CHI - UVF

$194 Find Cheap Flights from Chicago to Castries

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to Castries departing on 12/30. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to Castries

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Castries, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Castries, as well as popular online travel agencies
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41’299’237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest round-trip
$486
Overall average: $807
JetBlue
Tue 2/3Sun 2/8
ORD - UVF • 1 stop
Cheapest non-stop
$875
Typical prices: $1,090-$1,104
United Airlines
Sat 12/13Sat 12/20
ORD - UVF • Non-stop
Top airlines
JetBlue
Cheapest • from $486 (round-trip)
Delta
Best reviews • 7.9 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Top routes
ORD-UVF
Cheapest
ORD-UVF
Most popular
Insights
Insights
Insights
Insights
When to book
3 weeks
in advance
Our data shows that travelers who book at least 3 weeks in advance save around 19% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
January
Cheapest • 21% price drop
March
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Nonstop flights
1 day a week
There are direct flights from Chicago to Castries 1 day a week: Sat.
Direct flights
Direct flights
Direct flights
Direct flights
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We hope you love your trip to Castries!
Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Chicago to Castries (CHI-UVF)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago to Castries that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Chicago to Castries

Tue, Feb 3 - Sun, Feb 8
JetBlue Logo
9:40 am - 3:53 pmORD-UVF
28h 13m1 stop
JetBlue Logo
4:40 pm - 7:45 pmUVF-ORD
29h 05m1 stop
$486JetBlue
Find Deal
Sat, Jan 24 - Tue, Feb 3
American Airlines Logo
7:30 pm - 1:46 pmORD-UVF
16h 16m1 stop
American Airlines Logo
5:02 pm - 12:30 amUVF-ORD
9h 28m1 stop
$489American Airlines
Find Deal
Mon, Feb 9 - Thu, Feb 12
Delta Logo
1:26 pm - 3:05 pmMDW-UVF
23h 39m2 stops
Delta Logo
4:25 pm - 12:46 pmUVF-MDW
22h 21m2 stops
$494Delta
Find Deal
Sat, Jan 24 - Tue, Feb 3
American Airlines Logo
7:30 pm - 4:02 pmORD-UVF
18h 32m1 stop
American Airlines Logo
5:02 pm - 8:31 amUVF-ORD
17h 29m2 stops
$494American Airlines
Find Deal
Sun, Jan 11 - Sat, Jan 17
JetBlue Logo
9:15 am - 4:25 pmORD-UVF
29h 10m1 stop
JetBlue Logo
4:40 pm - 5:43 pmUVF-ORD
27h 03m1 stop
$495JetBlue
Find Deal
Sun, Jan 11 - Sun, Jan 18
Air Canada Logo
8:45 pm - 4:25 pmORD-UVF
17h 40m1 stop
Air Canada Logo
5:15 pm - 9:13 amUVF-ORD
17h 58m1 stop
$513Air Canada
Find Deal
Mon, Jan 19 - Mon, Jan 26
Delta Logo
5:30 am - 3:05 pmORD-UVF
7h 35m1 stop
Delta Logo
4:25 pm - 11:56 pmUVF-ORD
9h 31m1 stop
$519Delta
Find Deal
Sun, Jan 11 - Sun, Jan 18
Air Canada Logo
8:45 pm - 4:25 pmORD-UVF
17h 40m1 stop
Air Canada Logo
5:15 pm - 2:55 pmUVF-ORD
23h 40m2 stops
$523Air Canada
Find Deal
Sun, Jan 11 - Sun, Jan 18
Multiple Airlines Logo
1:49 pm - 4:25 pmMDW-UVF
24h 36m2 stops
Multiple Airlines Logo
5:15 pm - 1:09 pmUVF-MDW
21h 54m2 stops
$888Multiple Airlines
Find Deal
Sat, Mar 28 - Wed, Apr 1
Multiple Airlines Logo
9:30 am - 3:25 pmMDW-UVF
28h 55m2 stops
Multiple Airlines Logo
4:20 pm - 10:05 amUVF-MDW
18h 45m1 stop
$942Multiple Airlines
Find Deal
Booking Insights

KAYAK's insights & trends for Chicago to Castries flights

Get data-powered insights and trends into flights from Chicago to Castries to help you find the cheapest flights, the best time to fly and much more.

How much is a round-trip flight from Chicago to Castries?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Chicago to Castries departing in February.

What is the cheapest Chicago to Castries flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest return flight from Chicago to Castries costs $681 on the route between Chicago O'Hare Intl Airport (ORD) and Castries (UVF). It is also the most popular route.

