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Saint Thomas Island

$135+ 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 2/21. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — STT
Dec 10 — Dec 171
Wed 12/10
Wed 12/17
1 adult, Economy
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Cheap flight deals from Midway to Saint Thomas Island

Discover tips and strategies to find the most affordable flight options for your journey from Midway (MDW) to Saint Thomas Island (STT). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated November 10, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$322
(Kiwi.com)

One-way from

$135
(Kiwi.com)

Popular in

December

Cheapest in

September

Average price

$614
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. 8% potential increase in price ($57 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($24 potential savings vs. average RT price).
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Average for round-trip flights in November 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 November 10, 2025.

This Kiwi.com deal was found by Cheapflights users on 11/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/76:37 pmMDW - STT
1 stop18h 12mMultiple Airlines
Thu 12/183:23 pmSTT - MDW
1 stop8h 35mMultiple Airlines
Deal found 11/9$322
This Kiwi.com deal was found by Cheapflights users on 11/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/76:37 pmMDW - STT
1 stop18h 12mMultiple Airlines
Mon 12/153:54 pmSTT - MDW
2 stops18h 52mMultiple Airlines
Deal found 11/9$344
This Kiwi.com deal was found by Cheapflights users on 11/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/146:37 pmMDW - STT
1 stop18h 12mMultiple Airlines
Sat 12/2012:31 pmSTT - MDW
2 stops10h 33mMultiple Airlines
Deal found 11/9$349
This Kiwi.com deal was found by Cheapflights users on 11/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/58:42 pmMDW - STT
2 stops16h 07mMultiple Airlines
Thu 12/183:23 pmSTT - MDW
1 stop8h 35mMultiple Airlines
Deal found 11/9$350
This Kiwi.com deal was found by Cheapflights users on 11/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/47:23 pmMDW - STT
2 stops17h 26mMultiple Airlines
Thu 12/183:23 pmSTT - MDW
1 stop8h 35mMultiple Airlines
Deal found 11/9$376
This Kiwi.com deal was found by Cheapflights users on 11/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/58:42 pmMDW - STT
2 stops16h 07mMultiple Airlines
Mon 12/153:54 pmSTT - MDW
1 stop8h 04mMultiple Airlines
Deal found 11/9$379
This Kiwi.com deal was found by Cheapflights users on 11/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/47:23 pmMDW - STT
2 stops17h 26mMultiple Airlines
Mon 12/153:54 pmSTT - MDW
1 stop8h 04mMultiple Airlines
Deal found 11/9$406
This Kiwi.com deal was found by Cheapflights users on 11/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/172:49 pmMDW - STT
2 stops18h 42mMultiple Airlines
Sat 1/103:57 pmSTT - MDW
1 stop19h 16mMultiple Airlines
Deal found 11/9$413

Cheapflights Fare Finder

 
Customize your flight search to find flights from Midway to Saint Thomas Island that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated November 10, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to Saint Thomas Island that are best for you.

Fly from

Midway

Fly to

Saint Thomas Island

Route

Depart

Return

Price

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Sun 12/7

6:37 pm-2:49 pm

1 stop18h 12m

Saint Thomas Island Cyril E King

Mon 12/15

3:54 pm-8:46 am

2 stops18h 52m

$344

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Sun 12/14

6:37 pm-2:49 pm

1 stop18h 12m

Saint Thomas Island Cyril E King

Sat 12/20

12:31 pm-9:04 pm

2 stops10h 33m

$349

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Fri 12/5

8:42 pm-2:49 pm

2 stops16h 07m

Saint Thomas Island Cyril E King

Thu 12/18

3:23 pm-9:58 pm

1 stop8h 35m

$350

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Sun 12/7

7:27 pm-2:49 pm

2 stops17h 22m

Saint Thomas Island Cyril E King

Thu 12/18

3:23 pm-9:58 pm

1 stop8h 35m

$358

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Sat 1/3

2:16 pm-11:31 am

2 stops19h 15m

Saint Thomas Island Cyril E King

Sat 1/10

3:57 pm-9:13 am

1 stop19h 16m

$360

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Tue 1/6

6:45 am-4:10 pm

1 stop7h 25m

Saint Thomas Island Cyril E King

Fri 1/16

3:10 pm-10:09 pm

1 stop8h 59m

$509

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Thu 1/29

6:00 am-3:04 pm

1 stop7h 04m

Saint Thomas Island Cyril E King

Thu 2/5

4:15 pm-10:26 pm

1 stop8h 11m

$514

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Sun 2/1

6:00 am-3:04 pm

1 stop7h 04m

Saint Thomas Island Cyril E King

Fri 2/6

4:15 pm-10:26 pm

1 stop8h 11m

$519

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Fri 2/27

8:56 pm-2:31 pm

1 stop15h 35m

Saint Thomas Island Cyril E King

Sat 3/7

5:40 pm-10:33 am

2 stops18h 53m

$542

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Tue 3/10

6:00 am-1:55 pm

1 stop6h 55m

Saint Thomas Island Cyril E King

Wed 3/11

2:00 pm-9:46 pm

1 stop8h 46m

$569

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/7

Showing 1-10 of 18 results
1
2

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 November.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars
AranGrantPrice Accuracy2 starsTrust 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 60% of weekly flights between Chicago and Saint Thomas Island have experienced delays in the past year, with the average delay time being 68 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?

Monday 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

Get insights into the airlines that provide service to Saint Thomas Island. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Saint Thomas Island. Reviews last updated November 10, 2025.
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
8,004 reviews

Comfort

7.9

Crew

8.5

Food

7.3

Boarding

8.1

Overall

7.9

Entertainment

7.9

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
8,004 reviews
Delta
7.9
Good
8,004 reviews

Comfort

7.9

Crew

8.5

Food

7.3

Boarding

8.1

Overall

7.9

Entertainment

7.9

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.

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?

    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 $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

Traveling to a place near Saint Thomas Island?

Book flights to Saint Thomas Island if you plan to visit one of these locations
St. John

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Alternative routes for Midway to Saint Thomas Island

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Saint Thomas Island flights
O'Hare Intl to Christiansted flights

Top airline flying from Midway to Saint Thomas Island

Discover the top airline that operate flights from Midway to Saint Thomas Island. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated November 10, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$469Average$734FlexibilityNo cancel feeOn-timeN/A

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