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Saint Thomas Island

$124+ Cheap flights from Chicago (CHI) to Saint Thomas Island (STT)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/24. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — STT
nov. 1 — nov. 81
sáb. 11/1
sáb. 11/8
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Saint Thomas Island Cyril E King are usually found in September or November, booked 23 days in advance, depart on a Wednesday or Thursday and return on a Tuesday

Cheap flight deals from Chicago to Saint Thomas Island

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Saint Thomas Island (STT). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated octubre 2, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$228
(Cheapflightsfares)

One-way from

$124
(Cheapflightsfares)

Popular in

December

Cheapest in

September

Average price

$554

Good round-trip deal

$575 or less

Good one-way deal

$283 or less
Provider with most accurate pricing for Chicago (CHI)-Saint Thomas Island Cyril E King flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Saint Thomas Island Cyril E King flights.
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From Chicago (CHI) to Saint Thomas Island Cyril E King
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One-way flight from Chicago (CHI) to Saint Thomas Island Cyril E King
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Highest demand for flights based on searches. 6% potential increase in price ($42 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($20 potential savings vs. average RT price).
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Average for round-trip flights in October 2025
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Price to beat on a round-trip flight from Chicago (CHI) to Saint Thomas Island Cyril E King.
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Price to beat on a one-way flight from Chicago (CHI) to Saint Thomas Island Cyril E King.
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Find flight deals from Chicago to Saint Thomas Island

Cheapest flights from Chicago to Saint Thomas Island
Explore the most affordable flight options available from Chicago to Saint Thomas Island. Find the lowest fares from popular airlines and budget airlines, with prices last updated on octubre 2, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 10/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 10/227:43 pmORD - STT
1 stop13h 13mSpirit Airlines
mar. 10/2811:01 amSTT - ORD
1 stop15h 02mSpirit Airlines
Deal found 10/1$228
This Kiwi.com deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 10/227:43 pmORD - STT
1 stop13h 13mSpirit Airlines
jue. 10/302:40 pmSTT - ORD
1 stop7h 53mSpirit Airlines
Deal found 9/29$242
This Cheapflightsfares deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 10/227:43 pmORD - STT
1 stop13h 13mSpirit Airlines
sáb. 11/12:01 pmSTT - ORD
1 stop7h 16mSpirit Airlines
Deal found 9/30$255
This Cheapflightsfares deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 10/187:43 pmORD - STT
1 stop13h 13mSpirit Airlines
sáb. 10/252:01 pmSTT - ORD
1 stop8h 32mSpirit Airlines
Deal found 9/30$260
This Mytrip deal was found by Cheapflights users on 10/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 10/217:43 pmORD - STT
1 stop13h 13mSpirit Airlines
mar. 10/2811:01 amSTT - ORD
1 stop15h 02mSpirit Airlines
Deal found 10/1$263
This Cheapflightsfares deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 10/256:58 pmORD - STT
1 stop17h 37mSpirit Airlines
sáb. 11/12:01 pmSTT - ORD
1 stop7h 16mSpirit Airlines
Deal found 9/30$266
This Cheapflightsfares deal was found by Cheapflights users on 10/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 12/56:05 amORD - STT
1 stop7h 06mSpirit Airlines
dom. 12/71:33 pmSTT - ORD
1 stop12h 09mSpirit Airlines
Deal found 10/1$269
This Priceline deal was found by Cheapflights users on 10/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 10/267:43 pmORD - STT
1 stop13h 13mSpirit Airlines
jue. 10/302:40 pmSTT - ORD
1 stop7h 53mSpirit Airlines
Deal found 10/2$272
This Cheapflightsfares deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 11/165:59 pmORD - STT
1 stop16h 29mSpirit Airlines
mié. 11/191:33 pmSTT - ORD
1 stop12h 09mSpirit Airlines
Deal found 9/30$273
This Kiwi.com deal was found by Cheapflights users on 10/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 10/269:26 pmMDW - STT
2 stops35h 30mMultiple Airlines
jue. 10/302:40 pmSTT - MDW
1 stop18h 52mMultiple Airlines
Deal found 10/1$331
This Kiwi.com deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 11/71:37 pmMDW - STT
2 stops21h 23mMultiple Airlines
sáb. 11/154:19 pmSTT - MDW
1 stop18h 53mMultiple Airlines
Deal found 9/29$356
This Kiwi.com deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 10/175:28 pmMDW - STT
1 stop18h 31mMultiple Airlines
dom. 10/192:04 pmSTT - MDW
2 stops32h 42mMultiple Airlines
Deal found 9/30$423

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to Saint Thomas Island that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated octubre 2, 2025.
Use the filters below to find and compare flights from Chicago to Saint Thomas Island that are best for you.

