$102 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, Feb 15 - Tue, Feb 24
ORD
O'Hare Intl.
STT
Cyril E. King
$369 Roundtrip, found 1 day ago
$369
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Sun, Feb 15 from O'Hare Intl. to Cyril E. King, returning Tue, Feb 24, priced at $369 found 1 day ago
Sat, Feb 14 - Mon, Feb 16
MDW
Midway Intl.
STT
Cyril E. King
$766 Roundtrip, found 2 days ago
$766
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Sat, Feb 14 from Midway Intl. to Cyril E. King, returning Mon, Feb 16, priced at $766 found 2 days ago

Airfares from $102 One Way, $187 Round Trip from Chicago to St. Thomas

Prices starting at $187 for return flights and $102 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, Mar 11 - Wed, Mar 18
ORD
Chicago
STT
St. Thomas
$187 Roundtrip, found 5 days ago
$187
Roundtrip
found 5 days ago
Select Spirit Airlines flight, departing Wed, Mar 11 from Chicago to St. Thomas, returning Wed, Mar 18, priced at $187 found 5 days ago
Tue, May 12 - Wed, May 13
ORD
Chicago
STT
St. Thomas
$205 Roundtrip, found 6 days ago
$205
Roundtrip
found 6 days ago
Select Spirit Airlines flight, departing Tue, May 12 from Chicago to St. Thomas, returning Wed, May 13, priced at $205 found 6 days ago
Wed, Apr 15 - Tue, Apr 21
ORD
Chicago
STT
St. Thomas
$207 Roundtrip, found 3 days ago
$207
Roundtrip
found 3 days ago
Select Spirit Airlines flight, departing Wed, Apr 15 from Chicago to St. Thomas, returning Tue, Apr 21, priced at $207 found 3 days ago
Tue, Feb 24 - Wed, Mar 4
ORD
Chicago
STT
St. Thomas
$212 Roundtrip, found 6 days ago
$212
Roundtrip
found 6 days ago
Select Spirit Airlines flight, departing Tue, Feb 24 from Chicago to St. Thomas, returning Wed, Mar 4, priced at $212 found 6 days ago
Mon, Mar 30 - Mon, Apr 6
ORD
Chicago
STT
St. Thomas
$385 Roundtrip, found 1 day ago
$385
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Mon, Mar 30 from Chicago to St. Thomas, returning Mon, Apr 6, priced at $385 found 1 day ago

St. Thomas economy flight packages

Price found within the past 48 hours. Click for updated prices.
Bluebeard's Castle Resort
4.0-star property

Bluebeard's Castle Resort

No reviews

Mar 13 - Mar 21

8 night stay

Chicago (CHI) to St. Thomas (STT)

Spirit Airlines • Non-stop roundtrip • Coach
Price was $1,957, price is now $1,326 per person
$1,326
per person
found 1 day ago
Margaritaville Vacation Club - St. Thomas
4.0-star property

Margaritaville Vacation Club - St. Thomas

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

Mar 13 - Mar 21

8 night stay

Chicago (CHI) to St. Thomas (STT)

Spirit Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $4,198, price is now $2,709 per person
$2,709
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

Windward Passage Hotel
3.5-star property

Windward Passage Hotel

7/10 Good! (1,366 reviews)

Mar 13 - Mar 21

8 night stay

Chicago (CHI) to St. Thomas (STT)

Spirit Airlines • Non-stop roundtrip • Coach
Price was $2,206, price is now $1,637 per person
$1,637
per person
found 1 day ago
Reception was very friendly , clean and comfortable hotel

Reviewed on Dec 15, 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 17 - Mar 24

7 night stay

Chicago (ORD) to St. Thomas (STT)

Delta • Non-stop roundtrip • PremiumEconomy
Price was $2,081, price is now $1,586 per person
$1,586
per person
found 1 day ago
Reception was very friendly , clean and comfortable hotel

Reviewed on Dec 15, 2025

Margaritaville Vacation Club - St. Thomas
4.0-star property

Margaritaville Vacation Club - St. Thomas

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

Mar 17 - Mar 24

7 night stay

Chicago (ORD) to St. Thomas (STT)

Delta • Non-stop roundtrip • PremiumEconomy
Save 100% on your flight
Price was $3,759, price is now $2,483 per person
$2,483
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

Club Wyndham Elysian Beach Resort
3.5-star property

Club Wyndham Elysian Beach Resort

7.8/10 Good! (173 reviews)

Mar 17 - Mar 24

7 night stay

Chicago (ORD) to St. Thomas (STT)

Delta • Non-stop roundtrip • PremiumEconomy
Save 100% on your flight
Price was $4,573, price is now $3,598 per person
$3,598
per person
found 1 day ago
Its property is excellent to vacation . Cleaning , good tennis court and beach

Reviewed on Oct 27, 2024

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St. Thomas first class flight packages

Price found within the past 48 hours. Click for updated prices.
St John Inn
3.0-star property

St John Inn

9.2/10 Wonderful! (413 reviews)

Mar 22 - Mar 27

5 night stay

Chicago (CHI) to St. Thomas (STT)

American Airlines • Non-stop roundtrip • FirstClass
Price was $2,423, price is now $1,976 per person
$1,976
per person
found 19 hours ago
I loved the friendly, laid back atmosphere.

Reviewed on Jun 26, 2021

Wharfside Village Hotel
3.0-star property

Wharfside Village Hotel

9.8/10 Exceptional! (133 reviews)

Mar 16 - Mar 20

4 night stay

Chicago (ORD) to St. Thomas (STT)

American Airlines • Non-stop roundtrip • FirstClass
Price was $2,789, price is now $2,214 per person
$2,214
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)

Mar 16 - Mar 20

4 night stay

Chicago (ORD) to St. Thomas (STT)

American Airlines • Non-stop roundtrip • FirstClass
Price was $2,994, price is now $2,472 per person
$2,472
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.