$259 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.

Sun, Oct 4 - Fri, Oct 9
ORD
O'Hare Intl.
STT
Cyril E. King
$992 Roundtrip, found 13 hours ago
$992
Roundtrip
found 13 hours ago
Select American Airlines flight, departing Sun, Oct 4 from O'Hare Intl. to Cyril E. King, returning Fri, Oct 9, priced at $992 found 13 hours ago

Airfares from $259 One Way, $571 Round Trip from Chicago to St. Thomas

Prices starting at $571 for return flights and $259 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, Jan 28 - Sun, Feb 7
ORD
Chicago
STT
St. Thomas
$571 Roundtrip, found 19 hours ago
$571
Roundtrip
found 19 hours ago
Select American Airlines flight, departing Thu, Jan 28 from Chicago to St. Thomas, returning Sun, Feb 7, priced at $571 found 19 hours ago
Sun, Jan 17 - Sun, Jan 24
ORD
Chicago
STT
St. Thomas
$576 Roundtrip, found 6 hours ago
$576
Roundtrip
found 6 hours ago
Select American Airlines flight, departing Sun, Jan 17 from Chicago to St. Thomas, returning Sun, Jan 24, priced at $576 found 6 hours ago
Sun, Jan 17 - Sun, Jan 24
ORD
Chicago
STT
St. Thomas
$580 Roundtrip, found 6 hours ago
$580
Roundtrip
found 6 hours ago
Select American Airlines flight, departing Sun, Jan 17 from Chicago to St. Thomas, returning Sun, Jan 24, priced at $580 found 6 hours ago
Wed, Mar 24 - Wed, Mar 31
ORD
Chicago
STT
St. Thomas
$585 Roundtrip, found 1 day ago
$585
Roundtrip
found 1 day ago
Select American Airlines flight, departing Wed, Mar 24 from Chicago to St. Thomas, returning Wed, Mar 31, priced at $585 found 1 day ago
Fri, Jan 1 - Thu, Jan 7
ORD
Chicago
STT
St. Thomas
$590 Roundtrip, found 4 hours ago
$590
Roundtrip
found 4 hours ago
Select American Airlines flight, departing Fri, Jan 1 from Chicago to St. Thomas, returning Thu, Jan 7, priced at $590 found 4 hours ago

St. Thomas economy flight packages

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

Limetree Beach Resort by Club Wyndham

8.2/10 Very Good! (239 reviews)

Nov 6 - Nov 9

3 night stay

Chicago (CHI) to St. Thomas (STT)

American Airlines • Non-stop roundtrip • Coach
Price was $1,277, price is now $1,067 per person
$1,067
per person
found 1 day ago
10/10 highly recommend

Reviewed on Sep 12, 2026

Calichi at Picture Point
4.0-star property

Calichi at Picture Point

9.8/10 Exceptional! (84 reviews)

Nov 5 - Nov 11

6 night stay

Chicago (MDW) to St. Thomas (STT)

Southwest Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $4,320, price is now $3,349 per person
$3,349
per person
found 1 day ago
We stayed in Papaya. The view was amazing. The buildings were modern and looked well cared for. The room was clean and felt luxurious yet simple. We had an amazing time! I would definitely recommend and my wife is trying to find a way to trick me into taking her back.

Reviewed on Sep 22, 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)

Nov 3 - Nov 7

4 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 $1,882, price is now $1,539 per person
$1,539
per person
found 1 day ago

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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

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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.