HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Castries

$178+ 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 1/7. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — UVF
Nov 19 — Nov 261
Wed 11/19
Wed 11/26
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Chicago to Castries with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheapflights Tip: The best prices from Chicago to Castries Hewanorra are usually found in January or August, booked 39 days in advance, depart on a Tuesday or Monday and return on a Monday

Cheap 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 October 20, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$447
(Expedia)

One-way from

$178
(Priceline)

Popular in

December

Cheapest in

January

Average price

$770
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
High demand for flights, 1% potential price rise
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($22 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
Search Deals

Find 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 October 20, 2025.

This Expedia deal was found by Cheapflights users on 10/19. 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.
Fri 12/58:38 pmORD - UVF
1 stop16h 42mJetBlue
Thu 12/114:57 pmUVF - ORD
1 stop30h 55mJetBlue
Deal found 10/19$447
This Expedia deal was found by Cheapflights users on 10/19. 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.
Fri 12/58:38 pmORD - UVF
1 stop16h 42mJetBlue
Wed 12/104:57 pmUVF - ORD
2 stops19h 38mJetBlue
Deal found 10/19$464
This Mytrip deal was found by Cheapflights users on 10/19. 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.
Thu 10/3010:00 amORD - UVF
1 stop28h 25mMultiple Airlines
Mon 11/35:15 pmUVF - ORD
3 stops27h 19mMultiple Airlines
Deal found 10/19$561
This American Airlines deal was found by Cheapflights users on 10/19. 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.
Tue 12/25:00 amORD - UVF
1 stop8h 52mAmerican Airlines
Fri 12/263:53 pmUVF - ORD
1 stop9h 49mAmerican Airlines
Deal found 10/19$586
This American Airlines deal was found by Cheapflights users on 10/19. 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 12/68:50 pmORD - UVF
2 stops14h 29mAmerican Airlines
Thu 12/114:53 pmUVF - ORD
1 stop17h 56mAmerican Airlines
Deal found 10/19$591
This FlightHub deal was found by Cheapflights users on 10/19. 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.
Sat 12/68:15 pmORD - UVF
1 stop18h 10mAir Canada
Wed 12/105:15 pmUVF - ORD
1 stop18h 47mAir Canada
Deal found 10/19$604
This American Airlines deal was found by Cheapflights users on 10/20. 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.
Mon 11/175:00 amORD - UVF
1 stop8h 04mAmerican Airlines
Tue 11/254:04 pmUVF - ORD
1 stop9h 36mAmerican Airlines
Deal found 10/20$607
This American Airlines deal was found by Cheapflights users on 10/19. 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.
Thu 12/44:45 pmORD - UVF
1 stop18h 34mAmerican Airlines
Thu 12/114:53 pmUVF - ORD
1 stop9h 44mAmerican Airlines
Deal found 10/19$611
This Delta deal was found by Cheapflights users on 10/19. 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 12/56:00 amMDW - UVF
1 stop7h 36mDelta
Thu 12/114:56 pmUVF - MDW
1 stop8h 51mDelta
Deal found 10/19$632
This Delta deal was found by Cheapflights users on 10/18. 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 11/116:00 amMDW - UVF
1 stop7h 39mDelta
Wed 11/194:59 pmUVF - MDW
1 stop8h 41mDelta
Deal found 10/18$685
This Delta deal was found by Cheapflights users on 10/18. 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.
Mon 11/101:15 pmMDW - UVF
2 stops24h 24mDelta
Wed 11/194:59 pmUVF - MDW
2 stops17h 55mDelta
Deal found 10/18$690
This Delta deal was found by Cheapflights users on 10/18. 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 11/139:34 amMDW - UVF
2 stops28h 05mDelta
Wed 11/194:59 pmUVF - MDW
2 stops17h 55mDelta
Deal found 10/18$715

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 October 20, 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

