$100 Find Cheap Flights from Milwaukee to Kentucky - Compare and Save

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Cheap Flights from Milwaukee to Kentucky

Cheapest round-trip prices found by our users on KAYAK in the last 5 days
Louisville
Louisville1 stop$209
Lexington
Lexington1 stop$319
Nashville
Nashville1 stop$188
Louisville
Louisville1 stop$209
Lexington
Lexington1 stop$319
Nashville
Nashville1 stop$188
Booking Insights

KAYAK's insights & trends for Milwaukee to Kentucky flights

Get data-powered insights and trends into flights from Milwaukee to Kentucky to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest month to fly from Milwaukee to Kentucky?

The cheapest month for flights from Milwaukee to Kentucky is May, when tickets cost $288 (return) on average. On the other hand, the most expensive months are April and October, when the average cost of round-trip tickets is $646 and $412 respectively.

Good to know

Low season

November

Cheapest flight

$100
Best time to beat the crowds with an average 13% drop in price.
Most popular time to fly and prices are also 2% lower on average.
Flight from Milwaukee to Nashville

FAQs - booking Kentucky flights

  • How does KAYAK find such low prices on flights from Milwaukee to Kentucky?

    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 Milwaukee to Kentucky.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Milwaukee to Kentucky?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Milwaukee to Kentucky 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 Milwaukee to Kentucky?

    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 from Milwaukee to Kentucky with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Milwaukee to Kentucky?

    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 from Milwaukee to Kentucky up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Top tips for finding cheap flights to Kentucky

  • Looking for a cheap flight? 25% of our users found tickets from Milwaukee to the following destinations at these prices or less: Nashville $185 one-way - $326 round-trip

Reviews of the top 4 airlines serving from Milwaukee to Kentucky

 
Need help choosing which airline to fly with from Milwaukee 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 4190 reviews
8.1Boarding
8.0Comfort
8.6Crew
7.5Entertainment
7.0Food
Airline reviews

Wasn't expecting this, but, we actually ended up getting assigned to the first row of seats!!!!! The extra legroom came in handy

10.0 ExcellentAnonymous, Sep 2026
Read more Southwest reviews

Wasn't expecting this, but, we actually ended up getting assigned to the first row of seats!!!!! The extra legroom came in handy

Trash experience on all my flights this week. Delay after delay. The flight I’m waiting for has been delayed 6 times and nearly 3 hours.

Southwest has been a nightmare. Delayed flights, missed connections, systems down. Never again am I flying southwest.

had to check bag at gate when there was still overhead bin space. As usual the WIFI didn't really work.

Terrible delay today. also, waited 90 minutes for baggage to unload in Seattle earlier in the week.

Like new plane. Great crew. Comfortable. Clean. On time. Happy employees. Good organization and control of passengers.

Flight time kept changing and so did the gate. It was very frustrating

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

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

We were headed for Florida and anxious to get there. Everything was absolutely the best. This is our first time with Southwest and it’s now our go to airline. Best ever.

The flights were on time; all went as expected which is a big positive! No delays! There was no food or drink service in any legs, which I understand due to the short flight time.

The Delta assistsed services were awesome for my aunt. So very helpful.

Probably not the fault of Delta but there was delay after delay after delay and I ended up getting home 4 hours later then I should have at 1:30 in the morning

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!!

Staff was exceptional! Everyone was kind, professional and friendly making the trip very pleasant. Thank you!

Very late arrival at PWM. Late jet getting to ATL. Equipment problem with aircraft - could not get enough water onto plane., Another delay getting FAA approval for flight with bottled H2O. Not the crew’s problem.

A little bumpy ride . No food was being provided due the the turbulence. That was ok it was a short flight to my standards.

Pretty standard flight. Delta has a good selection of movies.

The flight was so late that I had to change connecting flights, turning a five-hour trip into a fourteen-hour nightmare.

Despite being delayed, we would still give a high score for this flight experience. For the first time in quite some time we had excellent customer service throughout our entire round trip. The flight attendants were the most polite we have experienced in our last ten flights at least (non of which were Delta and include business class). The food offered was a better selection than most—we just didn’t have any of it. Overall, almost as good as flying used to be. Thank you to Delta.

Plane congestion resulted in a 1 hr wait from landing to arrival at the gate. This was in addition to also experiencing extreme delays on my incoming flight.

Delayed too much. 1.5 hrs in the airport and another 1 hr in the runway. Got too late in the night. There was no proper food available.

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.

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

The flight was delayed by two de-icings. The seatbelt did not work correctly. It did not stay tight.

The seats on the aircraft are like sitting in a rock. During the boarding process they recognize Active Duty Military, why don’t they recognize Retired Military. I’ve always preferred Delta, this flight confirmed why I still prefer Delta.

It was literally one of the worst travel experiences ever. My flight got delayed by over an hour and there was no communication of this from the gate staff. I realized it by checking the screen periodically. Once on board the flight attendants continued to serve alcohol to a man who was clearly already drunk and that was making a bunch of commotion. Never again will I fly United!

At least the delays were short. Business class, even in the new planes is very crowded now with crappy tray tables

All good except paid for wifi that did not work

Flight cancelled due to fog. No other flights available for 36 hours. Directed by United to book passage on another carrier, and submit receipts for reimbursement. Did that. United now states they will not reimburse. Currently out 2 grand.

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.

Crew was helpful and cheerful especially when they had no refreshments to work with. The plane was never serviced and had nothing but limited water and coffee onboard. For the price point, a concern of services.

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.

I bought wifi and most of the flight could not even use it my apps would just spin. I couldn't even listen to music. super frustrating.

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.

There were several different delays but we ended up being delayed a total of 40 mins or so. It was annoying we had a gate change which made it take longer to leave DFW, and we had to check our carry on. Ugh

We were told we had no flights before our flight was continually delayed then cancelled.

More options for your flight from Milwaukee to Kentucky

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