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Castries

$139+ 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 3/28. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — UVF
Feb 26 — Mar 51
Thu 2/26
Thu 3/5
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 January 27, 2026.

This Air Canada 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/248:40 pm
ORD
-
UVF
1 stop17h 45m
Air Canada
Thu 3/264:15 pm
UVF
-
ORD
2 stops23h 40m
Air Canada
Deal found 1/25$472
This Air Canada 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/2412:50 pm
ORD
-
UVF
2 stops25h 35m
Air Canada
Mon 3/304:20 pm
UVF
-
ORD
2 stops19h 33m
Air Canada
Deal found 1/25$475
This Air Canada 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/246:04 pm
ORD
-
UVF
2 stops20h 16m
Air Canada
Thu 3/55:15 pm
UVF
-
ORD
1 stop23h 55m
Air Canada
Deal found 1/25$486
This FlightHub 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/241:12 pm
ORD
-
UVF
1 stop25h 08m
Multiple Airlines
Mon 3/25:23 pm
UVF
-
ORD
1 stop20h 26m
Multiple Airlines
Deal found 1/25$490
This Air Canada 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/113:40 pm
ORD
-
UVF
2 stops21h 30m
Air Canada
Fri 6/193:05 pm
UVF
-
ORD
2 stops19h 46m
Air Canada
Deal found 1/25$493
This FlightHub 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/188:40 pm
ORD
-
UVF
1 stop17h 45m
Air Canada
Wed 3/254:15 pm
UVF
-
ORD
2 stops20h 03m
Air Canada
Deal found 1/25$504
This Air Canada 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/228:40 pm
ORD
-
UVF
1 stop17h 45m
Air Canada
Thu 3/55:15 pm
UVF
-
ORD
2 stops23h 40m
Air Canada
Deal found 1/25$505
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/225:25 am
ORD
-
UVF
1 stop7h 40m
Delta
Wed 2/254:25 pm
UVF
-
ORD
1 stop18h 13m
Delta
Deal found 1/27$506
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/2510:35 am
ORD
-
UVF
2 stops27h 50m
Air Canada
Mon 3/304:20 pm
UVF
-
ORD
2 stops19h 33m
Air Canada
Deal found 1/25$508
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/227:59 pm
ORD
-
UVF
1 stop17h 06m
Delta
Fri 2/274:25 pm
UVF
-
ORD
2 stops22h 55m
Delta
Deal found 1/27$511
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/176:34 pm
MDW
-
UVF
2 stops18h 24m
Delta
Wed 3/253:18 pm
UVF
-
MDW
2 stops22h 11m
Delta
Deal found 1/25$551
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/226:40 pm
MDW
-
UVF
1 stop18h 25m
Delta
Wed 3/44:25 pm
UVF
-
MDW
2 stops22h 21m
Delta
Deal found 1/25$572

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 January 27, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$472
(Air Canada)

One-way from

$139
(Booking.com)

Popular in

June

Cheapest in

August

Average price

$660
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. 12% potential increase in price ($112 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($24 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 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 January 27, 2026.
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

