What is the cheapest airline to fly from Chicago Midway Airport to Saint Thomas Island round-trip?

Flying on Delta is currently your cheapest option to Saint Thomas Island, with prices starting at $524. Delta is 36% cheaper than the average price of flights available within the next 90 days to this destination.

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

Currently, September is the cheapest month in which you can book a flight from Chicago Midway Airport to Saint Thomas Island (average of $433). Flying from Chicago Midway Airport to Saint Thomas Island in June is currently the most expensive (average of $640). 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 day to fly from Chicago Midway Airport to Saint Thomas Island?

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

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

Tuesday is generally a great day to depart. Flying on this day could help you save up to 121%.

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

Travelers have found it’s best to book a flight 48 days in advance to save up to 72% compared to booking the same week of travel. As your travel date approaches, the cost of this flight route may potentially increase. While opting to book 48 days out may not be an option for all, there are still additional ways to secure a deal in the near future. You might find a flight from Chicago Midway Airport to Saint Thomas Island 1-2 weeks in advance for as low as $406, or $666 for flights within the next 24 hours.

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

September is one of the best times of the year to fly to Saint Thomas Island from Chicago Midway Airport. Prices for September average $609 per person but you can even find prices for as low as $179. The most expensive prices can be found in the month of March. Opting for a September flight can save you 42% on your journey compared to booking in March

What is the cheapest time of day to fly from MDW to STT?

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Chicago Midway Airport to Saint Thomas Island as you normally would.

Most accurate provider : When it comes to deals on Chicago Midway Airport-Saint Thomas Island flights, users find the pricing of AranGrant to be most consistent on Cheapflights vs. AranGrant Users can find the same prices on Chicago Midway Airport-Saint Thomas Island flight deals on Cheapflights vs. AranGrant >95% of the time. Price accuracy is based on data collected from Chicago Midway Airport-Saint Thomas Island flight searches over the past month and is updated monthly.

Most trusted provider : When it comes to deals on Chicago Midway Airport-Saint Thomas Island flights, Cheapflights users trust AranGrant the most. AranGrant 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 Midway Airport-Saint Thomas Island flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

What airport do you fly into for flights to Saint Thomas Island from Chicago Midway?

Most people fly into Saint Thomas Island Cyril E King (STT) if they book a flight to Saint Thomas Island from Chicago Midway. On average, Cyril E King has 0 inbound flights from Chicago Midway per day from 1 airline. Saint Thomas Island Cyril E King is conveniently located just 2.8 mi from Saint Thomas Island’s city center.

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

Yes. In addition to deals on Midway to Saint Thomas Island flights, Cheapflights offers vacation packages that include both flights and hotel.

How can I find direct flights from Midway 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 Midway to Saint Thomas Island.

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

Yes. Cheapflights offers flight deals from Midway 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.

$308+ Flights from Chicago Midway Airport to Saint Thomas Island

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1. Tell us where you want to go

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Cheap flight deals from Midway to Saint Thomas Island

Most accurate provider	AranGrant 3 stars
Most trusted provider	AranGrant 3 stars
Round-trip from	$479 (Mytrip)
One-way from	$308 (Delta)
Popular in	August
Cheapest in	June
Average price	$1,100

Provider with most accurate pricing for Chicago Midway-Saint Thomas Island Cyril E King flight deals.

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Provider most trusted by Cheapflights users for Chicago Midway-Saint Thomas Island Cyril E King flights.

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From Chicago Midway to Saint Thomas Island Cyril E King

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One-way flight from Chicago Midway to Saint Thomas Island Cyril E King

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Highest demand for flights based on searches. 11% potential increase in price ($104 potential increase over avg. RT price).

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Cheapest flight prices on average. 4% potential price decrease ($39 potential savings vs. average RT price).

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Average for round-trip flights in April 2025

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Find flight deals from Midway to Saint Thomas Island

Cheapest flights from Midway to Saint Thomas Island
Explore the most affordable flight options available from Midway to Saint Thomas Island. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 15, 2025.

Fri 6/68:36 pmMDW - STT

3 stops36h 21mMultiple Airlines

Sun 6/84:35 pmSTT - MDW

2 stops22h 28mMultiple Airlines

Deal found 4/15

$479

Wed 6/256:00 amMDW - STT

1 stop7h 51mDelta

Tue 7/11:19 pmSTT - MDW

1 stop9h 26mDelta

Deal found 4/15

$524

Best flights from Midway to Saint Thomas Island
Discover carefully curated flight deals from Midway to Saint Thomas Island that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated April 15, 2025.

Fri 6/68:36 pmMDW - STT

3 stops36h 21mMultiple Airlines

Sun 6/84:35 pmSTT - MDW

2 stops22h 28mMultiple Airlines

Deal found 4/15

$479

Wed 6/256:00 amMDW - STT

1 stop7h 51mDelta

Tue 7/11:19 pmSTT - MDW

1 stop9h 26mDelta

Deal found 4/15

$524

Last-minute flights from Midway to Saint Thomas Island
Discover last-minute flight deals from Midway to Saint Thomas Island. Data last updated April 15, 2025 and is based on user searches.

Mon 4/216:04 amMDW - STT

1 stop8h 01mDelta

Sat 4/261:55 pmSTT - MDW

1 stop9h 27mDelta

Deal found 4/15

$789

Sun 5/116:00 amMDW - STT

1 stop8h 10mDelta

Wed 5/212:51 pmSTT - MDW

1 stop7h 36mDelta

Deal found 4/15

$569

Fri 5/309:12 pmMDW - STT

1 stop15h 24mMultiple Airlines

Fri 6/61:21 pmSTT - MDW

2 stops32h 32mMultiple Airlines

Deal found 4/15

$512

One-way flights from Midway to Saint Thomas Island
Search for one-way flight options from Midway to Saint Thomas Island. Find affordable one-way fares based on user searches. Data last updated April 15, 2025.

