CHI - UVF

$157 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 4/11. 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
Travelers love KAYAK
41 299 237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest round-trip
$418
Overall average: $857
Air Canada
Sun 5/24Tue 6/2
ORD - UVF • 2 stops
Cheapest non-stop
$864
Typical prices: $932-$1,453
United Airlines
Sat 2/28Sat 3/7
ORD - UVF • Non-stop
Top airlines
Air Canada
Cheapest • from $418 (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 16% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
August
Cheapest • 23% price drop
November
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
Start a new search
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

Sun, May 24 - Tue, Jun 2
Air Canada Logo
6:23 pm - 2:05 pm
ORD
-
UVF
42h 42m
2 stops
Air Canada Logo
3:05 pm - 2:06 pm
UVF
-
ORD
24h 01m
1 stop
$418Air Canada
Fri, Mar 6 - Wed, Mar 11
JetBlue Logo
6:04 am - 3:58 pm
ORD
-
UVF
7h 54m
1 stop
JetBlue Logo
4:23 pm - 11:25 am
UVF
-
ORD
20h 02m
1 stop
$488JetBlue
Wed, Apr 15 - Wed, Apr 22
Air Canada Logo
6:40 pm - 3:25 pm
ORD
-
UVF
19h 45m
1 stop
Air Canada Logo
4:20 pm - 9:10 am
UVF
-
ORD
17h 50m
1 stop
$489Air Canada
Wed, Apr 15 - Wed, Apr 22
Air Canada Logo
6:40 pm - 3:25 pm
ORD
-
UVF
19h 45m
1 stop
Air Canada Logo
4:20 pm - 10:53 am
UVF
-
ORD
19h 33m
2 stops
$492Air Canada
Wed, Apr 15 - Wed, Apr 22
Air Canada Logo
6:40 pm - 3:25 pm
ORD
-
UVF
19h 45m
1 stop
Air Canada Logo
4:20 pm - 10:53 am
UVF
-
ORD
19h 33m
2 stops
$493Air Canada
Tue, Apr 7 - Thu, Apr 16
Air Canada Logo
6:40 pm - 3:20 pm
ORD
-
UVF
19h 40m
1 stop
Air Canada Logo
4:15 pm - 9:10 am
UVF
-
ORD
17h 55m
1 stop
$495Air Canada
Wed, Apr 15 - Wed, Apr 22
Air Canada Logo
6:40 pm - 3:25 pm
ORD
-
UVF
19h 45m
1 stop
Air Canada Logo
4:20 pm - 10:53 am
UVF
-
ORD
19h 33m
2 stops
$496Air Canada
Wed, Mar 4 - Wed, Mar 11
Multiple Airlines Logo
6:04 am - 4:01 pm
ORD
-
UVF
7h 57m
1 stop
Multiple Airlines Logo
4:20 pm - 5:48 pm
UVF
-
ORD
26h 28m
1 stop
$499Multiple Airlines
Mon, Mar 23 - Tue, Mar 31
Delta Logo
1:10 pm - 1:58 pm
MDW
-
UVF
23h 48m
2 stops
Delta Logo
3:18 pm - 5:54 pm
UVF
-
MDW
27h 36m
2 stops
$551Delta
Mon, Mar 2 - Mon, Mar 9
Delta Logo
6:40 pm - 3:05 pm
MDW
-
UVF
18h 25m
1 stop
Delta Logo
3:18 pm - 12:29 pm
UVF
-
MDW
22h 11m
2 stops
$581Delta
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.

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 $458 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 June and December, where the average cost of round-trip tickets is $1,047 and $1,011 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 1 stop layover the cheapest option at $728 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 3 weeks before departure, which saves you about 16% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 23 weeks before departure.

Good to know

Low seasonSeptember
Cheapest flight$157
Best time to beat the crowds but there is an average 11% increase in price.
Most popular time to fly and prices are also 15% 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 $157 for a one-way ticket and $418 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 $882 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 $359 or less one-way and $903 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 8169 reviews
8.5Crew
7.2Food
8.1Boarding
7.9Comfort
7.8Entertainment
Airline reviews

The flight was great as well as the airline staff

10.0 ExcellentPatty, Feb 2026
TPA - ATL
Read more Delta reviews

The flight was great as well as the airline staff

First class and monitors weren’t working for mine & my husbands. Eventually fixed, but quite annoyed as we bought first class. Also, No foot rests.

