Find cheap flights from New Windsor to Kentucky

Find cheap flights from New Windsor to Kentucky

Round-trip
Economy
New Windsor (SWF)
Kentucky
Tue 11/24
Tue 12/1
Any month
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Top tips for finding cheap flights to Kentucky

  • Book at least 2 weeks before departure in order to get a below-average price.
  • High season is considered to be January, November and December. The cheapest month to fly to Kentucky is August.
  • Morning departure is around 1,251% more expensive than an evening flight, on average*.
*Average of the lowest prices shown in KAYAK’s search results for departures within the next 30 days

FAQs - booking Kentucky flights

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Top airlines flying New Windsor Stewart to Kentucky

Scores according to KAYAK customer reviews

7.2
American Airlines
Overall score based on 44,870 reviews
7.5
Boarding
7.1
Comfort
7.8
Crew
6.8
Entertainment
6.7
Food
Airline reviews

Pros: "Even during a delay the crew remained professional. There was something wrong with the plan and I appreciate that safety was the main priority."
Cons: "My 1 hour layover turned into a four hours past 2am arrival."

Pros: "yes"
Cons: "nothing"

Pros: "Kind crew."

Pros: "The crew for the rear of the plane for this flight was fantastic."
Cons: "More Woodford reserve. Was only 1 available."

Cons: "Why on Earth does AA not offer televisions or charger plugs on flights across the US, but I have one on every hopper from Raleigh to Charlotte?!?!?!?"

Cons: "Flight was 2 hours late, and forced a full on sprint to get to a very distant gate in Philly for layover"

Pros: "Everything operated according to schedule."

Pros: "I love the inflight entertainment"

Pros: "The flight was on time"
Cons: "The crew, comfort, flight itself"

Cons: "Ability to download premade events apple calendar and apple wallet tickets was seemingly impossible. Send me one email with each of those items as it’s one of the number one thing customers care about"

Pros: "Not too much delay/ wait between flights"
Cons: "snacks ?"

Pros: "Seats were comfortable. Did not cramp anywhere entire flight. Great air vent control."
Cons: "Boarding was weird. Many Passengers in the last rows put their bags up by row 20 so that made boarding and disembarking slower and harder as we had to go forward extra rows to use the back empty bins and then fight against traffic to get back to our seats. Passing bags up when leaving or waiting to"

Pros: "Seats were roomy and comfortable."

Pros: "Boarding was fine and crew were friendly with one exception. The in flight entertainment is great idea, except that the wifi went down mid flight, mid movie."
Cons: "First and foremost seats are very uncomfortable. Would expect American to realize that passengers will be sitting for 9 hours and the seat needs to have some cushion. Could not get comfortable so could not sleep. Most of the crew were friendly and courteous, but was the 1 who was less so. Wifi quit"

Pros: "Arrived early. Friendly pilot."
Cons: "Attendant did not offer snack choice."

Pros: "That I could watch movies"
Cons: "How complicated it was to watch movies. Look at Netflix, they know how to do it right."

Cons: "After following out-of-date information to the furthest reaches of a sprawling and signage-deficient airport, I learned my departure gate was back where I’d come from. Having lost half an hour to my detour, I arrived panting and sweaty at the correct gate 12 minutes prior to departure - cutting it close, but before gate closing time. Or so American’s procedures say. The gate was deserted; they’d closed early."

Pros: "Crew was friendly"
Cons: "Delayed flight again. The American Airlines norm now. Seats are small. I ended up sharing part of mine with the man next to me. No food or snacks No entertainment. Not even a skymall magazine to keep me amused."

Pros: "American Airlines staff from checking to departation were very friendly."
Cons: "Sat behind a couple with a small dog that was very stressed and barked at anyone that walked by. It was a late flight and I could have used a few winks."

Pros: "The comfort of the plane and the continued update on my flight delay."
Cons: "The flight was delayed but no fault of American."

