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Saint Thomas Island

$253+ 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 12/13. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — STT
Oct 15 — Oct 221
Wed 10/15
Wed 10/22
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 September 15, 2025.

Round-trip from

$411
(Kiwi.com)

One-way from

$253
(Kiwi.com)

Popular in

December

Cheapest in

September

Average price

$539
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. 6% potential increase in price ($41 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($21 potential savings vs. average RT price).
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Average for round-trip flights in September 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 September 15, 2025.

This Kiwi.com deal was found by Cheapflights users on 9/12. 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 10/269:26 pmMDW - STT
2 stops35h 30mMultiple Airlines
Sun 11/23:37 pmSTT - MDW
1 stop18h 55mMultiple Airlines
Deal found 9/12$411
This Kiwi.com deal was found by Cheapflights users on 9/13. 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 12/42:15 pmMDW - STT
1 stop22h 56mMultiple Airlines
Thu 12/111:33 pmSTT - MDW
2 stops11h 32mMultiple Airlines
Deal found 9/13$418
This Kiwi.com deal was found by Cheapflights users on 9/14. 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 11/262:11 pmMDW - STT
2 stops20h 17mMultiple Airlines
Wed 12/34:06 pmSTT - MDW
1 stop23h 04mMultiple Airlines
Deal found 9/14$478
This Kiwi.com deal was found by Cheapflights users on 9/14. 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 12/72:15 pmMDW - STT
1 stop22h 56mMultiple Airlines
Fri 12/129:49 amSTT - MDW
2 stops12h 49mMultiple Airlines
Deal found 9/14$500
This Kiwi.com deal was found by Cheapflights users on 9/12. 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 12/72:15 pmMDW - STT
1 stop22h 56mMultiple Airlines
Sun 12/145:28 pmSTT - MDW
2 stops29h 10mMultiple Airlines
Deal found 9/12$542
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 9/2810:13 amMDW - STT
1 stop27h 44mMultiple Airlines
Wed 10/15:45 pmSTT - MDW
2 stops14h 26mMultiple Airlines
Deal found 9/15$624
This Delta deal was found by Cheapflights users on 9/14. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/186:00 amMDW - STT
1 stop7h 50mDelta
Sat 10/254:00 pmSTT - MDW
1 stop7h 14mDelta
Deal found 9/14$659
This Delta deal was found by Cheapflights users on 9/14. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/166:00 amMDW - STT
1 stop6h 40mDelta
Wed 11/193:50 pmSTT - MDW
1 stop9h 42mDelta
Deal found 9/14$689
This Delta deal was found by Cheapflights users on 9/14. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/156:00 amMDW - STT
1 stop7h 40mDelta
Sat 11/223:50 pmSTT - MDW
1 stop9h 42mDelta
Deal found 9/14$779
This Delta deal was found by Cheapflights users on 9/15. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/286:00 amMDW - STT
1 stop6h 33mDelta
Wed 10/12:43 pmSTT - MDW
1 stop7h 53mDelta
Deal found 9/15$809
This Delta deal was found by Cheapflights users on 9/14. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/136:00 amMDW - STT
1 stop7h 36mDelta
Sat 12/203:10 pmSTT - MDW
1 stop9h 06mDelta
Deal found 9/14$964

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 September 15, 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

Thu 12/4

2:15 pm-3:11 pm

1 stop22h 56m

Saint Thomas Island Cyril E King

Thu 12/11

1:33 pm-11:05 pm

2 stops11h 32m

$418

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Sun 12/7

2:15 pm-3:11 pm

1 stop22h 56m

Saint Thomas Island Cyril E King

Fri 12/12

9:49 am-8:38 pm

2 stops12h 49m

$500

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Sun 12/7

2:15 pm-3:11 pm

1 stop22h 56m

Saint Thomas Island Cyril E King

Sun 12/14

5:28 pm-8:38 pm

2 stops29h 10m

$542

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Sun 9/28

10:13 am-2:57 pm

1 stop27h 44m

Saint Thomas Island Cyril E King

Wed 10/1

5:45 pm-7:11 am

2 stops14h 26m

$624

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Sat 10/18

6:00 am-2:50 pm

1 stop7h 50m

Saint Thomas Island Cyril E King

Sat 10/25

4:00 pm-10:14 pm

1 stop7h 14m

$659

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Sun 11/16

6:00 am-2:40 pm

1 stop6h 40m

Saint Thomas Island Cyril E King

Wed 11/19

3:50 pm-11:32 pm

1 stop9h 42m

$689

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Fri 11/28

6:00 am-2:40 pm

1 stop6h 40m

Saint Thomas Island Cyril E King

Wed 12/3

3:54 pm-11:32 pm

1 stop9h 38m

$779

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Thu 10/2

6:00 am-1:33 pm

1 stop6h 33m

Saint Thomas Island Cyril E King

Mon 10/6

2:49 pm-10:14 pm

1 stop8h 25m

$779

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Sat 11/15

6:00 am-3:40 pm

1 stop7h 40m

Saint Thomas Island Cyril E King

Sat 11/22

3:50 pm-11:32 pm

1 stop9h 42m

$779

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Sun 9/28

6:00 am-1:33 pm

1 stop6h 33m

Saint Thomas Island Cyril E King

Wed 10/1

2:43 pm-9:36 pm

1 stop7h 53m

$809

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/14

Showing 1-10 of 20 results
1
2

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

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 September 15, 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
8.0
Very good
7,954 reviews

Boarding

8.2

Comfort

7.9

Overall

8.0

Crew

8.5

Food

7.3

Entertainment

7.9

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
7,954 reviews
Delta
8.0
Very good
7,954 reviews

Boarding

8.2

Comfort

7.9

Overall

8.0

Crew

8.5

Food

7.3

Entertainment

7.9

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

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 $487.

  • 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 $643). 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

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

Browse thousands of different options on Cheapflights for your next trip

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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 September 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$487Average$647FlexibilityNo cancel feeOn-timeN/A

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