CHI - UVF

$143 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 6/11. 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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Everything you should know

Cheapest round-trip
$392
Typical prices: $1,340-$747
Air Canada
Thu 6/18Fri 6/26
ORD - UVF • 1 stop
Cheapest non-stop
$721
Typical prices: $1,142-$923
United Airlines
Sat 7/4Sat 7/11
ORD - UVF • Non-stop
Nonstop flights
Sat
You can fly direct with United Airlines. Average duration is 5h 45m
Direct flights
Direct flights
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Direct flights
Direct flights
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Top airlines
Cheapest • from $392 (round-trip)
Best reviews • 7.9 score
Airline reviews
Airline reviews
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Airline reviews
Airline reviews
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Top layover airports
Cheapest • Avg $519 (round-trip)
Shortest trip • 7h 24m (one-way)
Insights
Insights
Insights
Insights
Top routes
Cheapest
Most popular
Insights
Insights
Insights
Insights
When to book
in advance
Our data shows that travelers who book at least 5 weeks in advance save around 9% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
Cheapest • 25% price drop
Most popular
Good to know
Good to know
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KAYAK searches 100s of sites at once to find you the best travel deals.
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

Thu, Jun 18 - Fri, Jun 26
Air Canada Logo
8:40 pm - 2:20 pm
ORD
-
UVF
16h 40m
1 stop
Air Canada Logo
3:05 pm - 12:11 pm
UVF
-
ORD
22h 06m
2 stops
$392Air Canada
Thu, Jun 18 - Fri, Jun 26
Air Canada Logo
6:22 pm - 2:20 pm
ORD
-
UVF
18h 58m
2 stops
Air Canada Logo
3:05 pm - 7:45 am
UVF
-
ORD
17h 40m
2 stops
$397Air Canada
Sun, Apr 19 - Thu, Apr 23
Air Canada Logo
2:00 pm - 3:20 pm
ORD
-
UVF
24h 20m
1 stop
Air Canada Logo
4:15 pm - 3:15 pm
UVF
-
ORD
24h 00m
1 stop
$449Air Canada
Sun, Apr 19 - Thu, Apr 23
Air Canada Logo
4:15 pm - 3:20 pm
ORD
-
UVF
22h 05m
1 stop
Air Canada Logo
4:15 pm - 2:55 pm
UVF
-
ORD
23h 40m
2 stops
$452Air Canada
Thu, Jun 18 - Fri, Jun 26
Air Canada Logo
8:40 pm - 2:20 pm
ORD
-
UVF
16h 40m
1 stop
Air Canada Logo
3:05 pm - 9:00 am
UVF
-
ORD
18h 55m
1 stop
$464Air Canada
Sun, Apr 19 - Thu, Apr 23
Air Canada Logo
9:05 am - 3:20 pm
ORD
-
UVF
29h 15m
1 stop
Air Canada Logo
4:15 pm - 2:01 pm
UVF
-
ORD
22h 46m
1 stop
$469Air Canada
Sun, Apr 19 - Thu, Apr 23
Air Canada Logo
4:15 pm - 3:20 pm
ORD
-
UVF
22h 05m
1 stop
Air Canada Logo
4:15 pm - 2:55 pm
UVF
-
ORD
23h 40m
2 stops
$472Air Canada
Thu, Jun 11 - Sun, Jun 14
Multiple Airlines Logo
9:55 am - 2:10 pm
ORD
-
UVF
27h 15m
1 stop
Multiple Airlines Logo
2:30 pm - 9:00 am
UVF
-
ORD
19h 30m
1 stop
$519Multiple Airlines
Tue, Aug 11 - Wed, Aug 12
Delta Logo
6:00 am - 2:08 pm
MDW
-
UVF
7h 08m
1 stop
Delta Logo
3:28 pm - 12:30 pm
UVF
-
MDW
22h 02m
2 stops
$681Delta
Tue, Aug 11 - Tue, Aug 18
Delta Logo
6:00 am - 2:08 pm
MDW
-
UVF
7h 08m
1 stop
Delta Logo
3:28 pm - 12:30 pm
UVF
-
MDW
22h 02m
2 stops
$732Delta
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 June.

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 $837 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 August, where tickets cost $605 (return) on average. On the other hand, the most expensive months are December and June, where the average cost of round-trip tickets is $1,096 and $1,058 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.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 2 stops layover the cheapest option at $788 on average.

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 5 weeks before departure, which saves you about 9% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 10 weeks before departure.

Good to know

Low seasonJuly
Cheapest flight$143
Best time to beat the crowds with an average 10% drop in price.
Most popular time to fly and prices are also 19% 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 $143 for a one-way ticket and $392 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 $716 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 $1,322 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 $923 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 8392 reviews
7.9Comfort
8.5Crew
7.2Food
7.8Entertainment
8.1Boarding
Airline reviews

The crew bent over backwards to thank us for flying and make us comfortable. The food service was quick and efficient. The Captain communicated and said goodbye and thank you as we departed. They really stood out!

10.0 ExcellentKathryn, Apr 2026
JFK - LAX
Read more Delta reviews

The crew bent over backwards to thank us for flying and make us comfortable. The food service was quick and efficient. The Captain communicated and said goodbye and thank you as we departed. They really stood out!