What is the cheapest month to fly from Chicago to Castries?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago to Castries, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Chicago to Castries is January, where tickets cost $600 (return) on average. On the other hand, the most expensive months are December and June, where the average cost of round-trip tickets is $1,056 and $999 respectively.

Can I save money by flying with a layover from Chicago to Castries?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $705, prices are generally cheapest when you fly direct.

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

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Chicago to Castries, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Chicago to Castries, you should book around 3 weeks before departure, which saves you about 19% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 8 weeks before departure.

Good to know

Low seasonSeptember
Cheapest flight$194
Best time to beat the crowds but there is an average 2% increase in price.
Most popular time to fly and prices are also 2% lower on average.
Flight from Chicago O'Hare Airport to Castries

When to book flights from Chicago to Castries

Are your dates flexible? Find out the best times to travel from Chicago to Castries based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking flights from Chicago to Castries

  • What is the cheapest flight from Chicago to Castries?

    In the last 3 days, the lowest price for a flight from Chicago to Castries was $194 for a one-way ticket and $486 for a round-trip.

  • Do I need a passport to fly between Chicago and Castries?

    A passport is required to fly from Chicago to Castries.

  • Which airports will I be using when flying from Chicago to Castries?

    When flying out of Chicago you will be using one of these airports: Chicago Midway or Chicago O'Hare Intl. You will be landing at Castries Hewanorra.

  • Which aircraft models fly most regularly from Chicago to Castries?

    The Boeing 737-700 is the aircraft model that flies most regularly on the Chicago to Castries flight route.

  • Which airline alliances offer flights from Chicago to Castries?

    SkyTeam, Star Alliance, and oneworld are the airline alliances operating flights between Chicago and Castries, with SkyTeam being the most commonly used for this route.

  • On which days can I fly direct from Chicago to Castries?

    You can catch a nonstop flight from Chicago to Castries on on Saturday.

  • Which is the best airline for flights from Chicago to Castries, Delta or United Airlines?

    The two airlines most popular with KAYAK users for flights from Chicago to Castries are Delta and United Airlines. With an average price for the route of $722 and an overall rating of 7.9, Delta is the most popular choice. United Airlines is also a great choice for the route, with an average price of $872 and an overall rating of 7.4.

  • How does KAYAK find such low prices on flights from Chicago to Castries?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago to Castries.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago to Castries?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Castries from Chicago is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago to Castries?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Castries with an airline and back to Chicago with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago to Castries?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Castries from Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

KAYAK’s top tips for finding a cheap flight from Chicago to Castries

  • Looking for a cheap flight? 25% of our users found flights on this route for $368 or less one-way and $771 or less round-trip.

Prefer to fly direct from Chicago to Castries?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Chicago to Castries Hewanorra.
Find which airlines fly direct from Chicago to Castries Hewanorra Airport, which days they fly and book direct flights.

Direct departures

Chicago to Castries Hewanorra

Saturday

United Airlines

United Airlines

See more direct flights

Direct returns

Castries Hewanorra to Chicago

Saturday

United Airlines

United Airlines

See more direct flights

Reviews of the top 3 airlines serving from Chicago to Castries

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Castries. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Chicago to Castries? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.9
DeltaOverall score based on 8010 reviews
8.5Crew
7.9Comfort
8.1Boarding
7.9Entertainment
7.3Food
Airline reviews

Staff was exceptional! Everyone was kind, professional and friendly making the trip very pleasant. Thank you!

10.0 ExcellentMary Heather, Nov 2025MKE - LGA
Read more Delta reviews

Staff was exceptional! Everyone was kind, professional and friendly making the trip very pleasant. Thank you!

No lunch on a x-country flight scheduled for 10:50 am departure, arrived 5+ hrs later. That requires a black box label before you pay for the tickets. Worst, when I checked in online, it's specifically said that lunch was served on his flight for economy Plus passengers.

We had a lot of really rough weather but that was not Delta's fault. Pilot was amazing.

First, Delta needs more flights to/from Miami. Second, a 1000pm leaving at 1230pm is unacceptable from their biggest airport world hub. Another aircraft could have been used such as the aircraft scheduled to be used in the morning for that exact same route. Yes, I did get me there but the lack of sleep the next day didn't help me enjoy my entire trip since I was busy with activities during the weekend. This can be and is expected from Spirit (going bankrupt) and Frontier (despite they're nickel and dimers). But from Delta's World Hub? That's totally unacceptable!

