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Castries

$277+ 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 1/10. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — UVF
Aug 25 — Sep 11
Mon 8/25
Mon 9/1
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Castries Hewanorra are usually found in October or January, 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 August 20, 2025.

Round-trip from

$460
(Expedia)

One-way from

$277
(Expedia)

Popular in

June

Cheapest in

October

Average price

$605
From Chicago (CHI) to Castries Hewanorra
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One-way flight from Chicago (CHI) to Castries Hewanorra
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Highest demand for flights based on searches. 11% potential increase in price ($101 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($23 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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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 August 20, 2025.

This Expedia deal was found by Cheapflights users on 8/20. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/25:44 amORD - UVF
1 stop30h 13mJetBlue
Thu 11/64:57 pmUVF - ORD
1 stop29h 55mJetBlue
Deal found 8/20$460
This Expedia deal was found by Cheapflights users on 8/20. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/176:44 amORD - UVF
1 stop30h 13mJetBlue
Fri 11/215:01 pmUVF - ORD
1 stop31h 49mJetBlue
Deal found 8/20$464
This Travelocity deal was found by Cheapflights users on 8/17. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/66:20 pmORD - UVF
1 stop18h 55mAir Canada
Fri 10/103:10 pmUVF - ORD
1 stop19h 04mAir Canada
Deal found 8/17$474
This Priceline deal was found by Cheapflights users on 8/17. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/118:34 amORD - UVF
1 stop28h 11mJetBlue
Fri 10/173:05 pmUVF - ORD
1 stop28h 19mJetBlue
Deal found 8/17$489
This Expedia deal was found by Cheapflights users on 8/20. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/166:44 amORD - UVF
1 stop30h 13mJetBlue
Thu 11/205:01 pmUVF - ORD
1 stop31h 49mJetBlue
Deal found 8/20$493
This Priceline deal was found by Cheapflights users on 8/19. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/112:00 pmORD - UVF
1 stop23h 15mAir Canada
Tue 9/233:10 pmUVF - ORD
1 stop18h 58mAir Canada
Deal found 8/19$508
This Mytrip deal was found by Cheapflights users on 8/18. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/299:20 amMDW - UVF
3 stops27h 30mWestJet
Sun 11/23:40 pmUVF - MDW
2 stops23h 28mWestJet
Deal found 8/18$1,011
This Delta deal was found by Cheapflights users on 8/19. 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 9/266:00 amMDW - UVF
1 stop7h 23mDelta
Tue 9/303:38 pmUVF - MDW
2 stops18h 02mDelta
Deal found 8/19$1,124
This Delta deal was found by Cheapflights users on 8/19. 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.
Sun 12/146:00 amMDW - UVF
1 stop7h 10mDelta
Sat 12/203:03 pmUVF - MDW
1 stop9h 02mDelta
Deal found 8/19$1,132
This Delta deal was found by Cheapflights users on 8/20. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/136:00 amMDW - UVF
1 stop7h 10mDelta
Wed 12/174:35 pmUVF - MDW
2 stops21h 57mDelta
Deal found 8/20$1,304
This Delta deal was found by Cheapflights users on 8/19. 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.
Sat 9/66:00 amMDW - UVF
1 stop7h 15mDelta
Sat 9/133:33 pmUVF - MDW
2 stops18h 07mDelta
Deal found 8/19$1,392
This Delta deal was found by Cheapflights users on 8/18. 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 8/286:00 amMDW - UVF
1 stop7h 15mDelta
Mon 9/13:35 pmUVF - MDW
2 stops21h 53mDelta
Deal found 8/18$1,488

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 August 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 11/2

