Which layover airport has the shortest travel time from Chicago to Saint Thomas Island?

Flights connecting via Orlando (MCO) have the shortest average one-way travel time: 6h 50m.

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

Generally, flights departing in the early afternoon tend to experience fewer delays. Flights in the morning have, in the past, seen delays more frequently in comparison.

Which airport is the most popular layover for flights between Chicago and Saint Thomas Island?

Fort Lauderdale (FLL) was the most common stop: 30% of momondo users choosing 1-stop flights on this route connected there.

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

Tuesday is statistically the day of the week which experiences the fewest number of delays on this flight route. Monday has historically seen more delays on average compared to the rest of the week.

What airlines fly to Saint Thomas Island?

American Airlines, United Airlines and Spirit Airlines are the top three most popular airlines that fly to Saint Thomas Island from Chicago according to our data. American Airlines is the first choice among our users, with 52% of people opting to fly with this airline when traveling to Saint Thomas Island. Keep in mind that there are 4 different airlines that fly to Saint Thomas Island on a routine basis, so you have a few additional options to choose from.

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

According to our data, United Airlines have had the least number of delays on this route over the last 12 months; with about 16% of their flights experiencing any sort of delay.

How many flights depart from Chicago to Saint Thomas Island on average per day?

The number of flights available between Chicago and Saint Thomas Island is 1 per day as of February 2026. The most frequent departure time is 9:00AM, with 100% of daily flights leaving at noon.

Which layover airport has the shortest connection time from Chicago to Saint Thomas Island?

Atlanta (ATL) has the shortest average layover time for this route: 1h 01m.

How many flights depart from Chicago to Saint Thomas Island on average per week?

As of February 2026, there are 9 flights per week flying from Chicago to Saint Thomas Island. The most common day of the week flights depart is Sat, with 22% of flights taking off on this day.

Which layover airport offers the lowest fares from Chicago to Saint Thomas Island?

Flights via Fort Lauderdale (FLL) offer the lowest average round-trip price of $183.

What is the cheapest airline that flies from Chicago to Saint Thomas Island Cyril E King?

Spirit Airlines and Southwest are the most popular carriers operating from Chicago to Saint Thomas Island Cyril E King

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

Historically, on average around 20% of flights between Chicago and Saint Thomas Island have experienced a delay on any given week. The average delay length over the past 12 months has been 128 minutes.

When did momondo last update prices for flights from Chicago to Saint Thomas Island Cyril E King Airport?

Prices for flights from Chicago to Saint Thomas Island Cyril E King Airport were last updated today.

How many operators does momondo search for flights from Chicago to Saint Thomas Island Cyril E King Airport?

As of February 2026, there are 4 operators available to choose from for flights from Chicago to Saint Thomas Island Cyril E King Airport.

How old do you have to be to fly from Chicago to Saint Thomas Island Cyril E King Airport?

The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Chicago to Saint Thomas Island Cyril E King Airport.

What documentation or ID do you need to fly to Saint Thomas Island Cyril E King Airport?

The travel and health documents required for your trip to Saint Thomas Island Cyril E King Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Saint Thomas Island Cyril E King Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

$75 Cheap Flights from Chicago to Saint Thomas Island in 2026

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Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

