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Cheap flights from Chicago Midway Airport to Castries from $320

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 6/20. 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
3:20 pm - 1:40 pm
MDW
-
UVF
21h 20m
1 stop
Multiple Airlines Logo
2:30 pm - 2:35 pm
UVF
-
MDW
25h 05m
1 stop
$598Multiple Airlines
Wed, May 20 - Thu, May 28
Multiple Airlines Logo
10:25 am - 1:40 pm
MDW
-
UVF
26h 15m
1 stop
Multiple Airlines Logo
2:30 pm - 9:40 am
UVF
-
MDW
20h 10m
1 stop
$669Multiple Airlines
Sat, May 23 - Thu, May 28
Multiple Airlines Logo
7:30 am - 1:40 pm
MDW
-
UVF
29h 10m
2 stops
Multiple Airlines Logo
2:30 pm - 9:40 am
UVF
-
MDW
20h 10m
1 stop
$733Multiple Airlines
Wed, May 20 - Thu, May 28
Multiple Airlines Logo
4:05 pm - 1:46 pm
MDW
-
UVF
20h 41m
1 stop
Multiple Airlines Logo
2:50 pm - 3:20 pm
UVF
-
MDW
25h 30m
1 stop
$745Multiple Airlines
Mon, Apr 6 - Thu, Apr 9
Multiple Airlines Logo
3:20 pm - 1:40 pm
MDW
-
UVF
21h 20m
1 stop
Multiple Airlines Logo
2:30 pm - 9:40 am
UVF
-
MDW
20h 10m
1 stop
$779Multiple Airlines
Wed, May 20 - Sun, May 24
Multiple Airlines Logo
11:00 am - 1:46 pm
MDW
-
UVF
25h 46m
1 stop
Multiple Airlines Logo
2:40 pm - 10:05 am
UVF
-
MDW
20h 25m
1 stop
$816Multiple Airlines
Wed, Mar 25 - Sun, Mar 29
Multiple Airlines Logo
10:25 am - 1:40 pm
MDW
-
UVF
26h 15m
1 stop
Multiple Airlines Logo
2:30 pm - 8:43 am
UVF
-
MDW
19h 13m
2 stops
$819Multiple Airlines
Sat, May 23 - Thu, May 28
Multiple Airlines Logo
12:55 pm - 1:46 pm
MDW
-
UVF
23h 51m
1 stop
Multiple Airlines Logo
2:50 pm - 3:20 pm
UVF
-
MDW
25h 30m
1 stop
$868Multiple Airlines
Sat, Apr 4 - Thu, Apr 9
Multiple Airlines Logo
6:34 pm - 1:46 pm
MDW
-
UVF
18h 12m
2 stops
Multiple Airlines Logo
2:50 pm - 3:20 pm
UVF
-
MDW
25h 30m
1 stop
$887Multiple Airlines
Mon, Apr 6 - Thu, Apr 9
Multiple Airlines Logo
12:55 pm - 1:46 pm
MDW
-
UVF
23h 51m
1 stop
Multiple Airlines Logo
2:50 pm - 8:53 am
UVF
-
MDW
19h 03m
2 stops
$939Multiple Airlines
Sat, Apr 4 - Thu, Apr 9

WestJet flights from Chicago Midway Airport to Castries

Our best WestJet deals on Chicago Midway Airport to Castries flight tickets
WestJet
May 13
MDW9:22 amChicago Midway
27h 18m
3 stops
UVF1:40 pmCastries Hewanorra
May 17
UVF2:30 pmCastries Hewanorra
19h 13m
2 stops
MDW8:43 amChicago Midway
$1,099
WestJet
May 16
MDW1:22 pmChicago Midway
23h 18m
2 stops
UVF1:40 pmCastries Hewanorra
May 24
UVF2:30 pmCastries Hewanorra
19h 13m
2 stops
MDW8:43 amChicago Midway
$1,100
WestJet
May 13
MDW9:22 amChicago Midway
27h 18m
3 stops
UVF1:40 pmCastries Hewanorra
May 17
UVF2:30 pmCastries Hewanorra
23h 12m
3 stops
MDW12:42 pmChicago Midway
$1,111

