$84 Find Cheap Flights from Milwaukee to Massachusetts - Compare and Save

1 adult
1 adult, Economy, 0 bags

Save 25% or more on flights. Compare deals from all over the web.

Never overpay with our price tracking tools.

Filter searches by price, airline and more to find your best flights.

Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Milwaukee to Massachusetts

Cheapest round-trip prices found by our users on KAYAK in the last 5 days
Boston
Boston1 stop$297
Albany
Albany1 stop$271
Boston
Boston1 stop$297
Albany
Albany1 stop$271
Booking Insights

KAYAK's insights & trends for Milwaukee to Massachusetts flights

Get data-powered insights and trends into flights from Milwaukee to Massachusetts 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 Massachusetts?

Flight prices are below average for this route right now.

Flights to Massachusetts from Milwaukee usually cost between $361 and $514 in December.
The lowest price found in the past 5 days was $297 on American Airlines (Dec 25-Dec 30).

What is the cheapest Milwaukee to Massachusetts flight route?

The cheapest ticket to Massachusetts from Milwaukee found in the last 5 days was to Boston, at $238 round-trip. The most popular route is from Milwaukee (MKE) to Boston (BOS), and the cheapest round-trip airline ticket found on this route in the last 5 days was $238.

What is the cheapest time of day to fly to Massachusetts?

The cheapest time of day to fly to Massachusetts is generally in the evening, when round-trip flights cost $294 on average. Morning departures are around 8% more expensive than evening flights, on average. The most expensive time of day to fly to Massachusetts is generally in the afternoon, which is peak travel time and where the average cost of a ticket is $483.

Can I save money by flying with a layover from Milwaukee to Massachusetts?

No, with an average price for the route of $419, prices are generally cheapest when you fly direct.

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

The cheapest month for flights from Milwaukee to Massachusetts is May, when tickets cost $235 (return) on average. On the other hand, the most expensive months are November and February, when the average cost of round-trip tickets is $435 and $419 respectively.

What’s the cheapest day of the week to fly from Milwaukee to Massachusetts?

When flying from Milwaukee to Massachusetts, you should consider leaving on a Saturday and avoid Mondays if you are looking for the best rates. For your return to Milwaukee, you’ll find the best rates on Saturdays and the most expensive ones on Mondays.

How far in advance should I book a flight from Milwaukee to Massachusetts?

To get a below average price on the flight from Milwaukee to Massachusetts, you should book around 3 weeks before departure, which saves you about 50% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 12 weeks before departure.

Good to know

Low season

February

Cheapest flight

$84
Best time to beat the crowds but there is an average 22% increase in price.
Most popular time to fly and prices are also 16% lower on average.
Flight from Milwaukee to Boston

FAQs - booking Massachusetts flights

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

    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 Massachusetts.

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

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

    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 Massachusetts 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 Massachusetts?

    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 Massachusetts 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 Massachusetts

 
Need help choosing which airline to fly with from Milwaukee to Massachusetts? 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.
7.9
SouthwestOverall score based on 4217 reviews
8.0Comfort
7.0Food
7.4Entertainment
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
Read more Southwest 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.

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.

Friendly crew. Snacks were carb-heavy. Flight was quite delaye

The service was fine, about the same as you get on most lower end airlines. I dont understand the perks of flying them much anymore for the cost.

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.

Great flight. Thank you for the upgrade to first class.

Flight was delayed and not a lot of communication on why until we got on the plane.

Horrible experience. Delta delayed the flight to 11pm which happens. Apparently the pilots were there but we were waiting for flight attendants to arrive from Detroit and they were delayed. They could have made arrangements but that’s fine. What was truly horrible was that at 10:50pm the pilot comes out and says the flight will be cancelled but hasn’t been cancelled yet in the system. It’s being cancelled because the pilots have timed out. As soon as that plane got delayed past 10:50pm delta knew it couldn’t fly. Yet they made us wait around for hours. When the flight finally got cancelled all the area hotels were booked and flights for the next day were unavailable until midday. All I wanted was to spend one day with my family before needing to fly abroad on another delta flight. That will be my last flight with them. I’ll take my 800k miles flown and annual spend to an airline that isn’t so thoughtless.

got ahead of the schedule, nothing else to like. crew management of boarding when overhead bag space was virtually gone in the midst of their priority zone 3 should have been better. but they absolutely did not care. ryanair crew is better than this!

