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Saint Thomas Island

$117+ 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 5/17. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — STT
Apr 6 — Apr 131
Sun 4/6
Sun 4/13
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 August, booked 46 days in advance, depart on a Wednesday or Sunday and return on a Wednesday

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 April 1, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$265
(CheapOair)

One-way from

$117
(Mytrip)

Popular in

March

Cheapest in

September

Average price

$537

Good round-trip deal

$736 or less

Good one-way deal

$398 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 ($44 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($18 potential savings vs. average RT price).
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Average for round-trip flights in April 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 April 1, 2025.

This CheapOair deal was found by Cheapflights users on 3/30. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/2611:45 amORD - STT
2 stops21h 15mSpirit Airlines
Sat 5/311:05 amSTT - ORD
1 stop14h 53mSpirit Airlines
Deal found 3/30$265
This Mytrip deal was found by Cheapflights users on 3/30. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/198:20 pmORD - STT
3 stops36h 40mMultiple Airlines
Sat 4/2612:29 pmSTT - ORD
2 stops21h 06mMultiple Airlines
Deal found 3/30$377
This American Airlines deal was found by Cheapflights users on 3/31. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/105:29 amORD - STT
1 stop8h 51mAmerican Airlines
Wed 6/181:44 pmSTT - ORD
1 stop9h 44mAmerican Airlines
Deal found 3/31$479
This United Airlines deal was found by Cheapflights users on 3/31. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/99:20 pmORD - STT
2 stops13h 55mUnited Airlines
Mon 5/122:10 pmSTT - ORD
1 stop10h 34mUnited Airlines
Deal found 3/31$533
This Delta deal was found by Cheapflights users on 3/31. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/245:45 amORD - STT
1 stop8h 06mDelta
Fri 6/273:00 pmSTT - ORD
1 stop7h 30mDelta
Deal found 3/31$544
This Delta deal was found by Cheapflights users on 3/31. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/236:00 amMDW - STT
1 stop6h 55mDelta
Sat 8/301:21 pmSTT - MDW
1 stop9h 26mDelta
Deal found 3/31$669

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 April 1, 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

Sat 4/26

11:45 am-10:00 am

2 stops21h 15m

Saint Thomas Island Cyril E King

Sat 5/3

11:05 am-12:58 am

1 stop14h 53m

$265

ChicagoSaint Thomas Island

ORD - STT

ORDSTT

Chicago O'Hare Intl

Sat 4/19

8:20 pm-10:00 am

3 stops36h 40m

Saint Thomas Island Cyril E King

Sat 4/26

12:29 pm-8:35 am

2 stops21h 06m

$377

ChicagoSaint Thomas Island

ORD - STT

ORDSTT

Chicago O'Hare Intl

Tue 6/10

5:29 am-3:20 pm

1 stop8h 51m

Saint Thomas Island Cyril E King

Wed 6/18

1:44 pm-10:28 pm

1 stop9h 44m

$479

ChicagoSaint Thomas Island

ORD - STT

ORDSTT

Chicago O'Hare Intl

Fri 5/9

9:20 pm-12:15 pm

2 stops13h 55m

Saint Thomas Island Cyril E King

Mon 5/12

2:10 pm-11:44 pm

1 stop10h 34m

$533

ChicagoSaint Thomas Island

ORD - STT

ORDSTT

Chicago O'Hare Intl

Tue 6/24

5:45 am-2:51 pm

1 stop8h 06m

Saint Thomas Island Cyril E King

Fri 6/27

3:00 pm-9:30 pm

1 stop7h 30m

$544

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Fri 6/6

6:00 am-3:10 pm

1 stop8h 10m

Saint Thomas Island Cyril E King

Thu 6/12

3:00 pm-9:38 pm

1 stop7h 38m

$669

ChicagoSaint Thomas Island

ORD - STT

ORDSTT

Chicago O'Hare Intl

Sat 5/17

5:05 am-2:54 pm

1 stop8h 49m

$117

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Fri 5/16

6:00 am-3:10 pm

1 stop8h 10m

$268

ChicagoSaint Thomas Island

ORD - STT

ORDSTT

Chicago O'Hare Intl

Thu 7/17

7:10 am-3:01 pm

1 stop6h 51m

$268

ChicagoSaint Thomas Island

ORD - STT

ORDSTT

Chicago O'Hare Intl

Sun 5/25

8:17 pm-10:55 am

2 stops13h 38m

$274

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/31

Showing 1-10 of 11 results
1
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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 April.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
AranGrantPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars
FlightnetworkPrice Accuracy-Trust 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 March 28, 2025.

Booking 46 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 $640). 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 April 1, 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.

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 April 1, 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
7,898 reviews

Entertainment

7.9

Comfort

7.9

Crew

8.5

Boarding

8.2

Food

7.3

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
Delta
8.0
Very good
7,898 reviews
Delta
8.0
Very good
7,898 reviews

Entertainment

7.9

Comfort

7.9

Crew

8.5

Boarding

8.2

Food

7.3

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
United Airlines
7.4
Good
8,615 reviews
Delta
8.0
Very good
7,898 reviews

Entertainment

7.9

Comfort

7.9

Crew

8.5

Boarding

8.2

Food

7.3

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,898 reviews

Entertainment

7.9

Comfort

7.9

Crew

8.5

Boarding

8.2

Food

7.3

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
Spirit Airlines
6.3
Okay
7,885 reviews
Delta
8.0
Very good
7,898 reviews

Entertainment

7.9

Comfort

7.9

Crew

8.5

Boarding

8.2

Food

7.3

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

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.

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

    According to our current data, Spirit Airlines ($265), American Airlines ($479), and United Airlines ($533) offers the cheapest pricing from Chicago to Saint Thomas Island. Spirit Airlines is priced at 56% lower than the current average price of a flight leaving 3 months from now.

  • What are the cheapest airlines to fly from Chicago to Saint Thomas Island one-way?

    The cheapest airlines for a one-way flight from Chicago to Saint Thomas Island are Spirit Airlines ($117), Delta ($268), and American Airlines ($274).

  • 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 $670, our data indicates the cheapest price to be $303. The most popular route (Chicago O'Hare Intl - Saint Thomas Island Cyril E King), is priced around $243.

  • 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 $640). 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

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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 April 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$189Average$331FlexibilityNo cancel feeOn-time65%
DeltaCheapest$402Average$734FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$463Average$650FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$483Average$755FlexibilityNo cancel feeOn-time69%

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