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Flight Deals
Cheap Flights from Milwaukee to Kentucky
Cheapest round-trip prices found by our users on KAYAK in the last 5 daysBook Cheap Milwaukee to Kentucky Plane Tickets
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Milwaukee to Kentucky 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 Milwaukee to Kentucky
Sat, Dec 12 - Mon, Dec 14
4:08 pm - 11:05 pmMKE Milwaukee-Mitchell-SDF Louisville Intl
5h 57m1 stop Atlanta Hartsfield-Jackson
3:02 pm - 9:02 pmSDF Louisville Intl-MKE Milwaukee-Mitchell
7h 00m1 stop Atlanta Hartsfield-Jackson
$223Delta
Mon, Dec 7 - Sat, Dec 12
7:01 am - 2:17 pmMKE Milwaukee-Mitchell-SDF Louisville Intl
6h 16m1 stop Atlanta Hartsfield-Jackson
6:35 am - 10:15 amSDF Louisville Intl-MKE Milwaukee-Mitchell
4h 40m1 stop Minneapolis St Paul
$223Delta
Tue, Nov 17 - Wed, Nov 18
6:47 am - 1:35 pmMKE Milwaukee-Mitchell-SDF Louisville Intl
5h 48m1 stop Chicago O'Hare Intl
10:37 am - 2:58 pmSDF Louisville Intl-MKE Milwaukee-Mitchell
5h 21m1 stop Chicago O'Hare Intl
$223United Airlines
Tue, Nov 17 - Tue, Nov 24
10:20 am - 4:54 pmMKE Milwaukee-Mitchell-SDF Louisville Intl
5h 34m1 stop Atlanta Hartsfield-Jackson
8:05 am - 11:37 amSDF Louisville Intl-MKE Milwaukee-Mitchell
4h 32m1 stop Atlanta Hartsfield-Jackson
$223Delta
Sat, Dec 12 - Mon, Dec 14
5:45 am - 10:15 amMKE Milwaukee-Mitchell-SDF Louisville Intl
3h 30m1 stop Chicago Midway
5:40 am - 11:00 amSDF Louisville Intl-MKE Milwaukee-Mitchell
6h 20m2 stops Baltimore/Washington Chicago Midway
$228Southwest
Tue, Nov 17 - Tue, Nov 24
8:00 am - 3:35 pmMKE Milwaukee-Mitchell-SDF Louisville Intl
6h 35m2 stops Lambert-St Louis Chicago Midway
8:25 am - 10:50 amSDF Louisville Intl-MKE Milwaukee-Mitchell
3h 25m1 stop Chicago Midway
$228Southwest
Wed, Dec 9 - Fri, Dec 11
10:38 am - 6:17 pmMKE Milwaukee-Mitchell-SDF Louisville Intl
6h 39m1 stop Chicago O'Hare Intl
9:00 am - 1:32 pmSDF Louisville Intl-MKE Milwaukee-Mitchell
5h 32m1 stop Chicago O'Hare Intl
$243United Airlines
Mon, Nov 23 - Sat, Nov 28
8:35 am - 1:35 pmMKE Milwaukee-Mitchell-SDF Louisville Intl
4h 00m1 stop Chicago O'Hare Intl
7:00 am - 10:11 amSDF Louisville Intl-MKE Milwaukee-Mitchell
4h 11m1 stop Chicago O'Hare Intl
$280United Airlines
Sat, Nov 21 - Sun, Nov 22
6:27 pm - 11:58 pmMKE Milwaukee-Mitchell-LEX Lexington Blue Grass
4h 31m1 stop Charlotte Douglas
5:55 pm - 11:52 pmLEX Lexington Blue Grass-MKE Milwaukee-Mitchell
6h 57m1 stop Charlotte Douglas
$319American Airlines
Fri, Jan 29 - Sun, Jan 31
12:10 pm - 6:47 pmMKE Milwaukee-Mitchell-LEX Lexington Blue Grass
5h 37m1 stop Charlotte Douglas
4:56 pm - 8:31 pmLEX Lexington Blue Grass-MKE Milwaukee-Mitchell
4h 35m1 stop Charlotte Douglas
$319American Airlines
Recent one-way flight deals from Milwaukee to Kentucky
Tue, Dec 8
4:20 pm - 8:35 pmMKE Milwaukee-Mitchell-SDF Louisville Intl
3h 15m1 stop Chicago Midway
