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Castries

$256+ Cheap flights from Chicago (CHI) 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 1/22. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — UVF
Jan 9 — Jan 161
Fri 1/9
Fri 1/16
1 adult, Economy
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Cheap flight deals from Chicago to Castries

Cheapest flights from Chicago to Castries
Explore the most affordable flight options available from Chicago to Castries. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 10, 2025.

This Expedia deal was found by Cheapflights users on 12/7. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/1011:25 amORD - UVF
2 stops25h 27mMultiple Airlines
Sun 12/145:15 pmUVF - ORD
2 stops21h 36mMultiple Airlines
Deal found 12/7$626
This Delta deal was found by Cheapflights users on 12/9. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/125:30 amORD - UVF
1 stop8h 06mDelta
Wed 12/174:56 pmUVF - ORD
1 stop17h 43mDelta
Deal found 12/9$798
This American Airlines deal was found by Cheapflights users on 12/10. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/138:50 pmORD - UVF
2 stops14h 29mAmerican Airlines
Sat 12/203:53 pmUVF - ORD
1 stop10h 06mAmerican Airlines
Deal found 12/10$808
This Delta deal was found by Cheapflights users on 12/8. 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 12/135:30 amORD - UVF
1 stop8h 06mDelta
Sat 12/204:53 pmUVF - ORD
1 stop9h 09mDelta
Deal found 12/8$828
This Delta deal was found by Cheapflights users on 12/8. 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 12/175:30 amORD - UVF
1 stop8h 06mDelta
Fri 12/264:50 pmUVF - ORD
1 stop9h 13mDelta
Deal found 12/8$831
This American Airlines deal was found by Cheapflights users on 12/7. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/106:35 pmORD - UVF
1 stop18h 27mAmerican Airlines
Sun 12/144:53 pmUVF - ORD
1 stop9h 44mAmerican Airlines
Deal found 12/7$833
This Delta deal was found by Cheapflights users on 12/7. 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 12/106:00 amMDW - UVF
1 stop7h 36mDelta
Sun 12/144:56 pmUVF - MDW
1 stop8h 51mDelta
Deal found 12/7$916
This Delta deal was found by Cheapflights users on 12/8. 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 12/175:30 amORD - UVF
1 stop8h 06mDelta
Sat 12/274:53 pmUVF - ORD
1 stop17h 54mDelta
Deal found 12/8$991
This Kiwi.com deal was found by Cheapflights users on 12/7. 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 12/1011:00 amMDW - UVF
1 stop25h 50mMultiple Airlines
Sun 12/143:40 pmUVF - MDW
2 stops32h 18mMultiple Airlines
Deal found 12/7$1,270
This Delta deal was found by Cheapflights users on 12/8. 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 12/186:00 amMDW - UVF
1 stop7h 36mDelta
Sat 12/273:00 pmUVF - MDW
1 stop9h 22mDelta
Deal found 12/8$1,825
This WestJet deal was found by Cheapflights users on 12/7. 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 WestJet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/1010:49 amMDW - UVF
2 stops26h 01mWestJet
Sun 12/143:40 pmUVF - MDW
2 stops23h 30mWestJet
Deal found 12/7$4,445

Find flight deals from Chicago to Castries

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) 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 December 10, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$489
(American Airlines)

One-way from

$256
(Trip.com)

Popular in

June

Cheapest in

January

Average price

$959
Provider with most accurate pricing for Chicago (CHI)-Castries Hewanorra flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Castries Hewanorra flights.
Search Deals
From Chicago (CHI) to Castries Hewanorra
Search Deals
One-way flight from Chicago (CHI) to Castries Hewanorra
Search Deals
Highest demand for flights based on searches. 9% potential increase in price ($78 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($20 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago 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 December 10, 2025.
Use the filters below to find and compare flights from Chicago to Castries that are best for you.

