$88 Find Cheap Flights from Massachusetts to Wisconsin - 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 Massachusetts to Wisconsin departing on 7/16. 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.
1 adult
1 adult, Economy, 0 bags

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Low seasonJanuary
Cheapest flight$88
Best time to beat the crowds with an average 6% drop in price.
Most popular time to fly with an average 4% increase in price.
Flight from Hartford to Minneapolis

FAQs for booking flights from Massachusetts to Wisconsin

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

    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 Massachusetts to Wisconsin.

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

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

    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 Massachusetts to Wisconsin 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 Massachusetts to Wisconsin?

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

  • Which airlines fly most frequently to Wisconsin?

    Massachusetts and Wisconsin are connected by different airlines. The airlines that fly that route the most regularly are Delta (22 flights per week), American Airlines (14 flights per week), and JetBlue (7 flights per week).

  • How many airports are there in Wisconsin?

    There are 8 airports in Wisconsin. The busiest airport is Milwaukee-Mitchell Airport (MKE), with 43% of all flights arriving there.

  • Which is the cheapest airport to fly into in Wisconsin?

    Prices will differ depending on the departure airport, but generally, the cheapest airport to fly to in Wisconsin is Milwaukee-Mitchell Airport (MKE), with an average flight price of $243.

  • What is the cheapest day to fly to Wisconsin?

    Based on KAYAK data, the cheapest day to fly to Wisconsin is Tuesday where round-trip tickets can be as cheap as $266. On the other hand, the most expensive day to fly is Monday, where round-trip prices are $428 on average.

  • What is the cheapest time of day to fly to Wisconsin?

    The cheapest time of day to fly to Wisconsin is generally in the afternoon, when round-trip flights cost $287 on average. Morning departures are around 11% cheaper than evening flights, on average. The most expensive time of day to fly to Wisconsin is generally in the evening, which is peak travel time and where the average cost of a ticket is $345.

  • What is the cheapest flight to Wisconsin?

    The cheapest ticket to Wisconsin from Massachusetts found in the last 5 days was to Milwaukee, at $113 round-trip. The most popular route is Boston (BOS) to Milwaukee (MKE) and the cheapest round-trip airline ticket found on this route in the last 5 days was $113.

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

    The cheapest month for flights from Massachusetts to Wisconsin is May, when tickets cost $70 (return) on average. On the other hand, the most expensive months are February and December, when the average cost of round-trip tickets is $113 and $113 respectively.

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

    To get a below average price on the flight from Massachusetts to Wisconsin, you should book around 3 weeks before departure, which saves you about 47% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 12 weeks before departure.

  • How many cities have direct flights to Wisconsin?

    From Massachusetts, there are direct flights to Wisconsin from 1 city. This city is Boston and there are 58 direct flights each week.

  • How many direct flights to Wisconsin are there each day?

    There are around 10 direct flights from within Massachusetts to Wisconsin every day. Most flights (58%) depart in the afternoon.

  • How many direct flights to Wisconsin are there each week?

    Each week there are around 67 direct flights from within Massachusetts to Wisconsin. The most common day for departures is Monday, with 16% of flights taking off on this day.

  • How long is the flight to Wisconsin?

    An average nonstop flight from Massachusetts to Wisconsin takes 6h 07m, covering a distance of 903 miles. The shortest route is Albany (ALB) to Chicago O'Hare Intl Airport (ORD) with an average flight time of 2h 23m.

  • How many long-haul flights are there to Wisconsin each week?

    There are not any long-haul (6-12 hour flight duration) or medium-haul (3-6 hour flight duration) flights to Wisconsin. Instead, there are 58 short-haul flights (up to 3 hour flight duration), with the most arriving from Boston.

  • What are the most popular destinations in Wisconsin?

    Based on KAYAK flight searches, the most popular destination is Chicago (67% of total searches to Wisconsin). The next most popular destinations are Minneapolis (16%) and Milwaukee (7%). Searches for flights to Madison (6%), to Green Bay (2%) and to Appleton (1%) are also popular.

