How long is the flight from Chicago Midway Airport to Saint Thomas Island?

Delta can get you from Chicago Midway Airport to Saint Thomas Island in just under 6h 29m. Your travel time can differ by up to . Airlines will cover a distance of 2101 mi.

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 $469.

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 eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Chicago Midway Airport-Saint Thomas Island flight deals on Cheapflights vs. eDreams >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 eDreams the most. eDreams 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.

$288+ Flights from Chicago Midway Airport to Saint Thomas Island

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Cheap 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 enero 2, 2026.

mié. 12/316:00 amMDW - STT

1 stop8h 25mDelta

mié. 1/74:15 pmSTT - MDW

1 stop7h 52mDelta

Deal found 12/30

$829

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 enero 2, 2026.

vie. 1/301:00 pmMDW - STT

1 stop23h 52mMultiple Airlines

vie. 2/65:42 pmSTT - MDW

2 stops44h 03mMultiple Airlines

Deal found 1/2

$343

mié. 4/226:30 amMDW - STT

1 stop6h 29mDelta

jue. 4/301:15 pmSTT - MDW

1 stop10h 14mDelta

Deal found 12/31

$509

vie. 3/66:15 amMDW - STT

1 stop30h 16mMultiple Airlines

mar. 3/102:36 pmSTT - MDW

1 stop28h 37mMultiple Airlines

Deal found 1/2

$507

dom. 2/226:00 amMDW - STT

1 stop7h 04mDelta

mié. 3/43:10 pmSTT - MDW

1 stop9h 21mDelta

Deal found 12/31

$509

sáb. 2/216:00 amMDW - STT

1 stop8h 22mDelta

vie. 2/274:15 pmSTT - MDW

1 stop8h 16mDelta

Deal found 12/31

$514

dom. 2/11:00 pmMDW - STT

1 stop23h 52mMultiple Airlines

jue. 2/52:22 pmSTT - MDW

2 stops9h 57mMultiple Airlines

Deal found 1/2

$548

vie. 1/306:00 amMDW - STT

1 stop8h 20mDelta

lun. 2/24:15 pmSTT - MDW

1 stop8h 07mDelta

Deal found 12/31

$559

dom. 2/86:00 amMDW - STT

1 stop7h 05mDelta

jue. 2/124:15 pmSTT - MDW

1 stop8h 16mDelta

Deal found 1/1

$570

lun. 3/306:25 amMDW - STT

1 stop7h 18mDelta

mar. 4/71:55 pmSTT - MDW

1 stop9h 36mDelta

Deal found 12/30

$584

Last-minute flights from Midway to Saint Thomas Island
Discover last-minute flight deals from Midway to Saint Thomas Island. Data last updated enero 2, 2026 and is based on user searches.

jue. 1/1511:27 amMDW - STT

1 stop25h 25mMultiple Airlines

lun. 1/193:57 pmSTT - MDW

2 stops22h 08mMultiple Airlines

Deal found 12/31

$508

jue. 1/226:00 amMDW - STT

1 stop8h 10mDelta

lun. 1/264:32 pmSTT - MDW

1 stop7h 50mDelta

Deal found 1/1

$650

sáb. 1/246:25 amMDW - STT

1 stop6h 40mDelta

dom. 2/14:15 pmSTT - MDW

1 stop8h 07mDelta

Deal found 12/31

$654

mar. 1/276:00 amMDW - STT

1 stop8h 20mDelta

mar. 2/33:10 pmSTT - MDW

1 stop9h 12mDelta

Deal found 12/30

$509

mar. 1/276:00 amMDW - STT

1 stop7h 05mDelta

jue. 2/53:10 pmSTT - MDW

1 stop9h 12mDelta

Deal found 1/1

$590

mar. 1/276:00 amMDW - STT

1 stop7h 05mDelta

mar. 2/104:15 pmSTT - MDW

1 stop8h 07mDelta

Deal found 1/1

$630

jue. 1/296:00 amMDW - STT

1 stop8h 20mDelta

jue. 2/53:10 pmSTT - MDW

1 stop9h 12mDelta

Deal found 1/1

$535

vie. 1/301:00 pmMDW - STT

1 stop23h 52mMultiple Airlines

vie. 2/65:42 pmSTT - MDW

2 stops44h 03mMultiple Airlines

Deal found 1/2

$343

vie. 1/306:00 amMDW - STT

1 stop8h 20mDelta

lun. 2/24:15 pmSTT - MDW

1 stop8h 07mDelta

Deal found 12/31

$559

vie. 1/301:00 pmMDW - STT

1 stop23h 52mMultiple Airlines

lun. 2/22:22 pmSTT - MDW

2 stops9h 57mMultiple Airlines

Deal found 1/1

$574

vie. 1/306:00 amMDW - STT

1 stop8h 20mDelta

vie. 2/63:10 pmSTT - MDW

1 stop9h 12mDelta

Deal found 1/2

$610

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 enero 2, 2026.

jue. 2/196:00 amMDW - STT

1 stop7h 04mDelta

Deal found 1/1

$288

lun. 3/232:41 pmMDW - STT

2 stops23h 47mMultiple Airlines

Deal found 12/30

$314

vie. 3/206:00 amMDW - STT

2 stops32h 28mMultiple Airlines

Deal found 12/30

$320

dom. 3/226:44 pmMDW - STT

2 stops19h 44mMultiple Airlines

Deal found 12/30

$334

sáb. 3/219:16 pmMDW - STT

3 stops41h 12mMultiple Airlines

Deal found 12/30

$359

vie. 3/206:25 amMDW - STT

1 stop7h 18mDelta

Deal found 12/30

$448

sáb. 3/286:25 amMDW - STT

1 stop7h 18mDelta

Deal found 1/2

$573

dom. 3/226:05 amMDW - STT

1 stop7h 05mSouthwest

Deal found 12/30

$598

Find flight deals from Midway to Saint Thomas Island

Most accurate provider	eDreams 3 stars
Most trusted provider	eDreams 3 stars
Round-trip from	$296 (Kiwi.com)
One-way from	$288 (Delta)
Popular in	December
Cheapest in	January
Average price	$536

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

Search Deals

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

Search Deals

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. 9% potential increase in price ($64 potential increase over avg. RT price).

