$154 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, Apr 26 - Thu, Apr 30
MDW
Midway Intl.
STT
Cyril E. King
$593 Roundtrip, found 1 day ago
$593
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Sun, Apr 26 from Midway Intl. to Cyril E. King, returning Thu, Apr 30, priced at $593 found 1 day ago
Sun, Apr 26 - Sat, May 2
ORD
O'Hare Intl.
STT
Cyril E. King
$618 Roundtrip, found 7 hours ago
$618
Roundtrip
found 7 hours ago
Select Spirit Airlines flight, departing Sun, Apr 26 from O'Hare Intl. to Cyril E. King, returning Sat, May 2, priced at $618 found 7 hours ago

Airfares from $154 One Way, $371 Round Trip from Chicago to St. Thomas

Prices starting at $371 for return flights and $154 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.

Wed, Aug 12 - Wed, Aug 19
ORD
Chicago
STT
St. Thomas
$371 Roundtrip, found 1 day ago
$371
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Wed, Aug 12 from Chicago to St. Thomas, returning Wed, Aug 19, priced at $371 found 1 day ago
Fri, Jul 10 - Tue, Jul 14
ORD
Chicago
STT
St. Thomas
$380 Roundtrip, found 4 hours ago
$380
Roundtrip
found 4 hours ago
Select Spirit Airlines flight, departing Fri, Jul 10 from Chicago to St. Thomas, returning Tue, Jul 14, priced at $380 found 4 hours ago
Sat, May 23 - Sat, May 30
ORD
Chicago
STT
St. Thomas
$388 Roundtrip, found 1 day ago
$388
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Sat, May 23 from Chicago to St. Thomas, returning Sat, May 30, priced at $388 found 1 day ago
Thu, Aug 13 - Mon, Aug 17
MDW
Chicago
STT
St. Thomas
$468 Roundtrip, found 5 days ago
$468
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Thu, Aug 13 from Chicago to St. Thomas, returning Mon, Aug 17, priced at $468 found 5 days ago
Tue, May 19 - Wed, May 27
ORD
Chicago
STT
St. Thomas
$580 Roundtrip, found 16 hours ago
$580
Roundtrip
found 16 hours ago
Select Delta flight, departing Tue, May 19 from Chicago to St. Thomas, returning Wed, May 27, priced at $580 found 16 hours 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! (167 reviews)

Jun 3 - Jun 7

4 night stay

Chicago (CHI) to St. Thomas (STT)

American Airlines • Non-stop • Coach

St. Thomas (STT) to Chicago (CHI)

Spirit Airlines • Non-stop • Coach
Price was $1,187, price is now $911 per person
$911
per person
found 1 day ago
Great breakfast and view

Reviewed on Dec 31, 2024

Sapphire Sanctuary by the Sea
3.0-star property

Sapphire Sanctuary by the Sea

9.2/10 Wonderful! (47 reviews)

Jun 13 - Jun 19

6 night stay

Chicago (CHI) to St. Thomas (STT)

Spirit Airlines • Non-stop roundtrip • Coach
Price was $1,462, price is now $1,096 per person
$1,096
per person
found 1 day ago
This is a MUST MUST stay!!!! We loved every single minute and everything is so convenient just like being at home. We will definitely be back.

Reviewed on Nov 15, 2022

The Hideaway Hull Bay
4.0-star property

The Hideaway Hull Bay

9.6/10 Exceptional! (58 reviews)

May 23 - May 25

2 night stay

Chicago (CHI) to St. Thomas (STT)

United • Coach

St. Thomas (STT) to Chicago (CHI)

Spirit Airlines • Coach
Price was $2,379, price is now $1,793 per person
$1,793
per person
found 1 day ago
Realy cool but isolated . Cant get any supplies on mondays everything closed. Go to the grocery store before you arrived also no check in so look for your text for access codes

Reviewed on Feb 24, 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.