$241 Cheap flight deals from Chicago (CHI) to St. Thomas (STT)

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Airfares from $241 One Way, $519 Round Trip from Chicago to St. Thomas

Prices starting at $519 for return flights and $241 for one-way flights to St. Thomas were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Fri, Aug 28 - Mon, Aug 31
ORD
Chicago
STT
St. Thomas
$519 Roundtrip, found 1 day ago
$519
Roundtrip
found 1 day ago
Select American Airlines flight, departing Fri, Aug 28 from Chicago to St. Thomas, returning Mon, Aug 31, priced at $519 found 1 day ago
Fri, Aug 28 - Mon, Aug 31
ORD
Chicago
STT
St. Thomas
$524 Roundtrip, found 1 day ago
$524
Roundtrip
found 1 day ago
Select American Airlines flight, departing Fri, Aug 28 from Chicago to St. Thomas, returning Mon, Aug 31, priced at $524 found 1 day ago
Sat, Aug 15 - Fri, Aug 21
ORD
Chicago
STT
St. Thomas
$525 Roundtrip, found 6 days ago
$525
Roundtrip
found 6 days ago
Select American Airlines flight, departing Sat, Aug 15 from Chicago to St. Thomas, returning Fri, Aug 21, priced at $525 found 6 days ago
Fri, Aug 28 - Mon, Aug 31
ORD
Chicago
STT
St. Thomas
$527 Roundtrip, found 1 day ago
$527
Roundtrip
found 1 day ago
Select American Airlines flight, departing Fri, Aug 28 from Chicago to St. Thomas, returning Mon, Aug 31, priced at $527 found 1 day ago
Fri, Aug 28 - Mon, Aug 31
ORD
Chicago
STT
St. Thomas
$532 Roundtrip, found 1 day ago
$532
Roundtrip
found 1 day ago
Select American Airlines flight, departing Fri, Aug 28 from Chicago to St. Thomas, returning Mon, Aug 31, priced at $532 found 1 day ago

St. Thomas economy flight packages

Price found within the past 48 hours. Click for updated prices.
Margaritaville Vacation Club - St. Thomas
4.0-star property

Margaritaville Vacation Club - St. Thomas

8/10 Very Good! (2,458 reviews)

Jul 29 - Aug 2

4 night stay

Chicago (CHI) to St. Thomas (STT)

American Airlines • Non-stop roundtrip • Coach
Price was $1,531, price is now $1,203 per person
$1,203
per person
found 1 day ago
Great property and friendly staff. Very clean and good location. Would definitely go back as the property exceeded my expectations.

Reviewed on May 30, 2026

Limetree Beach Resort by Club Wyndham
3.5-star property

Limetree Beach Resort by Club Wyndham

8.2/10 Very Good! (222 reviews)

Jul 29 - Aug 2

4 night stay

Chicago (CHI) to St. Thomas (STT)

American Airlines • Non-stop roundtrip • Coach
Price was $1,890, price is now $1,463 per person
$1,463
per person
found 1 day ago
excellent property and experience

Reviewed on May 27, 2025

Club Wyndham Elysian Beach Resort
3.5-star property

Club Wyndham Elysian Beach Resort

8/10 Very Good! (185 reviews)

Jul 29 - Aug 2

4 night stay

Chicago (CHI) to St. Thomas (STT)

American Airlines • Non-stop roundtrip • Coach
Price was $1,520, price is now $1,233 per person
$1,233
per person
found 1 day ago
Its property is excellent to vacation . Cleaning , good tennis court and beach

Reviewed on Oct 27, 2024

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St. Thomas first class flight packages

Price found within the past 48 hours. Click for updated prices.
Club Wyndham Elysian Beach Resort
3.5-star property

Club Wyndham Elysian Beach Resort

8/10 Very Good! (185 reviews)

Jul 23 - Jul 27

4 night stay

Chicago (CHI) to St. Thomas (STT)

United • Non-stop roundtrip • FirstClass
Price was $2,353, price is now $2,008 per person
$2,008
per person
found 1 day ago
Its property is excellent to vacation . Cleaning , good tennis court and beach

Reviewed on Oct 27, 2024

Wharfside Village Hotel
3.0-star property

Wharfside Village Hotel

9.8/10 Exceptional! (182 reviews)

Jul 23 - Jul 27

4 night stay

Chicago (CHI) to St. Thomas (STT)

United • Non-stop roundtrip • FirstClass
Price was $2,989, price is now $2,494 per person
$2,494
per person
found 1 day ago
Perfect location and great rooms! Staff was friendly and gave "local" suggestions of places to eat, things to do.

