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 American Airlines ($472) 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 is the cheapest day to fly from Chicago to Saint Thomas Island?

Travelers seeking maximum savings on their Chicago to Saint Thomas Island flight should consider departing on Wednesday afternoons when fares are most often at their lowest. Friday mornings flights should be avoided if possible as fares are typically the most expensive at this time.

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 $543, 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 $252.

What are the most popular airlines that fly from Chicago to Saint Thomas Island?

The most popular airlines flying from Chicago to Saint Thomas Island are American Airlines, Delta and Spirit Airlines. Something to consider prior to booking your flight.

What is the cheapest day to fly round-trip from Chicago to Saint Thomas Island?

It’s generally more expensive to depart on a Tuesday, if you have to leave on this day you can still search on Cheapflights to find great options that meet your needs.

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

Users have found that booking a flight from Chicago to Saint Thomas Island at least 24 days early can save you up to 119% on average compared to booking a flight this week. If booking 24 days before your flight isn’t an option for you, users have found flights from Chicago to Saint Thomas Island for as little as $436 when booking for a departure date within the next two weeks. You can also check prices now. Some users have found airline tickets as low as $631 for flights departing within the next 3 days.

What is the cheapest month to fly from Chicago to Saint Thomas Island?

Our data shows that September tends to be the cheapest month to fly to Saint Thomas Island from Chicago. Users have commonly found prices around $619 for the month, but tickets can be as low as $265. Due to multiple factors, prepare for potentially higher prices in March.

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.

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.

$112+ Cheap Flights from Chicago to Saint Thomas Island

Home Search by date Vacation packages Hotels Flight deals Car rental Travel tips & news

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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

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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

Round-trip from	$240 (FlightHub)
One-way from	$112 (Cheapflightsfares)
Popular in	March
Cheapest in	September
Average price	$573
Good round-trip deal	$510 or less
Good one-way deal	$428 or less

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. 5% potential increase in price ($37 potential increase over avg. RT price).

Search Deals

Cheapest flight prices on average. 2% potential price decrease ($15 potential savings vs. average RT price).

Search Deals

Average for round-trip flights in August 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.

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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 August 14, 2025.

