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Castries

$503+ Cheap flights from Midway (MDW) to Castries (UVF)

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 2/12. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — UVF
Feb 11 — Feb 181
Wed 2/11
Wed 2/18
1 adult, Economy
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Cheap flight deals from Midway to Castries

Discover tips and strategies to find the most affordable flight options for your journey from Midway (MDW) to Castries (UVF). 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 12, 2026.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$683
(Kiwi.com)

One-way from

$503
(Delta)

Popular in

December

Cheapest in

September
Provider with most accurate pricing for Chicago Midway-Castries Hewanorra flight deals.
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Provider most trusted by Cheapflights users for Chicago Midway-Castries Hewanorra flights.
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From Chicago Midway to Castries Hewanorra
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One-way flight from Chicago Midway to Castries Hewanorra
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Highest demand for flights based on searches. 33% potential increase in price ($417 potential increase over avg. RT price).
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Cheapest flight prices on average. 11% potential price decrease ($88 potential savings vs. average RT price).
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Find flight deals from Midway to Castries

Cheapest flights from Midway to Castries
Explore the most affordable flight options available from Midway to Castries. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 12, 2026.

This Delta deal was found by Cheapflights users on 1/10. 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.
Tue 8/46:00 am
MDW
-
UVF
1 stop7h 13m
Delta
Thu 8/63:30 pm
UVF
-
MDW
2 stops18h 12m
Delta
Deal found 1/10$631
This Delta deal was found by Cheapflights users on 1/10. 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.
Tue 8/49:30 am
MDW
-
UVF
2 stops27h 43m
Delta
Fri 8/73:30 pm
UVF
-
MDW
2 stops28h 01m
Delta
Deal found 1/10$677
This Kiwi.com deal was found by Cheapflights users on 1/10. 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.
Sat 4/2512:45 pm
MDW
-
UVF
1 stop23h 59m
Multiple Airlines
Thu 4/302:35 pm
UVF
-
MDW
1 stop19h 10m
Multiple Airlines
Deal found 1/10$683
This Delta deal was found by Cheapflights users on 1/10. 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.
Wed 7/291:00 pm
MDW
-
UVF
2 stops24h 13m
Delta
Thu 8/63:30 pm
UVF
-
MDW
2 stops22h 00m
Delta
Deal found 1/10$691
This Delta deal was found by Cheapflights users on 1/10. 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 8/11:00 pm
MDW
-
UVF
2 stops24h 13m
Delta
Thu 8/63:30 pm
UVF
-
MDW
2 stops22h 00m
Delta
Deal found 1/10$716
This Kiwi.com deal was found by Cheapflights users on 1/12. 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.
Wed 5/135:20 pm
MDW
-
UVF
1 stop19h 20m
Multiple Airlines
Sun 5/172:35 pm
UVF
-
MDW
1 stop26h 49m
Multiple Airlines
Deal found 1/12$739
This Kiwi.com deal was found by Cheapflights users on 1/11. 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 4/2211:00 am
MDW
-
UVF
1 stop25h 46m
Multiple Airlines
Sun 4/262:35 pm
UVF
-
MDW
1 stop20h 30m
Multiple Airlines
Deal found 1/11$747
This Delta deal was found by Cheapflights users on 1/10. 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 8/19:30 am
MDW
-
UVF
2 stops27h 43m
Delta
Fri 8/73:30 pm
UVF
-
MDW
2 stops22h 00m
Delta
Deal found 1/10$762
This Delta deal was found by Cheapflights users on 1/12. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 1/286:00 am
MDW
-
UVF
1 stop7h 05m
Delta
Mon 2/94:25 pm
UVF
-
MDW
2 stops22h 21m
Delta
Deal found 1/12$767
This Delta deal was found by Cheapflights users on 1/12. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/291:26 pm
MDW
-
UVF
2 stops23h 39m
Delta
Mon 2/94:25 pm
UVF
-
MDW
2 stops27h 30m
Delta
Deal found 1/12$792
This Kiwi.com deal was found by Cheapflights users on 1/11. 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.
Sat 3/2112:45 pm
MDW
-
UVF
1 stop24h 01m
Multiple Airlines
Thu 3/262:50 pm
UVF
-
MDW
1 stop20h 15m
Multiple Airlines
Deal found 1/11$794

Cheapflights Fare Finder

 
Customize your flight search to find flights from Midway to Castries 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 12, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to Castries that are best for you.