Pros: "The fact that they re-booked without me having to contact customer service."
Cons: "The connecting flight was cancelled while boarding was in progress at the start of the journey."

Pros: "The only good thing about this flight was the free plastic cup of water they gave us right before we landed. Thanks!"
Cons: "The stewardess was outright mean! I am disabled and showed up in a wheelchair. The woman had the nerve to ask me if I was really disabled or if I was using it to cut the line. It was really horrible!"

Cons: "Cramped seats, no great snacks"

Pros: "Friendly staff."
Cons: "Typically claustrophobic conditions. No in-flight entertainment."

Pros: "Crew"
Cons: "Comfort"

Cons: "Potable water was down so no coffee, tea, or more important... water to wash hands. Then they didn’t have my second choice of beverages after coffee either."

Pros: "great stable flight"
Cons: "my connecting flight left late"

Pros: "YYC is a nice airport. I have found I like Canadian's more then Americans when it come to air travel."
Cons: "LAX is not a convenient airport at all."

Pros: "It Was Great. Flight Attendant Rita Was Amazing. The Flight Was Quite And Relaxing."
Cons: "That It Didn’t Last Longer. It Was A Short Trip."

Pros: "Considerate flight attendants. Turned lights down for evening flight, so we could get some rest."
Cons: "Flight was not on time. Time was changed a day prior with no reason explained. No in flight entertainment on this flight."

Cons: "Comfort of plane!"

Pros: "The airplale MD 80 are old"

Pros: "+ Last minute aisle seat + Middle seat empty"
Cons: "- Food was passable (chicken and rice for lunch) - Mediocre breakfast"

Pros: "Can't really say much as I slept most of the flight."

Pros: "Smith flight."
Cons: "Nothing"

Pros: "I really like having the ability to upgrade to a more roomy seat the most. I am 6 foot 1in and leg room is so very important to me when i fly, it the difference between a good experience and a great experience. For just a few more dollars i was able to enjoy a great flight."
Cons: "I don't like not having the movies to watch on the back of the seats, although i do understand the cost cutting reasons. It's not a problem, just saying."

Pros: "Adequately handled the 13 hr delay."
Cons: "Flight delayed 13 hrs for mechanical problems. Seems to be an ongoing problem w/ American Airlines now."

Pros: "Tthe crew was very friendly"
Cons: "No food"

Cons: "see review headline above"

Pros: "Appreciated the extra legroom and food and drink service, even on a short flight. Crew seemed very friendly."
Cons: "It was way too cold. We shouldn't all be bundling up in scarves and jackets. I've noticed that European airlines manage nut to freeze the passengers, so three must be a way to adjust the standard temperature on planes a but more."

Pros: "Stewards were patient and attentive."

Pros: "Boarding was simple"
Cons: "For my whole three hour flight a child kicked my chair, i asked the mother politely if she could get her to stop. the woman didn't even apologize and the kicking continued for three hours."

Pros: "Everyone was so nice"
Cons: "They didn't give me a drink"

Pros: "Everything"
Cons: "Nothing"

Cons: "Flight was delayed for over 6 hours. Had to find an alternative way to get home"

Pros: "Nothing"
Cons: "No tv.. Rude customer service n my luggage got lost.. I will make to stay away from aa"

Pros: "Departed on time arrived a little early"
Cons: "Seats were not as comfortable as other flights I've been on."

Pros: "Everything went well. No problems."

Pros: "I had ample room and I really like the biscuits"

Pros: "Flight staff nice"

Pros: "The crew was amazing, super helpful, very friendly and understanding when it came to social distancing."
Cons: "The seats are not the most comfortable, but the price is right."

Pros: "Crew and plane ride."
Cons: "The seats hurt us."

Cons: "A plan to deal with a hostile mom with a screaming kid that was out of control."

Pros: "Crew was amazing"

Cons: "They charge $50 for a carry on bag!!!"