Sat 10/1811:52 amORD - STT

2 stops24h 07mSpirit Airlines

Sat 10/252:01 pmSTT - ORD

2 stops10h 44mSpirit Airlines

Deal found 8/14

$240

Sun 11/166:05 amORD - STT

1 stop7h 06mSpirit Airlines

Wed 11/194:06 pmSTT - ORD

1 stop7h 17mSpirit Airlines

Deal found 8/14

$252

Wed 11/55:59 pmORD - STT

1 stop16h 29mSpirit Airlines

Tue 11/111:33 pmSTT - ORD

1 stop9h 27mSpirit Airlines

Deal found 8/12

$259

Wed 11/55:59 pmORD - STT

1 stop16h 29mSpirit Airlines

Thu 11/134:06 pmSTT - ORD

1 stop7h 17mSpirit Airlines

Deal found 8/12

$260

Wed 9/106:44 pmORD - STT

1 stop14h 00mSpirit Airlines

Sat 9/2010:49 amSTT - ORD

1 stop7h 50mSpirit Airlines

Deal found 8/14

$262

Sat 10/256:40 pmORD - STT

1 stop17h 55mSpirit Airlines

Sat 11/12:01 pmSTT - ORD

1 stop8h 32mSpirit Airlines

Deal found 8/12

$263

Sat 11/86:05 amORD - STT

1 stop7h 06mSpirit Airlines

Tue 11/111:33 pmSTT - ORD

1 stop12h 09mSpirit Airlines

Deal found 8/14

$264

Tue 11/186:00 amMDW - STT

1 stop6h 22mDelta

Thu 11/273:32 pmSTT - MDW

1 stop8h 12mDelta

Deal found 8/13

$584

Fri 9/56:00 amMDW - STT

1 stop7h 10mDelta

Thu 9/112:43 pmSTT - MDW

1 stop7h 53mDelta

Deal found 8/13

$614

Sun 11/166:00 amMDW - STT

1 stop6h 22mDelta

Wed 11/193:32 pmSTT - MDW

1 stop8h 12mDelta

Deal found 8/14

$619

Wed 9/106:00 amMDW - STT

1 stop7h 10mDelta

Sat 9/202:43 pmSTT - MDW

1 stop7h 27mDelta

Deal found 8/12

$624

Wed 9/106:00 amMDW - STT

1 stop7h 10mDelta

Wed 9/172:43 pmSTT - MDW

1 stop7h 53mDelta

Deal found 8/12

$669

Best flights from Chicago to Saint Thomas Island
Discover carefully curated flight deals from Chicago to Saint Thomas Island that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 14, 2025.

Sat 10/1811:52 amORD - STT

2 stops24h 07mSpirit Airlines

Sat 10/252:01 pmSTT - ORD

2 stops10h 44mSpirit Airlines

Deal found 8/14

$240

Sat 10/2511:52 amORD - STT

2 stops24h 43mSpirit Airlines

Sat 11/12:01 pmSTT - ORD

2 stops12h 02mSpirit Airlines

Deal found 8/14

$254

Wed 11/55:59 pmORD - STT

1 stop16h 29mSpirit Airlines

Tue 11/111:33 pmSTT - ORD

1 stop9h 27mSpirit Airlines

Deal found 8/12

$259

Fri 9/56:00 amMDW - STT

1 stop7h 10mDelta

Thu 9/112:43 pmSTT - MDW

1 stop7h 53mDelta

Deal found 8/13

$614

Wed 11/55:59 pmORD - STT

1 stop16h 29mSpirit Airlines

Sat 11/81:33 pmSTT - ORD

1 stop9h 27mSpirit Airlines

Deal found 8/14

$260

Wed 11/55:59 pmORD - STT

1 stop16h 29mSpirit Airlines

Thu 11/134:06 pmSTT - ORD

1 stop7h 17mSpirit Airlines

Deal found 8/12

$260

Sat 11/86:05 amORD - STT

1 stop7h 06mSpirit Airlines

Sat 11/151:33 pmSTT - ORD

1 stop9h 27mSpirit Airlines

Deal found 8/13

$260

Wed 11/56:05 amORD - STT

1 stop7h 06mSpirit Airlines

Wed 11/121:33 pmSTT - ORD

1 stop12h 09mSpirit Airlines

Deal found 8/13

$261

Sat 9/66:00 amMDW - STT

1 stop8h 13mDelta

Thu 9/112:43 pmSTT - MDW

1 stop7h 53mDelta

Deal found 8/13

$614

Sun 9/76:00 amMDW - STT

1 stop7h 10mDelta

Thu 9/112:43 pmSTT - MDW

1 stop7h 53mDelta

Deal found 8/13

$619

Wed 9/106:00 amMDW - STT

1 stop7h 10mDelta

Sat 9/202:43 pmSTT - MDW

1 stop7h 27mDelta

Deal found 8/12

$624

Wed 9/106:00 amMDW - STT

1 stop7h 10mDelta

Wed 9/172:43 pmSTT - MDW

1 stop7h 53mDelta

Deal found 8/12

$669

Last-minute flights from Chicago to Saint Thomas Island
Discover last-minute flight deals from Chicago to Saint Thomas Island. Data last updated August 14, 2025 and is based on user searches.