Fly from

Midway

Fly to

Castries

Route

Depart

Return

Price

ChicagoCastries

MDW - UVF

MDWUVF

Chicago Midway

Wed 1/28

6:00 am-3:05 pm

1 stop7h 05m

Castries Hewanorra

Mon 2/9

4:25 pm-12:46 pm

2 stops22h 21m

$767

ChicagoCastries

MDW - UVF

MDWUVF

Chicago Midway

Sun 2/1

6:35 pm-3:05 pm

2 stops18h 30m

Castries Hewanorra

Mon 2/9

4:25 pm-5:55 pm

2 stops27h 30m

$767

ChicagoCastries

MDW - UVF

MDWUVF

Chicago Midway

Thu 1/29

6:00 am-3:05 pm

1 stop7h 05m

Castries Hewanorra

Mon 2/9

4:25 pm-5:55 pm

2 stops27h 30m

$792

ChicagoCastries

MDW - UVF

MDWUVF

Chicago Midway

Fri 1/30

6:00 am-3:05 pm

1 stop7h 05m

Castries Hewanorra

Mon 2/9

4:25 pm-5:55 pm

2 stops27h 30m

$792

ChicagoCastries

MDW - UVF

MDWUVF

Chicago Midway

Sat 3/21

12:45 pm-1:46 pm

1 stop24h 01m

Castries Hewanorra

Thu 3/26

2:50 pm-10:05 am

1 stop20h 15m

$794

ChicagoCastries

MDW - UVF

MDWUVF

Chicago Midway

Wed 1/21

9:50 am-2:50 pm

2 stops27h 00m

Castries Hewanorra

Sun 1/25

3:40 pm-10:10 am

1 stop20h 30m

$1,035

ChicagoCastries

MDW - UVF

MDWUVF

Chicago Midway

Thu 2/12

6:00 am-3:05 pm

1 stop7h 05m

$503

ChicagoCastries

MDW - UVF

MDWUVF

Chicago Midway

Sat 2/14

12:50 pm-10:05 am

3 stops43h 15m

$557

ChicagoCastries

MDW - UVF

MDWUVF

Chicago Midway

Sat 2/14

6:00 am-3:05 pm

1 stop7h 05m

$838

ChicagoCastries

MDW - UVF

MDWUVF

Chicago Midway

Wed 2/11

6:00 am-3:05 pm

1 stop7h 05m

$1,611

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/12

Showing 1-10 of 11 results
1
2

Compare providers for flights from Midway to Castries

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 Castries in January.
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-Castries 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-Castries flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Chicago Midway Airport-Castries flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago Midway Airport-Castries 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-Castries 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 Castries

Have a flexible travel schedule? Discover the best time to fly to Castries 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.

Related info for your journey

Find useful and relevant information for your journey from Midway to Castries. 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 Castries from Chicago Midway?

    Castries Hewanorra (UVF) is the airport you will fly into if you book a flight from Chicago Midway to Castries. You should not have trouble finding flights to Hewanorra from Chicago Midway; the airport handles an average of 0 inbound flights from Chicago Midway per day. You should also have plenty of airline options to choose from since 0 airlines have flights to the Castries airport from Chicago Midway. It is only a 19.3 mi journey from Hewanorra (UVF) to Castries’s city center.

  • How long is the flight from Chicago Midway Airport to Castries?

    A quick flight from Chicago Midway Airport to Castries can take about 7h 05m. Delta provides one of the quickest options available for as low as $767. Chicago Midway Airport and Castries are separated by a distance of 2514 mi.

  • Can I find deals for flights from Midway to Castries that include hotel bookings?

    Yes. In addition to deals on Midway to Castries flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Midway to Castries?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Midway to Castries.

  • Can I find deals for business class flights from Midway to Castries?

    Yes. Cheapflights offers flight deals from Midway to Castries 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

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Alternative routes for Midway to Castries

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O'Hare Intl to Castries flights
O'Hare Intl to Castries flights

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