12:44 pm - 2:31 pm

ORD

STT

23h 47m

1 stop

4:40 pm - 11:47 pm

STT

ORD

8h 07m

1 stop

$276Spirit Airlines

Fri, Mar 6 - Mon, Mar 9

6:10 pm - 1:26 pm

ORD

STT

18h 16m

2 stops

2:36 pm - 11:50 am

STT

ORD

22h 14m

3 stops

$277Spirit Airlines

Thu, Apr 9 - Mon, Apr 13

7:00 am - 4:34 pm

ORD

STT

7h 34m

1 stop

5:40 pm - 11:47 pm

STT

ORD

8h 07m

1 stop

$278Spirit Airlines

Mon, Feb 16 - Fri, Feb 20

5:15 am - 4:34 pm

ORD

STT

9h 19m

1 stop

4:40 pm - 11:47 pm

STT

ORD

8h 07m

1 stop

$279Spirit Airlines

Fri, Mar 6 - Mon, Mar 9

4:36 pm - 1:26 pm

ORD

STT

19h 50m

2 stops

2:36 pm - 11:50 am

STT

ORD

22h 14m

3 stops

$280Spirit Airlines

Tue, Mar 24 - Tue, Mar 31

8:16 pm - 2:31 pm

ORD

STT

16h 15m

2 stops

5:40 pm - 11:47 pm

STT

ORD

8h 07m

1 stop

$281Spirit Airlines

Thu, Feb 26 - Thu, Mar 5

4:36 pm - 1:26 pm

ORD

STT

19h 50m

2 stops

4:35 pm - 10:20 am

STT

ORD

18h 45m

2 stops

$283Spirit Airlines

Wed, Mar 18 - Wed, Mar 25

9:07 pm - 2:31 pm

ORD

STT

15h 24m

1 stop

5:40 pm - 6:18 pm

STT

ORD

26h 38m

2 stops

$284Multiple Airlines

Fri, Feb 20 - Mon, Feb 23

5:32 pm - 12:26 pm

ORD

STT

17h 54m

2 stops

1:21 pm - 11:41 pm

STT

ORD

11h 20m

2 stops

$285Spirit Airlines

Sat, Apr 18 - Tue, Apr 21

5:35 pm - 2:55 pm

MDW

STT

19h 20m

2 stops

1:50 pm - 8:50 pm

STT

MDW

8h 00m

1 stop

$468Southwest

Tue, Mar 3 - Tue, Mar 10

Spirit Airlines flights from Chicago to Saint Thomas Island

Our best Spirit Airlines deals on Chicago to Saint Thomas Island flight tickets

Spirit Airlines

Mar 6

ORD12:44 pmChicago O'Hare Intl

23h 47m

1 stop

STT2:31 pmSaint Thomas Island Cyril E King

Mar 9

STT4:40 pmSaint Thomas Island Cyril E King

8h 07m

1 stop

ORD11:47 pmChicago O'Hare Intl

$276

Spirit Airlines

Apr 9

ORD6:10 pmChicago O'Hare Intl

18h 16m

2 stops

STT1:26 pmSaint Thomas Island Cyril E King

Apr 13

STT2:36 pmSaint Thomas Island Cyril E King

22h 14m

3 stops

ORD11:50 amChicago O'Hare Intl

$277

Spirit Airlines

Feb 16

ORD7:00 amChicago O'Hare Intl

7h 34m

1 stop

STT4:34 pmSaint Thomas Island Cyril E King

Feb 20

STT5:40 pmSaint Thomas Island Cyril E King

8h 07m

1 stop

ORD11:47 pmChicago O'Hare Intl

$278

Southwest flights from Chicago to Saint Thomas Island

Our best Southwest deals on Chicago to Saint Thomas Island flight tickets

Southwest

Mar 3

MDW5:35 pmChicago Midway

19h 20m

2 stops

STT2:55 pmSaint Thomas Island Cyril E King

Mar 10

STT1:50 pmSaint Thomas Island Cyril E King

8h 00m

1 stop

MDW8:50 pmChicago Midway

$468

Southwest

Apr 19

MDW8:55 pmChicago Midway

15h 40m

2 stops

STT1:35 pmSaint Thomas Island Cyril E King

Apr 24

STT2:30 pmSaint Thomas Island Cyril E King

10h 00m

2 stops

MDW11:30 pmChicago Midway

$499

Southwest

Mar 3

MDW5:00 amChicago Midway

7h 55m

1 stop

STT2:55 pmSaint Thomas Island Cyril E King

Mar 10

STT1:50 pmSaint Thomas Island Cyril E King

8h 00m

1 stop

MDW8:50 pmChicago Midway

$514

momondo 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

Fri 3/6

12:44 pm-2:31 pm

1 stop23h 47m

Saint Thomas Island Cyril E King

Mon 3/9

4:40 pm-11:47 pm

1 stop8h 07m

$276

ChicagoSaint Thomas Island

ORD - STT

ORDSTT

Chicago O'Hare Intl

Thu 4/9

6:10 pm-1:26 pm

2 stops18h 16m

Saint Thomas Island Cyril E King

Mon 4/13

2:36 pm-11:50 am

3 stops22h 14m

$277

ChicagoSaint Thomas Island

ORD - STT

ORDSTT

Chicago O'Hare Intl

Mon 2/16

7:00 am-4:34 pm

1 stop7h 34m

Saint Thomas Island Cyril E King

Fri 2/20

5:40 pm-11:47 pm

1 stop8h 07m

$278

ChicagoSaint Thomas Island

ORD - STT

ORDSTT

Chicago O'Hare Intl

Fri 3/6

5:15 am-4:34 pm

1 stop9h 19m

Saint Thomas Island Cyril E King

Mon 3/9

4:40 pm-11:47 pm

1 stop8h 07m

$279

ChicagoSaint Thomas Island

ORD - STT

ORDSTT

Chicago O'Hare Intl

Tue 3/24

4:36 pm-1:26 pm

2 stops19h 50m

