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Cheap flights from Chicago to Castries from $248

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to Castries departing on 11/8. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

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Find the cheapest flights from Chicago to Castries

Cheap round-trip flights

Enter your travel dates to find the best prices.
Air Canada Logo
8:45 am - 2:10 pm
ORD
-
UVF
52h 25m
2 stops
Air Canada Logo
3:15 pm - 1:22 pm
UVF
-
ORD
23h 07m
1 stop
$382Air Canada
Sun, Jun 14 - Fri, Jun 19
Air Canada Logo
6:22 pm - 2:10 pm
ORD
-
UVF
42h 48m
2 stops
Air Canada Logo
3:15 pm - 7:45 am
UVF
-
ORD
17h 30m
2 stops
$388Air Canada
Sun, Jun 14 - Fri, Jun 19
Air Canada Logo
6:22 pm - 2:20 pm
ORD
-
UVF
18h 58m
2 stops
Air Canada Logo
3:15 pm - 7:45 am
UVF
-
ORD
17h 30m
2 stops
$398Air Canada
Thu, Jun 18 - Tue, Jun 23
Air Canada Logo
9:50 am - 2:20 pm
ORD
-
UVF
27h 30m
1 stop
Air Canada Logo
3:05 pm - 8:05 pm
UVF
-
ORD
30h 00m
2 stops
$424Air Canada
Thu, Jul 23 - Tue, Jul 28
Delta Logo
1:00 pm - 2:26 pm
MDW
-
UVF
24h 26m
2 stops
Delta Logo
3:41 pm - 8:45 am
UVF
-
MDW
18h 04m
2 stops
$868Delta
Wed, Oct 21 - Thu, Oct 29
Delta Logo
6:00 am - 2:26 pm
MDW
-
UVF
7h 26m
1 stop
Delta Logo
3:41 pm - 8:45 am
UVF
-
MDW
18h 04m
2 stops
$892Delta
Thu, Oct 22 - Thu, Oct 29
Multiple Airlines Logo
3:15 pm - 1:40 pm
MDW
-
UVF
21h 25m
1 stop
Multiple Airlines Logo
2:30 pm - 9:40 am
UVF
-
MDW
20h 10m
1 stop
$922Multiple Airlines
Wed, Jul 8 - Sun, Jul 12
Multiple Airlines Logo
3:15 pm - 1:40 pm
MDW
-
UVF
21h 25m
1 stop
Multiple Airlines Logo
2:30 pm - 9:08 am
UVF
-
MDW
19h 38m
2 stops
$1,023Multiple Airlines
Wed, Jul 8 - Sun, Jul 12
WestJet Logo
6:42 pm - 1:40 pm
MDW
-
UVF
41h 58m
2 stops
WestJet Logo
2:30 pm - 6:31 pm
UVF
-
MDW
29h 01m
2 stops
$2,814WestJet
Fri, Aug 28 - Sun, Sep 6
WestJet Logo
6:42 pm - 1:40 pm
MDW
-
UVF
41h 58m
2 stops
WestJet Logo
2:30 pm - 6:31 pm
UVF
-
MDW
29h 01m
2 stops
$2,865WestJet
Fri, Aug 28 - Sun, Sep 6

Air Canada flights from Chicago to Castries

Our best Air Canada deals on Chicago to Castries flight tickets
Air Canada
Jun 14
ORD8:45 amChicago O'Hare Intl
52h 25m
2 stops
UVF2:10 pmCastries Hewanorra
Jun 19
UVF3:15 pmCastries Hewanorra
23h 07m
1 stop
ORD1:22 pmChicago O'Hare Intl
$382
Air Canada
Jun 14
ORD6:22 pmChicago O'Hare Intl
42h 48m
2 stops
UVF2:10 pmCastries Hewanorra
Jun 19
UVF3:15 pmCastries Hewanorra
17h 30m
2 stops
ORD7:45 amChicago O'Hare Intl
$388
Air Canada
Jun 18
ORD6:22 pmChicago O'Hare Intl
18h 58m
2 stops
UVF2:20 pmCastries Hewanorra
Jun 23
UVF3:15 pmCastries Hewanorra
17h 30m
2 stops
ORD7:45 amChicago O'Hare Intl
$398

