$310 Find Cheap Flights from Milwaukee to The Big Island - Compare and Save

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Milwaukee to The Big Island departing on 10/17. 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.
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Cheap Flights from Milwaukee to The Big Island

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Kailua-Kona
Kailua-Kona2 stops$440
Hilo
Hilo2 stops$674
Kailua-Kona
Kailua-Kona2 stops$440
Hilo
Hilo2 stops$674

Book Cheap Milwaukee to The Big Island 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 The Big Island 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 The Big Island

Sun, Aug 23 - Fri, Aug 28
American Airlines Logo
5:16 am - 4:15 pm
MKE
-
KOA
15h 59m
2 stops
American Airlines Logo
9:45 pm - 1:54 pm
KOA
-
MKE
11h 09m
1 stop
$440American Airlines
Tue, Sep 15 - Thu, Sep 24
American Airlines Logo
5:03 am - 4:00 pm
MKE
-
KOA
15h 57m
2 stops
American Airlines Logo
9:45 pm - 2:05 pm
KOA
-
MKE
11h 20m
1 stop
$440American Airlines
Tue, Aug 25 - Tue, Sep 1
United Airlines Logo
10:35 am - 7:35 pm
MKE
-
KOA
14h 00m
2 stops
United Airlines Logo
1:08 pm - 7:07 am
KOA
-
MKE
12h 59m
2 stops
$445United Airlines
Tue, Aug 25 - Tue, Sep 1
Delta Logo
7:09 am - 7:17 pm
MKE
-
KOA
17h 08m
2 stops
Delta Logo
8:42 pm - 9:41 pm
KOA
-
MKE
19h 59m
2 stops
$445Delta
Wed, Nov 4 - Thu, Nov 5
Southwest Logo
6:45 am - 2:00 pm
MKE
-
KOA
11h 15m
1 stop
Southwest Logo
9:30 pm - 1:15 pm
KOA
-
MKE
11h 45m
1 stop
$494Southwest
Wed, Nov 4 - Thu, Nov 5
United Airlines Logo
9:33 am - 8:32 pm
MKE
-
KOA
14h 59m
2 stops
United Airlines Logo
8:25 pm - 1:34 pm
KOA
-
MKE
13h 09m
1 stop
$500United Airlines
Wed, Nov 4 - Thu, Nov 5
Southwest Logo
5:10 am - 9:25 pm
MKE
-
KOA
20h 15m
2 stops
Southwest Logo
9:30 pm - 1:55 pm
KOA
-
MKE
12h 25m
2 stops
$505Southwest
Thu, Sep 10 - Wed, Sep 16
Delta Logo
10:00 am - 7:15 pm
MKE
-
KOA
14h 15m
2 stops
Delta Logo
8:55 pm - 7:34 pm
KOA
-
MKE
17h 39m
2 stops
$522Delta
Tue, Aug 25 - Tue, Sep 1
Multiple Airlines Logo
3:05 pm - 1:24 pm
MKE
-
KOA
27h 19m
1 stop
Multiple Airlines Logo
7:15 pm - 11:59 pm
KOA
-
MKE
23h 44m
2 stops
$559Multiple Airlines
Tue, Aug 25 - Tue, Sep 1
Multiple Airlines Logo
7:02 am - 9:31 am
MKE
-
KOA
31h 29m
2 stops
Multiple Airlines Logo
6:00 am - 11:59 pm
KOA
-
MKE
12h 59m
2 stops
$597Multiple Airlines
Booking Insights

KAYAK's insights & trends for Milwaukee to The Big Island flights

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

Can I save money by flying with a layover from Milwaukee to The Big Island?

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 $429, prices are generally cheapest when you fly direct.

What is the cheapest month to fly from Milwaukee to The Big Island?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Milwaukee to The Big Island, 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 Milwaukee to The Big Island is February, when tickets cost $548 (return) on average. On the other hand, the most expensive months are June and December, when the average cost of round-trip tickets is $1,229 and $1,199 respectively.