Okay considering we had weather delays which the Pilot notified us of immediately!

Generally on time departures and arrivals, clean planes, sky miles membership provides great benefits (complimentary upgrades, etc).

Flight from Fort Wayne to Atlanta was the smallest in terms of cabin space that I've ever seen. A carry on I've used for 20 years BARELY fit in overhead compartment. I'm 5'10" and felt very cramped. Not the best experience.

I am writing to express my dissatisfaction with the poor service and unprofessional staff we encountered when traveling with an infant. Our flight was delayed, and the gate staff failed to manage the boarding process appropriately. Due to incorrect, unavailable, or missing 'pink tag' stroller and car seat check-in procedures at the gate, we were forced to board last. Furthermore, the gate staff was rude and dismissive, causing significant distress to our infant. To make matters worse, one of our checked items—an infant sleeper/lounger—was returned to us broken. Given the unsafe handling of essential equipment and unprofessional treatment, I expect a prompt resolution regarding compensation for the damaged items.

We departed and landed early which was a nice surprise. The boarding process was slow.

N Everything was perfect from boarding to assistance to baggage in Tampa

Subpar. The seating on the plane is almost unbearable. We are literally touching and/or sitting on each other which is totally unacceptable and shameful. Pilots and crew was very accommodating and friendly.

The boarding was organized and informative but the plane was tight meaning that you were sitting on one another and extremely uncomfortable. It’s disappointing that can’t have common seating comfort on the plane.

Loved the crew! Sucks that we went from 1 hour and 8 minute layover to a 3 hour layover. But weather sucks like that.

The boarding timing needs to be improved. The flight was delayed again because it took way too long to board. I was already exhausted from sleeping at the airport and spending all day there due to delay from my previous flight that connected in Chicago.

Great until we got to FRA. The next trip leg we were put in Business Class where seats had minimal padding!!!! They were awful and United Airlines needs to have their Lufthansa partner up their game or I won’t fly with them again!!

No meal service to the back of the plane as it started late or was too slow to get it out before it was time to land.

Terrible, if possible won't be flying again anytime soon!

Efficient boarding and early departure. Very smooth flight. Early arrival in ATL. Great flight.

Smooth and easy boarding, comfortable for the entire 5 hour flight, and the seat back entertainment was great! I appreciated all the features, from location info and maps, movies, the ability to connect with Bluetooth headphones, and good selection of movies. Food was good, normal airline snacks (I didn’t purchase anything)

Awful. No counter attendants. No dinner offered due to delays.

This trip did not start off well. The inbound flight was delayed about 20 minutes. Then, after initial onboarding, the passengers had to deplane due to a mechanical problem. That took about 30 minutes to fix and be cleared. Then, reboarding was chaotic. It took a long time to sort passengers and two passengers on standby were ticketed but there was no seat. So, they had to deplane. One of the flight crew was trying to help passengers figure out a place to put their carry-on bags and that took more time. In the end, our scheduled 10:30 am departure did not actually take off until about 12:05 pm CST. The flight itself was long but we got to Houston. Some passengers missed their connecting flights and had to rebook. Not the best of flights I've had.

We were delayed for about an hour from taking off due to traffic control procedures at the destination airport. But once in the air, the flight went well. The crew members were great and provided cabin service despite moderate turbulence during much of the flight.

Short flight, but no drink/snack service. The flights both going and coming were delayed.

Delays experienced in boarding/take off due to incoming plane delayed. However, the boarding time/depart time in the app was significantly delayed in providing these updates. Usually not updated until an hour after we should have already boarded. Poorly managed.

Moved to earlier flight which unexpectedly had maintenance issues initially indicated as quick fix to ultimately plane changes. Moved back to original flight, also delayed. In all cases customer updates and communication very unclear, no updates on drivers for delays.

Typical AA - late by 90+ mn. Gate changed twice... Changed the departure time 6 times No explanation, no communication on reasons for delay I travel with AA twice a year... and it is consistently very poor.. I will continue to use AA only when i have to.

The gate got changed several times and the flight was delayed over an hour. Awful experience

American continues to decline in their customer service and its beyond disappointing.

It was an older plane. First Class was not especially roomy or comfortable. It was a short flight so there were no meal but they did offer mixed nuts which used to be normal but now is rare. Crew member was very polite and professional.

Flight to Tampa was delayed taking off due to plane arriving late but no other issues

As previously stated the delay I experienced flying from Wichita to Chicago caused a host of issues. When I finally was able to be booked on the last remaining American flight from Chicago to Cincinnati, the gate changed four times with the last change occurring very near the scheduled boarding time. While I didn't have a problem moving from gate to gate, I did notice and make note of others that had mobility issues and had to move each time for the gate change.

Maintenance took a very long time and then we were in a holding pattern. While a one-off maintenance issue is standard, there were delays on both of my flights for this trip based on maintenance issues with the planes, which delayed both flights over 45 minutes. Thankfully, I didn't have any connections but it wasn't an experience that would make me pick AA if I have other options.

No Snacks or Entertainment. The flight was short, snacks should still be given.

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

Information on your arrival and departure airports