Thu 3/19

8:00 am-3:25 pm

1 stop30h 25m

Castries Hewanorra

Thu 3/26

4:15 pm-1:01 pm

1 stop21h 46m

$544

ChicagoCastries

ORD - UVF

ORDUVF

Chicago O'Hare Intl

Mon 3/23

7:59 pm-1:58 pm

1 stop16h 59m

Castries Hewanorra

Wed 3/25

3:18 pm-11:54 pm

1 stop9h 36m

$546

ChicagoCastries

ORD - UVF

ORDUVF

Chicago O'Hare Intl

Wed 4/22

1:55 pm-3:25 pm

2 stops24h 30m

Castries Hewanorra

Mon 4/27

4:15 pm-2:55 pm

2 stops23h 40m

$548

ChicagoCastries

ORD - UVF

ORDUVF

Chicago O'Hare Intl

Wed 3/18

5:30 am-1:58 pm

1 stop7h 28m

Castries Hewanorra

Tue 3/31

3:18 pm-4:43 pm

2 stops26h 25m

$551

ChicagoCastries

ORD - UVF

ORDUVF

Chicago O'Hare Intl

Tue 3/17

1:57 pm-1:58 pm

2 stops23h 01m

Castries Hewanorra

Tue 3/24

3:18 pm-11:54 pm

1 stop9h 36m

$551

ChicagoCastries

ORD - UVF

ORDUVF

Chicago O'Hare Intl

Wed 4/22

1:36 pm-2:02 pm

2 stops23h 26m

Castries Hewanorra

Wed 4/29

3:22 pm-6:52 pm

2 stops28h 30m

$551

ChicagoCastries

ORD - UVF

ORDUVF

Chicago O'Hare Intl

Tue 3/24

5:30 am-1:58 pm

1 stop7h 28m

Castries Hewanorra

Tue 3/31

3:18 pm-4:43 pm

2 stops26h 25m

$551

ChicagoCastries

ORD - UVF

ORDUVF

Chicago O'Hare Intl

Tue 3/17

1:57 pm-1:58 pm

2 stops23h 01m

Castries Hewanorra

Wed 3/25

3:18 pm-9:10 am

2 stops18h 52m

$551

ChicagoCastries

ORD - UVF

ORDUVF

Chicago O'Hare Intl

Wed 3/18

5:30 am-1:58 pm

1 stop7h 28m

Castries Hewanorra

Tue 3/24

3:18 pm-4:43 pm

2 stops26h 25m

$551

ChicagoCastries

MDW - UVF

MDWUVF

Chicago Midway

Tue 3/24

6:00 am-1:58 pm

1 stop6h 58m

Castries Hewanorra

Wed 3/25

3:18 pm-12:29 pm

2 stops22h 11m

$551

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/25

Showing 1-10 of 30 results
1
2
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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 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-Castries flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago-Castries flight deals on Cheapflights vs. FlightHub >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 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-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 January 23, 2026.

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, February is the cheapest month in which you can book a flight from Chicago to Castries (average of $519). Flying from Chicago to Castries in July is currently the most expensive (average of $636). 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 January 27, 2026.

When flying from Chicago to Castries, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

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 January 27, 2026.
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
8,118 reviews

Entertainment

7.8

Crew

8.5

Food

7.2

Overall

7.9

Comfort

7.9

Boarding

8.1

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
8,118 reviews
Delta
7.9
Good
8,118 reviews

Entertainment

7.8

Crew

8.5

Food

7.2

Overall

7.9

Comfort

7.9

Boarding

8.1

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
9,205 reviews
Delta
7.9
Good
8,118 reviews

Entertainment

7.8

Crew

8.5

Food

7.2

Overall

7.9

Comfort

7.9

Boarding

8.1

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
11,197 reviews
Delta
7.9
Good
8,118 reviews

Entertainment

7.8

Crew

8.5

Food

7.2

Overall

7.9

Comfort

7.9

Boarding

8.1

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 Air Canada and Delta fly from Chicago to Castries in about 16h 59m. The time it takes to get you to your destination can typically vary by up to 13h 26m. 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 ($546), American Airlines ($552), and United Airlines ($600) offers the cheapest pricing from Chicago to Castries. Delta is currently priced 30% 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 $359. While the most popular route (Chicago O'Hare Intl - Castries Hewanorra) can be booked for $536 on average, our data indicates $957 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, February is the cheapest month in which you can book a flight from Chicago to Castries (average of $519). Flying from Chicago to Castries in July is currently the most expensive (average of $636). 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

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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
O'Hare Intl to Castries flights
Midway 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 January 27, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$546Average$750FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$552Average$715FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$600Average$1,011FlexibilityNo cancel feeOn-time69%

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