JetBlue flights from Chicago to Castries

Our best JetBlue deals on Chicago to Castries flight tickets
JetBlue
Jul 11
ORD5:27 pmChicago O'Hare Intl
18h 00m
1 stop
UVF12:27 pmCastries Hewanorra
Jul 20
UVF4:40 pmCastries Hewanorra
17h 10m
1 stop
ORD8:50 amChicago O'Hare Intl
$584
JetBlue
Jul 11
ORD5:27 pmChicago O'Hare Intl
18h 00m
1 stop
UVF12:27 pmCastries Hewanorra
Jul 13
UVF4:40 pmCastries Hewanorra
17h 10m
1 stop
ORD8:50 amChicago O'Hare Intl
$616
JetBlue
Jul 8
ORD6:30 pmChicago O'Hare Intl
17h 06m
1 stop
UVF12:36 pmCastries Hewanorra
Jul 20
UVF4:40 pmCastries Hewanorra
17h 10m
1 stop
ORD8:50 amChicago O'Hare Intl
$619

momondo 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, momondo users made 832,500 searches. Data last updated May 25, 2026.
Use the filters below to find and compare flights from Chicago to Castries that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoCastries

ORD - UVF

ORDUVF

Chicago O'Hare Intl

Sun 6/14

8:45 am-2:10 pm

2 stops52h 25m

Castries Hewanorra

Fri 6/19

3:15 pm-1:22 pm

1 stop23h 07m

$382

ChicagoCastries

ORD - UVF

ORDUVF

Chicago O'Hare Intl

Sun 6/14

6:22 pm-2:10 pm

2 stops42h 48m

Castries Hewanorra

Fri 6/19

3:15 pm-7:45 am

2 stops17h 30m

$388

ChicagoCastries

ORD - UVF

ORDUVF

Chicago O'Hare Intl

Thu 6/18

6:22 pm-2:20 pm

2 stops18h 58m

Castries Hewanorra

Tue 6/23

3:15 pm-7:45 am

2 stops17h 30m

$398

ChicagoCastries

ORD - UVF

ORDUVF

Chicago O'Hare Intl

Thu 7/23

9:50 am-2:20 pm

1 stop27h 30m

Castries Hewanorra

Tue 7/28

3:05 pm-8:05 pm

2 stops30h 00m

$424

ChicagoCastries

MDW - UVF

MDWUVF

Chicago Midway

Wed 10/21

1:00 pm-2:26 pm

2 stops24h 26m

Castries Hewanorra

Thu 10/29

3:41 pm-8:45 am

2 stops18h 04m

$868
Quickest round-trip

ChicagoCastries

MDW - UVF

MDWUVF

Chicago Midway

Thu 10/22

6:00 am-2:26 pm

1 stop7h 26m

Castries Hewanorra

Thu 10/29

3:41 pm-8:45 am

2 stops18h 04m

$892

ChicagoCastries

MDW - UVF

MDWUVF

Chicago Midway

Wed 7/8

3:15 pm-1:40 pm

1 stop21h 25m

Castries Hewanorra

Sun 7/12

2:30 pm-9:40 am

1 stop20h 10m

$922

ChicagoCastries

MDW - UVF

MDWUVF

Chicago Midway

Wed 7/8

3:15 pm-1:40 pm

1 stop21h 25m

Castries Hewanorra

Sun 7/12

2:30 pm-9:08 am

2 stops19h 38m

$1,023

ChicagoCastries

MDW - UVF

MDWUVF

Chicago Midway

Fri 8/28

6:42 pm-1:40 pm

2 stops41h 58m

Castries Hewanorra

Sun 9/6

2:30 pm-6:31 pm

2 stops29h 01m

$2,814

ChicagoCastries

MDW - UVF

MDWUVF

Chicago Midway

Fri 8/28

6:42 pm-1:40 pm

2 stops41h 58m

Castries Hewanorra

Sun 9/6

2:30 pm-6:31 pm

2 stops29h 01m

$2,865

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Castries from

How to get the cheapest flight ticket from Chicago to Castries

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the typical price of a round-trip flight between Chicago and Castries?