Saint Thomas Island Cyril E King

Tue 3/31

2:36 pm-11:50 am

3 stops22h 14m

$280

ChicagoSaint Thomas Island

ORD - STT

ORDSTT

Chicago O'Hare Intl

Thu 2/26

8:16 pm-2:31 pm

2 stops16h 15m

Saint Thomas Island Cyril E King

Thu 3/5

5:40 pm-11:47 pm

1 stop8h 07m

$281

ChicagoSaint Thomas Island

ORD - STT

ORDSTT

Chicago O'Hare Intl

Wed 3/18

4:36 pm-1:26 pm

2 stops19h 50m

Saint Thomas Island Cyril E King

Wed 3/25

4:35 pm-10:20 am

2 stops18h 45m

$283

ChicagoSaint Thomas Island

ORD - STT

ORDSTT

Chicago O'Hare Intl

Fri 2/20

9:07 pm-2:31 pm

1 stop15h 24m

Saint Thomas Island Cyril E King

Mon 2/23

5:40 pm-6:18 pm

2 stops26h 38m

$284

ChicagoSaint Thomas Island

ORD - STT

ORDSTT

Chicago O'Hare Intl

Sat 4/18

5:32 pm-12:26 pm

2 stops17h 54m

Saint Thomas Island Cyril E King

Tue 4/21

1:21 pm-11:41 pm

2 stops11h 20m

$285

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Tue 3/3

5:35 pm-2:55 pm

2 stops19h 20m

Saint Thomas Island Cyril E King

Tue 3/10

1:50 pm-8:50 pm

1 stop8h 00m

$468

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Showing 1-10 of 20 resultsSorted by cheapest first

How to get the cheapest flight ticket from Chicago to Saint Thomas Island

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

Prices

Airlines

Delays

Layovers

Other information

What is the typical price of a round-trip flight between Chicago and Saint Thomas Island?

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

The month of September is another great option to travel to Saint Thomas Island, with average flight prices from Chicago averaging around $549.

What is the cheapest day to depart on your flight to Saint Thomas Island?

On average, the least expensive day to fly to Saint Thomas Island from Chicago is on a Thursday. momondo users have found tickets for Thursday departures for as low as $609. However, this price may fluctuate depending on the airline, the season, and holidays. When flying out on a Saturday, the most expensive travel day of the week, you can expect to see flight prices from Chicago to Saint Thomas Island for around $858.

What is the cheapest Chicago to Saint Thomas Island Cyril E King flight route?

Fly from Chicago O'Hare Intl to Saint Thomas Island Cyril E King for the best Chicago - Saint Thomas Island Cyril E King flight prices

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

You are more likely to see cheaper flights to Saint Thomas Island from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to Saint Thomas Island for around $650 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Saint Thomas Island from Chicago for as low as $507 on momondo.

What cabin class options are available on Chicago to Saint Thomas Island Cyril E King flights?

There are 2 cabin classes available to choose from on Chicago to Saint Thomas Island Cyril E King flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Chicago to Saint Thomas Island flights?

You could potentially save up to 38% on your flight if you consider stops on a Chicago to Saint Thomas Island flight.

How have Chicago to Saint Thomas Island flight prices changed over time?

When to book flights from Chicago to Saint Thomas Island

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago to Saint Thomas Island according to our flight data. Find out which month and days have the cheapest flights.

Estimated round-trip price

Cheap Chicago to Saint Thomas Island (CHI to STT) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago to Saint Thomas Island

Best Price Found	$352
Fastest flight time	4h 48m
Direct flights	Every day
Airports in Saint Thomas Island	1 airport

The best one-way flight to Saint Thomas Island from Chicago in the past 72 hours is $352. The best round-trip flight deal from Chicago to Saint Thomas Island found on momondo in the last 72 hours is $606.