Sat 5/106:00 amMDW - STT

1 stop8h 10mDelta

Deal found 4/15

$308

Cheapflights Fare Finder

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

Fly from

Fly to

Route

Depart

Return

Price

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Fri 6/6

8:36 pm-9:57 am

3 stops36h 21m

Saint Thomas Island Cyril E King

Sun 6/8

4:35 pm-2:03 pm

2 stops22h 28m

$479

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Wed 6/25

6:00 am-2:51 pm

1 stop7h 51m

Saint Thomas Island Cyril E King

Tue 7/1

1:19 pm-9:45 pm

1 stop9h 26m

$524

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Sat 5/10

6:00 am-3:10 pm

1 stop8h 10m

$308

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/15

Compare providers for flights from Midway to Saint Thomas Island

Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Midway to Saint Thomas Island in April.

Provider	Price Accuracy	Trust Score*
Expedia	Price Accuracy1 star	Trust Score*3 stars
FlightHub	Price Accuracy3 stars	Trust Score*2 stars
AranGrant	Price Accuracy3 stars	Trust Score*3 stars
eDreams	Price Accuracy3 stars	Trust 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 Midway Airport-Saint Thomas Island flights, users find the pricing of AranGrant to be most consistent on Cheapflights vs. AranGrant Users can find the same prices on Chicago Midway Airport-Saint Thomas Island flight deals on Cheapflights vs. AranGrant >95% of the time. Price accuracy is based on data collected from Chicago Midway Airport-Saint Thomas Island flight searches over the past month and is updated monthly.
Most trusted provider: When it comes to deals on Chicago Midway Airport-Saint Thomas Island flights, Cheapflights users trust AranGrant the most. AranGrant 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 Midway Airport-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 Midway to Saint Thomas Island

Have a flexible travel schedule? Discover the best time to fly to Saint Thomas Island from Midway 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.

Reviews of airlines servicing Saint Thomas Island

Delta

8.0

Very good

7,917 reviews

Reviews

1 / 20

10.0

Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

Delta

8.0

Very good

7,917 reviews

Delta

8.0

Very good

7,917 reviews

Reviews

1 / 20

10.0

Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

Related info for your journey

What airport do you fly into for flights to Saint Thomas Island from Chicago Midway?
Most people fly into Saint Thomas Island Cyril E King (STT) if they book a flight to Saint Thomas Island from Chicago Midway. On average, Cyril E King has 0 inbound flights from Chicago Midway per day from 1 airline. Saint Thomas Island Cyril E King is conveniently located just 2.8 mi from Saint Thomas Island’s city center.
What is the cheapest airline to fly from Chicago Midway Airport to Saint Thomas Island round-trip?
Flying on Delta is currently your cheapest option to Saint Thomas Island, with prices starting at $524. Delta is 36% cheaper than the average price of flights available within the next 90 days to this destination.
Can I find deals for flights from Midway to Saint Thomas Island that include hotel bookings?
Yes. In addition to deals on Midway to Saint Thomas Island flights, Cheapflights offers vacation packages that include both flights and hotel.
How can I find direct flights from Midway 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 Midway to Saint Thomas Island.
Can I find deals for business class flights from Midway to Saint Thomas Island?
Yes. Cheapflights offers flight deals from Midway 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 Midway Airport to Saint Thomas Island?
Currently, September is the cheapest month in which you can book a flight from Chicago Midway Airport to Saint Thomas Island (average of $433). Flying from Chicago Midway Airport to Saint Thomas Island in June is currently the most expensive (average of $640). 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

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Top airline flying from Midway to Saint Thomas Island

Airline	Cheapest	Average	Flexibility	On-time
Delta	Cheapest$487	Average$802	FlexibilityNo cancel fee	On-timeN/A

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$308+ Cheap flights from Midway (MDW) 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 5/10. Fares are subject to change and may not be available on all flights or dates of travel.

Find cheap flights from Midway to Saint Thomas Island with Cheapflights

1. Tell us where you want to go

2. Select your favorite providers

3. Compare prices and book

Cheap flight deals from Midway to Saint Thomas Island

Most accurate provider

Most trusted provider

Round-trip from

One-way from

Popular in

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Find flight deals from Midway to Saint Thomas Island

Cheapest flights from Midway to Saint Thomas IslandExplore the most affordable flight options available from Midway to Saint Thomas Island. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 15, 2025.

Explore the most affordable flight options available from Midway to Saint Thomas Island. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 15, 2025.

Cheapflights Fare Finder

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

Compare providers for flights from Midway 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 Midway to Saint Thomas Island in April.

Best time to book a flight from Midway to Saint Thomas Island

Have a flexible travel schedule? Discover the best time to fly to Saint Thomas Island from Midway with our price prediction graph.

Reviews of airlines servicing Saint Thomas Island

Related info for your journey

Find useful and relevant information for your journey from Midway 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 Midway?

What is the cheapest airline to fly from Chicago Midway Airport to Saint Thomas Island round-trip?

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

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

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

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

Traveling to a place near Chicago Midway Airport?

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Alternative routes for Midway to Saint Thomas Island

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Top airline flying from Midway to Saint Thomas Island

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Cheapest flights from Midway to Saint Thomas Island
Explore the most affordable flight options available from Midway to Saint Thomas Island. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 15, 2025.