Search Deals

Cheapest flight prices on average. 4% potential price decrease ($25 potential savings vs. average RT price).

Search Deals

Average for round-trip flights in January 2026

Search Deals

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

vie. 1/30

1:00 pm-2:52 pm

1 stop23h 52m

Saint Thomas Island Cyril E King

vie. 2/6

5:42 pm-11:45 am

2 stops44h 03m

$343

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

vie. 3/6

6:15 am-2:31 pm

1 stop30h 16m

Saint Thomas Island Cyril E King

mar. 3/10

2:36 pm-6:13 pm

1 stop28h 37m

$507

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

mié. 4/22

6:30 am-1:59 pm

1 stop6h 29m

Saint Thomas Island Cyril E King

jue. 4/30

1:15 pm-10:29 pm

1 stop10h 14m

$509

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

dom. 2/22

6:00 am-3:04 pm

1 stop7h 04m

Saint Thomas Island Cyril E King

mié. 3/4

3:10 pm-10:31 pm

1 stop9h 21m

$509

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

sáb. 2/21

6:00 am-4:22 pm

1 stop8h 22m

Saint Thomas Island Cyril E King

vie. 2/27

4:15 pm-10:31 pm

1 stop8h 16m

$514

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

dom. 2/1

1:00 pm-2:52 pm

1 stop23h 52m

Saint Thomas Island Cyril E King

jue. 2/5

2:22 pm-10:19 pm

2 stops9h 57m

$548

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

vie. 1/30

6:00 am-4:20 pm

1 stop8h 20m

Saint Thomas Island Cyril E King

lun. 2/2

4:15 pm-10:22 pm

1 stop8h 07m

$559

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

dom. 2/8

6:00 am-3:05 pm

1 stop7h 05m

Saint Thomas Island Cyril E King

jue. 2/12

4:15 pm-10:31 pm

1 stop8h 16m

$570

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

lun. 3/30

6:25 am-2:43 pm

1 stop7h 18m

Saint Thomas Island Cyril E King

mar. 4/7

1:55 pm-10:31 pm

1 stop9h 36m

$584

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

jue. 2/19

6:00 am-3:04 pm

1 stop7h 04m

$288

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/30

Showing 1-10 of 16 results

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 January.

Provider	Price Accuracy	Trust Score*
Expedia	Price Accuracy2 stars	Trust Score*3 stars
FlightHub	Price Accuracy3 stars	Trust Score*1 star
eDreams	Price Accuracy3 stars	Trust Score*3 stars
AranGrant	Price Accuracy2 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 eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Chicago Midway Airport-Saint Thomas Island flight deals on Cheapflights vs. eDreams >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 eDreams the most. eDreams 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.

Cheapflights Insights

Everything you need to know about your flight from Chicago Midway Airport to Saint Thomas Island

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

About 50% of weekly flights between Chicago and Saint Thomas Island have experienced delays in the past year, with the average delay time being 70 minutes.

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

Historically, flights departing in the early afternoon are less likely to be delayed, whereas flights leaving in the morning tend to experience delays more often.

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

Wednesday tends to have the lowest number of delays on this route, whereas Saturday has historically faced a higher average of delays compared to other days of the week.

Reviews of airlines servicing Saint Thomas Island

Read through reviews of airlines operating flights from Chicago Midway Airport to Saint Thomas Island, such as Delta. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.

Delta

7.9

Good

8,021 reviews

Reviews

1 / 20

6.0

Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.

Delta

7.9

Good

8,021 reviews

Delta

7.9

Good

8,021 reviews

Reviews

1 / 20

6.0

Good

Jim,Nov 2025

AVL - ATL

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.
How long is the flight from Chicago Midway Airport to Saint Thomas Island?
Delta can get you from Chicago Midway Airport to Saint Thomas Island in just under 6h 29m. Your travel time can differ by up to . Airlines will cover a distance of 2101 mi.
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 $469.
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.

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$469	Average$789	FlexibilityNo cancel fee	On-timeN/A

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$288+ 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 2/19. 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

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 enero 2, 2026.

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 enero 2, 2026.

Find flight deals from Midway to Saint Thomas Island

Most accurate provider

Most trusted provider

Round-trip from

One-way from

Popular in

Cheapest in

Average price

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 January.

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.

Cheapflights Insights

Everything you need to know about your flight from Chicago Midway Airport 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?

Reviews of airlines servicing Saint Thomas Island

Read through reviews of airlines operating flights from Chicago Midway Airport to Saint Thomas Island, such as Delta. 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 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?

How long is the flight from Chicago Midway Airport to Saint Thomas Island?

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?

Traveling to a place near Saint Thomas Island?

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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 enero 2, 2026.