$100 Find Cheap Flights from Milwaukee to Maine - 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 Maine departing on 10/30. 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 Maine

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Portland
Portland1 stop$325
Bangor
Bangor1 stop$271
Bar Harbor
Bar Harbor2 stops$734
Boston
Boston1 stop$188
Portland
Portland1 stop$325
Bangor
Bangor1 stop$271
Bar Harbor
Bar Harbor2 stops$734
Boston
Boston1 stop$188

Book Cheap Milwaukee to Maine 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 Maine 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 Maine

Fri, Oct 30 - Mon, Nov 2
Frontier Logo
8:03 pm - 10:09 am
MKE
-
BOS
13h 06m
1 stop
Frontier Logo
10:11 am - 7:08 pm
BOS
-
MKE
9h 57m
1 stop
$188Frontier
Sun, Aug 30 - Sat, Sep 5
Frontier Logo
12:10 pm - 9:09 am
MKE
-
BOS
19h 59m
1 stop
Frontier Logo
10:04 am - 11:13 am
BOS
-
MKE
26h 09m
1 stop
$198Frontier
Sat, Sep 12 - Mon, Sep 14
JetBlue Logo
10:55 am - 2:09 pm
MKE
-
BOS
2h 14mnonstop
JetBlue Logo
8:30 am - 10:02 am
BOS
-
MKE
2h 32mnonstop
$219JetBlue
Sat, Sep 12 - Tue, Sep 15
JetBlue Logo
10:55 am - 2:09 pm
MKE
-
BOS
2h 14mnonstop
JetBlue Logo
8:30 am - 10:02 am
BOS
-
MKE
2h 32mnonstop
$224JetBlue
Sat, Sep 12 - Tue, Sep 15
Delta Logo
2:35 pm - 6:07 pm
MKE
-
BOS
2h 32mnonstop
Delta Logo
4:15 pm - 5:52 pm
BOS
-
MKE
2h 37mnonstop
$227Delta
Sat, Sep 26 - Wed, Sep 30
Delta Logo
2:35 pm - 6:07 pm
MKE
-
BOS
2h 32mnonstop
Delta Logo
4:15 pm - 5:52 pm
BOS
-
MKE
2h 37mnonstop
$227Delta
Sat, Oct 31 - Tue, Nov 3
United Airlines Logo
6:18 pm - 12:46 am
MKE
-
BOS
5h 28m
1 stop
United Airlines Logo
6:00 am - 10:13 am
BOS
-
MKE
5h 13m
1 stop
$247United Airlines
Sat, Sep 12 - Tue, Sep 15
United Airlines Logo
6:47 pm - 1:10 am
MKE
-
BOS
5h 23m
1 stop
United Airlines Logo
10:38 am - 3:11 pm
BOS
-
MKE
5h 33m
1 stop
$247United Airlines
Tue, Sep 15 - Tue, Sep 22
Southwest Logo
3:05 pm - 9:30 pm
MKE
-
BOS
5h 25m
1 stop
Southwest Logo
2:45 pm - 9:00 pm
BOS
-
MKE
7h 15m
1 stop
$247Southwest
Wed, Sep 9 - Wed, Sep 16
Southwest Logo
4:25 pm - 10:20 pm
MKE
-
BOS
4h 55m
1 stop
Southwest Logo
1:05 pm - 8:00 pm
BOS
-
MKE
7h 55m
1 stop
$247Southwest
Booking Insights

KAYAK's insights & trends for Milwaukee to Maine flights

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

How much is a round-trip flight from Milwaukee to Maine?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Milwaukee to Maine departing in October.

Flight prices are below average for this route right now.

Flights to Maine from Milwaukee usually cost between $462 and $596 in October.
The lowest price found in the past 5 days was $325 on United Airlines (Oct 3-Oct 7).

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Milwaukee to Maine, 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 Maine is April, when tickets cost $210 (return) on average. On the other hand, the most expensive months are July and August, when the average cost of round-trip tickets is $550 and $529 respectively.

Good to know

Low season

February

Cheapest flight

$100
Best time to beat the crowds with an average 16% drop in price.
Most popular time to fly with an average 53% increase in price.
Flight from Milwaukee to Boston

FAQs - booking Maine flights

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

    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 Maine.

