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Saint Thomas Island

$138+ 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 2/15. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — STT
Feb 27 — Mar 61
Fri 2/27
Fri 3/6
1 adult, Economy
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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 January 28, 2026.

This Kiwi.com deal was found by Cheapflights users on 1/27. 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 2/127:30 am
MDW
-
STT
1 stop29h 01m
Multiple Airlines
Mon 2/165:40 pm
STT
-
MDW
2 stops27h 27m
Multiple Airlines
Deal found 1/27$407
This Kiwi.com deal was found by Cheapflights users on 1/27. 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.
Mon 2/21:00 pm
MDW
-
STT
1 stop23h 52m
Multiple Airlines
Wed 2/43:57 pm
STT
-
MDW
1 stop29h 55m
Multiple Airlines
Deal found 1/27$409
This Kiwi.com deal was found by Cheapflights users on 1/26. 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 2/11:00 pm
MDW
-
STT
1 stop23h 52m
Multiple Airlines
Thu 2/53:57 pm
STT
-
MDW
1 stop29h 55m
Multiple Airlines
Deal found 1/26$449
This Southwest deal was found by Cheapflights users on 1/27. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/245:00 am
MDW
-
STT
1 stop7h 55m
Southwest
Tue 3/33:55 pm
STT
-
MDW
1 stop7h 05m
Southwest
Deal found 1/27$468
This Southwest deal was found by Cheapflights users on 1/25. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/149:15 pm
MDW
-
STT
2 stops15h 20m
Southwest
Tue 5/192:10 pm
STT
-
MDW
1 stop8h 15m
Southwest
Deal found 1/25$484
This Southwest deal was found by Cheapflights users on 1/26. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/128:55 pm
MDW
-
STT
2 stops15h 40m
Southwest
Mon 4/202:30 pm
STT
-
MDW
1 stop10h 10m
Southwest
Deal found 1/26$499
This Southwest deal was found by Cheapflights users on 1/26. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/149:15 pm
MDW
-
STT
2 stops15h 20m
Southwest
Mon 5/182:30 pm
STT
-
MDW
2 stops9h 15m
Southwest
Deal found 1/26$500
This Southwest deal was found by Cheapflights users on 1/28. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/38:55 pm
MDW
-
STT
2 stops15h 40m
Southwest
Sat 5/92:05 pm
STT
-
MDW
1 stop7h 35m
Southwest
Deal found 1/28$504
This Kiwi.com deal was found by Cheapflights users on 1/26. 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.
Mon 2/97:00 pm
MDW
-
STT
1 stop17h 52m
Multiple Airlines
Thu 2/1212:01 pm
STT
-
MDW
2 stops12h 33m
Multiple Airlines
Deal found 1/26$506
This Southwest deal was found by Cheapflights users on 1/27. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/229:35 pm
MDW
-
STT
2 stops15h 20m
Southwest
Thu 2/262:10 pm
STT
-
MDW
2 stops9h 30m
Southwest
Deal found 1/27$514
This Southwest deal was found by Cheapflights users on 1/26. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/135:35 am
MDW
-
STT
1 stop7h 00m
Southwest
Mon 4/202:30 pm
STT
-
MDW
1 stop10h 10m
Southwest
Deal found 1/26$515
This Kiwi.com deal was found by Cheapflights users on 1/26. 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.
Mon 3/309:51 pm
MDW
-
STT
1 stop14h 35m
Multiple Airlines
Sun 4/54:35 pm
STT
-
MDW
2 stops30h 44m
Multiple Airlines
Deal found 1/26$519

Find 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 January 28, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$407
(Kiwi.com)

One-way from

$138
(Kiwi.com)

Popular in

December

Cheapest in

May

Average price

$556
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. 11% potential increase in price ($86 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($31 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals

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 January 28, 2026.
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

Tue 4/21

6:50 pm-1:20 pm

2 stops17h 30m

Saint Thomas Island Cyril E King

Tue 4/28

2:10 pm-7:35 am

2 stops18h 25m

$468

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Thu 5/14

9:15 pm-1:35 pm

2 stops15h 20m

Saint Thomas Island Cyril E King

Tue 5/19

2:10 pm-7:35 am

2 stops18h 25m

$484

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Thu 5/14

9:15 pm-1:35 pm

2 stops15h 20m

Saint Thomas Island Cyril E King

Mon 5/18

2:30 pm-11:40 pm

1 stop10h 10m

$484

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Sun 5/3

5:15 am-2:25 pm

1 stop8h 10m

Saint Thomas Island Cyril E King

Sat 5/9

2:05 pm-8:40 pm

1 stop7h 35m

$504

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Sun 2/22

7:30 am-2:31 pm

1 stop29h 01m

Saint Thomas Island Cyril E King

Thu 2/26

2:22 pm-10:29 pm

2 stops10h 07m

$506

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Sun 3/1

6:05 am-2:55 pm

1 stop6h 50m

Saint Thomas Island Cyril E King

Tue 3/10

1:50 pm-8:50 pm

1 stop8h 00m

$514

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Sun 2/22

9:20 pm-2:55 pm

2 stops15h 35m

Saint Thomas Island Cyril E King

Thu 2/26

2:10 pm-9:40 pm

2 stops9h 30m

$514

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Fri 4/10

5:35 am-1:35 pm

1 stop7h 00m

Saint Thomas Island Cyril E King

Wed 4/15

2:10 pm-11:05 pm

2 stops9h 55m

$514

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Sun 2/15

7:30 am-4:34 pm

2 stops31h 04m

$138

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Fri 4/10

8:30 pm-1:26 pm

1 stop15h 56m

$148

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/26

Showing 1-10 of 15 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 January.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
AranGrantPrice Accuracy2 starsTrust Score*2 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 FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago Midway Airport-Saint Thomas Island flight deals on Cheapflights vs. FlightHub >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 FlightHub the most. FlightHub 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 75% of weekly flights between Chicago and Saint Thomas Island have experienced delays in the past year, with the average delay time being 87 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.

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 0 airlines. 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?

    Southwest can get you from Chicago Midway Airport to Saint Thomas Island in just under 17h 30m. Your travel time can differ by up to . Airlines will cover a distance of 2101 mi.

  • 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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