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Saint Thomas Island

$131+ 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 4/9. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — STT
Apr 23 — Apr 301
Thu 4/23
Thu 4/30
1 adult, Economy
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Find cheap flights from Chicago to Saint Thomas Island with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

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3. Compare prices and book

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Cheapflights Tip: The best prices from Chicago to Saint Thomas Island Cyril E King are usually found in May or January, booked 34 days in advance, depart on a Thursday or Wednesday and return on a Tuesday

Cheap 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 March 24, 2026.

This CheapOair deal was found by Cheapflights users on 3/23. 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.
Fri 4/105:05 am
ORD
-
STT
1 stop9h 23m
Spirit Airlines
Tue 4/144:35 pm
STT
-
ORD
1 stop18h 01m
Spirit Airlines
Deal found 3/23$281
This Kiwi.com deal was found by Cheapflights users on 3/19. 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.
Thu 4/25:05 am
ORD
-
STT
1 stop9h 23m
Multiple Airlines
Wed 4/84:35 pm
STT
-
ORD
1 stop31h 15m
Multiple Airlines
Deal found 3/19$293
This CheapOair deal was found by Cheapflights users on 3/20. 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.
Fri 4/36:10 pm
ORD
-
STT
1 stop20h 18m
Spirit Airlines
Tue 4/74:35 pm
STT
-
ORD
1 stop28h 16m
Spirit Airlines
Deal found 3/20$297
This CheapOair deal was found by Cheapflights users on 3/24. 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.
Tue 4/145:05 am
ORD
-
STT
1 stop9h 23m
Spirit Airlines
Tue 4/215:10 pm
STT
-
ORD
1 stop17h 26m
Spirit Airlines
Deal found 3/24$299
This Expedia deal was found by Cheapflights users on 3/19. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/215:05 am
ORD
-
STT
1 stop10h 10m
Spirit Airlines
Tue 4/285:10 pm
STT
-
ORD
1 stop8h 14m
Spirit Airlines
Deal found 3/19$302
This CheapOair deal was found by Cheapflights users on 3/20. 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 4/47:17 am
ORD
-
STT
1 stop7h 11m
Spirit Airlines
Wed 4/84:35 pm
STT
-
ORD
1 stop7h 42m
Spirit Airlines
Deal found 3/20$304
This Cheapflightsfares deal was found by Cheapflights users on 3/23. 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.
Sat 4/187:15 pm
ORD
-
STT
1 stop15h 15m
Spirit Airlines
Wed 4/225:10 pm
STT
-
ORD
1 stop8h 14m
Spirit Airlines
Deal found 3/23$315
This CheapOair deal was found by Cheapflights users on 3/23. 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.
Mon 4/205:05 am
ORD
-
STT
1 stop10h 10m
Spirit Airlines
Thu 4/2312:25 pm
STT
-
ORD
1 stop12h 59m
Spirit Airlines
Deal found 3/23$317
This Kiwi.com deal was found by Cheapflights users on 3/19. 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.
Sun 4/262:00 pm
MDW
-
STT
1 stop18h 54m
Multiple Airlines
Sat 5/210:49 am
STT
-
MDW
2 stops12h 25m
Multiple Airlines
Deal found 3/19$374
This Kiwi.com deal was found by Cheapflights users on 3/23. 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.
Mon 4/136:00 am
MDW
-
STT
2 stops30h 26m
Multiple Airlines
Fri 4/2410:49 am
STT
-
MDW
1 stop8h 05m
Multiple Airlines
Deal found 3/23$376
This Kiwi.com deal was found by Cheapflights users on 3/19. 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.
Sun 4/262:00 pm
MDW
-
STT
1 stop18h 54m
Multiple Airlines
Fri 5/112:25 pm
STT
-
MDW
2 stops11h 01m
Multiple Airlines
Deal found 3/19$391
This Kiwi.com deal was found by Cheapflights users on 3/19. 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.
Thu 4/25:01 am
MDW
-
STT
1 stop7h 25m
Multiple Airlines
Tue 4/74:35 pm
STT
-
MDW
2 stops28h 32m
Multiple Airlines
Deal found 3/19$402

