$211 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, Aug 29 - Fri, Sep 4
ORD
O'Hare Intl.
STT
Cyril E. King
$896 Roundtrip, just found
$896
Roundtrip
just found
Select American Airlines flight, departing Sat, Aug 29 from O'Hare Intl. to Cyril E. King, returning Fri, Sep 4, priced at $896 just found
Sat, Aug 29 - Thu, Sep 3
MDW
Midway Intl.
STT
Cyril E. King
$1,020 Roundtrip, found 2 days ago
$1,020
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Sat, Aug 29 from Midway Intl. to Cyril E. King, returning Thu, Sep 3, priced at $1,020 found 2 days ago

Airfares from $211 One Way, $439 Round Trip from Chicago to St. Thomas

Prices starting at $439 for return flights and $211 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.

Sat, Jan 16 - Mon, Jan 25
ORD
Chicago
STT
St. Thomas
$439 Roundtrip, found 8 hours ago
$439
Roundtrip
found 8 hours ago
Select American Airlines flight, departing Sat, Jan 16 from Chicago to St. Thomas, returning Mon, Jan 25, priced at $439 found 8 hours ago
Wed, Oct 28 - Sun, Nov 1
ORD
Chicago
STT
St. Thomas
$452 Roundtrip, found 3 hours ago
$452
Roundtrip
found 3 hours ago
Select American Airlines flight, departing Wed, Oct 28 from Chicago to St. Thomas, returning Sun, Nov 1, priced at $452 found 3 hours ago
Sat, Jan 23 - Mon, Feb 1
ORD
Chicago
STT
St. Thomas
$456 Roundtrip, found 3 days ago
$456
Roundtrip
found 3 days ago
Select American Airlines flight, departing Sat, Jan 23 from Chicago to St. Thomas, returning Mon, Feb 1, priced at $456 found 3 days ago
Wed, Oct 28 - Sun, Nov 1
ORD
Chicago
STT
St. Thomas
$461 Roundtrip, found 3 hours ago
$461
Roundtrip
found 3 hours ago
Select American Airlines flight, departing Wed, Oct 28 from Chicago to St. Thomas, returning Sun, Nov 1, priced at $461 found 3 hours ago
Sat, Jan 23 - Mon, Feb 1
ORD
Chicago
STT
St. Thomas
$464 Roundtrip, found 3 days ago
$464
Roundtrip
found 3 days ago
Select American Airlines flight, departing Sat, Jan 23 from Chicago to St. Thomas, returning Mon, Feb 1, priced at $464 found 3 days ago

St. Thomas economy flight packages

Price found within the past 48 hours. Click for updated prices.
At Home in the Tropics
3.0-star property

At Home in the Tropics

9.8/10 Exceptional! (184 reviews)

Oct 7 - Oct 12

5 night stay

Chicago (CHI) to St. Thomas (STT)

American Airlines • Non-stop roundtrip • Coach
Price was $1,460, price is now $1,111 per person
$1,111
per person
found 1 day ago
Excellent place to stay on Saint Thomas. The owners are very responsive, friendly, and accommodating. Clean and spacious rooms a short walk from downtown Charlotte Amalie. This is a small, locally owned "hotel" that has an intimate, relaxed vibe. Easy access and parking.

Reviewed on Aug 3, 2026

Limetree Beach Resort by Club Wyndham
3.5-star property

Limetree Beach Resort by Club Wyndham

8.2/10 Very Good! (230 reviews)

Oct 7 - Oct 12

5 night stay

Chicago (CHI) to St. Thomas (STT)

American Airlines • Non-stop roundtrip • Coach
Price was $1,561, price is now $1,178 per person
$1,178
per person
found 1 day ago
We had a great stay the only issue is we had no wifi and no cell signal most of the time in our room, had to go elsewhere on the property to try and get signal/wifi.

Reviewed on Aug 23, 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)

Oct 7 - Oct 12

5 night stay

Chicago (CHI) to St. Thomas (STT)

American Airlines • Non-stop roundtrip • Coach
Price was $2,159, price is now $1,653 per person
$1,653
per person
found 1 day ago

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St. Thomas first class flight packages

Price found within the past 48 hours. Click for updated prices.
At Home in the Tropics
3.0-star property

At Home in the Tropics

9.8/10 Exceptional! (184 reviews)

Oct 4 - Oct 12

8 night stay

Chicago (ORD) to St. Thomas (STT)

Delta • Non-stop • FirstClass

St. Thomas (STT) to Chicago (ORD)

American Airlines • Non-stop • FirstClass
Price was $3,198, price is now $2,585 per person
$2,585
per person
found 11 hours ago
Excellent place to stay on Saint Thomas. The owners are very responsive, friendly, and accommodating. Clean and spacious rooms a short walk from downtown Charlotte Amalie. This is a small, locally owned "hotel" that has an intimate, relaxed vibe. Easy access and parking.

Reviewed on Aug 3, 2026

Margaritaville Vacation Club - St. Thomas
4.0-star property

Margaritaville Vacation Club - St. Thomas

8/10 Very Good! (2,511 reviews)

Oct 4 - Oct 12

8 night stay

Chicago (ORD) to St. Thomas (STT)

Delta • Non-stop • FirstClass

St. Thomas (STT) to Chicago (ORD)

American Airlines • Non-stop • FirstClass
Price was $3,172, price is now $2,596 per person
$2,596
per person
found 11 hours ago

Limetree Beach Resort by Club Wyndham
3.5-star property

Limetree Beach Resort by Club Wyndham

8.2/10 Very Good! (230 reviews)

Oct 4 - Oct 12

8 night stay

Chicago (ORD) to St. Thomas (STT)

Delta • Non-stop • FirstClass

St. Thomas (STT) to Chicago (ORD)

American Airlines • Non-stop • FirstClass
Price was $3,170, price is now $2,626 per person
$2,626
per person
found 11 hours ago
We had a great stay the only issue is we had no wifi and no cell signal most of the time in our room, had to go elsewhere on the property to try and get signal/wifi.

Reviewed on Aug 23, 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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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.