$140 Cheap Flights from St. Thomas (STT) to Chicago (ORD)

View $140 flight on Sat, May 17, 2025Opens in a new window

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

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Find available prices by choosing your travel dates.

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

Prices were available within the past 7 days and start at $140 for one-way flights and $291 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Spirit Airlines
Thu, May 15 - Sun, May 25
STT
St. Thomas
ORD
Chicago
$291 Roundtrip, found 6 hours ago
$291
Roundtrip
found 6 hours ago
Select Spirit Airlines flight, departing Thu, May 15 from St. Thomas to Chicago, returning Sun, May 25, priced at $291 found 6 hours ago
Spirit Airlines
Tue, Jun 17 - Tue, Jun 24
STT
St. Thomas
ORD
Chicago
$318 Roundtrip, found 2 days ago
$318
Roundtrip
found 2 days ago
Select Spirit Airlines flight, departing Tue, Jun 17 from St. Thomas to Chicago, returning Tue, Jun 24, priced at $318 found 2 days ago
Spirit Airlines
Fri, May 23 - Thu, May 29
STT
St. Thomas
ORD
Chicago
$322 Roundtrip, found 1 day ago
$322
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Fri, May 23 from St. Thomas to Chicago, returning Thu, May 29, priced at $322 found 1 day ago
Spirit Airlines
Thu, May 29 - Mon, Jun 2
STT
St. Thomas
ORD
Chicago
$325 Roundtrip, found 2 hours ago
$325
Roundtrip
found 2 hours ago
Select Spirit Airlines flight, departing Thu, May 29 from St. Thomas to Chicago, returning Mon, Jun 2, priced at $325 found 2 hours ago
Spirit Airlines
Fri, May 23 - Sun, May 25
STT
St. Thomas
ORD
Chicago
$329 Roundtrip, found 2 days ago
$329
Roundtrip
found 2 days ago
Select Spirit Airlines flight, departing Fri, May 23 from St. Thomas to Chicago, returning Sun, May 25, priced at $329 found 2 days ago
Spirit Airlines
Sat, May 31 - Mon, Jun 2
STT
St. Thomas
ORD
Chicago
$330 Roundtrip, found 4 days ago
$330
Roundtrip
found 4 days ago
Select Spirit Airlines flight, departing Sat, May 31 from St. Thomas to Chicago, returning Mon, Jun 2, priced at $330 found 4 days ago
JetBlue Airways
Sat, May 10 - Tue, May 13
STT
St. Thomas
ORD
Chicago
$422 Roundtrip, found 1 day ago
$422
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Sat, May 10 from St. Thomas to Chicago, returning Tue, May 13, priced at $422 found 1 day ago
United
Tue, Nov 4 - Sun, Nov 9
STT
St. Thomas
ORD
Chicago
$475 Roundtrip, found 5 days ago
$475
Roundtrip
found 5 days ago
Select United flight, departing Tue, Nov 4 from St. Thomas to Chicago, returning Sun, Nov 9, priced at $475 found 5 days ago
American Airlines
Tue, Oct 21 - Mon, Oct 27
STT
St. Thomas
ORD
Chicago
$479 Roundtrip, just found
$479
Roundtrip
just found
Select American Airlines flight, departing Tue, Oct 21 from St. Thomas to Chicago, returning Mon, Oct 27, priced at $479 just found
Delta
Tue, Oct 21 - Mon, Oct 27
STT
St. Thomas
ORD
Chicago
$499 Roundtrip, just found
$499
Roundtrip
just found
Select Delta flight, departing Tue, Oct 21 from St. Thomas to Chicago, returning Mon, Oct 27, priced at $499 just found

Frequently asked questions

How much does a flight from Cyril E. King Airport (STT) to O'Hare Intl. Airport (ORD) cost?
Cheap return fares from Cyril E. King Airport (STT) to O’Hare Intl. Airport (ORD) start from $780. 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 STT on April 26 2025 and touching down at ORD. The price was last updated on April 23 2025 and has not changed since.
What is the cheapest month to fly from STT to ORD?
The cheapest flights from STT to ORD 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 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 STT to ORD?
At the moment, the cheapest carrier operating one-way flights from STT to ORD is United. You can jet off on this route from $1047. This fare is based on the lowest price found on Expedia departing within the next three months. The flight takes off from STT on June 7 2025. Prices were last updated on April 23 2025 and have not changed since.
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.
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