CHI - UVF

$174 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 11/8. 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

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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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

Mon, Sep 22 - Fri, Sep 26
JetBlue Logo
6:45 am - 1:45 pmORD-UVF
30h 00m1 stop
JetBlue Logo
3:05 pm - 6:24 pmUVF-ORD
28h 19m1 stop
$418JetBlue
Find Deal
Mon, Sep 22 - Fri, Sep 26
Air Canada Logo
8:25 pm - 2:15 pmORD-UVF
16h 50m1 stop
Air Canada Logo
3:10 pm - 9:51 amUVF-ORD
19h 41m2 stops
$450Air Canada
Find Deal
Mon, Sep 22 - Fri, Sep 26
 Logo
11:13 am - 2:15 pmORD-UVF
26h 02m3 stops
 Logo
3:10 pm - 4:50 pmUVF-ORD
26h 40m3 stops
Sun, Nov 2 - Fri, Nov 7
American Airlines Logo
6:50 pm - 1:00 pmORD-UVF
16h 10m1 stop
American Airlines Logo
5:15 pm - 12:17 amUVF-ORD
9h 02m1 stop
$575American Airlines
Find Deal
Sun, Nov 2 - Fri, Nov 7
American Airlines Logo
6:54 pm - 1:00 pmORD-UVF
16h 06m2 stops
American Airlines Logo
5:15 pm - 8:42 amUVF-ORD
17h 27m1 stop
$580American Airlines
Find Deal
Sat, Aug 30 - Thu, Sep 4
Delta Logo
5:00 pm - 2:15 pmORD-UVF
20h 15m2 stops
Delta Logo
3:35 pm - 8:04 amUVF-ORD
17h 29m2 stops
$605Delta
Find Deal
Tue, Aug 12 - Fri, Aug 22
Delta Logo
5:45 am - 2:15 pmORD-UVF
7h 30m1 stop
Delta Logo
3:35 pm - 11:56 pmUVF-ORD
9h 21m1 stop
$617Delta
Find Deal
Sun, Aug 24 - Sun, Aug 31
 Logo
6:06 pm - 2:15 pmORD-UVF
43h 09m2 stops
 Logo
2:35 pm - 9:09 amUVF-ORD
19h 34m1 stop
Fri, Oct 31 - Tue, Nov 4
WestJet Logo
9:20 am - 2:48 pmMDW-UVF
52h 28m2 stops
WestJet Logo
3:40 pm - 6:07 pmUVF-MDW
28h 27m2 stops
$3,357WestJet
Find Deal
Wed, Nov 26 - Sun, Nov 30
WestJet Logo
2:00 pm - 2:48 pmMDW-UVF
22h 48m2 stops
WestJet Logo
3:40 pm - 1:09 pmUVF-MDW
23h 29m2 stops
$3,473WestJet
Find Deal
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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?

The cheapest price for flight routes found by users searching on KAYAK in the last 2 weeks for round-trip flights from Chicago to Castries.

Our data shows that the cheapest route for a return flight from Chicago to Castries cost $1,193 and was between Chicago O'Hare Intl Airport (ORD) and Castries (UVF). On average, the best prices are found if you fly this route. The average price for a return flight for this route is $1,193.

What’s the cheapest day of the week to fly from Chicago to Castries?

The average price of all round-trip flights from Chicago to Castries clicked on KAYAK for each day over the last 12 months.

If your flying dates are flexible, you should consider flying to Castries on a Wednesday, as we generally find the cheapest rates on that day for this route. On the other hand, Saturday is the most expensive day to fly from Chicago to Castries. For your return ticket, we recommend flying on a Friday and avoiding Saturdays for the best deals.

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 $603 (return) on average. On the other hand, the most expensive months are June and March, where the average cost of round-trip tickets is $999 and $935 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 $1,294, 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 5 weeks before departure. For the absolute cheapest price, our data suggests you should book 7 weeks before departure.

Good to know

Low seasonOctober
High seasonMarch
Cheapest flight$174
Best time to beat the crowds with an average 18% drop in price.
Most popular time to fly with an average 26% increase in price.
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 $174 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?

    Star Alliance is the only airline alliance operating flights between Chicago and Castries.

  • 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 $774 and an overall rating of 8.0, Delta is the most popular choice. United Airlines is also a great choice for the route, with an average price of $984 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 $373 or less one-way.

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.
8.0
DeltaOverall score based on 7952 reviews
8.2Boarding
8.5Crew
7.9Entertainment
7.9Comfort
7.3Food
Airline reviews

Everything was fine except the entertainment was not working for half of the flight.

8.0 ExcellentEileen, Jul 2025BOS - PBI
Read more Delta reviews

Everything was fine except the entertainment was not working for half of the flight.

Easy boarding with an extremely kind attendant. Seats were spacious and we had 3 seats for 2 people so we could stretch out. Comfortable air flow and very attentive and hospital attendants. Bathrooms and food were the only negative. Bathrooms were so small you could hardly get in and close the door. I don’t think an obese person would fit or a person with a movement disability. Food was the trending food for flights, nonexistent. We spent $40 getting sandwich and snack at airport for our 6 hour flught.

At first, we were on the runway for about an hour, literally. The Captain did explain that the Control Tower just had a change shift (sounds like an unrealistic excuse) and then that we had to change a runway. A regular economy seat is made for 12 yo twiggy. I understand Delta wants to push for an upgrade, but after sitting in a Comfort seat and in First class. I would say First class is not worthy of my money. The landing was delayed because of the weather in NYC, I don't hold that against Delta, of course. The Captain did alert us to that upon takeoff in Vegas and again as we reached NY.