$112Southwest
Wed, Dec 2
4:35 pm - 10:15 pmMKE Milwaukee-Mitchell-SDF Louisville Intl
4h 40m1 stop Baltimore/Washington
$112Southwest
Tue, Dec 8
6:20 am - 12:15 pmMKE Milwaukee-Mitchell-SDF Louisville Intl
4h 55m2 stops Chicago Midway Nashville Intl
$117Southwest
Wed, Dec 2
8:00 am - 3:35 pmMKE Milwaukee-Mitchell-SDF Louisville Intl
6h 35m2 stops Lambert-St Louis Chicago Midway
$117Southwest
Tue, Dec 8
12:30 pm - 8:59 pmMKE Milwaukee-Mitchell-LEX Lexington Blue Grass
7h 29m1 stop Charlotte Douglas
$263American Airlines
Tue, Dec 8
5:00 am - 4:33 pmMKE Milwaukee-Mitchell-LEX Lexington Blue Grass
10h 33m2 stops Chicago O'Hare Intl Charlotte Douglas
$268American Airlines
Tue, Dec 8
5:00 am - 9:59 pmMKE Milwaukee-Mitchell-SDF Louisville Intl
15h 59m3 stops Chicago O'Hare Intl Des Moines Houston George Bush Intcntl
$316United Airlines
Wed, Dec 2
5:00 am - 9:59 pmMKE Milwaukee-Mitchell-SDF Louisville Intl
15h 59m3 stops Chicago O'Hare Intl Des Moines Houston George Bush Intcntl
$336United Airlines
Sat, Nov 7
12:03 pm - 5:30 pmMKE Milwaukee-Mitchell-LEX Lexington Blue Grass
4h 27m1 stop Chicago O'Hare Intl
$384United Airlines
Tue, Dec 8
5:00 am - 10:15 pmMKE Milwaukee-Mitchell-LEX Lexington Blue Grass
16h 15m3 stops Chicago O'Hare Intl Des Moines Denver Intl
$1,195United Airlines
Recent last minute flight deals from Milwaukee to Kentucky
Sat, Oct 31 - Sun, Nov 1
6:45 am - 1:15 pmMKE Milwaukee-Mitchell-SDF Louisville Intl
5h 30m1 stop Tampa
7:05 am - 9:45 amSDF Louisville Intl-MKE Milwaukee-Mitchell
3h 40m1 stop Nashville Intl
$657Southwest
Sat, Oct 31 - Sun, Nov 1
6:35 am - 4:35 pmMKE Milwaukee-Mitchell-SDF Louisville Intl
9h 00m2 stops Chicago Midway Nashville Intl
7:55 pm - 10:10 pmSDF Louisville Intl-MKE Milwaukee-Mitchell
3h 15m1 stop Chicago Midway
$662Southwest
Sat, Oct 31 - Sun, Nov 1
6:35 am - 3:25 pmMKE Milwaukee-Mitchell-SDF Louisville Intl
7h 50m2 stops Chicago Midway Baltimore/Washington
5:10 pm - 11:55 pmSDF Louisville Intl-MKE Milwaukee-Mitchell
7h 45m2 stops Baltimore/Washington Nashville Intl
$667Southwest
Sat, Oct 31 - Sun, Nov 1
7:00 am - 12:38 pmMKE Milwaukee-Mitchell-LEX Lexington Blue Grass
4h 38m1 stop Charlotte Douglas
8:11 pm - 11:56 pmLEX Lexington Blue Grass-MKE Milwaukee-Mitchell
4h 45m1 stop Charlotte Douglas
$688American Airlines
Sat, Oct 31 - Sun, Nov 1
7:45 am - 5:25 pmMKE Milwaukee-Mitchell-LEX Lexington Blue Grass
8h 40m2 stops Chicago O'Hare Intl Charlotte Douglas
8:11 pm - 11:56 pmLEX Lexington Blue Grass-MKE Milwaukee-Mitchell
4h 45m1 stop Charlotte Douglas
$693American Airlines
Sat, Oct 31 - Sun, Nov 1
8:45 am - 5:25 pmMKE Milwaukee-Mitchell-LEX Lexington Blue Grass
7h 40m2 stops Chicago O'Hare Intl Charlotte Douglas
5:00 am - 11:08 amLEX Lexington Blue Grass-MKE Milwaukee-Mitchell
7h 08m2 stops Charlotte Douglas Chicago O'Hare Intl
$874American Airlines
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.