What is the cheapest month to fly to Castries?

The month of April is, on average, the cheapest month to fly to Castries from Chicago, with most prices found around $363. The month of August is another great option to travel to Castries, with average flight prices from Chicago averaging around $368.

What is the cheapest Chicago to Castries Hewanorra flight route?

Fly from Chicago O'Hare Intl to Castries Hewanorra for the best Chicago - Castries Hewanorra flight prices

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

You are more likely to see cheaper flights to Castries from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to Castries for around $865 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Castries from Chicago for as low as $617 on momondo.

What cabin class options are available on Chicago to Castries flights?

There is only 1 cabin class available to choose from on Chicago to Castries flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Chicago to Castries flights?

You could potentially save up to 18% on your flight if you consider stops on a Chicago to Castries flight.

When to book flights from Chicago to Castries

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago to Castries according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Chicago to Castries (CHI to UVF) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago to Castries

Best Price Found

$488

Fastest flight time

5h 33m

Direct flights

Sun

Airports in Castries

1 airport
The best one-way flight to Castries from Chicago in the past 72 hours is $488. The best round-trip flight deal from Chicago to Castries found on momondo in the last 72 hours is $928.
The fastest flight from Chicago to Castries takes 5h 33m
Direct flights go from Chicago to Castries on Sunday. The only airline offering direct flights is United Airlines.
There is 1 airport in Castries. From Chicago there are direct flights to Castries Hewanorra (UVF).
Search flight deals

Frequently asked questions about flying from Chicago to Castries

  • How far is Chicago to Castries Hewanorra by plane?

    Castries Hewanorra is 2496.8 mi away from Chicago. A reasonable flight in good conditions will take 5h 33m.

  • When did momondo last update prices for flights from Chicago to Castries Hewanorra Airport?

    Prices for flights from Chicago to Castries Hewanorra Airport were last updated today.

  • How many operators does momondo search for flights from Chicago to Castries Hewanorra Airport?

  • How old do you have to be to fly from Chicago to Castries Hewanorra Airport?

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago to Castries Hewanorra Airport.

  • What documentation or ID do you need to fly to Castries Hewanorra Airport?

    The travel and health documents required for your trip to Castries Hewanorra Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Castries Hewanorra Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

  • What is the most popular plane model from Chicago to Castries?

  • What is the most popular airline from Chicago to Castries?

Best airlines flying from Chicago to Castries

Compare and see reviews for airlines that fly from Chicago to Castries with momondo
Airline
Rating
Free Cancellation
Price
American AirlinesPriceFrom $552Free CancellationRating
7.1
11,629 reviews
Search American Airlines flights
DeltaPriceFrom $565Free CancellationRating
7.9
8,434 reviews
Search Delta flights
United AirlinesPriceFrom $608Free CancellationRating
7.4
9,747 reviews
Search United Airlines flights

  • United Airlines Flights From Chicago to Castries

    United Airlines flight deals from Chicago to Castries start from $608 round-trip. Over the 1 United Airlines flight for this route in a normal week, average airfare is usually $1,183 round-trip - but some users have found much cheaper deals with momondo.

Traveling to a place near Castries?

Book flights to Castries if you plan to visit one of these locations
Vieux Fort

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Castries?

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Chicago to Castries for you.

Can I find flights from Chicago to Castries with flexible booking policies on momondo?

Yes. momondo allows you to filter the results for Chicago to Castries flights to just show those with flexible booking policies.

How can momondo help me find flights from Chicago to Castries?

Once all potential Chicago to Castries flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

I’m not ready to book a flight from Chicago to Castries right now. Can momondo alert me if prices change?

Yes. momondo can track prices for Chicago to Castries flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.

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Find better results for your trip to Saint Lucia

Airports servicing Saint Lucia

Castries George F. L. Charle Airport