Reviews of the top 5 airlines serving from Massachusetts to Wisconsin

 
Need help choosing which airline to fly with from Massachusetts to Wisconsin? 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 4246 reviews
8.6Crew
8.1Boarding
7.0Food
8.0Comfort
7.5Entertainment
Airline reviews

SW can't get their wifi right. I upgrade to insure wifi service but the last two trips had intermittent service. Not worth the extra costs.

6.0 GoodAnonymous, Jun 2026
TPA - DAL
Read more Southwest reviews

SW can't get their wifi right. I upgrade to insure wifi service but the last two trips had intermittent service. Not worth the extra costs.

The flight was late. The crew was rude. There was no food. Cramped and uncomfortable. Nothing about this flight was good.

Crew was rude, flight was late, wifi didn't work, no food, basically nothing about this flight was good.

It was just okay, no frills, basic transportation with no luxury. No screens on the seats, no water or drinks on a short flight. Full flight but at least it was on time.

Flight was constantly delayed with significant changes in time, it was supposed to get to Colorado Springs at 8:30 PM but it got there after midnight.

Slow boarding, limited food and drink portions. Bad delays and turbulence

The entire travel day was a disaster from beginning to end. Woke up at two in the morning to make it to San Juan airport in time for a 5:30 am flight to Milwaukee which connected in Baltimore. Massive delays lead to me missing original connection out of Baltimore. Sixteen hours of delays/rebooking/layover time later, arrived in Milwaukee to find that only one of two checked bags made it there (despite the fact that Southwest brought another 737 jet to San Juan to fly us out to our original Baltimore connection—-not squeezed into another booked flight). The flight from Baltimore to Milwaukee was barely half full, so there was no logical reason to ship my bags out of Baltimore on a different flight to Chicago to then ship to Milwaukee. Southwest decided that my bags should not have been on the same connecting flight I WAS ON to Milwaukee, and then proceeded to accidentally leave my larger bag with the important items in Chicago. Terrible logic and support all around. Extremely angered and disappointed with SW. What a clownish operation your company has become!

WiFi was not working and didn’t have a beverage service

Great flight. Outstanding Service. Southwest was able to put us on a direct flight to Denver when the connection could have been affected by a later arrival to Baltimore. The direct flight was less expensive that the flight with the connection in Baltimore.

Flights delayed by 4-6 hours. Boarding was a mess and unclear. Bags were not at arrival airport and had never even been put on the plane. No idea when I’ll get them. Don’t fly into Denver!

I thought the service was very nice and pleasant. There were no hiccups and no issues so overall a good experience.

It was a pleasant surprise to have complimentary Wi-Fi on the flight

Flight was delayed, we could have been notified earlier and in a consistent manner. App was not refreshing for another passenger to get the latest flight status. We could have stayed and waited at the hotel instead of waiting at the airport had we known the flight was going to delayed for more than 5 hours. The toilet is too tight, and needs to be cleaned more frequently (every hour). The entertainment screen froze, the touch screen not responding to touch. We were upgraded to comfort, it is more comfortable than regular economy seats.

Mechanical Delay of over an hour with multiple gate changes. Entertainment system down for rejuvenation.

Love delta smaller commuter plane so no entertainment and paid wifi on MKE-LGA leg was extremely unreliable and slow

My flight was cancelled with no explanation after I had already cleared security. I was given 4 options to rebook, only one being non-stop like I had paid for. I grabbed it. It was 4 plus hours later and then took off even later. Biggest complaint is that I booked early and had an aisle seat. They gave me a "window" seat in front of the exit row, so the seat did not decline. I weigh all of 103 #s and it was tight for me! For what I paid, I feel I was kind of ripped off. I think they should have given me the empty comfort seat for the inconvenience. There was no apology nor any explanation as to why the flight was cancelled. My guess is it benefitted Delta in some way.

The dear was very limited in space. I could put my water bottle in seat basket. Also, there was no inflight entertainment in the delta app?

Wifi did not work and they only served water, coffee, or tea.

