$221 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, Jul 5 - Thu, Jul 9
ORD
O'Hare Intl.
STT
Cyril E. King
$1,070 Roundtrip, found 10 hours ago
$1,070
Roundtrip
found 10 hours ago
Select Delta flight, departing Sun, Jul 5 from O'Hare Intl. to Cyril E. King, returning Thu, Jul 9, priced at $1,070 found 10 hours ago
Fri, Jul 3 - Tue, Jul 7
MDW
Midway Intl.
STT
Cyril E. King
$1,510 Roundtrip, found 1 day ago
$1,510
Roundtrip
found 1 day ago
Select Delta flight, departing Fri, Jul 3 from Midway Intl. to Cyril E. King, returning Tue, Jul 7, priced at $1,510 found 1 day ago

Airfares from $221 One Way, $467 Round Trip from Chicago to St. Thomas

Prices starting at $467 for return flights and $221 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
MDW
Chicago
STT
St. Thomas
$467 Roundtrip, found 6 days ago
$467
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Thu, Sep 10 from Chicago to St. Thomas, returning Mon, Sep 14, priced at $467 found 6 days ago
Tue, Nov 10 - Tue, Nov 17
ORD
Chicago
STT
St. Thomas
$492 Roundtrip, found 14 hours ago
$492
Roundtrip
found 14 hours ago
Select American Airlines flight, departing Tue, Nov 10 from Chicago to St. Thomas, returning Tue, Nov 17, priced at $492 found 14 hours ago
Tue, Nov 10 - Tue, Nov 17
ORD
Chicago
STT
St. Thomas
$496 Roundtrip, found 14 hours ago
$496
Roundtrip
found 14 hours ago
Select American Airlines flight, departing Tue, Nov 10 from Chicago to St. Thomas, returning Tue, Nov 17, priced at $496 found 14 hours ago
Thu, Sep 10 - Mon, Sep 14
ORD
Chicago
STT
St. Thomas
$497 Roundtrip, found 3 days ago
$497
Roundtrip
found 3 days ago
Select American Airlines flight, departing Thu, Sep 10 from Chicago to St. Thomas, returning Mon, Sep 14, priced at $497 found 3 days ago
Thu, Sep 10 - Mon, Sep 14
ORD
Chicago
STT
St. Thomas
$509 Roundtrip, found 3 days ago
$509
Roundtrip
found 3 days ago
Select American Airlines flight, departing Thu, Sep 10 from Chicago to St. Thomas, returning Mon, Sep 14, priced at $509 found 3 days ago

St. Thomas economy flight packages

Price found within the past 48 hours. Click for updated prices.
Sapphire Sanctuary by the Sea
3.0-star property

Sapphire Sanctuary by the Sea

9.2/10 Wonderful! (47 reviews)

Aug 23 - Aug 27

4 night stay

Chicago (CHI) to St. Thomas (STT)

Southwest Airlines • Non-stop roundtrip • Coach
Price was $1,080, price is now $862 per person
$862
per person
found 23 hours ago
The condo was great! Clean and plenty of space for my family of 5!

Reviewed on Dec 6, 2025

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 23 - Aug 27

4 night stay

Chicago (CHI) to St. Thomas (STT)

Southwest Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $2,484, price is now $1,942 per person
$1,942
per person
found 23 hours ago

Calichi at Picture Point
4.0-star property

Calichi at Picture Point

9.8/10 Exceptional! (83 reviews)

Aug 22 - Aug 29

7 night stay

Chicago (CHI) to St. Thomas (STT)

Southwest Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $3,217, price is now $2,621 per person
$2,621
per person
found 1 day ago
Our villa was great with incredible views. Any issues or questions we had were quickly resolved. Would highly recommend Calichi to anyone looking to stay on the quiet side of the island.

Reviewed on Jun 15, 2026

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St. Thomas first class flight packages

Price found within the past 48 hours. Click for updated prices.
Boundless Bliss Hotel
2.5-star property

Boundless Bliss Hotel

7/10 Good! (172 reviews)

Aug 5 - Aug 8

3 night stay

Chicago (CHI) to St. Thomas (STT)

Delta • Non-stop • FirstClass

St. Thomas (STT) to Chicago (CHI)

United • Non-stop • FirstClass
Price was $3,175, price is now $3,020 per person
$3,020
per person
found 24 hours ago
Ocean view is misleading property is out of the way on top of a hill.Shuttle and taxis do not want the fare.Sole staff member was fantastic.Rooms are outdated 1960’s .

Reviewed on Jun 28, 2026

Limetree Beach Resort by Club Wyndham
3.5-star property

Limetree Beach Resort by Club Wyndham

8.2/10 Very Good! (222 reviews)

Aug 5 - Aug 8

3 night stay

Chicago (CHI) to St. Thomas (STT)

Delta • Non-stop • FirstClass

St. Thomas (STT) to Chicago (CHI)

United • Non-stop • FirstClass
Price was $3,393, price is now $3,228 per person
$3,228
per person
found 24 hours ago
I only took away a star because the WiFi was down the entire time we were there. Other than that we truly enjoyed this resort.

Reviewed on Jul 1, 2026

Margaritaville Vacation Club - St. Thomas
4.0-star property

Margaritaville Vacation Club - St. Thomas

8/10 Very Good! (2,471 reviews)

Aug 5 - Aug 8

3 night stay

Chicago (CHI) to St. Thomas (STT)

Delta • Non-stop • FirstClass

St. Thomas (STT) to Chicago (CHI)

United • Non-stop • FirstClass
Price was $3,278, price is now $3,135 per person
$3,135
per person
found 24 hours ago
Beautiful property with amazing views. We had a great time!

Reviewed on Jul 1, 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

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Cheap Air Ticket Prices Guaranteed

Orbitz is your number one source for low fares for Chicago to St. Thomas flights. Our low price guarantee on domestic and international air tickets give you great savings for a perfect trip to St. Thomas. Need hotels too? You can book them last minute on your mobile phone.

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.