Prices
Airlines
More
Good to know
Low season | January |
|---|---|
High season | October |
Cheapest flight | $112 |
FAQs - booking Kentucky flights
Top tips for finding cheap flights to Kentucky
Reviews of the top 4 airlines serving from Milwaukee to Kentucky
See real verified KAYAK customer reviews for airlines flying from Milwaukee to Kentucky. 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.
7.9
SouthwestOverall score based on 4225 reviews
7.0Food
7.4Entertainment
8.0Comfort
8.1Boarding
8.6Crew
Airline reviews
Flight was delayed about 50 minutes and completely full. they did the usual demand for people to check carry-ons. they called all groups to board very fast only to stand in the gangway after having boarding passes scanned. Why don't airlines board from the back to front - since they now have assigned seats? our stewardess got drink orders confused, so she just called out "cranberry". etc.,.. I wish they wouldn't serve pretzels snacks with a powdered coating, as it sticks to your hands and they don't have wet wipes. don't want to lick my fingers after hanging out in the terminal for over an hour.
8.0 ExcellentLinda, Oct 2026
Flight was delayed about 50 minutes and completely full. they did the usual demand for people to check carry-ons. they called all groups to board very fast only to stand in the gangway after having boarding passes scanned. Why don't airlines board from the back to front - since they now have assigned seats? our stewardess got drink orders confused, so she just called out "cranberry". etc.,.. I wish they wouldn't serve pretzels snacks with a powdered coating, as it sticks to your hands and they don't have wet wipes. don't want to lick my fingers after hanging out in the terminal for over an hour.
Delayed over 3 hours, extremely rough landing on all four flights. Would not recommend
Boarding, crew and inflight entertainment was great. Could have better food options for a long flight. Paid money and got a seat with extra leg space but was asked to keep my carry on under the seat in front of me which defeats the purpose of buying a extra space seat.
On time departure and arrival. Had to be the oldest plane in the SWA fleet but it got me where I needed to be.
Flight was delayed out of BWI unexpectedly / without a reason given but otherwise ok.
I got a bit sick on the flight, and was so grateful when the male flight attendant explained to me they keep the back row open for cases like mine. He took such great care of me! I was incredibly grateful.
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.
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.
Good, our flight was delayed but that was totally out of their control due to weather and a presidential visit.
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.
awful delay, awful communication, zero updates throughout the experience of a giant delay
My luggage was lost at some point during my layover between Chicago and LHR. I landed Tuesday morning, and did not get it until Thursday night. Ironically, the people at the ticket desk had added a “priority” sticker to my tracking tag.
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.
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.
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
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Cabin class types available on flights to Kentucky
Cabin classes available on flights to Kentucky. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.
Flights from other airports in Milwaukee to Kentucky
Flights from all airports in Milwaukee to Kentucky. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.
Flights to other popular destinations
The most popular flights on KAYAK according to clicks in the last 2 weeks. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.
Flights from Milwaukee to popular cities in Kentucky
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