Fly from

Chicago

Fly to

Castries

Route

Depart

Return

Price

ChicagoCastries

ORD - UVF

ORDUVF

Chicago O'Hare Intl

Sat 1/24

7:56 pm-3:03 pm

1 stop17h 07m

Castries Hewanorra

Tue 2/3

5:02 pm-9:05 am

1 stop18h 03m

$489

ChicagoCastries

ORD - UVF

ORDUVF

Chicago O'Hare Intl

Sun 3/1

7:13 pm-4:00 pm

1 stop18h 47m

Castries Hewanorra

Thu 3/5

4:25 pm-9:05 am

1 stop18h 40m

$489

ChicagoCastries

ORD - UVF

ORDUVF

Chicago O'Hare Intl

Tue 3/17

5:40 am-2:04 pm

1 stop7h 24m

Castries Hewanorra

Wed 3/25

3:24 pm-8:57 am

2 stops18h 33m

$494

ChicagoCastries

ORD - UVF

ORDUVF

Chicago O'Hare Intl

Sat 1/31

7:56 pm-3:03 pm

1 stop17h 07m

Castries Hewanorra

Sat 2/7

5:02 pm-9:05 am

1 stop18h 03m

$519

ChicagoCastries

ORD - UVF

ORDUVF

Chicago O'Hare Intl

Mon 1/19

8:50 pm-3:03 pm

2 stops16h 13m

Castries Hewanorra

Mon 1/26

2:46 pm-11:08 pm

1 stop10h 22m

$524

ChicagoCastries

ORD - UVF

ORDUVF

Chicago O'Hare Intl

Fri 1/23

7:30 pm-2:10 pm

1 stop16h 40m

Castries Hewanorra

Fri 1/30

5:02 pm-9:01 am

2 stops17h 59m

$524

ChicagoCastries

MDW - UVF

MDWUVF

Chicago Midway

Fri 3/13

5:38 pm-2:04 pm

1 stop19h 26m

Castries Hewanorra

Sun 3/22

3:24 pm-4:53 pm

1 stop26h 29m

$1,415

ChicagoCastries

MDW - UVF

MDWUVF

Chicago Midway

Wed 4/1

1:09 pm-2:04 pm

2 stops23h 55m

Castries Hewanorra

Fri 4/10

3:24 pm-9:55 am

1 stop19h 31m

$1,474

ChicagoCastries

MDW - UVF

MDWUVF

Chicago Midway

Sat 5/30

6:00 am-2:08 pm

1 stop7h 08m

Castries Hewanorra

Sat 6/6

3:25 pm-12:30 pm

2 stops22h 05m

$1,505

ChicagoCastries

MDW - UVF

MDWUVF

Chicago Midway

Wed 3/4

9:50 am-2:46 pm

2 stops26h 56m

Castries Hewanorra

Sun 3/8

2:40 pm-10:05 am

1 stop20h 25m

$1,531

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/8

Showing 1-10 of 25 results
1
2
3

Compare providers for flights from Chicago 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 Chicago to Castries in December.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
AranGrantPrice Accuracy2 starsTrust Score*3 stars
eDreamsPrice Accuracy3 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-Castries flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Chicago-Castries flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Chicago-Castries flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago-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-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 Chicago to Castries

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

How far ahead should I book a flight from Chicago to Castries?

Use this chart to determine the optimal time to book a round-trip flight from Chicago to Castries. Price data was last updated on December 5, 2025.

The best time to book flights from Chicago to Castries is 40 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.

What is the cheapest month to book a flight from Chicago to Castries?

Currently, August is the cheapest month in which you can book a flight from Chicago to Castries (average of $535). Flying from Chicago to Castries in December is currently the most expensive (average of $675). 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.

What is the cheapest time of day to fly from CHI to UVF?

Find hourly flight availability from Chicago to Castries. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated December 10, 2025.

It’s optimal to fly from Chicago to Castries at noon. By choosing this option you can save up to 32% on the cost of your flight, compared to a flight in the evening.

Reviews of airlines servicing Castries

Get insights into the airlines that provide service to Castries. 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 Castries. Reviews last updated December 10, 2025.
Read through reviews of airlines operating flights from Chicago to Castries, such as Delta, United Airlines, and American Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Delta
7.9
Good
8,007 reviews

Boarding

8.1

Overall

7.9

Crew

8.5

Food

7.3

Comfort

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
8,007 reviews
Delta
7.9
Good
8,007 reviews

Boarding

8.1

Overall

7.9

Crew

8.5

Food

7.3

Comfort

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.
United Airlines
7.4
Good
9,092 reviews
Delta
7.9
Good
8,007 reviews

Boarding

8.1

Overall

7.9

Crew

8.5

Food

7.3

Comfort

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.
American Airlines
7.2
Good
11,048 reviews
Delta
7.9
Good
8,007 reviews

Boarding

8.1

Overall

7.9

Crew

8.5

Food

7.3

Comfort

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 Chicago 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?

    If you book a flight to Castries from Chicago, you will be flying to Hewanorra, which is the city’s only airport. Castries Hewanorra (UVF) is located 19.3 mi from the center of Castries. There are 0 flights from Chicago to Hewanorra per day from 3 different airlines.

  • How long is the flight from Chicago to Castries?

    Airlines like American Airlines and Delta fly from Chicago to Castries in about 7h 24m. The time it takes to get you to your destination can typically vary by up to 9h 43m. Chicago and Castries are separated by a distance of 2529 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What are the cheapest airlines flying from Chicago to Castries round-trip?

    According to our current data, Delta ($555), United Airlines ($558), and American Airlines ($565) offers the cheapest pricing from Chicago to Castries. Delta is currently priced 26% below the average price you’ll pay for this route.

  • What are the cheapest flights from Chicago to Castries?

    Looking at all options, your cheapest flight can be booked for $368. While the most popular route (Chicago O'Hare Intl - Castries Hewanorra) can be booked for $499 on average, our data indicates $831 when flying from Chicago to Castries.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Chicago 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.

  • What is the cheapest month to book a flight from Chicago to Castries?

    Currently, August is the cheapest month in which you can book a flight from Chicago to Castries (average of $535). Flying from Chicago to Castries in December is currently the most expensive (average of $675). 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.

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Alternative routes for Chicago to Castries

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Castries flights
St. Louis to Castries flights
Midway to Castries flights
O'Hare Intl to Castries flights
Moline to Castries flights

Top 3 airlines flying from Chicago to Castries

Discover the top 3 airlines that operate flights from Chicago to Castries. 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 December 10, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$555Average$766FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$565Average$739FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$570Average$912FlexibilityNo cancel feeOn-time69%

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