No one fussed at me about my pap machine as a 3rd pice on the plane. Boarding was pleasant and smooth. The boarding agent in Anchorage was a fun character- he could be in a movie. :~) The on-board crew were downright pleasant. No militant attitudes on Delta. Like all planes these days the seats are too narrow for standard Americans and at 5’2” there is barely enough leg room. I don’t know how tall people fold themselves into the seats. But that’s nothing specific to Delta

Great. Very smooth. Plenty of information. However, wish they would give out a menu in advance of making a dinner choice like other international airlines. The flight attendant says chicken or pasta and there are details about ingredients or spices requiring the passenger to ask which requires the flight attendant to answer many times. So easy to solve this problem. P

I'm a tall guy and even the seats with more leg room were not as comfortable as I had hoped.

My husband upgraded our seats and I don't know if it was due to the type of planet was or if they didn't upgrade our seats. We were supposed to be in I believe comfort seats and they were just as tight as any other seat- no leg room and we are very tall people but at least it wasn't extremely cold. My husband did put in a complaint about our seating because he paid extra and if we would have known that the space and the tightness would have been the same, we just would have gotten the emergency row emergency row seats that we normally get. We love Delta but both our flights coming home we're not good. Oh I forgot to mention that on our flight to Hawaii our luggage wheels got broke and we had to purse new luggage on vacation then we never had this problem so we didn't know protocol and reported it after we got home only for them to tell is we only had 24hrs to report the damage. Not sure what was going on with Delta this vacation trip.

My flight was extremely cold. I had a jacket and a cover was left in each seat. The cover was extremely thin and I have a disability, fibromyalgia and arthrithis and AC air is the worst. I closed my vent and my husbands vent and it still was frigid. I asked the attendant if I could get another cover and she quickly almost dismissively and totally unconcerned stating, (I quote) (one per chair) and walked off so quickly that I didn't get a chance to explain to her that I literally have adisability. I didnt want to make a seen so I set on that flight for over 5 hours in pain, joints locking up and extremely uncomfortable. When my fibromyalgia flares up my joints not only ache but they will lock up also and it takes me days to get back to my regular self even though I take medication for it. I felt like it would not have hurt anyone at all for her to just give me an extra cover because I'm sure they have all types of medical issues in people that fly every day.

After all the weather issues at least they got me to my destination the next day

My flight was canceled after being rescheduled for four days canceling my trip. Kayak and everyone affiliated with it I.e the airlines, and just fly have been excruciating to deal with. My trip to visit family had to be canceled as there was no way to make it. I am furious at all of you.

It was great, I’m very grateful for the pilots and crew flight attendants for everything.

Evidently, my seat had the only broken TV. I couldn’t plug it in, get it to come on, or watch anything, and of course, no one could fix it while we were on the plane. The service was good and the boarding was quick

The boarding of took of late.The presentation of the food was horrable as was the tast of the food was cold and tastless.

Delay and keep changing gates. I have to run around from B to C then to E.

I was charged for my daughters bag when I am supposed to receive two free checked bags with my United Explorer card.

The schedule to Moline changed 5 times. The gate changed 6 times. That is a pathetic way to run an airline. No wonder that no one in our company flies on United Express to or from Moline. Changes happen most of the time. I learned my lesson on this trip…never again!

Flight was great. Efficient boarding. Short flight. Early arrival. Friendly flight crew. The entertainment system did not work well. Could not access it until the aircraft reached 10K feet or more. Lots of glitches.

A bit rush for transit. Food and entertainment are not available

Boarding was a little difficult. The gate area at O'Hare was very small and crowded due to multiple gates in the area. Could not hear the intercom, so had to rely on signage to see when my group was boarding and the signage was blocked by passengers standing in the gate. Flight was great and we arrived in Montreal on time.

Smooth boarding process. Early departure, smooth flight, early arrival. The entertainment package has very good recent movie options. The flight crew were friendly and professional.

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

Excellent! The gate agents were kind enough to rebook me on an earlier flight saving me from a 6 hour layover. Even my luggage made it despite the fact that the connection was technically too narrow. The flight itself was very comfortable, roomy, and clean. Plenty of space for my carryon items with plugs to charge my phone. After a long international flight of 14 hours, this was an excellent way to end my travels!

Great experience. Flight boarded easily. Departed early. Smooth flight. Great arrival in DC--almost no taxing! Almost direct to gate from runway. Crew was terrific. Same cookies and beverages in main cabin. I did not use the entertainment system on this flight.

This particular flight wasn't very full at the back, so there were three seats available for spreading out and getting relatively comfortable

Most of the delay was due to weather which is not what was at issue here. One delay was due to a missing flashlight and in the end the flashlight was actually found on the plane. The entertainment system is very limited. Live TV options offer only a few channels that are not very appealing. Boarding and deplaning are always difficult. It just takes too much time to get on and off the plane. On the plus side, I missed my connecting flight, but was easily able to book a later flight from the app while enroute.

You were more on time than United. I'm so over united delays.

The meals were mediocre and the alcohol selection was poor. I enjoyed the selection of movies and other entertainment.

I chatted with the captain before the flight, and similarly during the welcome announcement, he warned of a turbulent flight that may impact the in-flight service. However, once at altitude, he announced that the weather changed and he immediately turned off the seatbelt sign. But it appeared the cabin crew had already decided to take off this flight. They remained seated and then just chatted in the galley. The flight was fully catered, but only first class received service.

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

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