Thu 8/218:47 pmORD - STT

2 stops16h 01mSpirit Airlines

Mon 8/252:43 pmSTT - ORD

1 stop8h 39mSpirit Airlines

Deal found 8/12

$358

Thu 8/216:04 amMDW - STT

1 stop7h 06mDelta

Mon 8/253:23 pmSTT - MDW

1 stop7h 21mDelta

Deal found 8/12

$959

Fri 8/228:12 pmORD - STT

1 stop14h 01mSpirit Airlines

Tue 8/2612:18 pmSTT - ORD

1 stop12h 41mSpirit Airlines

Deal found 8/12

$386

Fri 8/226:04 amMDW - STT

1 stop7h 06mDelta

Tue 8/263:23 pmSTT - MDW

1 stop7h 21mDelta

Deal found 8/12

$794

Sat 8/2311:36 amORD - STT

2 stops25h 12mSpirit Airlines

Sat 8/302:43 pmSTT - ORD

2 stops10h 16mSpirit Airlines

Deal found 8/12

$380

Sat 8/236:04 amMDW - STT

1 stop7h 07mDelta

Sat 8/301:51 pmSTT - MDW

1 stop8h 21mDelta

Deal found 8/14

$709

Thu 9/45:17 pmORD - STT

1 stop20h 40mSpirit Airlines

Mon 9/810:49 amSTT - ORD

1 stop7h 50mSpirit Airlines

Deal found 8/14

$299

Thu 9/45:17 pmORD - STT

1 stop20h 40mSpirit Airlines

Sun 9/710:49 amSTT - ORD

1 stop25h 03mSpirit Airlines

Deal found 8/14

$307

Fri 9/56:44 pmORD - STT

1 stop14h 00mSpirit Airlines

Tue 9/910:49 amSTT - ORD

1 stop7h 50mSpirit Airlines

Deal found 8/12

$302

Fri 9/56:00 amMDW - STT

1 stop7h 10mDelta

Thu 9/112:43 pmSTT - MDW

1 stop7h 53mDelta

Deal found 8/13

$614

Sun 9/76:00 amMDW - STT

1 stop7h 10mDelta

Thu 9/112:43 pmSTT - MDW

1 stop7h 53mDelta

Deal found 8/13

$619

Wed 9/106:44 pmORD - STT

1 stop14h 00mSpirit Airlines

Sat 9/2010:49 amSTT - ORD

1 stop7h 50mSpirit Airlines

Deal found 8/14

$262

One-way flights from Chicago to Saint Thomas Island
Search for one-way flight options from Chicago to Saint Thomas Island. Find affordable one-way fares based on user searches. Data last updated August 14, 2025.