This flight was straightforward and without difficulty. Service was OK, but I continue to be underwhelmed by level of attention given to Sky Priority passengers.

It would’ve been nice for all that money to have a more substantial snack for free. I remember once upon a time getting a very nice turkey sandwich with Swiss cheese on whole wheat bread for no charge along with a drink. I guess those days are gone. it’s a little insulting being given a cookie or a bag of baked chips Going forward I’ll just bring my own.

Great. Seamless. Check in agent at kiosk international was amazing and extremely helpful.

Our flight from SFO to MSP was right on time on 11/15/2025. No delays. As we approached MSP at about 8 pm, we circled in the air until 8:40 pm so I don't call that efficient for MSP. I think the captain should announce the delay and why. (as if we all don't know that we are just circling around the area, slowing down, speeding up, slowing down.) Thank you. Marilyn Fischer

Service in business class was not impressive. I ordered coffee with dinner and then watched other people get 2 refills before I got my 1 cup of coffee, and only after I pressed the attendant button overhead. Furthermore, the seats in the forward cabin need maintenance on this 737-800: the upholstery is detaching from the seat frame, at least on the backs of seats 1C, 1D.

Plenty of leg room, temperature was great and staff was excellent. Would do it more often.

Very nice flight love the small aircraft. We had a wonderful flight attendant. Nice to see someone that really enjoys her job. Don't have her name but had a southern accent.

Very thoughtful flight attendant offered me water immediately since I had run to make my connection.

Seats in waiting area and on plane hard as rock. Fast internet on the flight was great! Crew was kind.

Always wish for more healthy, gluten free options. We have to bring our own.

Having a long layover, I was very appreciative of the ability to stand by for an earlier flight. Other airlines like Delta have refused this to me in the past, just to be mean (because my ticket class wasn't high enough). United went out of their way to help me get to my destination early, which I really appreciated given that it was the third leg of a 24+ hour journey for me.

Other than a way way too cold cabinets for the entire flight, all was great

One bag is incorrect and not acceptable for an international flight. The food was not just good. I won't fly with them again.

Excellent flight. Smooth, efficient boarding. Quick flight. Arrived early at STL.

Not the fault of United—weather, reroute around weather, time sitting on tarmac, arrived couple hours late, too late for train into city necessitating a much pricier cab but weather…can’t be helped.

I will never book a flight through Cheap fare. They booked me from Portland Main . And would not give me a refund, so I bought 2 tickets one for 299. From Portland Main to ORD. Then I had to buy a ticket from Oregon PDX to ORD that was another 440. So Just so you know they even told me it was there fault but no refund. Bad bussniess. I did inform United but they said they couldn't help me due to the fact I booked through Cheap Tickets. Never again. And I'm spreding the word. I let everyone know at my 50th class reunion

We loved the steward on the plane. He made the night enjoyable

The plane was late, when we did board the plane was as cold as a freezer. I was freezing the entire flight, no blankets. Lost miserable flight I’ve ever had.

My wife and I love to travel, so we fly a lot. We've already logged 381,075 miles and with practically every major airline. But this flight was very disappointing. It started off well, with no delays and a new plane. But when lunchtime approached, all that good impression was ruined. Instead of white tablecloths, we were offered small, dark placemats, which, as it turned out, were perfectly adequate for the food. All the food offered—and my wife and I only took fish, and the meat—was not just bad, it was downright disgusting and not heated enough. The same applies to the appetizers. This was the first time in many years of traveling that we've been offered such disgusting food.

Lost luggage stuck no clothes and no word after 2 days leaving on cruise no stuff or clothes

3 hour weather delay followed by 1 hour (and counting) maintenance delay. UGH!

After we'd boarded , they canceled the flight. The crew didn't even know , we just all received text messages. Then after they deplaned us , AA was just like "too bad, go F your self, we sure ain't gonna help you"

After a two hour delay, my flight was CANCELLED! No pilot available. Such BS.

Amazing food, great staff, with one noticable detail missing ...but no seat entertainment in any of aircraft ...I am not a fan

I wish American Airlines would change the airline industry by loading the plane back to front instead of front to back. Planes would board so much more smoothly and quickly.

I have long legs, my foot was out in the aisle and when a flight attendant came walking by and I didn't notice, instead of saying "excuse me" or anything like that, she kicked my foot. Extremely rude

Everything you need to know for your flight from Chicago to Castries

Information on your arrival and departure airports