$113 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, Mar 1 - Fri, Mar 6
ORD
O'Hare Intl.
STT
Cyril E. King
$382 Roundtrip, found 1 day ago
$382
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Sun, Mar 1 from O'Hare Intl. to Cyril E. King, returning Fri, Mar 6, priced at $382 found 1 day ago
Fri, Feb 27 - Sun, Mar 1
MDW
Midway Intl.
STT
Cyril E. King
$838 Roundtrip, found 1 day ago
$838
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Fri, Feb 27 from Midway Intl. to Cyril E. King, returning Sun, Mar 1, priced at $838 found 1 day ago

Airfares from $113 One Way, $255 Round Trip from Chicago to St. Thomas

Prices starting at $255 for return flights and $113 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, May 16 - Tue, May 19
ORD
Chicago
STT
St. Thomas
$255 Roundtrip, found 1 hour ago
$255
Roundtrip
found 1 hour ago
Select Spirit Airlines flight, departing Sat, May 16 from Chicago to St. Thomas, returning Tue, May 19, priced at $255 found 1 hour ago
Tue, Apr 28 - Tue, May 5
ORD
Chicago
STT
St. Thomas
$261 Roundtrip, found 6 days ago
$261
Roundtrip
found 6 days ago
Select Spirit Airlines flight, departing Tue, Apr 28 from Chicago to St. Thomas, returning Tue, May 5, priced at $261 found 6 days ago
Sat, May 2 - Wed, May 6
ORD
Chicago
STT
St. Thomas
$262 Roundtrip, found 12 hours ago
$262
Roundtrip
found 12 hours ago
Select Spirit Airlines flight, departing Sat, May 2 from Chicago to St. Thomas, returning Wed, May 6, priced at $262 found 12 hours ago
Wed, May 13 - Mon, May 18
ORD
Chicago
STT
St. Thomas
$263 Roundtrip, found 5 days ago
$263
Roundtrip
found 5 days ago
Select Spirit Airlines flight, departing Wed, May 13 from Chicago to St. Thomas, returning Mon, May 18, priced at $263 found 5 days ago
Sat, May 16 - Tue, May 19
ORD
Chicago
STT
St. Thomas
$265 Roundtrip, found 1 hour ago
$265
Roundtrip
found 1 hour ago
Select Spirit Airlines flight, departing Sat, May 16 from Chicago to St. Thomas, returning Tue, May 19, priced at $265 found 1 hour ago

St. Thomas economy flight packages

Price found within the past 48 hours. Click for updated prices.
Windward Passage Hotel
3.5-star property

Windward Passage Hotel

7/10 Good! (1,366 reviews)

Apr 1 - Apr 7

6 night stay

Chicago (CHI) to St. Thomas (STT)

Spirit Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $1,593, price is now $1,131 per person
$1,131
per person
found 1 day ago
I had a very nice room, and the hotel is centrally located right in town. Staff was great, and I did not experience any issues. Would definitely stay at Windward again.

Reviewed on Feb 12, 2026

Margaritaville Vacation Club - St. Thomas
4.0-star property

Margaritaville Vacation Club - St. Thomas

8/10 Very Good! (2,299 reviews)

Apr 1 - Apr 7

6 night stay

Chicago (CHI) to St. Thomas (STT)

Spirit Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $2,757, price is now $1,780 per person
$1,780
per person
found 1 day ago
The villa was good, but the master bath fan ran continuously, and the air handler quit the last night. We reported the fan issue, but no repair was done. Staff were great. Shuttle up the hill was good to have.

Reviewed on Feb 9, 2026

Wharfside Village Hotel
3.0-star property

Wharfside Village Hotel

9.8/10 Exceptional! (133 reviews)

Apr 1 - Apr 7

6 night stay

Chicago (CHI) to St. Thomas (STT)

Spirit Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $2,988, price is now $2,146 per person
$2,146
per person
found 1 day ago
Perfect location and great rooms! Staff was friendly and gave "local" suggestions of places to eat, things to do.

Reviewed on May 13, 2025

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St. Thomas packages with premium economy flights

Price found within the past 48 hours. Click for updated prices.
Windward Passage Hotel
3.5-star property

Windward Passage Hotel

7/10 Good! (1,366 reviews)

Mar 29 - Apr 5

7 night stay

Chicago (ORD) to St. Thomas (STT)

Delta • Non-stop roundtrip • PremiumEconomy
Price was $2,461, price is now $2,019 per person
$2,019
per person
found 9 hours ago
I had a very nice room, and the hotel is centrally located right in town. Staff was great, and I did not experience any issues. Would definitely stay at Windward again.

Reviewed on Feb 12, 2026

Margaritaville Vacation Club - St. Thomas
4.0-star property

Margaritaville Vacation Club - St. Thomas

8/10 Very Good! (2,299 reviews)

Mar 29 - Apr 5

7 night stay

Chicago (ORD) to St. Thomas (STT)

Delta • Non-stop roundtrip • PremiumEconomy
Price was $4,047, price is now $3,018 per person
$3,018
per person
found 8 hours ago
The villa was good, but the master bath fan ran continuously, and the air handler quit the last night. We reported the fan issue, but no repair was done. Staff were great. Shuttle up the hill was good to have.

Reviewed on Feb 9, 2026

Wharfside Village Hotel
3.0-star property

Wharfside Village Hotel

9.8/10 Exceptional! (133 reviews)

Mar 29 - Apr 5

7 night stay

Chicago (ORD) to St. Thomas (STT)

Delta • Non-stop roundtrip • PremiumEconomy
Price was $4,194, price is now $3,248 per person
$3,248
per person
found 9 hours ago
Perfect location and great rooms! Staff was friendly and gave "local" suggestions of places to eat, things to do.

Reviewed on May 13, 2025

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St. Thomas first class flight packages

Price found within the past 48 hours. Click for updated prices.
Margaritaville Vacation Club - St. Thomas
4.0-star property

Margaritaville Vacation Club - St. Thomas

8/10 Very Good! (2,299 reviews)

Apr 16 - Apr 21

5 night stay

Chicago (ORD) to St. Thomas (STT)

American Airlines • Non-stop • FirstClass

St. Thomas (STT) to Chicago (ORD)

United • Non-stop • FirstClass
Price was $3,378, price is now $2,677 per person
$2,677
per person
found 1 day ago
The villa was good, but the master bath fan ran continuously, and the air handler quit the last night. We reported the fan issue, but no repair was done. Staff were great. Shuttle up the hill was good to have.

Reviewed on Feb 9, 2026

Wharfside Village Hotel
3.0-star property

Wharfside Village Hotel

9.8/10 Exceptional! (133 reviews)

Apr 16 - Apr 21

5 night stay

Chicago (ORD) to St. Thomas (STT)

American Airlines • Non-stop • FirstClass

St. Thomas (STT) to Chicago (ORD)

United • Non-stop • FirstClass
Price was $3,662, price is now $2,978 per person
$2,978
per person
found 1 day ago
Perfect location and great rooms! Staff was friendly and gave "local" suggestions of places to eat, things to do.

Reviewed on May 13, 2025

Limetree Beach Resort by Club Wyndham
3.5-star property

Limetree Beach Resort by Club Wyndham

8.2/10 Very Good! (202 reviews)

Apr 16 - Apr 21

5 night stay

Chicago (ORD) to St. Thomas (STT)

American Airlines • Non-stop • FirstClass

St. Thomas (STT) to Chicago (ORD)

United • Non-stop • FirstClass
Price was $3,833, price is now $3,298 per person
$3,298
per person
found 1 day ago
excellent property and experience

Reviewed on May 27, 2025

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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.