The fastest flight from Chicago to Saint Thomas Island takes 4h 48m

Direct flights go from Chicago to Saint Thomas Island every day.

There is 1 airport in Saint Thomas Island. From Chicago there are direct flights to Saint Thomas Island Cyril E King (STT).

Search flight deals

How far is Chicago to Saint Thomas Island Cyril E King by plane?
Chicago and Saint Thomas Island Cyril E King are 2102.2 mi apart from one another. Flights usually cover this in 4h 48m, depending on flying conditions and air traffic around both airports.
When did momondo last update prices for flights from Chicago to Saint Thomas Island Cyril E King Airport?
Prices for flights from Chicago to Saint Thomas Island Cyril E King Airport were last updated today.
How many operators does momondo search for flights from Chicago to Saint Thomas Island Cyril E King Airport?
As of February 2026, there are 4 operators available to choose from for flights from Chicago to Saint Thomas Island Cyril E King Airport.
How old do you have to be to fly from Chicago to Saint Thomas Island Cyril E King Airport?
The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Chicago to Saint Thomas Island Cyril E King Airport.
What documentation or ID do you need to fly to Saint Thomas Island Cyril E King Airport?
The travel and health documents required for your trip to Saint Thomas Island Cyril E King Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Saint Thomas Island Cyril E King Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.
What is the most popular plane model from Chicago to Saint Thomas Island?
Based on momondo bookings for this flight route, the most popular plane model on flight routes from Chicago to Saint Thomas Island is Boeing 737 MAX 8 (55.94% of total bookings). The next most popular plane models are Airbus A319 (37.90%), Airbus A320-100/200 (2.05%), and Boeing 737-800 (1.83%).
What is the most popular airline from Chicago to Saint Thomas Island?
momondo data reveals that the most frequently booked airline on the route from Chicago to Saint Thomas Island is American Airlines, representing 39% of all bookings. The subsequent popular airlines are United Airlines at 28%, Spirit Airlines at 25%, and Delta at 7%.

Best airlines flying from Chicago to Saint Thomas Island

Compare and see reviews for airlines that fly from Chicago to Saint Thomas Island with momondo

Airline	Rating	Free Cancellation	Price
Spirit Airlines	PriceFrom $176	Free Cancellation	Rating 6.3 8,407 reviews	Search Spirit Airlines flights
Delta	PriceFrom $359	Free Cancellation	Rating 7.9 8,138 reviews	Search Delta flights
United Airlines	PriceFrom $414	Free Cancellation	Rating 7.4 9,236 reviews	Search United Airlines flights
American Airlines	PriceFrom $488	Free Cancellation	Rating 7.2 11,218 reviews	Search American Airlines flights

United Airlines Flights From Chicago to Saint Thomas Island
United Airlines flight deals from Chicago to Saint Thomas Island start from $414 round-trip. Over the 6 United Airlines flights for this route in a normal week, average airfare is usually $708 round-trip - but some users have found much cheaper deals with momondo.
American Airlines Flights From Chicago to Saint Thomas Island
American Airlines is also a popular choice for this route. American Airlines flight deals for Chicago to Saint Thomas Island start from as low as $488 round-trip, depending on your selected dates, with average American Airlines deals seen on momondo around $678. American Airlines operates 3 flights to Saint Thomas Island from Chicago in an average week. Users have rated it 7.2/10 across 11,216 reviews.

St. John

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Saint Thomas Island?

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Chicago to Saint Thomas Island. Millions of users trust and use momondo every year so you are in good hands.

Can I find flights from Chicago to Saint Thomas Island with flexible booking policies on momondo?

Yes. All flights to Saint Thomas Island from Chicago on momondo can be compared and filtered by various policies on offer, including flexible booking.

How can momondo help me find flights from Chicago to Saint Thomas Island?

momondo helps you find the best flight between Chicago and Saint Thomas Island by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

I’m not ready to book a flight from Chicago to Saint Thomas Island right now. Can momondo alert me if prices change?

Yes momondo offers price alerts on flights to Saint Thomas Island from Chicago. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.

