CHI - UVF

$251 Find Cheap Flights from Chicago to Castries - Compare and Save

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 7/25. 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

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Everything you should know

Cheapest round-trip
$551
Typical prices: $705-$1,112
Air Canada
Wed 10/21Sun 10/25
ORD - UVF • 2 stops
Cheapest non-stop
$1,100
United Airlines
Sat 7/18Sat 7/25
ORD - UVF • Non-stop
Nonstop flights
1 day a week
Sat
You can fly direct with United Airlines. Average duration is 5h 45m
Direct flights
Direct flights
+1
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Direct flights
Direct flights
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Top airlines
Cheapest • from $551 (round-trip)
Best reviews • 7.8 score
Airline reviews
Airline reviews
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Airline reviews
Airline reviews
+1
Top layover airports
Cheapest • Avg $475 (round-trip)
Shortest trip • 7h 26m (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 4 weeks in advance save around 37% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
Cheapest • 23% price drop
Most popular
Good to know
Good to know
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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

Wed, Oct 21 - Sun, Oct 25
Air Canada Logo
3:40 pm - 2:15 pm
ORD
-
UVF
45h 35m
2 stops
Air Canada Logo
4:40 pm - 6:20 pm
UVF
-
ORD
50h 40m
2 stops
$551Air Canada
Fri, Oct 23 - Mon, Nov 2
Air Canada Logo
2:01 pm - 3:40 pm
ORD
-
UVF
48h 39m
2 stops
Air Canada Logo
5:40 pm - 4:44 pm
UVF
-
ORD
25h 04m
1 stop
$558Air Canada
Fri, Oct 23 - Mon, Nov 2
Air Canada Logo
5:56 pm - 3:40 pm
ORD
-
UVF
44h 44m
2 stops
Air Canada Logo
5:40 pm - 7:50 am
UVF
-
ORD
16h 10m
2 stops
$561Air Canada
Sun, Nov 1 - Mon, Nov 9
Air Canada Logo
8:35 pm - 4:40 pm
ORD
-
UVF
18h 05m
1 stop
Air Canada Logo
5:40 pm - 9:23 am
UVF
-
ORD
17h 43m
1 stop
$572Air Canada
Sun, Nov 1 - Mon, Nov 9
Air Canada Logo
8:50 pm - 4:40 pm
ORD
-
UVF
17h 50m
1 stop
Air Canada Logo
5:40 pm - 9:23 am
UVF
-
ORD
17h 43m
1 stop
$574Air Canada
Sun, Nov 1 - Mon, Nov 9
Air Canada Logo
3:45 pm - 4:40 pm
ORD
-
UVF
22h 55m
2 stops
Air Canada Logo
5:40 pm - 9:23 am
UVF
-
ORD
17h 43m
1 stop
$575Air Canada
Sun, Nov 1 - Mon, Nov 9
Air Canada Logo
3:45 pm - 4:40 pm
ORD
-
UVF
22h 55m
2 stops
Air Canada Logo
5:40 pm - 9:23 am
UVF
-
ORD
17h 43m
1 stop
$577Air Canada
Sun, Nov 1 - Mon, Nov 9
Air Canada Logo
3:45 pm - 4:40 pm
ORD
-
UVF
22h 55m
2 stops
Air Canada Logo
5:40 pm - 11:07 am
UVF
-
ORD
19h 27m
2 stops
$578Air Canada
Fri, Sep 4 - Wed, Sep 9
Delta Logo
6:05 am - 2:14 pm
MDW
-
UVF
7h 09m
1 stop
Delta Logo
3:32 pm - 10:45 pm
UVF
-
MDW
8h 13m
1 stop
$698Delta
Wed, Sep 9 - Mon, Sep 14
Delta Logo
6:05 am - 2:12 pm
MDW
-
UVF
7h 07m
1 stop
Delta Logo
3:32 pm - 10:45 pm
UVF
-
MDW
8h 13m
1 stop
$738Delta
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 October.

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 $728 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 April, where tickets cost $363 (return) on average. On the other hand, the most expensive months are September and August, where the average cost of round-trip tickets is $685 and $565 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 $759 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 4 weeks before departure, which saves you about 37% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 10 weeks before departure.

Good to know

Low seasonSeptember
Cheapest flight$251
Best time to beat the crowds with an average 10% drop 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

  • How many flights are there between Chicago and Castries per day?

    There is a maximum of 1 nonstop flight a day that takes off from Chicago and lands in Castries, with an average flight time of 5h 45m. The most common departure time is 8:00 am and most flights take off in the morning. Each week, there are 1 flights.

  • What is the cheapest flight from Chicago to Castries?

    In the last 5 days, the lowest price for a flight from Chicago to Castries was $251 for a one-way ticket and $551 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 $795 and an overall rating of 7.8, Delta is the most popular choice. United Airlines is also a great choice for the route, with an average price of $1,239 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 $848 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.
7.8
DeltaOverall score based on 8453 reviews
7.2Food
7.8Comfort
8.5Crew
7.8Entertainment
8.1Boarding
Airline reviews

The crew was very inconsiderate and rude. My flight was scheduled to depart at 6:00am. I received a call from the crew at 5:40am, asking if I was going to make the flight because I was the only one that hasn't boarded yet and boarding ends at 5:50am. I let them know that I will be at the gate in a few minutes, before the 5:50am cutoff. When I arrived at the gate at 5:45am the gate was closed. Departing early on last minute notice without having all passengers on board is inconsiderate and unprofessional.