Sun 2/8

7:30 pm-1:47 pm

1 stop16h 17m

Castries Hewanorra

Fri 2/13

4:45 pm-9:02 am

1 stop18h 17m

$565

ChicagoCastries

ORD - UVF

ORDUVF

Chicago O'Hare Intl

Wed 4/1

5:50 am-2:04 pm

1 stop7h 14m

Castries Hewanorra

Tue 4/7

3:24 pm-8:39 am

1 stop18h 15m

$565

ChicagoCastries

ORD - UVF

ORDUVF

Chicago O'Hare Intl

Tue 2/17

8:25 pm-2:15 pm

2 stops15h 50m

Castries Hewanorra

Tue 2/24

5:00 pm-7:21 am

2 stops16h 21m

$570

ChicagoCastries

ORD - UVF

ORDUVF

Chicago O'Hare Intl

Mon 1/19

5:50 am-3:04 pm

1 stop7h 14m

Castries Hewanorra

Mon 1/26

4:24 pm-11:54 pm

1 stop9h 30m

$590

ChicagoCastries

ORD - UVF

ORDUVF

Chicago O'Hare Intl

Thu 1/22

7:30 pm-1:47 pm

1 stop16h 17m

Castries Hewanorra

Tue 1/27

4:05 pm-11:27 pm

1 stop9h 22m

$590

ChicagoCastries

ORD - UVF

ORDUVF

Chicago O'Hare Intl

Fri 1/30

5:50 am-3:04 pm

1 stop7h 14m

Castries Hewanorra

Fri 2/6

4:24 pm-11:54 pm

1 stop9h 30m

$590

ChicagoCastries

ORD - UVF

ORDUVF

Chicago O'Hare Intl

Fri 2/27

5:50 am-3:04 pm

1 stop7h 14m

Castries Hewanorra

Sat 3/7

4:24 pm-11:54 pm

1 stop9h 30m

$615

ChicagoCastries

ORD - UVF

ORDUVF

Chicago O'Hare Intl

Thu 12/4

8:50 pm-1:19 pm

2 stops14h 29m

Castries Hewanorra

Thu 12/11

4:53 pm-7:19 am

2 stops16h 26m

$616

ChicagoCastries

ORD - UVF

ORDUVF

Chicago O'Hare Intl

Wed 1/14

7:48 pm-1:47 pm

2 stops15h 59m

Castries Hewanorra

Tue 1/20

5:02 pm-8:22 am

2 stops17h 20m

$620

ChicagoCastries

MDW - UVF

MDWUVF

Chicago Midway

Fri 12/5

6:00 am-3:36 pm

1 stop7h 36m

Castries Hewanorra

Thu 12/11

4:56 pm-11:47 pm

1 stop8h 51m

$632

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/18

Showing 1-10 of 27 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 October.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
AranGrantPrice Accuracy3 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 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 October 17, 2025.

The best time to book flights from Chicago to Castries is 39 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, June is the cheapest month in which you can book a flight from Chicago to Castries (average of $476). Flying from Chicago to Castries in July is currently the most expensive (average of $631). 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 October 20, 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.

How much does it cost to fly round-trip from Chicago to Castries?

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 October 20, 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
7,978 reviews

Boarding

8.2

Comfort

7.9

Crew

8.5

Entertainment

7.9

Food

7.3

Overall

7.9

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
Delta
7.9
Good
7,978 reviews
Delta
7.9
Good
7,978 reviews

Boarding

8.2

Comfort

7.9

Crew

8.5

Entertainment

7.9

Food

7.3

Overall

7.9

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
United Airlines
7.4
Good
8,991 reviews
Delta
7.9
Good
7,978 reviews

Boarding

8.2

Comfort

7.9

Crew

8.5

Entertainment

7.9

Food

7.3

Overall

7.9

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
American Airlines
7.2
Good
11,024 reviews
Delta
7.9
Good
7,978 reviews

Boarding

8.2

Comfort

7.9

Crew

8.5

Entertainment

7.9

Food

7.3

Overall

7.9

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.

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 14m. The time it takes to get you to your destination can typically vary by up to 9h 03m. 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 ($568) offers the cheapest pricing from Chicago to Castries. Delta is currently priced 28% below the average price you’ll pay for this route.

  • What are the cheapest airlines to fly from Chicago to Castries one-way?

    The cheapest airlines for a one-way flight from Chicago to Castries are Air Canada ($214), JetBlue ($277), and American Airlines ($443).

  • What are the cheapest flights from Chicago to Castries?

    Looking at all options, your cheapest flight can be booked for $600. While the most popular route (Chicago O'Hare Intl - Castries Hewanorra) can be booked for $426 on average, our data indicates $1,183 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, June is the cheapest month in which you can book a flight from Chicago to Castries (average of $476). Flying from Chicago to Castries in July is currently the most expensive (average of $631). 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

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
Midway to Castries flights
O'Hare Intl to Castries flights
St. Louis 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 October 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$555Average$766FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$558Average$864FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$568Average$734FlexibilityNo cancel feeOn-time71%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.