Delta flights from Chicago Midway Airport to Castries

Our best Delta deals on Chicago Midway Airport to Castries flight tickets
Delta
May 14
MDW1:22 pmChicago Midway
23h 43m
2 stops
UVF2:05 pmCastries Hewanorra
May 27
UVF3:25 pmCastries Hewanorra
18h 18m
2 stops
MDW8:43 amChicago Midway
$634
Delta
May 14
MDW1:22 pmChicago Midway
23h 43m
2 stops
UVF2:05 pmCastries Hewanorra
May 21
UVF3:25 pmCastries Hewanorra
18h 18m
2 stops
MDW8:43 amChicago Midway
$646
Delta
May 13
MDW9:22 amChicago Midway
27h 43m
2 stops
UVF2:05 pmCastries Hewanorra
May 27
UVF3:25 pmCastries Hewanorra
18h 18m
2 stops
MDW8:43 amChicago Midway
$703

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 March 1, 2026.
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

Wed 5/20

3:20 pm-1:40 pm

1 stop21h 20m

Castries Hewanorra

Thu 5/28

2:30 pm-2:35 pm

1 stop25h 05m

$598

ChicagoCastries

MDW - UVF

MDWUVF

Chicago Midway

Sat 5/23

10:25 am-1:40 pm

1 stop26h 15m

Castries Hewanorra

Thu 5/28

2:30 pm-9:40 am

1 stop20h 10m

$669

ChicagoCastries

MDW - UVF

MDWUVF

Chicago Midway

Wed 5/20

7:30 am-1:40 pm

2 stops29h 10m

Castries Hewanorra

Thu 5/28

2:30 pm-9:40 am

1 stop20h 10m

$733

ChicagoCastries

MDW - UVF

MDWUVF

Chicago Midway

Mon 4/6

4:05 pm-1:46 pm

1 stop20h 41m

Castries Hewanorra

Thu 4/9

2:50 pm-3:20 pm

1 stop25h 30m

$745

ChicagoCastries

MDW - UVF

MDWUVF

Chicago Midway

Wed 5/20

3:20 pm-1:40 pm

1 stop21h 20m

Castries Hewanorra

Sun 5/24

2:30 pm-9:40 am

1 stop20h 10m

$779

ChicagoCastries

MDW - UVF

MDWUVF

Chicago Midway

Wed 3/25

11:00 am-1:46 pm

1 stop25h 46m

Castries Hewanorra

Sun 3/29

2:40 pm-10:05 am

1 stop20h 25m

$816

ChicagoCastries

MDW - UVF

MDWUVF

Chicago Midway

Sat 5/23

10:25 am-1:40 pm

1 stop26h 15m

Castries Hewanorra

Thu 5/28

2:30 pm-8:43 am

2 stops19h 13m

$819

ChicagoCastries

MDW - UVF

MDWUVF

Chicago Midway

Sat 4/4

12:55 pm-1:46 pm

1 stop23h 51m

Castries Hewanorra

Thu 4/9

2:50 pm-3:20 pm

1 stop25h 30m

$868

ChicagoCastries

MDW - UVF

MDWUVF

Chicago Midway

Mon 4/6

6:34 pm-1:46 pm

2 stops18h 12m

Castries Hewanorra

Thu 4/9

2:50 pm-3:20 pm

1 stop25h 30m

$887

ChicagoCastries

MDW - UVF

MDWUVF

Chicago Midway

Sat 4/4

12:55 pm-1:46 pm

1 stop23h 51m

Castries Hewanorra

Thu 4/9

2:50 pm-8:53 am

2 stops19h 03m

$939

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 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 $1,012. If your travel schedule is flexible, try to avoid departing on a Saturday because tickets tend to average around $1,147. These prices are subject to change though, so be sure to set up a Price Alert for flights to Castries.

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

6h 58m

Direct flights

None
The fastest flight from Chicago Midway Airport to Castries takes 6h 58m
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 6h 58m 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