Fly from

Chicago

Fly to

Saint Thomas Island

Route

Depart

Return

Price

ChicagoSaint Thomas Island

ORD - STT

ORDSTT

Chicago O'Hare Intl

sáb. 11/1

11:55 am-1:00 pm

1 stop24h 05m

Saint Thomas Island Cyril E King

mar. 11/4

1:55 pm-6:34 pm

2 stops30h 39m

$339

ChicagoSaint Thomas Island

ORD - STT

ORDSTT

Chicago O'Hare Intl

dom. 1/25

6:05 am-3:11 pm

1 stop7h 06m

Saint Thomas Island Cyril E King

jue. 1/29

1:33 pm-9:44 am

2 stops22h 11m

$472

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

mié. 2/18

6:00 am-3:54 pm

1 stop7h 54m

Saint Thomas Island Cyril E King

mié. 2/25

4:00 pm-9:46 pm

1 stop7h 46m

$509

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

mar. 1/6

6:00 am-2:55 pm

1 stop6h 55m

Saint Thomas Island Cyril E King

vie. 1/16

3:00 pm-9:46 pm

1 stop8h 46m

$509

ChicagoSaint Thomas Island

ORD - STT

ORDSTT

Chicago O'Hare Intl

mié. 3/4

7:10 am-3:54 pm

1 stop6h 44m

Saint Thomas Island Cyril E King

mié. 3/11

1:00 pm-9:14 pm

1 stop9h 14m

$509

ChicagoSaint Thomas Island

ORD - STT

ORDSTT

Chicago O'Hare Intl

dom. 1/25

9:30 am-4:18 pm

Nonstop4h 48m

Saint Thomas Island Cyril E King

jue. 1/29

3:05 pm-6:45 pm

Nonstop5h 40m

$510

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

jue. 1/1

6:00 am-4:25 pm

1 stop8h 25m

Saint Thomas Island Cyril E King

jue. 1/8

3:00 pm-9:46 pm

1 stop8h 46m

$514

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

dom. 1/18

6:00 am-3:54 pm

1 stop7h 54m

Saint Thomas Island Cyril E King

dom. 1/25

4:00 pm-9:46 pm

1 stop7h 46m

$514

ChicagoSaint Thomas Island

ORD - STT

ORDSTT

Chicago O'Hare Intl

mié. 12/10

6:20 pm-1:12 pm

2 stops16h 52m

Saint Thomas Island Cyril E King

vie. 12/19

3:05 pm-6:45 pm

Nonstop5h 40m

$527

ChicagoSaint Thomas Island

ORD - STT

ORDSTT

Chicago O'Hare Intl

mié. 12/10

9:05 pm-1:12 pm

2 stops14h 07m

Saint Thomas Island Cyril E King

lun. 12/22

5:20 pm-11:44 pm

1 stop8h 24m

$527

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/29

Showing 1-10 of 38 results
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Compare providers for flights from Chicago to Saint Thomas Island

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Chicago to Saint Thomas Island in October.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
AranGrantPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Chicago-Saint Thomas Island flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago-Saint Thomas Island flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago-Saint Thomas Island flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago-Saint Thomas Island flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago-Saint Thomas Island flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Chicago to Saint Thomas Island

Have a flexible travel schedule? Discover the best time to fly to Saint Thomas Island from Chicago with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Chicago to Saint Thomas Island

How far ahead should I book a flight from Chicago to Saint Thomas Island?

Use this chart to determine the optimal time to book a round-trip flight from Chicago to Saint Thomas Island. Price data was last updated on September 26, 2025.

Booking 23 days in advance of your planned departure date is, on average, the best time to get cheap flights from Chicago to Saint Thomas Island. The general trend is that the closer you book to the departure date, the more expensive your flight will be.

What is the cheapest month to book a flight from Chicago to Saint Thomas Island?

Currently, September is the cheapest month in which you can book a flight from Chicago to Saint Thomas Island (average of $433). Flying from Chicago to Saint Thomas Island in June is currently the most expensive (average of $643). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from CHI to STT?

Find hourly flight availability from Chicago to Saint Thomas Island. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated octubre 2, 2025.

It’s typically best to fly out from Chicago to Saint Thomas Island in the afternoon. Doing so could potentially save you 49% on the flight price compared to flying in the morning, which is usually more expensive.

How much does it cost to fly round-trip from Chicago to Saint Thomas Island?

What’s the top layover airport for flights from Chicago to Saint Thomas Island?

Share of 1-stop round-trip flights from Chicago to Saint Thomas Island chosen by Cheapflights users in the past 12 months, using the same layover each way.

Fort Lauderdale (FLL) – chosen by Cheapflights users on 67% of 1-stop itineraries from Chicago to Saint Thomas Island on Cheapflights.