How far in advance should I book a flight from Milwaukee to The Big Island?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Milwaukee to The Big Island, 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 Milwaukee to The Big Island, you should book around 3 weeks before departure, which saves you about 49% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 10 weeks before departure.

Good to know

Low season

July

Cheapest flight

$310
Best time to beat the crowds with an average 13% drop in price.
Most popular time to fly with an average 51% increase in price.
Flight from Milwaukee to Kailua-Kona

FAQs - booking The Big Island flights

  • How does KAYAK find such low prices on flights from Milwaukee to The Big Island?

    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 The Big Island.

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

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

    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 The Big Island 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 The Big Island?

    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 The Big Island up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top 5 airlines serving from Milwaukee to The Big Island

 
See real verified KAYAK customer reviews for airlines flying from Milwaukee to The Big Island. 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 Milwaukee to The Big Island? 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 4226 reviews
7.5Entertainment
8.0Comfort
8.1Boarding
8.6Crew
7.0Food
Airline reviews

No wifi, seems to be very common with Southwest currently. Everything else was normal.

8.0 ExcellentSean, Jul 2026
HOU - LGB
Read more Southwest reviews

No wifi, seems to be very common with Southwest currently. Everything else was normal.

The crew was very kind and made going to Hawaii relaxing and fun to look forward to! Thank you Southwest for a pleasant flight!

I liked the crew member who gave flight instructions on "in case of a problem:. The seats are so small that only a young teenager could sit in middle seat.

I recently flew Southwest from San Jose to Honolulu. I was very impressed with the flight crew, especially the flight attendant in charge of the front of the plane. She came through the aisle at least five times for drinks and water, and two times for snacks. I have not seen such service since I flew first class. Also, for the first time, they gave us the correct baggage claim number, and the luggage came out quickly. I can't wait for Southwest to have assigned seating! I absolutely hate the Cattle Call boarding procedure and the mad dash to get seats and overhead bins. However, the boarding was efficient.

Much better than the.last. flight on SW on Thanksgiving day

Unfortunately it was not a good experience. There was a rude stewardess.

Boarding was well explained and smooth. The flight was short, so there was no time for snacks. They did offer water or juice, though.

The flight was very short, 45 mins, therefore no snacks/drinks were provided; there should be a NA option for food and entertainment survey questions. Also, there were no charging ports onboard for cell phones. My experience was overall positive.

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.

Price was right. Add power to the seats, television, larger plane to accommodate a long flight to improve mental health and overall comfort for a 5 hour flight.

Now that Spirit is not around Alaska took over the title of cheap and worse airlines with high prices for garbage cheap planes. Seats recline the entire 2”. What’s the purpose? Just make the stationary. Crew is on steroids. Food is like McDonald’s happy meal. Only happy in the name rest is garbage

It was good. Too long for older people. Service and support was great! Friendly crew!

The flight attendant and first class were very friendly, efficient, and wanted to make sure that service was great. Highly recommend this airline.

Check in went smooth, flight was on time and our checked bag was delivered in a timely fashion.

Full, attentive service from the fist class cabin flight attendant was superb. Really exceeded expectations.

Direct and non stop. We were late checking in but had paid for our luggage to be checked and they easily took the bags at the gate for us. We unfortunately had to take our bags through TSA and lost a few items...

Oh the days of yore when there was some space. Wedged in by an extremely overweight passenger and sitting cramped for 4 hours is no one’s dream trip. One shouldn’t have to pay more for 1st class just to survive the trip. Literally the 1 day is ruined with recovery. Hugely obese need more room and should pay more for the required space. Staff were very nice, no hitches with baggage. I really dread flying., related to comfort.

My TSA precheck did not appear on my boarding pass, even though I entered my TTN at time of purchase and verified it was on the Alaska Airlines website under my reservation.

