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Saint Thomas Island

$128+ 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 1/6. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — STT
Jan 8 — Jan 151
Thu 1/8
Thu 1/15
1 adult, Economy
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Find cheap flights from Chicago to Saint Thomas Island with Cheapflights

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Cheapflights Tip: The best prices from Chicago to Saint Thomas Island Cyril E King are usually found in September or January, booked 23 days in advance, depart on a Thursday or Wednesday and return on a Wednesday

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 December 9, 2025.

This Kiwi.com deal was found by Cheapflights users on 12/6. 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.
Wed 12/313:26 pmORD - STT
1 stop18h 05mSpirit Airlines
Wed 1/712:31 pmSTT - ORD
1 stop10h 28mSpirit Airlines
Deal found 12/6$363
This Kiwi.com deal was found by Cheapflights users on 12/7. 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.
Tue 12/305:35 amORD - STT
2 stops54h 53mMultiple Airlines
Fri 1/93:57 pmSTT - ORD
1 stop29h 20mMultiple Airlines
Deal found 12/7$385
This Kiwi.com deal was found by Cheapflights users on 12/6. 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.
Tue 12/307:01 pmORD - STT
1 stop17h 27mMultiple Airlines
Wed 1/712:31 pmSTT - ORD
1 stop10h 28mMultiple Airlines
Deal found 12/6$398
This Kiwi.com deal was found by Cheapflights users on 12/6. 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.
Wed 12/313:10 pmMDW - STT
1 stop21h 18mMultiple Airlines
Fri 1/93:57 pmSTT - MDW
1 stop9h 12mMultiple Airlines
Deal found 12/6$406
This Expedia deal was found by Cheapflights users on 12/7. 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.
Sun 12/141:52 pmORD - STT
2 stops22h 57mSpirit Airlines
Thu 12/1812:31 pmSTT - ORD
1 stop8h 08mSpirit Airlines
Deal found 12/7$427
This Priceline deal was found by Cheapflights users on 12/7. 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.
Mon 12/1511:25 amORD - STT
2 stops24h 55mMultiple Airlines
Fri 12/193:23 pmSTT - ORD
2 stops11h 07mMultiple Airlines
Deal found 12/7$428
This Kiwi.com deal was found by Cheapflights users on 12/6. 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.
Wed 12/313:26 pmORD - STT
1 stop18h 05mSpirit Airlines
Thu 1/85:42 pmSTT - ORD
1 stop8h 04mSpirit Airlines
Deal found 12/6$431
This Expedia deal was found by Cheapflights users on 12/7. 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.
Sun 12/141:52 pmORD - STT
2 stops22h 57mSpirit Airlines
Fri 12/1912:31 pmSTT - ORD
1 stop13h 59mSpirit Airlines
Deal found 12/7$439
This Kiwi.com deal was found by Cheapflights users on 12/7. 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.
Tue 12/305:35 amORD - STT
2 stops54h 53mMultiple Airlines
Tue 1/612:31 pmSTT - ORD
1 stop24h 43mMultiple Airlines
Deal found 12/7$442
This Kiwi.com deal was found by Cheapflights users on 12/7. 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.
Tue 12/303:10 pmMDW - STT
1 stop21h 18mMultiple Airlines
Fri 1/93:57 pmSTT - MDW
1 stop9h 12mMultiple Airlines
Deal found 12/7$492
This Kiwi.com deal was found by Cheapflights users on 12/8. 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.
Tue 12/303:10 pmMDW - STT
1 stop21h 18mMultiple Airlines
Tue 1/612:31 pmSTT - MDW
2 stops11h 46mMultiple Airlines
Deal found 12/8$558
This Kiwi.com deal was found by Cheapflights users on 12/6. 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 12/223:10 pmMDW - STT
1 stop21h 18mMultiple Airlines
Tue 12/303:23 pmSTT - MDW
1 stop8h 35mMultiple Airlines
Deal found 12/6$583

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 December 9, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$271
(Cheapflightsfares)

One-way from

$128
(Kiwi.com)

Popular in

December

Cheapest in

September

Average price

$916

Good round-trip deal

$580 or less

Good one-way deal

$406 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. 9% potential increase in price ($69 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($25 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
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 December 9, 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