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

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

    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 Maine 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 Maine?

    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 Maine 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 Maine

  • Looking for a cheap flight? 25% of our users found tickets from Milwaukee to the following destinations at these prices or less: Boston $143 one-way - $223 round-trip

Reviews of the top 4 airlines serving from Milwaukee to Maine

 
See real verified KAYAK customer reviews for airlines flying from Milwaukee to Maine. 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 Maine? 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 4229 reviews
8.6Crew
8.0Comfort
7.5Entertainment
8.1Boarding
7.0Food
Airline reviews

Boarding process of asking for volunteers to check bags goes against the system you had before with 2 bags checked free. This process is more of a guilt trip than a caring attitude toward the customer. In addition bag-size scrutiny has increased which also slows down the process of boarding. My wife said she will not fly on your airline again unless there is no other option.

10.0 ExcellentDenis, Aug 2026
MDW - ATL
Read more Southwest reviews

Boarding process of asking for volunteers to check bags goes against the system you had before with 2 bags checked free. This process is more of a guilt trip than a caring attitude toward the customer. In addition bag-size scrutiny has increased which also slows down the process of boarding. My wife said she will not fly on your airline again unless there is no other option.

Eveeyrime I fly they are begging for bags due to cabin overhead space. What they should so ia take the bags that are clearly too big to fit wheels first on their side. And those of us who give up the bag should really get their bags first. When boarding, nobody wants stupid jokes about how hot it is on board. Give us some cool air. Im usually sick from the heat by the time we take off.

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

Poor customer service, no accommodation for passengers when the flight was delayed over 5 hours.

Friendly crew kept coming by to make sure all was ok, provide additional refreshments, etc.

It was good. Last flight was delayed but I always say that is in God's plan

Red eye from San Diego. Temperature of the cabin was way too warm and the air duct flowed very little air.

Overall good, just screaming kids in the area the whole flight.

My experience will Southwest was good. I wish there was more entertainment and the boarding process was slow at time but other than that my experience was great definitely will be flying with SouthWest again.

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.

Comfortable seats. Nice service online. Short flight, so not a lot of time to enjoy.

Awful. There was an unexpected delay of nearly three hours because there were not enough flight attendants. I understand this is likely due to FAA regulations; but in that case, Delta should coordinate with smaller airports such as RDU to have extra flight attendants on the ground and "on call". In addition, this was the second 2-hour+ delay to Boston on this route in one week.

It was strange that the flight attendant was so adamant about having phones turned to airplane mode that he was calling out names from networks shown and waiting until they were all gone. I've never experienced that before, and after already working through an hour+ delay, it felt tone deaf. I take dozens of flights per year and have never experienced anything similar.

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

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.

Flight staff and all was fine. Food always sucks on planes so nothing new.

The flight crew were very helpful. The seats were very close together. There was barely room to sit without touching the person next to you.

I’m an EP on AA every year for more than a decade but this was a very pleasant and surprising experience. Clean and sizable plane for HOU to CHI. 5 row first class. And excellent food in first class the steak option was really good. Your flight attendants even better. Seat 5A

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.

My wallet fell out of my pocket ( my fault). Staff claimed they looked while cleaning. Said they didn't find it, but was actually found in Washington DC on the plane. Which mean either they didn't look or don't do a good job of cleaning. Now I have to pay 27 dollars to get it shipped back and have no wallet for my entire vacation

Although there were two delays, they were communicated clearly and the boarding process was expedited. The crew was pleasant and efficient.

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.

Seating was horrible. Small seats. Access to flight information and extras very iser unfriendly. Kept losing internet after paying for it. Staff in madison was as unprofessional and unhelpful.

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

The counter/baggage counter was busy and so many people missed flights. We got stuck sitting on the plane over 2 hours at the gate while they were doing an inspection is wrong. Many of us missed our connecting flights because of it.

Our flight was changed from Madison to DC to Madison to Charlotte.

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

Boarding was relatively fast and easy and the crew was attentive throughout.

90 min delay for a food cart that needed to be fixed.

Everything you need to know for your flight from Milwaukee to Maine

Information on your arrival and departure airports