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Cheap flights from Chicago Midway Airport to Castries from $367

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 Midway Airport to Castries departing on 1/3. 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 Midway Airport to Castries

Cheap round-trip flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
6:35 pm - 1:46 pm
MDW
-
UVF
18h 11m2 stops
Multiple Airlines Logo
2:40 pm - 10:05 am
UVF
-
MDW
20h 25m1 stop
$1,304Multiple Airlines
Sat, Mar 28 - Sun, Apr 5
Multiple Airlines Logo
12:45 pm - 1:46 pm
MDW
-
UVF
24h 01m1 stop
Multiple Airlines Logo
2:40 pm - 10:05 am
UVF
-
MDW
20h 25m1 stop
$1,310Multiple Airlines
Sat, Mar 28 - Sun, Apr 5
Delta Logo
1:09 pm - 2:04 pm
MDW
-
UVF
23h 55m2 stops
Delta Logo
3:24 pm - 9:55 am
UVF
-
MDW
19h 31m1 stop
$1,492Delta
Mon, Mar 23 - Thu, Apr 2
Delta Logo
5:38 pm - 2:04 pm
MDW
-
UVF
19h 26m1 stop
Delta Logo
3:24 pm - 9:55 am
UVF
-
MDW
19h 31m1 stop
$1,602Delta
Mon, Mar 23 - Thu, Apr 2
Delta Logo
5:40 pm - 1:58 pm
MDW
-
UVF
19h 18m1 stop
Delta Logo
3:18 pm - 4:55 pm
UVF
-
MDW
26h 37m1 stop
$1,615Delta
Sun, Mar 29 - Sun, Apr 5
Delta Logo
5:38 pm - 2:04 pm
MDW
-
UVF
19h 26m1 stop
Delta Logo
3:24 pm - 12:02 pm
UVF
-
MDW
21h 38m1 stop
$1,701Delta
Wed, Mar 25 - Thu, Apr 2
Delta Logo
4:30 pm - 1:58 pm
MDW
-
UVF
20h 28m1 stop
Delta Logo
3:18 pm - 9:56 am
UVF
-
MDW
19h 38m1 stop
$1,742Delta
Sat, Mar 28 - Sat, Apr 4
Delta Logo
6:00 am - 2:05 pm
MDW
-
UVF
7h 05m1 stop
Delta Logo
3:30 pm - 12:30 pm
UVF
-
MDW
22h 00m2 stops
$1,755Delta
Wed, Jun 10 - Sun, Jun 14
Delta Logo
5:40 pm - 1:58 pm
MDW
-
UVF
19h 18m1 stop
Delta Logo
3:18 pm - 4:55 pm
UVF
-
MDW
26h 37m1 stop
$1,865Delta
Fri, Mar 27 - Sun, Apr 5
Delta Logo
5:40 pm - 1:58 pm
MDW
-
UVF
19h 18m1 stop
Delta Logo
3:18 pm - 9:56 am
UVF
-
MDW
19h 38m1 stop
$1,889Delta
Sun, Mar 29 - Fri, Apr 3

Delta flights from Chicago Midway Airport to Castries

Our best Delta deals on Chicago Midway Airport to Castries flight tickets
Delta
Dec 27
MDW6:00 amChicago Midway
7h 33m
1 stop
UVF3:33 pmCastries Hewanorra
Dec 31
UVF4:50 pmCastries Hewanorra
18h 15m
1 stop
MDW9:05 amChicago Midway
$1,575
Find similar
Delta
Dec 27
MDW6:00 amChicago Midway
7h 33m
1 stop
UVF3:33 pmCastries Hewanorra
Dec 31
UVF4:50 pmCastries Hewanorra
17h 59m
2 stops
MDW8:49 amChicago Midway
$1,580
Find similar
Delta
Mar 29
MDW5:40 pmChicago Midway
19h 18m
1 stop
UVF1:58 pmCastries Hewanorra
Apr 4
UVF3:18 pmCastries Hewanorra
19h 38m
1 stop
MDW9:56 amChicago Midway
$1,615
Find similar

WestJet flights from Chicago Midway Airport to Castries

Our best WestJet deals on Chicago Midway Airport to Castries flight tickets
WestJet
Mar 28
MDW1:09 pmChicago Midway
23h 37m
2 stops
UVF1:46 pmCastries Hewanorra
Apr 5
UVF2:40 pmCastries Hewanorra
22h 49m
2 stops
MDW12:29 pmChicago Midway
$3,606
Find similar
WestJet
Jan 11
MDW6:30 pmChicago Midway
42h 20m
2 stops
UVF2:50 pmCastries Hewanorra
Jan 18
UVF3:40 pmCastries Hewanorra
23h 06m
2 stops
MDW12:46 pmChicago Midway
$3,612
Find similar
WestJet
Jan 16
MDW1:28 pmChicago Midway
47h 22m
2 stops
UVF2:50 pmCastries Hewanorra
Jan 27
UVF3:40 pmCastries Hewanorra
28h 15m
2 stops
MDW5:55 pmChicago Midway
$3,620
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Chicago Midway Airport 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 December 20, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to Castries that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoCastries

MDW - UVF

MDWUVF

Chicago Midway

Sat 3/28

6:35 pm-1:46 pm

2 stops18h 11m

Castries Hewanorra

Sun 4/5

2:40 pm-10:05 am

1 stop20h 25m

$1,304

ChicagoCastries

MDW - UVF

MDWUVF

Chicago Midway

Sat 3/28

12:45 pm-1:46 pm

1 stop24h 01m

Castries Hewanorra

Sun 4/5

2:40 pm-10:05 am

1 stop20h 25m

$1,310

ChicagoCastries

MDW - UVF

MDWUVF

Chicago Midway

Mon 3/23

1:09 pm-2:04 pm

2 stops23h 55m

Castries Hewanorra

Thu 4/2

3:24 pm-9:55 am

1 stop19h 31m

$1,492

ChicagoCastries

MDW - UVF

MDWUVF

Chicago Midway

Mon 3/23

5:38 pm-2:04 pm

1 stop19h 26m

Castries Hewanorra

Thu 4/2

3:24 pm-9:55 am

1 stop19h 31m

$1,602

ChicagoCastries

MDW - UVF

MDWUVF

Chicago Midway

Sun 3/29

5:40 pm-1:58 pm

1 stop19h 18m

Castries Hewanorra

Sun 4/5

3:18 pm-4:55 pm

1 stop26h 37m

$1,615

ChicagoCastries

MDW - UVF

MDWUVF

Chicago Midway

Wed 3/25

5:38 pm-2:04 pm

1 stop19h 26m

Castries Hewanorra

Thu 4/2

3:24 pm-12:02 pm

1 stop21h 38m

$1,701

ChicagoCastries

MDW - UVF

MDWUVF

Chicago Midway

Sat 3/28

4:30 pm-1:58 pm

1 stop20h 28m

Castries Hewanorra

Sat 4/4

3:18 pm-9:56 am

1 stop19h 38m

$1,742

ChicagoCastries

MDW - UVF

MDWUVF

Chicago Midway

Wed 6/10

6:00 am-2:05 pm

1 stop7h 05m

Castries Hewanorra

Sun 6/14

3:30 pm-12:30 pm

2 stops22h 00m

$1,755

ChicagoCastries

MDW - UVF

MDWUVF

Chicago Midway

Fri 3/27

5:40 pm-1:58 pm

1 stop19h 18m

Castries Hewanorra

Sun 4/5

3:18 pm-4:55 pm

1 stop26h 37m

$1,865

ChicagoCastries

MDW - UVF

MDWUVF

Chicago Midway

Sun 3/29

5:40 pm-1:58 pm

1 stop19h 18m

Castries Hewanorra

Fri 4/3

3:18 pm-9:56 am

1 stop19h 38m

$1,889

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 11 resultsSorted by cheapest first
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See travel insights to Castries from

How to get the cheapest flight ticket from Chicago Midway Airport 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 cheapest day to depart on your flight to Castries?

The cheapest day to depart from Chicago Midway Airport to Castries is on a Wednesday when prices can be found for as low as $630. If your travel schedule is flexible, try to avoid departing on a Saturday because tickets tend to average around $997. These prices are subject to change though, so be sure to set up a Price Alert for flights to Castries.

What is the cheapest time of day to depart on your flight to Castries?

According to our data, the cheapest time of day to fly to Castries is at noon. momondo users have found flights departing from Chicago Midway Airport to Castries at noon for as low as $496. Keep in mind that these prices may fluctuate based on what airline you choose and the time of year you plan to travel. Flights to Castries are more costly in the morning, with an average ticket price of $897. Departure times in the morning fall within the peak daily travel times, which is why tickets can be more expensive.

When to book flights from Chicago Midway Airport to Castries

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

Cheap Chicago Midway Airport to Castries (MDW to UVF) flight deals and tips

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

Fastest flight time

7h 05m

Direct flights

None
The fastest flight from Chicago Midway Airport to Castries takes 7h 05m
There are no direct flights from Chicago Midway Airport to Castries. There are no popular flight routes from Chicago Midway Airport to Castries.
Search flight deals

  • How far is Chicago Midway to Castries Hewanorra by plane?

    A flight from Chicago Midway to Castries Hewanorra will travel around 2497.1 mi. Typically, this will take 7h 05m by plane in normal conditions.

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

    Prices for flights from Chicago Midway Airport to Castries Hewanorra Airport refresh daily.

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

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Chicago Midway Airport to Castries Hewanorra Airport.

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

    The travel and health documents you'll need for your trip to Castries Hewanorra Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Castries Hewanorra Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

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?

All flight searches from Chicago to Castries on momondo can be filtered to show those which offer flexible booking policies.

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

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Castries from Chicago.

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