$185 Find Cheap Flights from Portland to Kentucky - Compare and Save

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Cheap Flights from Portland to Kentucky

Cheapest round-trip prices found by our users on KAYAK in the last 5 days
Louisville
Louisville1 stop$335
Lexington
Lexington1 stop$369
Nashville
Nashville1 stop$323
Louisville
Louisville1 stop$335
Lexington
Lexington1 stop$369
Nashville
Nashville1 stop$323
Booking Insights

Price, demand and travel trends for Portland to Kentucky flights

Use KAYAK data on prices, travel dates, airlines and seasonal trends to compare options and book flights with more confidence.

What are the cheapest fares from Portland to Kentucky recently?

The cheapest fares from Portland to Kentucky on KAYAK in the last week were to Louisville Intl (SDF) from $335 round-trip and to Lexington Blue Grass (LEX) from $369 round-trip.

How do fares into airports in Kentucky compare?

According to KAYAK data from the last 12 months, the cheapest airports to fly into Kentucky from Portland are:

• Louisville Intl (SDF) (avg. price $441)
• Lexington Blue Grass (LEX) (avg. price $460)

What's the cheapest month to fly from Portland to Kentucky?

March is typically the cheapest month to fly from Portland to Kentucky, with round-trip fares averaging $398. April and January are usually the most expensive, averaging $807 and $482, respectively.

How do fares from Portland to Kentucky vary by day of the week?

On average, Thursday is the cheapest day to fly from Portland to Kentucky and Monday is the most expensive. Looking at the past 12 months of KAYAK data, it's 18% more expensive to fly on a Monday compared to Thursday.

What's the best time of day to fly from Portland to Kentucky?

It's cheapest to fly to Kentucky in the evening with average prices of $439. The morning is the most expensive time to fly, with average prices of $466.

Key details for Portland to Kentucky flights

Low season

January

Cheapest flight

$185
Beat the crowds with an average 45% drop in travelers.
The most popular month to fly with an average 60% increase in travelers.
One-way flight from Portland to Louisville

Your Portland to Kentucky flight questions, answered

Find helpful answers about this route, including flight times, airports, airlines and booking tips.

  • Is now a good time to book a flight from Portland to Kentucky?

    Yes. Fares from Portland to Kentucky are low right now. As a rule of thumb, a round-trip under $366 (cheaper than most fares this year) is a good deal, so if you spot one at or below that, it's a good time to book.

  • How much should I budget for a flight from Portland to Kentucky?

    Over the past 12 months, round-trip fares from Portland to Kentucky have typically cost between $366 and $491.

  • What are the main airports serving Kentucky?

    There are 10 airports in Kentucky. 78% of KAYAK users choose Louisville Intl (SDF) as their arrival airport, while 22% choose Lexington Blue Grass (LEX).

  • Which airlines fly nonstop from Portland to Kentucky?

    Based on the flight schedule for the next 3 months, no airline regularly operates nonstop flights from Portland to Kentucky. One-stop options include:

    • Delta
    • Southwest
    • American Airlines

  • Which destinations in Kentucky can I fly nonstop from Portland?

    Based on the flight schedule for the next 3 months, there are no nonstop flights from Portland to Kentucky. The most popular destination you can reach with one stop is Louisville.

  • Which cabin classes are available from Portland to Kentucky?

    On flights from Portland to Kentucky you can book Economy Class or First Class.

  • What are some popular landmarks around Kentucky?

    Kentucky is home to many popular sights. KAYAK travelers' favorites include:

    • Louisville Waterfront Park
    • Masonic Widows and Orphans Home

Your guide to booking Portland to Kentucky flights

Get tips on when to book, when to fly and what to know before your trip.
  • Flexible with your dates? Fly in March to save some money. It's typically the cheapest month on this route, while flights in April will cost you the most.
  • Fly out on a Thursday to get the cheapest fares. Avoid Monday flights, which are about 18% more expensive.
  • If you're watching your budget, fly into Louisville Intl (SDF) which has the lowest average airfare in the region. Just remember to budget for any onward travel by bus, car or domestic flight.
  • Start your trip in Louisville, the most popular destination in Kentucky. From there, it's easy to continue on to other popular spots such as Lexington, Bowling Green and Florence.

Reviews of the top 4 airlines serving from Portland to Kentucky

 
Need help choosing which airline to fly with from Portland to Kentucky? 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
SouthwestOverall score based on 4218 reviews
7.0Food
8.6Crew
8.1Boarding
8.0Comfort
7.5Entertainment
Airline reviews

Terrible, decided to delay our flight since another flight require a flight captain

2.0 MediocreChih Hsuan, Nov 2026
Read more Southwest reviews

Terrible, decided to delay our flight since another flight require a flight captain

staff and crew were great but the flight delays for the last few flights are insane. After a long day of work and you will get a notification of flights delay is not the message we want to see. And for some reason it keeps happening often this year.

I love southwest. I can not wait until all the planes convert to the upgraded planes. I love the charging option and the newer seats. Thank you from a very loyal Southwest customer.

My return flight was much better than the flight there! I paid for seat to Veagas but not the return. Thankgoodness they assigned me a seat with additional leg room as I have back and leg problems. I really appreciate it. With the flight already being super expensive due to gas prices and having to pay for bags (now) I needed to save some money.

My first flight from LGA to STL was not good. They didn't do service until over halfway through the flight, the internet didn't really work, and the crew all seemed like they didn't want to be there.

