$118 Cheap Flights from St. Thomas (STT) to Chicago (ORD)

View $118 flight on Sat, Dec 6, 2025Opens in a new window

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

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

Prices were available within the past 7 days and start at $118 for one-way flights and $242 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

American Airlines
Thu, Dec 25 - Tue, Dec 30
STT
St. Thomas
ORD
Chicago
$242 Roundtrip, found 3 days ago
$242
Roundtrip
found 3 days ago
Select American Airlines flight, departing Thu, Dec 25 from St. Thomas to Chicago, returning Tue, Dec 30, priced at $242 found 3 days ago
American Airlines
Thu, Dec 25 - Tue, Dec 30
STT
St. Thomas
ORD
Chicago
$247 Roundtrip, found 3 days ago
$247
Roundtrip
found 3 days ago
Select American Airlines flight, departing Thu, Dec 25 from St. Thomas to Chicago, returning Tue, Dec 30, priced at $247 found 3 days ago
Spirit Airlines
Mon, Feb 2 - Mon, Feb 9
STT
St. Thomas
ORD
Chicago
$249 Roundtrip, found 10 hours ago
$249
Roundtrip
found 10 hours ago
Select Spirit Airlines flight, departing Mon, Feb 2 from St. Thomas to Chicago, returning Mon, Feb 9, priced at $249 found 10 hours ago
Delta
Thu, Feb 5 - Tue, Feb 24
STT
St. Thomas
ORD
Chicago
$251 Roundtrip, found 3 days ago
$251
Roundtrip
found 3 days ago
Select Delta flight, departing Thu, Feb 5 from St. Thomas to Chicago, returning Tue, Feb 24, priced at $251 found 3 days ago
Spirit Airlines
Sat, Jan 10 - Sun, Jan 25
STT
St. Thomas
ORD
Chicago
$265 Roundtrip, found 2 days ago
$265
Roundtrip
found 2 days ago
Select Spirit Airlines flight, departing Sat, Jan 10 from St. Thomas to Chicago, returning Sun, Jan 25, priced at $265 found 2 days ago
Spirit Airlines
Fri, Jan 23 - Fri, Jan 30
STT
St. Thomas
ORD
Chicago
$269 Roundtrip, found 6 days ago
$269
Roundtrip
found 6 days ago
Select Spirit Airlines flight, departing Fri, Jan 23 from St. Thomas to Chicago, returning Fri, Jan 30, priced at $269 found 6 days ago
Spirit Airlines
Mon, Feb 2 - Mon, Feb 9
STT
St. Thomas
ORD
Chicago
$270 Roundtrip, found 10 hours ago
$270
Roundtrip
found 10 hours ago
Select Spirit Airlines flight, departing Mon, Feb 2 from St. Thomas to Chicago, returning Mon, Feb 9, priced at $270 found 10 hours ago
United
Thu, Dec 4 - Sat, Jan 10
STT
St. Thomas
ORD
Chicago
$273 Roundtrip, found 4 days ago
$273
Roundtrip
found 4 days ago
Select United flight, departing Thu, Dec 4 from St. Thomas to Chicago, returning Sat, Jan 10, priced at $273 found 4 days ago
Spirit Airlines
Fri, Dec 5 - Sat, Jan 10
STT
St. Thomas
ORD
Chicago
$275 Roundtrip, found 4 days ago
$275
Roundtrip
found 4 days ago
Select Spirit Airlines flight, departing Fri, Dec 5 from St. Thomas to Chicago, returning Sat, Jan 10, priced at $275 found 4 days ago
JetBlue Airways
Fri, Dec 19 - Wed, Dec 31
STT
St. Thomas
ORD
Chicago
$381 Roundtrip, found 2 days ago
$381
Roundtrip
found 2 days ago
Select JetBlue Airways flight, departing Fri, Dec 19 from St. Thomas to Chicago, returning Wed, Dec 31, priced at $381 found 2 days ago

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

April is typically the cheapest month to fly

From $213 - $667 per traveler.

