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

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

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

Flights connecting via Miami (MIA) have the shortest average one-way travel time: 6h 46m.

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 28m.

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

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

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 $147.

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 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 24% of their flights experiencing any sort of delay.

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

Historically, on average around 27% 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 133 minutes.

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 48% 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 airport is the most popular layover for flights between Chicago and Saint Thomas Island?

Miami (MIA) was the most common stop: 25% of momondo users choosing 1-stop flights on this route connected there.

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 May 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.

$175 Cheap Flights from Chicago to Saint Thomas Island in 2026

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Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Chicago to Saint Thomas Island

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

5:30 pm - 12:28 pm

ORD

STT

17h 58m

1 stop

2:29 pm - 12:25 pm

STT

ORD

22h 56m

1 stop

$360Multiple Airlines

Tue, Aug 25 - Tue, Sep 1

5:10 am - 1:23 pm

ORD

STT

7h 13m

1 stop

2:29 pm - 11:08 pm

STT

ORD

9h 39m

1 stop

$384Spirit Airlines

Sat, Aug 22 - Sat, Aug 29

5:10 am - 1:23 pm

ORD

STT

7h 13m

1 stop

2:29 pm - 11:08 pm

STT

ORD

9h 39m

1 stop

$391Spirit Airlines

Tue, Aug 25 - Tue, Sep 1

5:10 am - 1:27 pm

ORD

STT

7h 17m

1 stop

2:32 pm - 11:59 pm

STT

ORD

10h 27m

1 stop

$403Spirit Airlines

Tue, Jul 14 - Tue, Jul 21

5:10 am - 1:27 pm

ORD

STT

7h 17m

1 stop

2:32 pm - 11:59 pm

STT

ORD

10h 27m

1 stop

$404Spirit Airlines

Sat, Jul 11 - Thu, Jul 16

5:11 pm - 2:16 pm

ORD

STT

20h 05m

1 stop

3:21 pm - 10:14 pm

STT

ORD

7h 53m

1 stop

$415Multiple Airlines

Sat, May 30 - Mon, Jun 8

8:45 pm - 1:50 pm

MDW

STT

16h 05m

2 stops

2:45 pm - 9:15 pm

STT

MDW

7h 30m

1 stop

$504Southwest

Thu, Sep 24 - Thu, Oct 1

5:00 am - 1:50 pm

MDW

STT

7h 50m

1 stop

2:35 pm - 9:55 pm

STT

MDW

8h 20m

2 stops

$520Southwest

Fri, Aug 21 - Fri, Aug 28

6:00 am - 1:44 pm

MDW

STT

6h 44m

1 stop

2:54 pm - 9:46 pm

STT

MDW

7h 52m

1 stop

$580Delta

Tue, Sep 22 - Tue, Sep 29

6:00 am - 1:52 pm

MDW

STT

6h 52m

1 stop

4:10 pm - 9:46 pm

STT

MDW

6h 36m

1 stop

$585Delta

Sun, Aug 16 - Sat, Aug 29

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JetBlue flights from Chicago to Saint Thomas Island