Reviewed on May 13, 2025

Two Sandals – A Boutique Hotel
3.5-star property

Two Sandals – A Boutique Hotel

8.8/10 Excellent! (513 reviews)

Jul 23 - Jul 27

4 night stay

Chicago (CHI) to St. Thomas (STT)

United • Non-stop roundtrip • FirstClass
Price was $2,300, price is now $2,011 per person
$2,011
per person
found 1 day ago
Beautiful place with a pretty view. It is also near a noisy water plant. The owner has put noise canceling machines in every room so that helps. The road to town is somewhat dangerous (no crosswalk and no sidewalks in parts) but is is close to town if you can handle that and a very, very steep driveway.

Reviewed on Feb 25, 2023

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More About Flying To St. Thomas from Chicago

Route Information for Flights from Chicago to St. Thomas

Origin Airport IATA Code
CHI
Destination Airport IATA Code
STT
Distance
Direct Flight Airlines
Earliest Flight Arrival
Latest Flight Arrival

Chicago to St. Thomas

If you are looking to get guaranteed low prices for Chicago to St. Thomas flights then Orbitz is the place to go. We use cutting edge mobile tools to find the best deals on air tickets and to keep you updated on delays and changes.

Get Package Savings by Booking Flights and Hotels at the Same Time

Using the Orbitz Matrix display, you can see how much you will save on flights from Chicago to St. Thomas if the discount fare is combined with a hotel. You can also look at hotel reviews, photos and maps of the area, so it will be convenient to make your budget travel plans.

Orbitz for Business Helps Corporations save Money

Orbitz can assist all businesses from the small to major corporations with discounts on flights from Chicago to St. Thomas. We fine- tune your needs for Chicago to St. Thomas flights and optimize your plans by assessing your business and coming up with ways for you to save on air tickets.

Using Online Check-In Makes Flying Simple

You can use the Orbitz website to check-in for your flights from Chicago to St. Thomas. You can also make changes to your schedule or even cancel a flight.

Frequently asked questions

Are there non-stop flights from Chicago to St. Thomas?
United Airlines will fly you nonstop from O'Hare Intl. Airport (ORD) to Cyril E. King Airport (STT), which means you won't have to stress about switching planes or missing your next flight on this route.
What is the shortest flight from Chicago to St. Thomas?
The shortest flight from Chicago, IL (ORD-O'Hare Intl.) to Cyril E. King Airport is 5 hours and 18 minutes. Order your favorite tipple from the drink cart, write in your travel journal or get to know your seat mate — you'll have enough time on this medium-haul journey.
What airlines fly from Chicago to St. Thomas most frequently?
United Airlines is the most frequent airline operating on the Chicago to St. Thomas route. You can select from 4 flights every month with this carrier.
What is the cheapest day of the week to fly?
Consider flying out early in the week to save on your airfare. Orbitz data from 2021 shows that Monday is the cheapest day to depart, followed by Tuesday. Saturday showed the highest average ticket prices likely because many travelers prefer to start their vacation on a weekend.
What is the cheapest month to fly?
We won't keep you guessing, according to Orbitz data from 2021, the cheapest month to fly is February. Perfect for those who need a weekend getaway, or just a break from it all in the shortest month of the year. Be aware that the most expensive time to fly is during the height of summer in July, and in the holiday month of December.*According to flight demand on Orbitz.com from January to December 2021. Savings are subject to change based on departure location, date and destination.

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Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.