Pros: "The crew were very friendly."
Cons: "the seats were pretty uncomfortable, that was my main problem with the flight."

Pros: "Crew was nice."
Cons: "Not having so many extra charges and having to pay for a carry on"

Pros: "Quick direct flight that wasn't packed"
Cons: "The woman that checked my bag kept calling me "sir" and after I corrected her a second time she rolled her eyes and said "oh, I don't even look up" I am not a man. For Pete's sake pay attention."

Cons: "Bad turbulence throughout the entire flight. Hot temperature during majority of flight."

Pros: "We had about a 45 minute weather delay but those things can't be helped. The Captain kept us informed and he flew like superman getting us through all that crazy wind coming into Las Vegas. The plane was new and clean, the crew was great. Love that wide aisle...it eliminates that sardine feeling!!"

Pros: "Great crew. Good on-time flight (early, actually). Smooth boarding."
Cons: "Standard no-frills gripes. Seat is tolerable but basic, no recline. No power, zero inflight entertainment, etc etc. They won't even give you a sip of water for free, which is just absurd in my opinion. They did give me a free cup of ice... so I guess ice + time = free water..."

Pros: "Crew was good, quite friendly and helpful. Seats are a bit uncomfortable but what airline isn't."
Cons: "Both flights of this trip were delayed over an hour with no explanation. Major impact was my transportation arrangements on the return were impacted and forced a rental expense."

Pros: "All wa great"
Cons: "Nothing"

Pros: "the staff was nice."
Cons: "the soda can was 2$ and for a rum and coke 20$, the plane was uncomfortable"

Pros: "Crew friendly and professional"
Cons: "Everything is extra, even water or soda. Seats are narrow so glad im not a heavier person"

Pros: "Early out and early in."

Cons: "Long delays"

Pros: "The flight attendants, the space on the plane, the prompt departure and arrival!"
Cons: "Media has not been reflective of my great experience."

Pros: "Boarding was better than other airlines."
Cons: "Seats are uncomfortable and do NOT recline!"

Pros: "Going in & out of small airports."
Cons: "We arrived late. Pricing system."

Pros: "Flight left early and was at destination 30 minutes earlier!"
Cons: "On the return trip, I had to wait 30 minutes for my luggage."

Pros: "On time"
Cons: "initially assigned to center seat."

Cons: "Paying extra for EVERYTHING"

Pros: "I have never experienced this before. You stand in line to get a tag for your bag. Then you stand in line to check your bag. Then you stand in a Disney style HUGE line just to get to the escalator to take you to the second floor so you can go through security. Thank goodness for TSA precheck! That line was long but not very long like the other line."

Pros: "The flight was delayed for almost 4 hrs, but the staff was excellent. From the check-in agent, the gate agent, the flight attendants and pilots - everybody was upbeat and helpful."
Cons: "Just the continual delays, but the mobile notices were so helpful in not coming to the airport for a delayed flight. As always, the fact that the seats don’t recline makes the trip more uncomfortable."

Pros: "Passengers were fun"
Cons: "Need entertainment"

Cons: "Flight was very late. Have to pay $45 for a carry-on bag. Seats were uncomfortable and have to pay for all snacks and drinks including water."

Pros: "Crew likes to have fun with their passengers -- making the whole experience that much more enjoyable. It's a budget airline so you have to pay for things like refreshments and snacks (also, carryons and if you want you boarding pass printed at the airport) -- but don't let that sway you! All it takes is a little prior organization (we packed a couple of sandwiches and printed our passes at home, plus packed very light). Overall a great experience."

Pros: "It was easy to book. And they helped me make changes to my flight schedule without charging me"
Cons: "Everything else is charged... from the in service beverage cart, to your boarding pass. Your baggage. Everything you have to pay for. So just be prepared for that."

