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Saint Thomas Island

$244+ 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 7/30. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — STT
Jul 9 — Jul 161
Thu 7/9
Thu 7/16
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 May or January, booked 65 days in advance, depart on a Thursday or Wednesday and return on a Saturday

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 June 9, 2026.

This FlightHub deal was found by Cheapflights users on 6/4. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/138:10 pm
ORD
-
STT
1 stop16h 53m
JetBlue
Tue 7/212:53 pm
STT
-
ORD
2 stops20h 13m
JetBlue
Deal found 6/4$474
This FlightHub deal was found by Cheapflights users on 6/4. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/138:20 pm
ORD
-
STT
1 stop16h 43m
JetBlue
Tue 8/182:58 pm
STT
-
ORD
2 stops20h 08m
JetBlue
Deal found 6/4$486
This FlightHub deal was found by Cheapflights users on 6/6. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/308:10 pm
ORD
-
STT
1 stop16h 49m
JetBlue
Tue 8/42:58 pm
STT
-
ORD
2 stops20h 08m
JetBlue
Deal found 6/6$495
This FlightHub deal was found by Cheapflights users on 6/7. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/288:20 pm
ORD
-
STT
1 stop15h 39m
JetBlue
Sat 9/52:00 pm
STT
-
ORD
2 stops20h 59m
JetBlue
Deal found 6/7$506
This FlightHub deal was found by Cheapflights users on 6/4. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/147:00 am
ORD
-
STT
2 stops31h 17m
JetBlue
Tue 8/182:58 pm
STT
-
ORD
2 stops20h 08m
JetBlue
Deal found 6/4$519
This FlightHub deal was found by Cheapflights users on 6/8. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/38:10 pm
ORD
-
STT
1 stop16h 53m
JetBlue
Tue 8/112:58 pm
STT
-
ORD
2 stops20h 08m
JetBlue
Deal found 6/8$524
This FlightHub deal was found by Cheapflights users on 6/7. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/108:10 pm
ORD
-
STT
1 stop15h 49m
JetBlue
Tue 7/142:53 pm
STT
-
ORD
2 stops20h 13m
JetBlue
Deal found 6/7$545
This FlightHub deal was found by Cheapflights users on 6/8. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/138:10 pm
ORD
-
STT
1 stop16h 53m
JetBlue
Fri 7/172:49 pm
STT
-
ORD
2 stops22h 27m
JetBlue
Deal found 6/8$547
This American Airlines deal was found by Cheapflights users on 6/7. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/28:30 pm
ORD
-
STT
2 stops16h 45m
American Airlines
Mon 11/94:18 pm
STT
-
ORD
2 stops17h 23m
American Airlines
Deal found 6/7$548
This Delta deal was found by Cheapflights users on 6/8. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/226:05 am
MDW
-
STT
1 stop6h 39m
Delta
Tue 9/292:54 pm
STT
-
MDW
1 stop8h 31m
Delta
Deal found 6/8$580
This Delta deal was found by Cheapflights users on 6/8. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/166:05 am
MDW
-
STT
1 stop6h 29m
Delta
Sat 8/294:13 pm
STT
-
MDW
1 stop7h 23m
Delta
Deal found 6/8$585
This Delta deal was found by Cheapflights users on 6/4. 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.
Mon 8/106:05 am
MDW
-
STT
1 stop6h 29m
Delta
Thu 8/202:49 pm
STT
-
MDW
1 stop8h 47m
Delta
Deal found 6/4$650

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 June 9, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$474
(FlightHub)

One-way from

$244
(Justfly.com)

Popular in

December

Cheapest in

May

Average price

$631

Good round-trip deal

$661 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. 10% potential increase in price ($70 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($24 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in June 2026
Search Deals
Price to beat on a round-trip 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 June 9, 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

