flights from St. Thomas to Chicago with Expedia's search tool and vast selection of airlines.

The best time to book a flight from St. Thomas to Chicago

Sunday is one of the best days to book for cheap flights from St. Thomas to Chicago: 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 St. Thomas to Chicago

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 St. Thomas to Chicago in 2024. You can also book with separate airlines for your outbound and return journeys, from $113 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 St. Thomas to Chicago 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 St. Thomas to Chicago 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 is a one-way flight from STT to ORD?
Prepare to score a top deal, because St. Thomas flights to Chicago start from only $113. This is based on the best price found on Expedia for this route with a departure date during the next three months. This airfare is for an Spirit Airlines flight, leaving from Cyril E. King Airport (STT) on October 30 2024 and landing at O’Hare Airport. The price of this airfare was updated on September 23 2024 and has not changed since.
How long does it take to fly from STT to O'Hare Intl. Airport (ORD)?
A direct flight with United Airlines takes roughly 5 hours and 26 minutes. Lock in a seat on the 2:24PM flight from STT and touch down at O’Hare Intl. Airport (ORD) at 6:50PM. Pick up a superb deal on this and other routes when you use Expedia to book your journey.
Is it cheaper to buy a plane ticket from Cyril E. King Airport to ORD last minute?
Being the spontaneous type is a wonderful way to travel the globe, but it’s not necessarily the wisest way to nab a cheap fare. It’s better to book your Cyril E. King Airport (STT) to ORD journey ahead of time instead of leaving it to the last minute. Based on flight pricing and demand studies in 2022, we have found that the best time to book domestic flights is between 28 – 35 days ahead of the departure date, and international flights three to four months in advance. Leave all that spontaneity for when you get to your destination!
What is the cheapest airline flying from Cyril E. King Airport (STT) to O'Hare Intl. Airport (ORD) in the next 90 days?
With tickets starting at $113 for a flight from St. Thomas to Chicago, Spirit Airlines is the cheapest airline found on Expedia. This price is based on airfares found on Expedia with a departure date within the next 90 days and was last updated on September 23 2024 and has not changed since. The flight leaves Cyril E. King Airport (STT) on October 30 2024 and lands at O’Hare Intl. Airport (ORD).
What's the cheapest price for a flight from STT to ORD next month?
With a one-way flight from St. Thomas to Chicago on offer for $168, you’ll have more dough left in your wallet for fun stuff like sightseeing. This fare was found after looking at all available flights on Expedia within the next 30 days. This particular service sets off from Cyril E. King Airport (STT) on October 12 2024, comes in to land at O’Hare Intl. Airport (ORD) and is operated by Spirit Airlines. The price was last updated on September 23 2024 and has not changed since.
What airline has the least delays from Cyril E. King Airport to O'Hare Intl. Airport (ORD)?
If you’d prefer not to be waiting for hours — or worse, your travel plans left in tatters because of a flight delay — travel with United Airlines. Around 77% of its Cyril E. King Airport (STT) to O’Hare Airport services are on time. You can review your flight status before traveling to the airport through the free Expedia App. It’ll also provide you with real-time alerts about other helpful info, such as any gate changes, baggage carousel numbers and how to get to your hotel. Everything you need to know is right there in your pocket!
What airports do you fly into for Chicago from Charlotte Amalie?
With O’Hare Intl. Airport (ORD), Midway Intl. Airport (MDW) and Lewis University Airport (LOT) to choose from, flying from Charlotte Amalie to Chicago is a snap. The city’s major hub, O’Hare Intl. Airport (ORD), is about 16 mi northwest of the center. Besides the price of fares, consider factors like bus or train options from the airport and the distance to your hotel before making your decision. Get your Chicago vacation off to a superb start by visiting Wrigley Field and Millennium Park.
What are the most popular departure times for flights from Cyril E. King Airport (STT) to O'Hare Airport?
For United Airlines flights setting off from STT to ORD, the most popular departure times are between 2:00 PM - 3:00 PM. If you want to avoid any delays, book the earliest flight. This gives you a better chance to miss the air traffic that builds up in the afternoon and evening.
Can I change the date of my flight from STT to ORD?
Sometimes life gets in the way of plans, so Expedia is here to help make things easy. First, find your STT to O’Hare Intl. Airport (ORD) itinerary through the Expedia Trips portal and browse the fare rules about change fees or other charges. If you booked your ticket in the last 24 hours, some airlines will let you cancel for free and book new flights. If you booked more than 24 hours ago, get in touch with us through our Customer Service portal to learn more about your options.
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*Available to One Key members.