Prior to takeoff, the pilot told us there was a possibility of not being able to land and going to Portland. Well that happened, we took off and then did 8 loops around Spokane before the pilot told us we ran out of fuel and had to go to Portland. So for a 35 minute flight we have now been on the plane for 3 hours (boarded at 6:50 am and landed in Portland at 10:30). Then, we just sat in Portland's airport with no updates of when we can start heading back. All of a sudden, our pilots and crew just left, leaving us stranded in a different city and state. We continued to sit in Portland until we finally got a new crew assigned and boarded the plane (This was from 10:30-2). We then sat on the plane for an additional hour before take off because they had to count us multiple times. We finally landed in Spokane at 3:55 PM. So a flight that should have taken at max an hour took us 10 hours and we missed the majority of the recruiting event we went for.

It was delayed but other than that it was great.

Got on the plane and sat there for an hour before departure.

Second flight in a row where the entertainment system is broken. 5 hour long flight with no entertainment and flight attendants did not seem interested in resolving the matter. Very shocked to be treated this poorly considering I paid for a first class experience and have Diamond Medallion status.

They double booked seats, the gate staff changed my ticket as I was boarding she went over to the computer and changed it without telling me. She messed up an entire three row section for me and others. Other travelers were outraged but the gate staff were so rude, so condescending saying it wasn't their problem to solve. I would rate this a zero if I could. Will not fly Delta again I'll stick with United and American.

It was nt delta. It was aeromexo. Service was awful. They served a very small drink and NO snack for a 3hr and 35min flight. Then for the first 30 min of the flight is was talk and talk over head interruption the movie/ show i picked to watch.

Comfort seating was on the tight side. Maybe it was a smaller plane(?)

I was given middle seat on this flight and prior Boston to Seoul flight That is a problem for long flights, Kayak system did not give me a change to select my seats and assigned me middle seats regardless of my elevated status in Delta. This needs immediate attention.

Not being stranded in Chicago for her airport to 11:30 tomorrow morning the 3rd

I was fully checked in the prior night and i was unchecked and then didn’t have a seat when I boarded. Instead of an aisle seat, I was out in the middle seat of the very last row of the plane.

In overall it was a good experience, the only down point was that the entertainment screen was working properly.

They lost my luggage, so, not happy. The crew was nice but my suitcases never made it, still trying to find out what happened!

I understand weather is an issue, but making us chase our plane down at five scheduled gates across three terminals in an airport the size of O'Hare was unfair. They'd have probably been better off to leave gates as TBD until the inbound plane is in final approach instead of running us all over the place. Also, props to the consistently-unprepared ground crew in Richmond for once again leaving my lane parked short of the gate because they couldn't have a crew in place on time with 2 hours notice...

cabin crew was OK, food was OK, the trip from the US to Munich was actually pretty bad comfort wise. Noisy aircraft, lights never dimmed even in Business class (night flight) barely sufficient amenities for the price. I have millions of miles with United but TBH American is gaining ground and Delta has always been marginally better then United although on paper United has more longes and cheaper upgrades.

Essy to get on. The hostess gave very little pop, the plane was late getting in, and we are still waiting for our bags. This sucks. :/

Not United Airlines' fault. It's ORL airport's fault.

Great flight. On time boarding. Smooth flight and on time arrival at EWR. The flight crew was marvelous and there was a great selection of movies on the entertainment system. Our bags were at the carousel before we got there. Another excellent flight from United.

I liked the snacks and the flight attendants were friendly.

Delayed an hour due to operational issues. Minimal apologies or care for the significant inconvenience caused. Landed at nearly 1am and they still couldn’t find ground staff to get us off the plane promptly.

The aircraft had several problems - from excess fuel to non operational ac. Two hours of delay in Chicago could have been avoided with proper planning and aircraft maintenance.

Crew in Columbia was not prepared for landing. It was a bit of a disaster and getting bags took forever.

We were upgraded to First Class and it was a great flight

We experienced gate changes and a long delay. My seat was dirty when I boarded and I had to use wipes to clean it myself. There was an unpleasant and overpowering cleaning product scent on the plane as well that lingered through the flight.

My carry on baggage was damaged. Entire trip, I had to carry the baggage. When complained to the boarding crew, they got mad at me and still asked me to valet check in the cabin baggage. Rude boarding crew!!!

Crew were all friendly and helpful. It was a short flight so just a beverage service with a cookie. After we were boarded the plane took about 45 minutes to leave the gate but it was New Year’s Eve so not shocking there was some delay. Overall good experience and very grateful.

The boarding process needs to be fixed. The zone don't work, especially when there is hardly anyone in zones 3, 4,and 5, leaving the majority of the passengers backed up in the aisle, especially because passengers seated near the front are blocking passengers who are seated in the rear of the plane. It would also help if the size of carry on bags was more strictly enforced.

The boarding by groups is pointless. The first two groups worked fine, but almost Noone boarded in goups three thru five leaving the vast majority boarding when group six was called. It defeated the purpose of spreading out the crowd.

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

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

Information on your arrival and departure airports