$128 Find Cheap Flights from Milwaukee to Maine - Compare and Save

1 adult
1 adult, Economy, 0 bags

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Cheap Flights from Milwaukee to Maine

Cheapest round-trip prices found by our users on KAYAK in the last 5 days
Sort by: Cheapest
Portland
4h 30m2 stops
from $255per person
Boston
2h 13mNonstop
from $258per person
Bangor
4h 47m2 stops
from $321per person
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?

Flight prices are below average for this route right now.

Flights to Maine from Milwaukee usually cost between $370 and $573 in October.
The lowest price found in the past 5 days was $255 on American Airlines (Oct 14-Oct 21).

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

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 December, when the average cost of round-trip tickets is $528 and $462 respectively.

Good to know

Low season

February

Cheapest flight

$128
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 Portland

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 $153 one-way - $280 round-trip

Reviews of the top 4 airlines serving from Milwaukee to Maine

 
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 4190 reviews
8.6Crew
8.0Comfort
8.1Boarding
7.5Entertainment
7.0Food
Airline reviews

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

6.0 GoodAnonymous, Sep 2026
Read more Southwest reviews

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.

Flights delays were communicated timely and helpfully, but there was a significant delay without any real effort to make up for that. Also, the in-flight WiFi was very spotty. That said, this was my first time with Southwest and I was quite happy with the service and staff otherwise.

Delayed and once landed waited very long for the luggage

Nice managed … it was a smaller plane, so the seating wasn’t as comfortable.

The Southwest airline was ok. A big thank you to Kayak team (David), who worked with me on Sunday afternoon to rebook my travel from Burbank, CA, to CVG. My original flight on Sunday was delayed, so I had to cancel Sunday flight and rebook my travel to Monday. Could not have done it without help from David from Kayak team. Ante Soda GE Aerospace

Seated at front bulkhead for a smidge extra leg room away from home and on flight back home. Away crew was very proactive about assuring our carryons had space close behind us (because no seat in front of us our personal items had to be in a small bin overhead). They actively required passengers place overhead luggage on its side so more items could fit in bins. Home crew made no such efforts. I had to struggle back rows to get overhead bags upon landing, no crew help then either, and some disgruntled passengers as I and others retrieved our bags. There was a system that worked pretty well. The home bound crew just didn't feel like working.

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

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.

It’s a 3 hour flight with no entertainment and no WiFi due to Delta using old planes on this route and food is cold. Today we were told no potable water on the flight to even make coffee or tea. Ridiculous service in this direct route for business travelers and non business travelers

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

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.

awesome team work seen since on board till off plane in my destination. thanks you so much.

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

The flight could have actually taken place. Canceled flight and no option to rebook that day.

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.

More options for your flight from Milwaukee to Maine

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