Find 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 March 24, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$281
(CheapOair)

One-way from

$131
(CheapOair)

Popular in

December

Cheapest in

May

Average price

$683

Good round-trip deal

$598 or less

Good one-way deal

$318 or less
Provider with most accurate pricing for Chicago (CHI)-Saint Thomas Island Cyril E King flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Saint Thomas Island Cyril E King flights.
Search Deals
From Chicago (CHI) to Saint Thomas Island Cyril E King
Search Deals
One-way flight from Chicago (CHI) to Saint Thomas Island Cyril E King
Search Deals
Highest demand for flights based on searches. 14% potential increase in price ($106 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($35 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 2026
Search Deals
Price to beat on a round-trip flight from Chicago (CHI) to Saint Thomas Island Cyril E King.
Search Deals
Price to beat on a one-way flight from Chicago (CHI) to Saint Thomas Island Cyril E King.
Search Deals

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 March 24, 2026.
Use the filters below to find and compare flights from Chicago to Saint Thomas Island that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoSaint Thomas Island

ORD - STT

ORDSTT

Chicago O'Hare Intl

Tue 4/21

9:30 am-3:31 pm

Nonstop5h 01m

Saint Thomas Island Cyril E King

Tue 4/28

1:22 pm-8:37 pm

1 stop8h 15m

$576

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Mon 7/13

6:05 am-3:20 pm

1 stop8h 15m

Saint Thomas Island Cyril E King

Tue 7/21

1:21 pm-10:15 pm

1 stop9h 54m

$580

ChicagoSaint Thomas Island

ORD - STT

ORDSTT

Chicago O'Hare Intl

Fri 4/17

9:30 am-3:31 pm

Nonstop5h 01m

Saint Thomas Island Cyril E King

Fri 4/24

4:45 pm-11:43 pm

1 stop7h 58m

$601

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Sat 5/2

5:40 am-2:48 pm

1 stop8h 08m

Saint Thomas Island Cyril E King

Tue 5/12

1:16 pm-9:09 pm

1 stop8h 53m

$605

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Fri 5/8

5:35 am-1:35 pm

1 stop7h 00m

Saint Thomas Island Cyril E King

Tue 5/12

2:10 pm-9:50 pm

2 stops8h 40m

$614

ChicagoSaint Thomas Island

ORD - STT

ORDSTT

Chicago O'Hare Intl

Mon 4/27

10:55 pm-12:20 pm

2 stops12h 25m

Saint Thomas Island Cyril E King

Thu 4/30

2:10 pm-7:26 am

2 stops18h 16m

$632

ChicagoSaint Thomas Island

ORD - STT

ORDSTT

Chicago O'Hare Intl

Thu 4/16

9:30 am-3:31 pm

Nonstop5h 01m

Saint Thomas Island Cyril E King

Tue 4/21

1:22 pm-8:37 pm

1 stop8h 15m

$634
Quickest round-trip

ChicagoSaint Thomas Island

ORD - STT

ORDSTT

Chicago O'Hare Intl

Mon 4/20

9:30 am-3:31 pm

Nonstop5h 01m

Saint Thomas Island Cyril E King

Thu 4/23

2:10 pm-6:44 pm

Nonstop5h 34m

$641

ChicagoSaint Thomas Island

ORD - STT

ORDSTT

Chicago O'Hare Intl

Sun 4/19

9:30 am-3:31 pm

Nonstop5h 01m

Saint Thomas Island Cyril E King

Sun 4/26

2:10 pm-6:44 pm

Nonstop5h 34m

$662

ChicagoSaint Thomas Island

ORD - STT

ORDSTT

Chicago O'Hare Intl

Sat 5/16

10:59 am-5:00 pm

Nonstop5h 01m

Saint Thomas Island Cyril E King

Sat 5/23

4:45 pm-11:26 pm

1 stop7h 41m

$676

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/21

Showing 1-10 of 39 resultsSorted by cheapest first
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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 March.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
AranGrantPrice Accuracy2 starsTrust Score*2 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 13, 2026.