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Cheap flights from Chicago to Saint Thomas Island from $75

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to Saint Thomas Island departing on 2/25. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

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Spirit Airlines flights from Chicago to Saint Thomas Island

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

See travel insights to Saint Thomas Island from

How to get the cheapest flight ticket from Chicago to Saint Thomas Island

What is the typical price of a round-trip flight between Chicago and Saint Thomas Island?

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

The month of September is another great option to travel to Saint Thomas Island, with average flight prices from Chicago averaging around $549.

What is the cheapest day to depart on your flight to Saint Thomas Island?

What is the cheapest Chicago to Saint Thomas Island Cyril E King flight route?

Fly from Chicago O'Hare Intl to Saint Thomas Island Cyril E King for the best Chicago - Saint Thomas Island Cyril E King flight prices

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

What cabin class options are available on Chicago to Saint Thomas Island Cyril E King flights?

There are 2 cabin classes available to choose from on Chicago to Saint Thomas Island Cyril E King flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Chicago to Saint Thomas Island flights?

You could potentially save up to 38% on your flight if you consider stops on a Chicago to Saint Thomas Island flight.

How have Chicago to Saint Thomas Island flight prices changed over time?

What is the cheapest airline that flies from Chicago to Saint Thomas Island Cyril E King?

Spirit Airlines and Southwest are the most popular carriers operating from Chicago to Saint Thomas Island Cyril E King

What airlines fly to Saint Thomas Island?

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

Historically, on average around 20% of flights between Chicago and Saint Thomas Island have experienced a delay on any given week. The average delay length over the past 12 months has been 128 minutes.

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

Generally, flights departing in the early afternoon tend to experience fewer delays. Flights in the morning have, in the past, seen delays more frequently in comparison.

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

Tuesday is statistically the day of the week which experiences the fewest number of delays on this flight route. Monday has historically seen more delays on average compared to the rest of the week.

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

According to our data, United Airlines have had the least number of delays on this route over the last 12 months; with about 16% of their flights experiencing any sort of delay.

Which airport is the most popular layover for flights between Chicago and Saint Thomas Island?

Fort Lauderdale (FLL) was the most common stop: 30% of momondo users choosing 1-stop flights on this route connected there.

Which layover airport offers the lowest fares from Chicago to Saint Thomas Island?

Flights via Fort Lauderdale (FLL) offer the lowest average round-trip price of $183.

Which layover airport has the shortest travel time from Chicago to Saint Thomas Island?

Flights connecting via Orlando (MCO) have the shortest average one-way travel time: 6h 50m.

Which layover airport has the shortest connection time from Chicago to Saint Thomas Island?

Atlanta (ATL) has the shortest average layover time for this route: 1h 01m.

How many flights depart from Chicago to Saint Thomas Island on average per day?

The number of flights available between Chicago and Saint Thomas Island is 1 per day as of February 2026. The most frequent departure time is 9:00AM, with 100% of daily flights leaving at noon.

How many flights depart from Chicago to Saint Thomas Island on average per week?

As of February 2026, there are 9 flights per week flying from Chicago to Saint Thomas Island. The most common day of the week flights depart is Sat, with 22% of flights taking off on this day.

When to book flights from Chicago to Saint Thomas Island

Cheap Chicago to Saint Thomas Island (CHI to STT) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago to Saint Thomas Island

Best Price Found

Fastest flight time

Direct flights

Airports in Saint Thomas Island

How far is Chicago to Saint Thomas Island Cyril E King by plane?

When did momondo last update prices for flights from Chicago to Saint Thomas Island Cyril E King Airport?

How many operators does momondo search for flights from Chicago to Saint Thomas Island Cyril E King Airport?

How old do you have to be to fly from Chicago to Saint Thomas Island Cyril E King Airport?

What documentation or ID do you need to fly to Saint Thomas Island Cyril E King Airport?

What is the most popular plane model from Chicago to Saint Thomas Island?

What is the most popular airline from Chicago to Saint Thomas Island?

Best airlines flying from Chicago to Saint Thomas Island

Compare and see reviews for airlines that fly from Chicago to Saint Thomas Island with momondo

United Airlines Flights From Chicago to Saint Thomas Island

American Airlines Flights From Chicago to Saint Thomas Island

Traveling to a place near Saint Thomas Island?

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Saint Thomas Island?

Can I find flights from Chicago to Saint Thomas Island with flexible booking policies on momondo?