Checking in at the airport the agent only booked the first keg of my trip and had my checked luggage going to the airport with a layover! Never was issued a boarding pass for the second leg or received sticker fir my checked bag. All was well in the end! Delta agents helped to resolve the situation!!!

Had assistance at airport getting from arrivals gate to departure gate; I couldn't have managed without that extra help. Thank you Delta.

Boarding was great, and the crew were very friendly. The seats must have been a bit on the older side and you could feel some of the seat components through the padding. Also, the plugs did not work on the row's entertainment screen or charging ports. Checked bag was transferred for connecting flight, and we appreciated how early we had the connecting gate information.

Food was great. Staff was phenomenal. Seats were a bit hard and could use a lot more entertainment options as far as movies to choose from. WiFi was good. Overall great trip.

The flight was delayed, they didn’t even have water for the toilets or for drinks

It’s always a great time flying with united airlines.

Very old flight - time to retire it for newer airplanes

2+ hours delayed Outlet in row 12 did not work Tv monitors did not work Lights kept off the entire flight for at 5pm-7pm flight

Deplaning was delayed because of Jetbridge equipment issues in MKE, causing an issue on an otherwise great flight.

Delays took 2hours and thirty minutes making me miss my connecting flight and make me sit in the Chicago airport for 9 hours

No real agent onsite helping you for missing luggage there. Not like the other airline next to UA desk, they have staff attending in their desk assisting answer/helping luggage issue, even after midnight.

The wi-fi was awful. I paid $8 each way and got little , except frustration. .

not sure why you ask about food, I n3ver get food on flights except maybe cookies or pretzels. wifi was slow and in and out most of the flight not good.

there are no options s for snack besides cookies would ve nice to have a salty option n

Never ontime and always delays. Long waits for customer service and often app doesn’t work

We were upgraded to First Class and it was a great flight

it was fine, decent flight... dont get food besides cookies or pretzels so not sure why you ask about food. same for entertainment..

this plane was really old, had exit row seats and tray was in arm of seat so super uncomfortable to use. another seat they could t even use the tray it was broke. seat i. front of me had duct tape on it cause seat was ripped open... this plane should either be updated or retired.

We loved the steward on the plane. He made the night enjoyable

American airlines suck they delay the flights all the time made me sleep in an airport because my flight was delayed and I miss my connecting flight

Very poor delay in dfw was really bad n long

I didn't like that my paid for seat was changed 2 hours before my flight.

Flight left 2 hours late with no explanation as to the delay

Whole experience was poor. Delayed 2 hours. Lied about the delays. Was all jet blues fault and tried to blame on air traffic control. Sent out other let trips and wouldn't allow people to switch aircraft.

My bag was not loaded on my flight. it was not communicated to me until i was waiting for my bag at my destination. there was no confirmation of when my bag was arriving and no way to track it.

The gate attendant in Boston had a high raspy voice and spoke much too fast to be understood. Not pleasant.

It was fine for what it was. It’s not luxury travel but it was efficient, for the most part. Having my carry-on transferred into luggage however, was unwelcome.

We had better-than-average leg room and I loved the access to shows and movies. During boarding, we could not hear the agent even though we were close to the boarding door, which was kind of scary when we realized that half of the passengers had already boarded. Also, the entertainment was awesome, but I could not hear the movie as well as I would have liked, because my headphones were crappy. It would have been better if I could connect my own ear buds via Bluetooth or if JetBlue provided headphones.

I was seated next to an autistic child who was out of control and had a child behind me kicking my seat for most of the trip. I will never fly JetBlue again. Ever. I don't care how cheap it is. It's terrible.

Great price, easy check in, love the free drinks and snacks, and nice crew. The only negative part was waiting for your seat assignment 5 minutes before boarding, and the seats are a bit uncomfortable.

What a great flight. Seats were more comfortable than other airlines. Flight was full but very easy to navigate. No stress no drama

All airline travel outside of First or Business class is an ordeal to be endured. This trip was ok, small o, small k.

Everything you need to know for your flight to Wisconsin

Cabin class types available on flights to Massachusetts

Cabin classes available on flights to Massachusetts. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.