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

Flying on Frontier is currently your cheapest option to Saint Thomas Island, with prices starting at $450. Another option worth looking into is Delta, starting at $514 round trip. Frontier is 45% 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 $650). 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 24 days in advance to save up to 107% 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 24 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 $436, 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 $618 per person but you can even find prices for as low as $256. The most expensive prices can be found in the month of March. Opting for a September flight can save you 34% 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.

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.

$328+ Flights from Chicago Midway Airport to Saint Thomas Island

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

Find cheap flights from Midway to Saint Thomas Island with Cheapflights

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.

Cheap flight deals from Midway to Saint Thomas Island

Round-trip from	$389 (Mytrip)
One-way from	$328 (Delta)
Popular in	August
Cheapest in	June
Average price	$487

From Chicago Midway to Saint Thomas Island Cyril E King

Search Deals

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

Search Deals

Highest demand for flights based on searches. 18% potential increase in price ($189 potential increase over avg. RT price).

Search Deals

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

Search Deals

Average for round-trip flights in June 2025

Search Deals

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 June 12, 2025.

Fri 7/1810:31 amMDW - STT

2 stops22h 17mMultiple Airlines

Sun 7/204:05 pmSTT - MDW

2 stops22h 59mMultiple Airlines

Deal found 6/11

$389

Fri 7/256:20 amMDW - STT

2 stops9h 09mFrontier

Fri 8/15:14 pmSTT - MDW

2 stops28h 08mFrontier

Deal found 6/9

$450

Mon 11/36:00 amMDW - STT

1 stop6h 32mDelta

Wed 11/123:32 pmSTT - MDW

1 stop8h 12mDelta

Deal found 6/9

$509

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 June 12, 2025.

Fri 7/1810:31 amMDW - STT

2 stops22h 17mMultiple Airlines

Sun 7/204:05 pmSTT - MDW

2 stops22h 59mMultiple Airlines

Deal found 6/11

$389

Fri 7/256:20 amMDW - STT

2 stops9h 09mFrontier

Fri 8/15:14 pmSTT - MDW

2 stops28h 08mFrontier

Deal found 6/9

$450

Wed 8/136:04 amMDW - STT

1 stop7h 06mDelta

Mon 8/183:23 pmSTT - MDW

1 stop7h 26mDelta

Deal found 6/10

$514

Last-minute flights from Midway to Saint Thomas Island
Discover last-minute flight deals from Midway to Saint Thomas Island. Data last updated June 12, 2025 and is based on user searches.

Wed 6/186:00 amMDW - STT

1 stop6h 49mDelta

Sun 6/223:00 pmSTT - MDW

1 stop7h 45mDelta

Deal found 6/10

$1,785

Fri 7/1810:31 amMDW - STT

2 stops22h 17mMultiple Airlines

Sun 7/204:05 pmSTT - MDW

2 stops22h 59mMultiple Airlines

Deal found 6/11

$389

Fri 7/256:20 amMDW - STT

2 stops9h 09mFrontier

Fri 8/15:14 pmSTT - MDW

2 stops28h 08mFrontier

Deal found 6/9

$450

Wed 7/306:00 amMDW - STT

1 stop8h 00mDelta

Sun 8/31:27 pmSTT - MDW

1 stop9h 15mDelta

Deal found 6/12

$719

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 June 12, 2025.

Sat 7/266:00 amMDW - STT

1 stop8h 00mDelta

Deal found 6/11

$328

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 7/18

10:31 am-9:48 am

2 stops22h 17m

Saint Thomas Island Cyril E King

Sun 7/20

4:05 pm-2:04 pm

2 stops22h 59m

$389

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Fri 7/25

6:20 am-4:29 pm

2 stops9h 09m

Saint Thomas Island Cyril E King

Fri 8/1

5:14 pm-8:22 pm

2 stops28h 08m

$450

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Mon 11/3

6:00 am-2:32 pm

1 stop6h 32m

Saint Thomas Island Cyril E King

Wed 11/12

3:32 pm-9:44 pm

1 stop8h 12m

$509

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Sat 7/26

6:00 am-3:00 pm

1 stop8h 00m

$328

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/11

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

7,946 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

7,946 reviews

Delta

8.0

Very good

7,946 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!

Frontier

6.0

Okay

3,295 reviews

Delta

8.0

Very good

7,946 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 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 are the cheapest airlines flying from Chicago Midway Airport to Saint Thomas Island round-trip?
Flying on Frontier is currently your cheapest option to Saint Thomas Island, with prices starting at $450. Another option worth looking into is Delta, starting at $514 round trip. Frontier is 45% 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 $650). 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 airline flying from Midway to Saint Thomas Island

Airline	Cheapest	Average	Flexibility	On-time
Delta	Cheapest$487	Average$734	FlexibilityNo cancel fee	On-timeN/A

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.

$328+ 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 7/26. 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

Round-trip from

One-way from

Popular in

Cheapest in

Average price

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 June 12, 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 June 12, 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.

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 are the cheapest airlines flying 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?

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Midway to Saint Thomas Island

See prices for flight routes from nearby airports that may be better suited for you.

Top airline flying from Midway to Saint Thomas Island

100% Free

Book with Flexibility

Travel Smart

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 June 12, 2025.