2.0 MediocreJean, Jun 2026
MDW - ATL
Read more Delta reviews

The crew was very inconsiderate and rude. My flight was scheduled to depart at 6:00am. I received a call from the crew at 5:40am, asking if I was going to make the flight because I was the only one that hasn't boarded yet and boarding ends at 5:50am. I let them know that I will be at the gate in a few minutes, before the 5:50am cutoff. When I arrived at the gate at 5:45am the gate was closed. Departing early on last minute notice without having all passengers on board is inconsiderate and unprofessional.

Very easy to use and convenient, you can perform any action within the same portal

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

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.

Everything could have benn better. Short fly, no food, no entertainment and no wifi.

Stop changing gates. Stop cancelling flights Stop moving my seat.

The staff was frielndly. The plane was terrible, it was too small and should be decommissioned. There were no back seat screens at all. The only beverages we had a choice from was coffee, tea or water. The only bathroom in the back was behind the flight attendant's jump seat and wasn't working. And I literally felt like I was sitting on top of the guy next to me. It was terribly hot in the plane and we had to sit on the tarmac in Chicago for 1/2 hour due to congestion in Mpls. Wouldn't they have know that before they even boarded us so that we could have sat in comfort in the terminal?

This was one of the worst flights I’ve been on in years. I upgraded to comfort and had such an uncomfortable experience. The person next to me was oversized - which I understand - however, they took up their space and mine. I could only use about 50% of my seat space to not be physically touching this person the entire flight and there was no spatial awareness. I also could not use the seat outlet because their body was obstructing it. It was very inconvenient. Their body kept touching me repeatedly during the flight and I felt very uncomfortable. To pay more for an upgraded space and then not even being able to use it was highly disappointing.

It was very cold because the air conditioner was on high power, and my son got sick.

Horrible. Flight ORD to CGH was okay, but Paris was a nightmare. Old planes, delays, involuntary downgrades, broken planes, terrible communication. CGH to CPT was my worst flight ever.

The flight was delayed by a hour and I wish they had communicated it sooner. No issues on the plane, it did take a while for food to come.

Know that the movies that you are going to be offered are the oldest be rated movies they could possibly get. They may have one or two new movies that they keep advertising but when you’re flying 15 hours, there is nothing to see past the first new movie.

Agents at gate were not immediately available to solve problems and once they did they didn’t fix all the fight connections

Great experience. Boarding was fast, staff were very nice and funny, everything at the seat worked well.

Horrible! Several delays and then was cancelled! I spent over 24 hours in the airport and was unable to get a hotel or food voucher.

Smooth travel. Immediate update prior flight delay so I can arrange myself properly without too rush.

Boarded early; and arrived home 40 mins early. After a long flight, it’s nice to be back home early. These flights have no amenities; no snacks. So need to bring your own

A long delay. Don't travel late in the day.

Super friendly with lots of drink options an entertainment. Friendly crew.

The crew was great. Very friendly and responsive. The plane was old, small and tight. We ran out of overhead space and I had to check. Middle seat was particularly tight.

The seat was not even cleaned. It has full of cookie crums probably from last flight's passenger. Its basic expectation that, seats are clean.

Very turbulent flight, no drinks, very little service, unorganized boarding, gate changed multiple times

The flight was delayed significantly. Communication during the flight was abrupt and caused some panic as we were navigating turbulence. It was also too loud and every announcement felt startling. The flight attendants did not offer any assurances and I felt unsettled most of the flight. The seats, floor and tray table was very dirty. The seat next to me was broken and the passenger sitting there was very uncomfortable. He had a spring in his back and his seat made terrible squeaking noises through the flight.

Significant delays on my trip to Chicago and my trip back to NY

Delayed by 5 hours and I had to wit in the airport for more than 6+ hours.

I’ve got 31F seat and window seat . My 2 co passengers was AA crew members and they were very rude attitude and when I was going to use bathroom their gestures was very different and awkward and the guy beside me completely occupied the hand rest and I was really uncomfortable

It was so much better than expected, Ohare is not such a pleasant experience but American Airlines with the new, clean aeroplane and free Wi-Fi was outstanding and the crew so pleasant and helpful.

It wa sort of on time; the cab was left with some trash

My pillow had a shoe print on it, when I asked if I can have another pillow, I was told “I’m sorry but it is one pillow per guest, do YOU want to turn it inside out” to which I responded , no thanks I will go without. This is generally not ok, but For the price tag I paid flying business this is absolutely unacceptable. Hopefully American Airlines can update their accommodations to bedding that is not tossed on the ground and stepped on, or at least have a couple of extra pillows in hand, incase someone had decided to step on the pillows for what ever reason

American Airlines II: Delay Boogaloo. Multiple gate changes, delays, boarded and then MORE delays. I hate to say this won’t matter, but posting stuff about major corporations in 2026 is a post-modern “scream into the void.” Was multiple hours late coming home, so there you go.

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

Information on your arrival and departure airports