Sat 9/136:44 pmORD - STT

1 stop14h 00mSpirit Airlines

Deal found 8/14

$112

Mon 9/156:44 pmORD - STT

1 stop14h 00mSpirit Airlines

Deal found 8/14

$128

Wed 9/106:44 pmORD - STT

1 stop14h 00mSpirit Airlines

Deal found 8/14

$129

Tue 10/217:29 pmORD - STT

1 stop13h 27mSpirit Airlines

Deal found 8/13

$134

Tue 11/115:59 pmORD - STT

1 stop16h 29mSpirit Airlines

Deal found 8/14

$135

Mon 11/106:05 amORD - STT

1 stop7h 06mSpirit Airlines

Deal found 8/14

$136

Thu 9/116:44 pmORD - STT

1 stop14h 00mSpirit Airlines

Deal found 8/12

$143

Tue 10/147:29 pmORD - STT

1 stop13h 27mSpirit Airlines

Deal found 8/14

$146

Tue 10/218:05 amMDW - STT

2 stops24h 51mMultiple Airlines

Deal found 8/13

$203

Tue 10/216:00 amMDW - STT

1 stop6h 39mDelta

Deal found 8/13

$328

Cheapflights Fare Finder

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

ChicagoSaint Thomas Island

ORD - STT

ORDSTT

Chicago O'Hare Intl

Sat 10/18

11:52 am-12:59 pm

2 stops24h 07m

Saint Thomas Island Cyril E King

Sat 10/25

2:01 pm-11:45 pm

2 stops10h 44m

$240

ChicagoSaint Thomas Island

ORD - STT

ORDSTT

Chicago O'Hare Intl

Sat 10/25

11:52 am-1:35 pm

2 stops24h 43m

Saint Thomas Island Cyril E King

Sat 11/1

2:01 pm-1:03 am

2 stops12h 02m

$254

ChicagoSaint Thomas Island

ORD - STT

ORDSTT

Chicago O'Hare Intl

Wed 11/5

5:59 pm-12:28 pm

1 stop16h 29m

Saint Thomas Island Cyril E King

Tue 11/11

1:33 pm-9:00 pm

1 stop9h 27m

$259

ChicagoSaint Thomas Island

ORD - STT

ORDSTT

Chicago O'Hare Intl

Wed 11/5

5:59 pm-12:28 pm

1 stop16h 29m

Saint Thomas Island Cyril E King

Sat 11/8

1:33 pm-9:00 pm

1 stop9h 27m

$260

ChicagoSaint Thomas Island

ORD - STT

ORDSTT

Chicago O'Hare Intl

Wed 11/5

5:59 pm-12:28 pm

1 stop16h 29m

Saint Thomas Island Cyril E King

Thu 11/13

4:06 pm-9:23 pm

1 stop7h 17m

$260

ChicagoSaint Thomas Island

ORD - STT

ORDSTT

Chicago O'Hare Intl

Sat 11/8

6:05 am-3:11 pm

1 stop7h 06m

Saint Thomas Island Cyril E King

Sat 11/15

1:33 pm-9:00 pm

1 stop9h 27m

$260

ChicagoSaint Thomas Island

ORD - STT

ORDSTT

Chicago O'Hare Intl

Wed 11/5

6:05 am-3:11 pm

1 stop7h 06m

Saint Thomas Island Cyril E King

Wed 11/12

1:33 pm-11:42 pm

1 stop12h 09m

$261

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Fri 9/5

6:00 am-2:10 pm

1 stop7h 10m

Saint Thomas Island Cyril E King

Thu 9/11

2:43 pm-9:36 pm

1 stop7h 53m

$614

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Sat 9/6

6:00 am-3:13 pm

1 stop8h 13m

Saint Thomas Island Cyril E King

Thu 9/11

2:43 pm-9:36 pm

1 stop7h 53m

$614

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Sun 9/7

6:00 am-2:10 pm

1 stop7h 10m

Saint Thomas Island Cyril E King

Thu 9/11

2:43 pm-9:36 pm

1 stop7h 53m

$619

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/14

Showing 1-10 of 27 results

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?

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 $648). 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?

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?

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?

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?

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?

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

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

7,980 reviews

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

7,980 reviews

Delta

8.0

Very good

7,980 reviews

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

8,916 reviews

Delta

8.0

Very good

7,980 reviews

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

10,000 reviews

Delta

8.0

Very good

7,980 reviews

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

8,045 reviews

Delta

8.0

Very good

7,980 reviews

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

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 ($182), Delta ($359), and American Airlines ($472) 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 $543, 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 $252.
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 $648). 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

St. John

Browse thousands of different options on Cheapflights for your next trip

Top 4 airlines flying from Chicago to Saint Thomas Island

Airline	Cheapest	Average	Flexibility	On-time
Spirit Airlines	Cheapest$182	Average$304	FlexibilityNo cancel fee	On-time65%
Delta	Cheapest$359	Average$679	FlexibilityNo cancel fee	On-timeN/A
American Airlines	Cheapest$472	Average$665	FlexibilityNo cancel fee	On-time71%
United Airlines	Cheapest$479	Average$731	FlexibilityNo cancel fee	On-time69%

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$112+ 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 9/13. Fares are subject to change and may not be available on all flights or dates of travel.

Find cheap flights from Chicago to Saint Thomas Island with Cheapflights

1. Tell us where you want to go

2. Select your favorite providers

3. Compare prices and book

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

Round-trip from

One-way from

Popular in

Cheapest in

Average price

Good round-trip deal

Good one-way deal

Find flight deals from Chicago to Saint Thomas Island

Cheapest flights from Chicago to Saint Thomas IslandExplore 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 August 14, 2025.

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 August 14, 2025.

Cheapflights Fare Finder

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

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.

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 August 8, 2025.

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

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 August 14, 2025.

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.

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.

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.

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.

Reviews of airlines servicing Saint Thomas Island

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.

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?

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

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

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

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

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

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

Traveling to a place near Saint Thomas Island?

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Alternative routes for Chicago to Saint Thomas Island

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Top 4 airlines flying from Chicago to Saint Thomas Island

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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 August 14, 2025.