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

JetBlue

Jul 2

ORD8:20 pmChicago O'Hare Intl

17h 03m

1 stop

STT2:23 pmSaint Thomas Island Cyril E King

Jul 10

STT2:58 pmSaint Thomas Island Cyril E King

23h 01m

2 stops

ORD12:59 pmChicago O'Hare Intl

$460

JetBlue

Aug 25

ORD6:27 pmChicago O'Hare Intl

20h 05m

2 stops

STT3:32 pmSaint Thomas Island Cyril E King

Sep 1

STT2:58 pmSaint Thomas Island Cyril E King

20h 08m

2 stops

ORD10:06 amChicago O'Hare Intl

$486

JetBlue

Aug 25

ORD6:27 pmChicago O'Hare Intl

20h 05m

2 stops

STT3:32 pmSaint Thomas Island Cyril E King

Sep 1

STT2:58 pmSaint Thomas Island Cyril E King

20h 08m

2 stops

ORD10:06 amChicago O'Hare Intl

$488

Delta flights from Chicago to Saint Thomas Island

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

Delta

Sep 22

MDW6:00 amChicago Midway

6h 44m

1 stop

STT1:44 pmSaint Thomas Island Cyril E King

Sep 29

STT2:54 pmSaint Thomas Island Cyril E King

7h 52m

1 stop

MDW9:46 pmChicago Midway

$580

Delta

Aug 16

MDW6:00 amChicago Midway

6h 52m

1 stop

STT1:52 pmSaint Thomas Island Cyril E King

Aug 29

STT3:02 pmSaint Thomas Island Cyril E King

7h 44m

1 stop

MDW9:46 pmChicago Midway

$585

Delta

Jul 9

MDW6:00 amChicago Midway

8h 20m

1 stop

STT3:20 pmSaint Thomas Island Cyril E King

Jul 13

STT3:33 pmSaint Thomas Island Cyril E King

7h 42m

1 stop

MDW10:15 pmChicago Midway

$590

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

Cheapest round-trip

ChicagoSaint Thomas Island

ORD - STT

ORDSTT

Chicago O'Hare Intl

Tue 8/25

5:30 pm-12:28 pm

1 stop17h 58m

Saint Thomas Island Cyril E King

Tue 9/1

2:29 pm-12:25 pm

1 stop22h 56m

$360

ChicagoSaint Thomas Island

ORD - STT

ORDSTT

Chicago O'Hare Intl

Sat 8/22

5:10 am-1:23 pm

1 stop7h 13m

Saint Thomas Island Cyril E King

Sat 8/29

2:29 pm-11:08 pm

1 stop9h 39m

$384

ChicagoSaint Thomas Island

ORD - STT

ORDSTT

Chicago O'Hare Intl

Tue 8/25

5:10 am-1:23 pm

1 stop7h 13m

Saint Thomas Island Cyril E King

Tue 9/1

2:29 pm-11:08 pm

1 stop9h 39m

$391

ChicagoSaint Thomas Island

ORD - STT

ORDSTT

Chicago O'Hare Intl

Tue 7/14

5:10 am-1:27 pm

1 stop7h 17m

Saint Thomas Island Cyril E King

Tue 7/21

2:32 pm-11:59 pm

1 stop10h 27m

$403

ChicagoSaint Thomas Island

ORD - STT

ORDSTT

Chicago O'Hare Intl

Sat 7/11

5:10 am-1:27 pm

1 stop7h 17m

Saint Thomas Island Cyril E King

Thu 7/16

2:32 pm-11:59 pm

1 stop10h 27m

$404

ChicagoSaint Thomas Island

ORD - STT

ORDSTT

Chicago O'Hare Intl

Sat 5/30

5:11 pm-2:16 pm

1 stop20h 05m

Saint Thomas Island Cyril E King

Mon 6/8

3:21 pm-10:14 pm

1 stop7h 53m

$415

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Thu 9/24

8:45 pm-1:50 pm

2 stops16h 05m

Saint Thomas Island Cyril E King

Thu 10/1

2:45 pm-9:15 pm

1 stop7h 30m

$504

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Fri 8/21

5:00 am-1:50 pm

1 stop7h 50m

Saint Thomas Island Cyril E King

Fri 8/28

2:35 pm-9:55 pm

2 stops8h 20m

$520

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Tue 9/22

6:00 am-1:44 pm

1 stop6h 44m

Saint Thomas Island Cyril E King

Tue 9/29

2:54 pm-9:46 pm

1 stop7h 52m

$580

Quickest round-trip

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Sun 8/16

6:00 am-1:52 pm

1 stop6h 52m

Saint Thomas Island Cyril E King

Sat 8/29

4:10 pm-9:46 pm

1 stop6h 36m

$585

Flights are sorted by cheapest round-trip flights first.

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

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 June is another great option to travel to Saint Thomas Island, with average flight prices from Chicago averaging around $88.

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 $610. 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 $772.

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 from Chicago 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 $635 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 $526 on momondo.

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

You could potentially save up to 34% on your flight if you consider stops on a Chicago to Saint Thomas Island flight.

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	$328
Fastest flight time	4h 48m
Direct flights	Mon and Sun
Airports in Saint Thomas Island	1 airport

The best one-way flight to Saint Thomas Island from Chicago in the past 72 hours is $328. The best round-trip flight deal from Chicago to Saint Thomas Island found on momondo in the last 72 hours is $684.

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

Direct flights go from Chicago to Saint Thomas Island on Monday and Sunday. There are no airlines offering direct flights.

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

Frequently asked questions about flying from Chicago to Saint Thomas Island

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 May 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 (59.81% of total bookings). The next most popular plane models are Airbus A319 (29.67%), Airbus A220-300 (2.87%), and Boeing 737-700 (1.91%).
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 36% of all bookings. The subsequent popular airlines are Spirit Airlines at 30%, United Airlines at 29%, and Delta at 5%.

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 $219	Free Cancellation	Rating 6.3 8,634 reviews	Search Spirit Airlines flights
Delta	PriceFrom $359	Free Cancellation	Rating 7.9 8,460 reviews	Search Delta flights
United Airlines	PriceFrom $376	Free Cancellation	Rating 7.4 9,683 reviews	Search United Airlines flights
American Airlines	PriceFrom $500	Free Cancellation	Rating 7.1 11,670 reviews	Search American Airlines flights

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 $175

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 5/27. 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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JetBlue flights from Chicago to Saint Thomas Island

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

Delta flights from Chicago to Saint Thomas Island

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

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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?

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?

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

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

What is the cheapest airline that flies 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?

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

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

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

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

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

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

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

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

Frequently asked questions about flying 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

Traveling to a place near Saint Thomas Island?

Why use momondo?

An easier way to manage your Saint Thomas Island trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

Find better results for your trip to the U.S. Virgin Islands

Airports servicing U.S. Virgin Islands

Fly your favorite airline to Saint Thomas Island

Airlines are sorted and displayed according to clicks in the past 7 days on momondo

Cabin classes currently available on flights to Saint Thomas Island

List of cabin classes available on flights landing in Saint Thomas Island. Availability may vary depending on flight origin and airline.

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