Booking 34 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, June is the cheapest month in which you can book a flight from Chicago to Saint Thomas Island (average of $171). Flying from Chicago to Saint Thomas Island in December is currently the most expensive (average of $438). 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 March 24, 2026.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Chicago to Saint Thomas Island as you normally would.

Weekly flight availability from Chicago to Saint Thomas Island

Explore weekly flight availability from Chicago to Saint Thomas Island. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated March 24, 2026.

The most flights from CHI to STT are scheduled on a Monday (2 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (2 on average).

How often are flights from Chicago to Saint Thomas Island delayed?

About 21% of weekly flights between Chicago and Saint Thomas Island have experienced delays in the past year, with the average delay time being 131 minutes.

What is the most punctual flight time for Chicago to Saint Thomas Island flights?

Historically, flights departing in the early afternoon are less likely to be delayed, whereas flights leaving in the morning tend to experience delays more often.

What day of the week experiences the fewest flight delays on this route?

Tuesday tends to have the lowest number of delays on this route, whereas Monday has historically faced a higher average of delays compared to other days of the week.

Which airline has the best punctuality record on Chicago to Saint Thomas Island flights?

Over the last year, United Airlines have had the lowest number of delays on this route, with just 18% of flights being delayed.

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 March 24, 2026.
Read through reviews of airlines operating flights from Chicago to Saint Thomas Island, such as Delta,United Airlines, andAmerican Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Delta
7.9
Good
8,321 reviews

Boarding

8.1

Food

7.2

Overall

7.9

Comfort

7.9

Crew

8.5

Entertainment

7.8

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Delta
7.9
Good
8,321 reviews
Delta
7.9
Good
8,321 reviews

Boarding

8.1

Food

7.2

Overall

7.9

Comfort

7.9

Crew

8.5

Entertainment

7.8

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
United Airlines
7.4
Good
9,470 reviews
Delta
7.9
Good
8,321 reviews

Boarding

8.1

Food

7.2

Overall

7.9

Comfort

7.9

Crew

8.5

Entertainment

7.8

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
American Airlines
7.1
Good
11,491 reviews
Delta
7.9
Good
8,321 reviews

Boarding

8.1

Food

7.2

Overall

7.9

Comfort

7.9

Crew

8.5

Entertainment

7.8

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Spirit Airlines
6.3
Okay
8,535 reviews
Delta
7.9
Good
8,321 reviews

Boarding

8.1

Food

7.2

Overall

7.9

Comfort

7.9

Crew

8.5

Entertainment

7.8

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.

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 2 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 5h 01m. 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 ($173), Delta ($359), and United Airlines ($376) offers the cheapest pricing from Chicago to Saint Thomas Island. Spirit Airlines is priced at 72% 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 ($136), American Airlines ($278), and United Airlines ($283).

  • 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 $525, our data indicates the cheapest price to be $304. The most popular route (Chicago O'Hare Intl - Saint Thomas Island Cyril E King), is priced around $281.

  • 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, June is the cheapest month in which you can book a flight from Chicago to Saint Thomas Island (average of $171). Flying from Chicago to Saint Thomas Island in December is currently the most expensive (average of $438). 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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Alternative routes for Chicago to Saint Thomas Island

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Saint Thomas Island flights
St. Louis to Saint Thomas Island flights
Peoria to Saint Thomas Island flights
Moline to Saint Thomas Island flights

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 March 24, 2026.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$173Average$337FlexibilityNo cancel feeOn-time65%
DeltaCheapest$359Average$590FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$376Average$708FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$500Average$675FlexibilityNo cancel feeOn-time71%

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