$199 Find Cheap Flights from Wisconsin to Maine - Compare and Save

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Low season

January

Cheapest flight

$199
Best time to beat the crowds with an average 18% drop in price.
Most popular time to fly with an average 11% increase in price.
Flight from Milwaukee to Portland

FAQs for booking flights from Wisconsin to Maine

  • How does KAYAK find such low prices on flights from Wisconsin 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 Wisconsin to Maine.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Wisconsin 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 Wisconsin 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 Wisconsin 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 Wisconsin 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 Wisconsin to Maine up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • How many airports are there in Maine?

    There are 6 airports in Maine. The busiest airport is Portland Airport (PWM), with 70% of all flights arriving there.

  • What is the cheapest month to fly from Wisconsin to Maine?

    The cheapest month for flights from Wisconsin to Maine is January, when tickets cost $193 (return) on average. On the other hand, the most expensive months are November and March, when the average cost of round-trip tickets is $468 and $389 respectively.

  • How long is the flight to Maine?

    An average nonstop flight from Wisconsin to Maine takes 9h 34m, covering a distance of 993 miles. The shortest route is Milwaukee (MKE) to Boston (BOS) with an average flight time of 2h 19m.

  • What are the most popular destinations in Maine?

    Based on KAYAK flight searches, the most popular destination is Boston (89% of total searches to Maine). The next most popular destinations are Portland (9%) and Bangor (2%). Searches for flights to Bar Harbor (0%) are also popular.

Reviews of the top 4 airlines serving from Wisconsin to Maine

 
Need help choosing which airline to fly with from Wisconsin 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 4218 reviews
8.1Boarding
8.0Comfort
7.0Food
8.6Crew
7.4Entertainment
Airline reviews

I love southwest. I can not wait until all the planes convert to the upgraded planes. I love the charging option and the newer seats. Thank you from a very loyal Southwest customer.

10.0 ExcellentMichelle, Nov 2026
Read more Southwest reviews

I love southwest. I can not wait until all the planes convert to the upgraded planes. I love the charging option and the newer seats. Thank you from a very loyal Southwest customer.

My return flight was much better than the flight there! I paid for seat to Veagas but not the return. Thankgoodness they assigned me a seat with additional leg room as I have back and leg problems. I really appreciate it. With the flight already being super expensive due to gas prices and having to pay for bags (now) I needed to save some money.

My first flight from LGA to STL was not good. They didn't do service until over halfway through the flight, the internet didn't really work, and the crew all seemed like they didn't want to be there.

We were stressed about landing as our connecting flight was about to start boarding, being unfamiliar with the airport or where the gates were. We exited the plane to discover we were at the gate we needed. We would be getting back on the same plane but nobody told us we could have just stayed onboard. My wife and I were seated on aisle seats across from each other. We asked if there was a way we could sit together. Once we were at cruising altitude they let us move to an unoccupied row so that was nice.

It’s Southwest. The seats are small, the snacks are meh, it’s $50 to check a bag. It’s exactly fine. Could have been better. Could have been worse. It’s not Spirit

They delayed my flight all day but didn't try to reschedule me until all other options were gone. Ended up on a red eye. Not happy. Lesson learned, don't book the last flight from SJC to RDU.

Every single flight I take with southwest is delayed by at least one hour. Unbelievable

When I made my reservation it would have been nice if kayak would have included my luggage. Unaware that I had to pay $45 each way. Should have asked at reservation time if luggage was being checked

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.

My experience with Delta is always pleasant. My return flight #1426 from ATL to RIC was very delayed with departure and landing. It also took a substantial amount of time for baggage claim. It was already late at night, so the delays made for a very long day. I did not get home until after 12 midnight.

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.

Check in went smoothly. Flight attendant who was assigned my area barely paid any attention to me! She acted as though she was extremely busy and flustered. Maybe she was new?! I told her to change the language on my screen, she said she’d come back to help me but never did so I was able to solve the problem on my own. She came back and said she’d made adjustments on her end. Highly doubt it because I found the setting to change the language! Also, I noticed everyone was eating before we landed so I pushed my help button and she never came so I got up to find her to ask her if I can have breakfast. She said they are not serving breakfast but I can have a sandwich. Yes, that was her response as I saw everyone eating breakfast!!!

United staff were very communicative, the new starlink Wifi is amazing as I was able to work easily.

Good, our flight was delayed but that was totally out of their control due to weather and a presidential visit.

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

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.

The flight was delayed multiple times. Breakfast was not served and only an apology given and statement that we could find better pastries in Paris. Seats were extremely narrow and uncomfortable.

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.

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

More options for your flight to Maine

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