5:44 am-1:57 pm

1 stop30h 13m

Castries Hewanorra

Thu 11/6

4:57 pm-8:52 pm

1 stop29h 55m

$460

ChicagoCastries

ORD - UVF

ORDUVF

Chicago O'Hare Intl

Mon 11/17

6:44 am-2:57 pm

1 stop30h 13m

Castries Hewanorra

Fri 11/21

5:01 pm-10:50 pm

1 stop31h 49m

$464

ChicagoCastries

ORD - UVF

ORDUVF

Chicago O'Hare Intl

Mon 10/6

6:20 pm-2:15 pm

1 stop18h 55m

Castries Hewanorra

Fri 10/10

3:10 pm-9:14 am

1 stop19h 04m

$474

ChicagoCastries

ORD - UVF

ORDUVF

Chicago O'Hare Intl

Sat 10/11

8:34 am-1:45 pm

1 stop28h 11m

Castries Hewanorra

Fri 10/17

3:05 pm-6:24 pm

1 stop28h 19m

$489

ChicagoCastries

ORD - UVF

ORDUVF

Chicago O'Hare Intl

Sun 11/16

6:44 am-2:57 pm

1 stop30h 13m

Castries Hewanorra

Thu 11/20

5:01 pm-10:50 pm

1 stop31h 49m

$493

ChicagoCastries

ORD - UVF

ORDUVF

Chicago O'Hare Intl

Wed 10/29

6:44 am-1:57 pm

1 stop30h 13m

Castries Hewanorra

Sun 11/2

4:57 pm-8:52 pm

1 stop29h 55m

$504

ChicagoCastries

ORD - UVF

ORDUVF

Chicago O'Hare Intl

Thu 9/11

2:00 pm-2:15 pm

1 stop23h 15m

Castries Hewanorra

Tue 9/23

3:10 pm-9:08 am

1 stop18h 58m

$508

ChicagoCastries

MDW - UVF

MDWUVF

Chicago Midway

Sun 2/1

5:59 pm-3:04 pm

2 stops19h 05m

Castries Hewanorra

Thu 2/5

4:24 pm-9:23 am

1 stop18h 59m

$580

ChicagoCastries

MDW - UVF

MDWUVF

Chicago Midway

Mon 2/2

9:30 am-3:04 pm

2 stops27h 34m

Castries Hewanorra

Wed 2/4

4:24 pm-9:23 am

1 stop18h 59m

$580

ChicagoCastries

MDW - UVF

MDWUVF

Chicago Midway

Sun 2/1

5:59 pm-3:04 pm

2 stops19h 05m

Castries Hewanorra

Fri 2/6

4:24 pm-9:23 am

1 stop18h 59m

$580

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/18

Showing 1-10 of 26 results
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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 August 8, 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, January is the cheapest month in which you can book a flight from Chicago to Castries (average of $556). Flying from Chicago to Castries in December is currently the most expensive (average of $730). 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 August 20, 2025.

It’s optimal to fly from Chicago to Castries at noon. By choosing this option you can save up to 44% on the cost of your flight, compared to a flight in the morning.

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 August 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
8.0
Very good
7,982 reviews

Food

7.3

Entertainment

7.9

Boarding

8.2

Crew

8.5

Comfort

7.9

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Delta
8.0
Very good
7,982 reviews
Delta
8.0
Very good
7,982 reviews

Food

7.3

Entertainment

7.9

Boarding

8.2

Crew

8.5

Comfort

7.9

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
United Airlines
7.4
Good
8,928 reviews
Delta
8.0
Very good
7,982 reviews

Food

7.3

Entertainment

7.9

Boarding

8.2

Crew

8.5

Comfort

7.9

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,982 reviews

Food

7.3

Entertainment

7.9

Boarding

8.2

Crew

8.5

Comfort

7.9

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

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 JetBlue, Air Canada, and Delta fly from Chicago to Castries in about 18h 55m. The time it takes to get you to your destination can typically vary by up to 11h 18m. 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 ($558), and United Airlines ($570) offers the cheapest pricing from Chicago to Castries. Delta is currently priced 27% below the average price you’ll pay for this route.

  • 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, January is the cheapest month in which you can book a flight from Chicago to Castries (average of $556). Flying from Chicago to Castries in December is currently the most expensive (average of $730). 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
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 August 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$546Average$733FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$558Average$724FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$570Average$877FlexibilityNo cancel feeOn-time69%

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