Alternative airports near Chicago

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

Select flight to O'Hare Intl. ORD. Cheapest option available. Average driving time to city center is 23 minutes. Flights from $740
ORD
O'Hare Intl.
Cheapest
Average driving time to city center23 min
Flights from $740

Frequently asked questions

How much does a flight from Cyril E. King Airport (STT) to O'Hare Intl. Airport (ORD) cost?
Lock in a cheap one-way flight from $118 or cheap return flight from $242 from Cyril E. King Airport (STT) to O'Hare Intl. Airport (ORD) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to find our cheapest flight offers on this route.
What is the cheapest month to fly from Cyril E. King Airport (STT) to O'Hare Intl. Airport (ORD)?
Planning your getaway for December may help you find better deals, as it's the cheapest month for flights between STT and ORD. You'll often find the lowest prices during off-peak months.
Which airlines fly direct from Cyril E. King Airport (STT) to O'Hare Intl. Airport (ORD)?
Hop on a nonstop flight with United Airlines and travel straight from Cyril E. King Airport (STT) to O'Hare Intl. Airport (ORD).
What is the cheapest airline that flies from Cyril E. King Airport (STT) to O'Hare Intl. Airport (ORD)?
The cheapest airline to offer flights between Cyril E. King Airport (STT) and O'Hare Intl. Airport (ORD) will change depending on when you want to travel. American Airlines and United Airlines are just some good options offering competitive fares. Use Expedia's filter tool to compare airlines in one place and find the right STT to ORD flight for your budget.
How many flights per day from Cyril E. King Airport (STT) to O'Hare Intl. Airport (ORD)?
On average, you can choose from 4 direct flights per week from Cyril E. King Airport (STT) to O'Hare Intl. Airport (ORD). To expand your choices, consider flights with layovers. Just enter your dates on Expedia and then filter your search to show one or more stops.
What are the most popular departure times for flights from Cyril E. King Airport (STT) to O'Hare Intl. Airport (ORD)?
More people fly between STT and ORD at 3 PM than at any other point in the day. Rather skip the crowds? Pick a flight outside the busiest times and you're likely to save on your ticket as well.
What day of the week has the most flights from STT to ORD?
Saturday has the most flights from Cyril E. King Airport (STT) to O'Hare Intl. Airport (ORD). Consider jetting off on this day and you'll have a greater chance of finding a departure that fits your schedule.
What is the earliest flight from Cyril E. King Airport (STT) to O'Hare Intl. Airport (ORD)?
Cyril E. King Airport (STT)'s earliest flight to O'Hare Intl. Airport (ORD) is at approximately 3:00PM UTC-4. With a total travel time of 5h 35m, you'll land at around 6:35PM UTC-6.
How long does it take to fly from Cyril E. King Airport (STT) to O'Hare Intl. Airport (ORD)?
The average flight time from STT to ORD is 5 hours and 35 minutes, covering a total distance of 2,100 mi.
What is the best time to fly from Cyril E. King Airport (STT) to O'Hare Intl. Airport (ORD)?
To touch down at O'Hare Intl. Airport (ORD) without delays, pick a flight that leaves from Cyril E. King Airport (STT) 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 Chicago from Cyril E. King Airport (STT)?
O'Hare Intl. Airport (ORD) is the only airport in Chicago with direct flights from Cyril E. King Airport (STT). Consider the options and find affordable fares on Expedia.
Is it cheaper to buy a plane ticket from Cyril E. King Airport (STT) to O'Hare Intl. Airport (ORD) last-minute?
Last-minute bookings from STT to ORD are generally more expensive. For the best rates, start searching for flights well in advance. That said, if your travel plans are flexible, it's possible to land a cheap fare right before you leave.
Is it cheaper to book a STT to ORD flight and hotel package?
Securing a STT to ORD flight and hotel package tends to be cheaper than booking separately. With Expedia, you can enjoy the convenience of organizing your travels in one place. Pick from our impressive range of hotels and then add car rentals, flights and activities to your booking. Bundle everything together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from Cyril E. King Airport (STT) to O'Hare Intl. Airport (ORD)?
Typically, it's possible to reschedule or cancel your STT to ORD flight. However, if it's been more than 24 hours since booking, additional charges may apply. Refer to your airline's policies in your itinerary to see what changes are possible and if any costs are involved. You'll also find further details on our Customer Service portal.

Travel information

Origin airport
Cyril E. King
Destination airport
O'Hare Intl.
Airlines serving
American Airlines, Delta, JetBlue Airways, Southwest Airlines, Spirit Airlines, United
Roundtrip price
$242
Distance
2117 mi
Average flight time
3 hours 38 mins

Book with confidence

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 December. 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 2025. You can also book with separate airlines for your outbound and return journeys, from $118 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.

 

St. Thomas to Chicago Flights

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