The crew were very respectful. And also they were welcoming.they did help us locate our seats.i enjoyed.

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.

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

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.

Please stop those idiotic and unrelenting announcements, commercials and stupid credit card drivel. All together about 15 minutes of stupidness that annoys each passenger.

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

My service dog and I were asked to deplane just before they closed the door - clearly very last minute they couldn’t find the documentation that I have filled out many many times before that is for flying service animals. I purposely purchase 3seats (a whole row) since he is large and not all passengers want to sit next to a dog on a cross country flight. The plane departed with my husband on it!!! They made me fill out a hard copy of the same form and had to reschedule me on a later flight where they could find 3 seats together!! I’ve done this so many times before - clearly the error was on their part in a technology glitch - but really people - do better!! Very traumatic - and my husband had to wait for us when he landed ….so bad. Poor pup was confused and tired.

Super friendly with lots of drink options an entertainment. Friendly crew.

I like flying first class, and United has a nice one

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

United airlines has the best customer experience from booking to arrival. I always fly United airlines. The mileage program is excellent

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

Great flight. Best in years. Very clean craft. Easy boarding. Communicative pilot. Friendly flight attendants. Absolutely smooth take off, in flight and landing. Very comfortable seats. Smoothest flight I've experienced in years. THANK YOU JET BLUE!

I was asked to pony up an additional $239 (over the $735 paid originally) for a one way middle seat, which was very uncomfortable. Where did you expect me to sit?

Late boarding, had to check the bag even though there was space on the flight and I was I row 7

Unacceptable pre-boarding ticket issues. Paid for and reserved Mint seat approximately a month in advance. Checked in to flight in Mint seat 24 hours before flight. Shortly before flight, was bumped out of Mint entirely, even though other Mint seats were still available and for sale. Was told it was "operational", however seats were still available/being sold. Got to gate and they could not explain it, but the gate agent was able to put me back into Mint (however to a different seat). Nothing proactive done by Jetblue, I would have been bumped had I not arrived at gate early enough to have a helpful gate agent rectify. No explanations from Jetblue.

Diana at the gate was unhelpful which was fine, but she was also rude which I did not appreciate at all.

Forced to check bag, even though plenty of space in overhead bins. Did not appreciate having to wait at baggage claim to retrieve suitcase.

They lost my luggage and have ruined first day of my vacation. Still don’t have it. I have nothing. I also paid for a seat I did not get. They changed both our seats with no notice. Will never fly this airline again.

The flight attendant was snarky and the flight took off very late. I know it was an issue with air traffic control and the runways in Boston, so not really anyone's fault, but very frustrating, I missed an important meeting because of rgr delay. They didn't offer headphones to watch the TV, but luckily I remembered my own and was able to enjoy watching a movie.

Flight was delayed 3 hours. No food on plane besides snacks

Nice plane, with TV, comfortable seats and leg room. Updated regularly on time changes

Staff announced flight was delayed. Then after passengers took the extra time to get food etc, announced it was on time. Not enough overhead space for a full flight Seats were super small and crammed. Crew welcomed us aboard to another "on time gate departure” only to sit on the tarmac for two hours. They made 2 announcements as to why that no one could understand. NO ENTERTAINMENT- food was a bag of old pretzrks. After landing, sat on the tarmac for another 20 minutes “looking for a parking spot”. I never fly American due to past poor performance. I had to that day due to departure time. American never fails to disappoint.

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 crew was wonderful, the plane was fine. We left the gate on time, but we had to wait 40 minutes on the tarmac because of all the congestion at Boston.

Had to pay for WiFi, delayed start, and sat on the runway forever.

On time departure was much appreciated. However, as a frequent flyer and American Advantage member, I was as disappointed not to get an aisle seat.

Flight was cancelled due to a myriad of operational issues. You guys really suck

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 Massachusetts

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