Fri 1/30

12:44 pm-2:52 pm

1 stop24h 08m

Saint Thomas Island Cyril E King

Sat 2/7

5:42 pm-11:22 am

1 stop19h 40m

$320

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Fri 1/30

1:00 pm-2:52 pm

1 stop23h 52m

Saint Thomas Island Cyril E King

Sat 2/7

3:57 pm-11:45 am

2 stops21h 48m

$324

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Sun 1/11

4:21 pm-2:52 pm

1 stop20h 31m

Saint Thomas Island Cyril E King

Thu 1/15

3:57 pm-9:09 am

1 stop19h 12m

$325

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Sat 1/31

9:38 am-2:52 pm

2 stops27h 14m

Saint Thomas Island Cyril E King

Thu 2/12

3:36 pm-7:50 pm

1 stop30h 14m

$372

ChicagoSaint Thomas Island

ORD - STT

ORDSTT

Chicago O'Hare Intl

Sat 1/17

7:20 am-4:37 pm

1 stop7h 17m

Saint Thomas Island Cyril E King

Wed 1/21

2:00 pm-5:43 pm

2 stops29h 43m

$378

ChicagoSaint Thomas Island

ORD - STT

ORDSTT

Chicago O'Hare Intl

Thu 2/12

3:33 pm-2:31 pm

2 stops20h 58m

Saint Thomas Island Cyril E King

Wed 2/25

5:40 pm-12:18 am

1 stop8h 38m

$418

ChicagoSaint Thomas Island

ORD - STT

ORDSTT

Chicago O'Hare Intl

Thu 2/12

9:30 am-4:18 pm

Nonstop4h 48m

Saint Thomas Island Cyril E King

Wed 2/25

3:05 pm-6:45 pm

Nonstop5h 40m

$500

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Tue 12/30

6:14 am-11:31 am

2 stops27h 17m

Saint Thomas Island Cyril E King

Fri 1/9

3:57 pm-11:09 pm

1 stop9h 12m

$503

ChicagoSaint Thomas Island

ORD - STT

ORDSTT

Chicago O'Hare Intl

Wed 2/18

8:14 am-2:55 pm

Nonstop4h 41m

Saint Thomas Island Cyril E King

Sun 2/22

6:36 pm-9:02 am

1 stop16h 26m

$505

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Tue 1/6

6:45 am-3:05 pm

1 stop6h 20m

Saint Thomas Island Cyril E King

Fri 1/16

4:15 pm-10:07 pm

1 stop7h 52m

$509

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/8

Showing 1-10 of 37 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 December.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars
AranGrantPrice Accuracy2 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 eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Chicago-Saint Thomas Island flight deals on Cheapflights vs. eDreams >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 eDreams the most. eDreams 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 December 5, 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, 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 $441). 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 December 9, 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.

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 50% 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.

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

About 12% of weekly flights between Chicago and Saint Thomas Island have experienced delays in the past year, with the average delay time being 138 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 9% 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 December 9, 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
7.9
Good
8,011 reviews

Comfort

7.9

Food

7.3

Crew

8.5

Entertainment

7.9

Boarding

8.1

Overall

7.9

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
8,011 reviews
Delta
7.9
Good
8,011 reviews

Comfort

7.9

Food

7.3

Crew

8.5

Entertainment

7.9

Boarding

8.1

Overall

7.9

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
9,089 reviews
Delta
7.9
Good
8,011 reviews

Comfort

7.9

Food

7.3

Crew

8.5

Entertainment

7.9

Boarding

8.1

Overall

7.9

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
7.2
Good
11,045 reviews
Delta
7.9
Good
8,011 reviews

Comfort

7.9

Food

7.3

Crew

8.5

Entertainment

7.9

Boarding

8.1

Overall

7.9

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
8,168 reviews
Delta
7.9
Good
8,011 reviews

Comfort

7.9

Food

7.3

Crew

8.5

Entertainment

7.9

Boarding

8.1

Overall

7.9

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 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 41m. 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 ($182), Delta ($359), and United Airlines ($470) offers the cheapest pricing from Chicago to Saint Thomas Island. Spirit Airlines is priced at 71% 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 ($121), 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 $530, our data indicates the cheapest price to be $323. The most popular route (Chicago O'Hare Intl - Saint Thomas Island Cyril E King), is priced around $271.

  • 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 $441). 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 December 9, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$182Average$321FlexibilityNo cancel feeOn-time65%
DeltaCheapest$359Average$695FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$475Average$730FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$479Average$677FlexibilityNo cancel feeOn-time71%

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