What’s the cheapest layover airport for flights from Chicago to Saint Thomas Island?

Average round-trip fare for 1-stop flights from Chicago to Saint Thomas Island, chosen by Cheapflights users in the past 12 months, with the same layover each way.

Orlando (MCO) is the most affordable 1-stop option, with an average round-trip price of $220.

What’s the fastest layover option from Chicago to Saint Thomas Island?

Shortest average travel time for 1-stop one-way flights from Chicago to Saint Thomas Island, based on itineraries clicked by Cheapflights users over the past 12 months, grouped by layover airport.

Flights via Orlando (MCO) have the shortest average one-way travel time for 1-stop routes: 10h 47m.

Which airport typically offers the quickest layover for flights from Chicago to Saint Thomas Island?

Average layover duration for 1-stop one-way flights from Chicago to Saint Thomas Island, chosen by Cheapflights users in the last 12 months, grouped by stopover airport.

Flights via Orlando (MCO) offer the fastest connection on this route, with an average layover time of 4h 12m.

Reviews of airlines servicing Saint Thomas Island

Get insights into the airlines that provide service to Saint Thomas Island. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Saint Thomas Island. Reviews last updated octubre 2, 2025.
Read through reviews of airlines operating flights from Chicago to Saint Thomas Island, such as Delta, United Airlines, and American Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,962 reviews

Boarding

8.2

Entertainment

7.9

Comfort

7.9

Food

7.3

Overall

8.0

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Delta
8.0
Very good
7,962 reviews
Delta
8.0
Very good
7,962 reviews

Boarding

8.2

Entertainment

7.9

Comfort

7.9

Food

7.3

Overall

8.0

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
United Airlines
7.4
Good
8,933 reviews
Delta
8.0
Very good
7,962 reviews

Boarding

8.2

Entertainment

7.9

Comfort

7.9

Food

7.3

Overall

8.0

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
American Airlines
7.2
Good
11,033 reviews
Delta
8.0
Very good
7,962 reviews

Boarding

8.2

Entertainment

7.9

Comfort

7.9

Food

7.3

Overall

8.0

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Spirit Airlines
6.3
Okay
8,070 reviews
Delta
8.0
Very good
7,962 reviews

Boarding

8.2

Entertainment

7.9

Comfort

7.9

Food

7.3

Overall

8.0

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

Related info for your journey

Find useful and relevant information for your journey from Chicago to Saint Thomas Island. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to Saint Thomas Island from Chicago?

    Saint Thomas Island Cyril E King (STT) is the airport you will fly into if you book a flight from Chicago to Saint Thomas Island. You should not have trouble finding flights to Cyril E King from Chicago; the airport handles an average of 0 inbound flights from Chicago per day. You should also have plenty of airline options to choose from since 4 airlines have flights to the Saint Thomas Island airport from Chicago. It is only a 2.8 mi journey from Cyril E King (STT) to Saint Thomas Island’s city center.

  • How long is the flight from Chicago to Saint Thomas Island?

    Departing from Chicago to Saint Thomas Island will take you 4h 48m. Airlines will cover a distance of 2116 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What are the cheapest airlines flying from Chicago to Saint Thomas Island round-trip?

    According to our current data, Spirit Airlines ($184), Delta ($359), and American Airlines ($479) offers the cheapest pricing from Chicago to Saint Thomas Island. Spirit Airlines is priced at 70% lower than the current average price of a flight leaving 3 months from now.

  • What are the cheapest flights from Chicago to Saint Thomas Island?

    Looking for the cheapest flight from Chicago to Saint Thomas Island? While on average our users pay $805, our data indicates the cheapest price to be $283. The most popular route (Chicago O'Hare Intl - Saint Thomas Island Cyril E King), is priced around $262.

  • Can I find deals for flights from Chicago to Saint Thomas Island that include hotel bookings?

    Yes. In addition to deals on Chicago to Saint Thomas Island flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Saint Thomas Island?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Saint Thomas Island.

  • Can I find deals for business class flights from Chicago to Saint Thomas Island?

    Yes. Cheapflights offers flight deals from Chicago to Saint Thomas Island by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chicago to Saint Thomas Island?

    Currently, September is the cheapest month in which you can book a flight from Chicago to Saint Thomas Island (average of $433). Flying from Chicago to Saint Thomas Island in June is currently the most expensive (average of $643). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Saint Thomas Island?

Book flights to Saint Thomas Island if you plan to visit one of these locations
St. John

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Top 4 airlines flying from Chicago to Saint Thomas Island

Discover the top 4 airlines that operate flights from Chicago to Saint Thomas Island. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated octubre 2, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$184Average$320FlexibilityNo cancel feeOn-time65%
DeltaCheapest$359Average$651FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$479Average$722FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$479Average$679FlexibilityNo cancel feeOn-time71%

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