MDW - STT

MDWSTT

Chicago Midway

Mon 8/10

6:05 am-1:34 pm

1 stop6h 29m

Saint Thomas Island Cyril E King

Sat 8/22

4:13 pm-10:36 pm

1 stop7h 23m

$585

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Thu 8/13

6:05 am-1:34 pm

1 stop6h 29m

Saint Thomas Island Cyril E King

Sat 8/22

4:13 pm-10:36 pm

1 stop7h 23m

$590

ChicagoSaint Thomas Island

ORD - STT

ORDSTT

Chicago O'Hare Intl

Fri 8/28

9:40 pm-12:58 pm

2 stops14h 18m

Saint Thomas Island Cyril E King

Sat 9/5

4:45 pm-7:41 am

2 stops15h 56m

$606

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Mon 8/10

6:05 am-1:34 pm

1 stop6h 29m

Saint Thomas Island Cyril E King

Thu 8/20

2:49 pm-10:36 pm

1 stop8h 47m

$650

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Tue 8/11

6:05 am-1:34 pm

1 stop6h 29m

Saint Thomas Island Cyril E King

Wed 8/19

2:49 pm-10:36 pm

1 stop8h 47m

$650

ChicagoSaint Thomas Island

ORD - STT

ORDSTT

Chicago O'Hare Intl

Wed 8/12

5:28 am-1:34 pm

1 stop7h 06m

Saint Thomas Island Cyril E King

Thu 8/20

2:49 pm-12:02 am

1 stop10h 13m

$650

ChicagoSaint Thomas Island

ORD - STT

ORDSTT

Chicago O'Hare Intl

Tue 8/11

5:28 am-1:34 pm

1 stop7h 06m

Saint Thomas Island Cyril E King

Wed 8/19

2:49 pm-12:02 am

1 stop10h 13m

$650

ChicagoSaint Thomas Island

ORD - STT

ORDSTT

Chicago O'Hare Intl

Thu 8/13

5:28 am-1:34 pm

1 stop7h 06m

Saint Thomas Island Cyril E King

Tue 8/18

2:49 pm-8:50 pm

1 stop7h 01m

$655

ChicagoSaint Thomas Island

ORD - STT

ORDSTT

Chicago O'Hare Intl

Fri 7/10

6:35 am-3:20 pm

1 stop7h 45m

Saint Thomas Island Cyril E King

Tue 7/14

3:33 pm-11:53 pm

1 stop9h 20m

$675
Quickest round-trip

ChicagoSaint Thomas Island

ORD - STT

ORDSTT

Chicago O'Hare Intl

Sat 8/1

8:53 am-2:54 pm

Nonstop5h 01m

Saint Thomas Island Cyril E King

Sat 8/8

4:45 pm-11:31 pm

1 stop7h 46m

$680

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/8

Showing 1-10 of 38 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 June.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
AranGrantPrice Accuracy3 starsTrust Score*3 stars
JustAirTicketPrice Accuracy-Trust Score*1 star
CheapTicketsDealPrice Accuracy1 starTrust 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

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

Currently, April is the cheapest month in which you can book a flight from Chicago to Saint Thomas Island (average of $80). Flying from Chicago to Saint Thomas Island in June is currently the most expensive (average of $287). 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 June 9, 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.

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.

Orlando (MCO) – 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 $520.

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: 6h 20m.

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 1h 15m.

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

About 26% of weekly flights between Chicago and Saint Thomas Island have experienced delays in the past year, with the average delay time being 135 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?

Wednesday tends to have the lowest number of delays on this route, whereas Friday 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 24% of flights being delayed.

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

Booking 22 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.

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 June 9, 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
8,394 reviews

Crew

8.5

Food

7.2

Comfort

7.8

Overall

7.9

Entertainment

7.8

Boarding

8.1

Reviews

1 / 20
10.0
Excellent

Anonymous,May 2026

SEA - KOA

The snacks were not very good, not everyone was very friendly and professional
Delta
7.9
Good
8,394 reviews
Delta
7.9
Good
8,394 reviews

Crew

8.5

Food

7.2

Comfort

7.8

Overall

7.9

Entertainment

7.8

Boarding

8.1

Reviews

1 / 20
10.0
Excellent

Anonymous,May 2026

SEA - KOA

The snacks were not very good, not everyone was very friendly and professional
United Airlines
7.4
Good
9,796 reviews
Delta
7.9
Good
8,394 reviews

Crew

8.5

Food

7.2

Comfort

7.8

Overall

7.9

Entertainment

7.8

Boarding

8.1

Reviews

1 / 20
10.0
Excellent

Anonymous,May 2026

SEA - KOA

The snacks were not very good, not everyone was very friendly and professional
American Airlines
7.1
Good
11,640 reviews
Delta
7.9
Good
8,394 reviews

Crew

8.5

Food

7.2

Comfort

7.8

Overall

7.9

Entertainment

7.8

Boarding

8.1

Reviews

1 / 20
10.0
Excellent

Anonymous,May 2026

SEA - KOA

The snacks were not very good, not everyone was very friendly and professional

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 3 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 6h 29m. Airlines will cover a distance of 2101 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, Delta ($359), United Airlines ($376), and American Airlines ($500) offers the cheapest pricing from Chicago to Saint Thomas Island. Delta is priced at 41% 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 $870, our data indicates the cheapest price to be $580. The most popular route (Chicago O'Hare Intl - Saint Thomas Island Cyril E King), is priced around $493.

  • 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, April is the cheapest month in which you can book a flight from Chicago to Saint Thomas Island (average of $80). Flying from Chicago to Saint Thomas Island in June is currently the most expensive (average of $287). 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
Moline to Saint Thomas Island flights
Peoria to Saint Thomas Island flights

Top 3 airlines flying from Chicago to Saint Thomas Island

Discover the top 3 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 June 9, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$359Average$677FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$376Average$706FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$500Average$672FlexibilityNo cancel feeOn-time71%

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