$246 Cheap flight deals from Chicago (CHI) to St. Thomas (STT)

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This Weekend's Flight Deals from Chicago to St. Thomas

This weekend's flight prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Sat, Jul 18 - Tue, Jul 21
ORD
O'Hare Intl.
STT
Cyril E. King
$1,013 Roundtrip, found 3 days ago
$1,013
Roundtrip
found 3 days ago
Select American Airlines flight, departing Sat, Jul 18 from O'Hare Intl. to Cyril E. King, returning Tue, Jul 21, priced at $1,013 found 3 days ago
Sat, Jul 18 - Tue, Jul 21
MDW
Midway Intl.
STT
Cyril E. King
$1,091 Roundtrip, found 3 days ago
$1,091
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Sat, Jul 18 from Midway Intl. to Cyril E. King, returning Tue, Jul 21, priced at $1,091 found 3 days ago

Airfares from $246 One Way, $484 Round Trip from Chicago to St. Thomas

Prices starting at $484 for return flights and $246 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.

Thu, Sep 10 - Mon, Sep 14
ORD
Chicago
STT
St. Thomas
$484 Roundtrip, found 3 days ago
$484
Roundtrip
found 3 days ago
Select American Airlines flight, departing Thu, Sep 10 from Chicago to St. Thomas, returning Mon, Sep 14, priced at $484 found 3 days ago
Thu, Sep 10 - Mon, Sep 14
ORD
Chicago
STT
St. Thomas
$487 Roundtrip, found 3 days ago
$487
Roundtrip
found 3 days ago
Select American Airlines flight, departing Thu, Sep 10 from Chicago to St. Thomas, returning Mon, Sep 14, priced at $487 found 3 days ago
Sat, Dec 5 - Fri, Dec 11
ORD
Chicago
STT
St. Thomas
$490 Roundtrip, found 4 days ago
$490
Roundtrip
found 4 days ago
Select American Airlines flight, departing Sat, Dec 5 from Chicago to St. Thomas, returning Fri, Dec 11, priced at $490 found 4 days ago
Fri, Aug 21 - Fri, Aug 28
ORD
Chicago
STT
St. Thomas
$492 Roundtrip, found 6 days ago
$492
Roundtrip
found 6 days ago
Select American Airlines flight, departing Fri, Aug 21 from Chicago to St. Thomas, returning Fri, Aug 28, priced at $492 found 6 days ago
Wed, Sep 2 - Wed, Sep 9
ORD
Chicago
STT
St. Thomas
$528 Roundtrip, found 5 days ago
$528
Roundtrip
found 5 days ago
Select JetBlue Airways flight, departing Wed, Sep 2 from Chicago to St. Thomas, returning Wed, Sep 9, priced at $528 found 5 days ago

St. Thomas economy flight packages

Price found within the past 48 hours. Click for updated prices.
Bluebeard's Castle Resort
4.0-star property

Bluebeard's Castle Resort

9/10 Wonderful! (546 reviews)

Aug 31 - Sep 7

7 night stay

Chicago (CHI) to St. Thomas (STT)

Southwest Airlines • Non-stop • Coach

St. Thomas (STT) to Chicago (CHI)

American Airlines • Non-stop • Coach
Price was $1,430, price is now $965 per person
$965
per person
found 1 day ago
Thought the room was great, clean , comfortable. Good location.

Reviewed on Jul 15, 2026

Great Bay Condominiums located at The Ritz-Carlton Club, St Thomas
4.5-star property

Great Bay Condominiums located at The Ritz-Carlton Club, St Thomas

9.2/10 Wonderful! (34 reviews)

Aug 31 - Sep 7

7 night stay

Chicago (CHI) to St. Thomas (STT)

Southwest Airlines • Non-stop • Coach

St. Thomas (STT) to Chicago (CHI)

American Airlines • Non-stop • Coach
Save 100% on your flight
Price was $4,089, price is now $2,419 per person
$2,419
per person
found 1 day ago

Limetree Beach Resort by Club Wyndham
3.5-star property

Limetree Beach Resort by Club Wyndham

8.2/10 Very Good! (222 reviews)

Aug 31 - Sep 7

7 night stay

Chicago (CHI) to St. Thomas (STT)

Southwest Airlines • Non-stop • Coach

St. Thomas (STT) to Chicago (CHI)

American Airlines • Non-stop • Coach
Price was $1,847, price is now $1,312 per person
$1,312
per person
found 1 day ago
The beach was beautiful but rocky. The standard room was dirty, the sofa was filthy, when we pulled it out to use the sofa bed the floor underneath was black. Did not have room cleaned by anyone even after requesting cleaning for 6 days. The ladies at the check in desk were not helpful at all with an issue at check in about the not getting the room that we paid for through Expedia, they blamed it on Expedia stating they did not have any studio suites only standard rooms and this is not true. I will never stay at a Wyndham hotel resort ever again!!!

Reviewed on Jul 7, 2026

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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

Whether you want to book cheap flights from Chicago to St. Thomas or are looking for the perfect package holiday, Orbitz is your one-stop source. Taking the stress and expense out of travel, Orbitz helps you find the best fares for Chicago to St. Thomas flights.

Make the Most of Your Vacation

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Book your flights from Chicago to St. Thomas wherever you are with the Orbitz app for Android and iPhone. Or simply use m.orbitz.com on your mobile browser to search and book the Chicago to St. Thomas flights that you want. And if you’re running late, you check your flight status and baggage claim information on your mobile device too too.

Craft Your Perfect Vacation

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Keep Informed With Orbitz

With Orbitz’s free alerts service, you will stay informed of flight or services disruptions to your Chicago to St. Thomas flights. The alerts can be sent straight to your mobile phone or email.

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.

More Destinations

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.