We were stressed about landing as our connecting flight was about to start boarding, being unfamiliar with the airport or where the gates were. We exited the plane to discover we were at the gate we needed. We would be getting back on the same plane but nobody told us we could have just stayed onboard. My wife and I were seated on aisle seats across from each other. We asked if there was a way we could sit together. Once we were at cruising altitude they let us move to an unoccupied row so that was nice.

It’s Southwest. The seats are small, the snacks are meh, it’s $50 to check a bag. It’s exactly fine. Could have been better. Could have been worse. It’s not Spirit

The seats were a bit cramped and worn, but otherwise okay.

Boarded the plane in Portland and sat on the tarmac for four hours before being given clearance to take off. Apparently a "scratch" was detected on the preflight inspection. This delay resulted in me missing my connection in Baltimore. I therefore had to stay overnight and then catch an early flight this morning, which resulted in my missing a mandatory class. I would like a refund / voucher to cover the cost of the missed flight. And additional voucher for the time spent on the plane in Portland would also be appreciated.

Since the flight wasn’t full, we had some extra room. Crew was great

The app could have worked in any way to enable re booking, which I did by downloading 2 other apps and ignoring Kayak.

flight was hot, it was delayed and there was no wifi.

being late for poor reasons, bad chairs, being regulated to a terrible gate in LAX

As an Elevance employee, don't we get priority boarding? Also, I boarded zone 5 and could not get normal carry on in luggage space. There were many Delta employees on the flight and their bags, which were large and could only fit two bags per compartment, got preference over customers so I had to check my bag.

Everything went smoothly, WiFi connection was strong. Time to upgrade the regional planes, we are all on top of each other. No room to comfortably do anything.

The bathroom is disgustingly dirty. It looks like the crew members didn’t clean it on a regular basis. Also, who made the bathroom so small?. I am not a big girl but I still feel very cramped inside. Def unpleasant experience to use the bathroom.

My experience with Delta is always pleasant. My return flight #1426 from ATL to RIC was very delayed with departure and landing. It also took a substantial amount of time for baggage claim. It was already late at night, so the delays made for a very long day. I did not get home until after 12 midnight.

I had a great flight with delta. Plane was clean and the staff was nice, I would fly again with delta.

Lady Pilot was perfect in every way wheels up to wheels down communication, professionalism, excellent on time departure and on time arrival, excellent communication! Fantastic job with Superb attitude!!

Delta did an awful job w logistics at DTW. Missed connection. We were there an hour early. SUCKED

We had missed our scheduled connecting flight to Casper and was on the late arrival of 10:15. The plane pulled up to the gangway and nobody was getting off after waiting several minutes. The pilot made an announcement that he needed to start the engines and make a circle back to the parking spot 6 inches closer. Overall, it took 45 minutes to get off the plane that usually takes less than 15. Because of the flight delays out of Casper at the beginning of our trip and on the way home, we booked our next trip out of Denver which is a four hour drive each way.

Flight delay for something to do with an accident on a runway. Our connection time was scheduled for 1 hour and 11 minutes which wasn’t enough with the departure time. We eventually got to our home airport 3 hours late.

The plane to Casper is of the two by two variety which has small bag only overhead. So many passengers try to put oversized bags overhead and causes delays for the flight. Hand checked bags for all with anything larger than a purse or briefcase would make boarding easier.

Our trip from MSP to DEN was 15 minutes early arriving and made us feel a little better while walking from B19 to B94. We checked the Departure board midway to make sure the gate was still assigned to our flight. Just before we arrived, we checked the board and now it said B62 which was back up a stairway and around a long corner. We were exhausted!

It was great. The staff is always helpful and polite. The app is great and makes the whole trip and process so easy. They even offer a step to step guide to your correct terminal. And they keep all the information you'll need updated. Anything you can think of! Great experience.

It was hot and not as comfortable as the flight to Chicago. Must have been a different plane that needs to be worked on or replaced.

Both my flight where delayed Had 25min to make it to my transfer flight

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

I just got back from a trip with 3 flights each way. The flights were good and we were happy with out experience. There was one steward on our first flight that was harsh and grump with passengers. It did not leave a good impression. All of the other flight crews were great on the other five flights.

They changed my flight 5 hours before it took off and changed my connecting airport messing up my entire 1st day in Japan.

awful delay, awful communication, zero updates throughout the experience of a giant delay

Our flight was delayed to Louisville. What made this worse was they did not have another flight attendant to service the flight. This caused an even longer delay. Then when a flight attendant did show up, she chose to "swap" flights with another flight attendant. Therefore, we had to wait longer for the other flight attendant to come to our flight. This is information that the gate attendant should not have shared. Processes and execution at American are broken. Passengers are feeling it. Fixing this starts at the top of the organization.

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

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.

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

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.

My Internet did not work for Outlook email or basically anything. I paid for one hour of in-flight usage and it was terrible. I spent a lot of time on different sites and browsers with no luck and a lot of frustration. Other than that, the flight was on time, crew was nice, service was fine. Seat was OK even though I paid for the extra 6 inches. I cannot imagine how tight the seats in the back must be.

The plane was probably full boarding was easy. We were able to check our carry-on luggage for free. It was a return flight through Philly to LA. Never saw a stewardess do a demonstration of emergency Procedures. I think my flight was pretty full

Flight was delayed after boarding and no idea when it would take off. Crew in Portland did arrange for transport to Boston for a different set of flights to my destination.

Seats are so close together. Middle seats should be discounted.

More options for your flight from Portland to Kentucky

Complete your trip to Kentucky with a hotel stay or car rental