Very friendly staff, very responsive to complaints about the cabin temperature. 😁

First class only upgrades seat width. The bottom cushion of the seat sloped forward so much that I was constantly sliding out of my seat. The meal was awful, granola and dried fruit? Seriously, for what I paid to upgrade? I can bring my own sawdust and rotten fruit for a whole lot less. Priority boarding is great except when you have a hundred economy passengers stranding in the aisle slamming you in the face with their enormous carry ons and smelly asses right under your nose. I want my money back for that leg of my trip. It wasn’t worth the money for such a minimal upgrade.

Seats were not bad enough and uncomfortable good legroom in the emergency exit row we were in, but we were forbidden to hold my grandson on my lap for a little while, and the stewardess passed us saying it was against regulations which makes little or no sense when you’re 36,000 feet. The food snacks were really bad. Tasteless tasted like wallpaper, but we’re supposed to be protein bars, and the announcements were all completely incoherent because of the noise of the airplane and the lowness and crackly nature of the PA system.. this was disgraceful. No one in our party could understand a word of what the captain or the flight attendant were saying —not a word! The landing was a little hairy in a pretty stiff crosswind -we bounced before the plane stabilized on the runway

Crew was nice, meal was good. Entertainment had to be rebooted 3 times and still did not work. Turns out there was residue on screen, it needed to be cleaned to prevent the touchscreen buttons from continuously activating. I had entertainment for the last 45 minutes of a 5 hour 45 minute flight. Really unacceptable for first class. Flight attendent indicated your cleaning solution creates this problem. Seems as if this is widely known, you should be using a different product or cleaning better. Really really disappointing which simply added to the wi fi on your planes with reliably never ever works.

Long flight but comfortable and not freezing as I have experienced on Hawaiian flights to the islands. They gave us blankets just in case. Nice touch.

NEVER MADE THE FLIGHT BECAUSE DELTA SAID THEY CAN NOT

Everything I mentioned earlier - the airbus was more comfortable indeed and the experience was further enhanced.

First class and monitors weren’t working for mine & my husbands. Eventually fixed, but quite annoyed as we bought first class. Also, No foot rests.

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

It would be nice if was given wires ear buds. Overall was a good experience was able to sleep on the plane

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

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.

Great staff. Clean plane, but we were delayed for more than an hour due to maintenance issues and had to board another plane.

Overall a good experience, but no wifi available for free or for purchase and we got wet from condensation or other water source during descent.

I’m so sorry, I can’t remember her name, I believe it was Dimpti. She was stellar, also a mature Asian flight attendant, lots of flowers in her hair, just as amazing! But literally the crew was AWESOME . Only downside is there weren’t any charging outlets. Maybe I needed to ask a flight attendant , but it would’ve been nice to have one easily accessible.

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

Older aircraft, no meal, only food was for purchase. Not impressed United.

Stuck on tarmac for two hours plus a 5.5 hour flight. Rude flight attendant. And no meals, not even for purchase!

I learned that seating towards the end of plane that a line forms for the restroom and people use your chair as a hand railing, bumping your seat consistently. I was seated in the aisle. I think that next time if I am towards the back row I would want to sit in the middle or window seat.

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!

All good except paid for wifi that did not work

Flight pulled out on time but sat on runway for 30 mins. It was extremely cold in the aircraft despite wearing a winter coat. Surprisingly they had a vegetarian meal but could have some better snack choices for a 8 hour flight.

For a 5 1/2 hour flite i considered the "business class" to be subpar. The seats were just ok, no amenities, really nothing more than a long domestic flight. Frankly disappointed.

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.

More choices on snacks. Built-in video screen to enjoy entertainment choices.

Almost a 6 hour flight and the only food option is a cheese plate… and chips. Also how is it there are no options for texting on American. I’ll be going back to delta and united.

Angela was the best fa ever. She made that 8 hour flight a breeze

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

Crew were attentive and friendly. Flight was smooth and early! I enjoyed the less crowded plane. Thank you!

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

Everything you need to know for your flight to The Big Island

Information on your arrival and departure airports