Pros: "Cost"
Cons: "Left late"

Pros: "Great flight. On time. Easy on. Easy off. And amazing fares."
Cons: "Everything great"

Pros: "Flight was cancelled due to Irma in Florida. Customer service agent was fantastic. I was able to rebook die the following week without any hassle."
Cons: "I didn't get to fly to Florida when I first chose."

Pros: "Boarding speed and flight"
Cons: "Uncomfortable seats, does not recline, even water is for sale."

Pros: "My wife said that this was the smoothest airplane ride she had ever had."
Cons: "The first lady at the check in desk told us the wrong gate. We wound up taking a tram to another terminal, found out that we were in the wrong place, and then made it back just in time to board with a few minutes to spare. Anyway, the airline itself was o.k. and next time I'll check the arrival/departure board. Since we were traveling with only a carry on, it was a good price after all the "frills" were added (pay for carry on, pay to select seat). we still had a price lower than any other airline. So all in all, once we got on the plane it was a pleasant experience."

Cons: "All of the hidden fees. I was initially charged more than $200 over the price I was quoted on Kayak.com and then had to pay an extra $45 to bring 1 carry-on each. I do not plan to use Kayak.com again for these reasons and will not recommend this site to anyone"

Pros: "Cost of tickets, airport locations-and more convenient travel utilizing smaller airports."
Cons: "Baggage fees are outrageous, no complimentary amenities or refreshments. Flight attendants were rude in asking parties to return to assigned seats, while there were several completely open rows towards the back, (no obvious or explained reason aside from "assigned ticket seats" that they should remain empty. Families or companions could have traveled together- seemed unnecessary to prevent this, only gain noticed was Flight attendants satisfaction at denying seat relocation."

Pros: "The friendly staff made our daughters 21 to Vegas absolutely perfect"

Cons: "Both original and 2nd plane had malfunctions which caused extensive delays and doubled boarding time"

Pros: "Cleanliness, friendliness, on time."
Cons: "Charging for drinks and snacks snacks.."

Pros: "Very efficient service... for a first experience we were pretty impressed because your review overall were not that great. Good job."
Cons: "The airline nickel and dimes for everything."

Cons: "No wifi"

Cons: "Worst plane trip. I am a bigger girl, and I could not even buckle my seat belt due to the size of the chair. I have never had this issue on any other plane flight. It was incredibly noisy, and rough ride. I will not travel again."

Pros: "It's convenient and inexpensive for one of my regular destinations. Though, over the years, I've experienced a few cranky employees at the Punta Gorda location. Just the opposite in Asheville, where friendly was apparently invented."

Pros: "Everything was good"
Cons: "Could of had more selections on the flight for snacks"

Pros: "The price of the flight was cheap, but i know why. You ended up paying for your carry on luggage, ypu pay for seat assignment if you want to guarentee sitting with you party, you pay for soda. My flight was 1.5 hours late, due to mechanical problem. Plane was janky and it felt like it STILL needed repairs."
Cons: "Low airfare."

Pros: "Quick flight."
Cons: "You have to pay extra for everything."

Pros: "pleasant flight got there and back safely"

Pros: "The flight attendants were great. Pilots attention to detail..Great."
Cons: "Charging for every little thing including seat choice, bags, snacks. No complimentary beverages or peanuts. Not even water! In the long run, I didn't save money on this trip."

Pros: "flight attendants"
Cons: "flight was delayed 4 hrs"

Read more about American Airlines
COVID-19 information

Safety measures for airlines flying from New Windsor to Kentucky

Airlines flying from New Windsor to Kentucky have enacted additional safety measures and adjusted policies to better accommodate travelers. Policies vary by airline.

Heightened sanitation

Daily cleaning, installation of cabin HEPA filters

Mandatory masks

Masks required on board, masks provided

Social distancing seating

Middle seats unavailable to book

Pre-flight testing

Testing for antibodies, testing for symptoms

Book cheap flights from New Windsor to Kentucky

Recent round-trip flight deals

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