$55 Find Cheap Flights from Massachusetts to Wisconsin

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Low seasonJanuary
High seasonAugust
Cheapest flight$55
Best time to beat the crowds with an average 0% drop in price.
Most popular time to fly and prices are also 12% lower on average.
Flight from Boston to Chicago O'Hare Airport

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 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 $213.

  • What is the cheapest day to fly to Wisconsin?

    Based on KAYAK data, the cheapest day to fly to Wisconsin is Wednesday where round-trip tickets can be as cheap as $296. On the other hand, the most expensive day to fly is Sunday, where round-trip prices are $387 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 $288 on average. Morning departures are around 2% more expensive than evening flights, on average. The most expensive time of day to fly to Wisconsin is generally at night, which is peak travel time and where the average cost of a ticket is $403.

  • What is the cheapest flight to Wisconsin?

    The cheapest ticket to Wisconsin from Massachusetts found in the last 72 hours was to Milwaukee, at $98 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 72 hours was $98.

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

    The cheapest month for flights from Massachusetts to Wisconsin is February, when tickets cost $356 (return) on average. On the other hand, the most expensive months are October and March, when the average cost of round-trip tickets is $714 and $678 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 4 weeks before departure. For the absolute cheapest price, our data suggests you should book 26 weeks before departure.

  • How long is the flight to Wisconsin?

    An average nonstop flight from Massachusetts to Wisconsin takes 6h 03m, 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.

  • What are the most popular destinations in Wisconsin?

    Based on KAYAK flight searches, the most popular destination is Chicago (62% of total searches to Wisconsin). The next most popular destinations are Minneapolis (20%) and Milwaukee (12%). Searches for flights to Madison (3%), to Green Bay (1%) 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.
8.0
SouthwestOverall score based on 4241 reviews
8.0Comfort
8.1Boarding
7.0Food
8.6Crew
7.6Entertainment
Airline reviews

Worst experience I had on Southwest. Still better than most, but the seating was barely tolerable.

4.0 OkayBobby, Jul 2025BNA - MDW
Read more Southwest reviews

Worst experience I had on Southwest. Still better than most, but the seating was barely tolerable.

The Southwest employees (all two of them) were very nice and cheerful despite the fact the line to self-check a bag (simply drop it off) was hundreds of people long. Thank God I arrived early to the airport because I stood in this line for at least an hour. Once on the flight that had been delayed by an hour, we had no Wi-Fi and thus no entertainment. Finally, I hope the investor strong arm tactics against Southwest pay off in a short-term windfall to your C-Suite because the rest of you are screwed. I have been a faithful Southwest customer for 15 years due to everything you just got rid of. I'm flying to Idaho and Washington in October, both places I used to simply book with Southwest without a second thought now with Frontier (Washington) and United (Idaho) because they offer everything the "new" Southwest does but cheaper and at better times, destinations, etc. This really makes me sad...

It was okay. The plane was delayed from earlier in the day, but they kept updating the departure time, sometimes later, sometimes earlier. That was stressful. Once we finally got on and took off, it was fine. I was supposed to have a connection in Chicago to Los Angeles, and the time for so late I was rebooked to arrive in LA 3 hours late. The departure time to Chicago later became early enough to have taken my original connection and arrive earlier but that wasn't an option.

It was one and half hour late... Not sure if any other experience matters.

Delayed flight. Nicest crew member was a SW pilot flying seated next to me who kindly move to seat the final passenger. Flight extra delayed. My cup of refreshment of ginger ale was so packed with ice it was literally 2 sips.

For my birthday trip this was my second time ever flying, this trip was the best.

after landing, we stay 2 hours on the taxi way before reaching the gate The airline and the crew were good though

No trays in our seats, we sat in first row, purchased a business class fare. Had to hold our drinks and snack in our hands. No plugs for our cell phones. Had to pay for it a drink cocktail each. Seats so uncomfortable.

Flight wasn’t even full, but too many carry-ons caused us to run out of bin space. New bag fee has folks who would usually check their bags carrying on. Watching Southwest morph into Spirit/Frontier is so sad to watch

Sat on tarmac for 2 hours and then missed my connecting flight

There was no problems, just a little uncomfortable with seats that do not lay back a little

Always good but we must do something about people in rows ahead of you that don't put their seats back up when they are suppose to. And It's rough to not be able to even lean over to get something out of my purse.

Flight was delayed, 30+ bags had to be gate checked. Crew were very friendly!

Everything was good until we were boarding our connection flight in Atlanta, we were told to gate check our carry-on, but when we got inside the plane, there was plenty of room in the overhead.

Did not know my son and I had different seating arrangements. He was fine, but it was disappointing.

Flight was canceled, and no effort was made to help with rebooking, no hotel vouchers, no car transportation and minimal food voucher and most places for food were closed by the time the voucher was given. Waited for 3 hours for bags. Simply the worst travel experience I have ever had

Food was surprisingly good but the WiFi was not great

this crew didn't care much. bumping carts into seats more times than i care to remember

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.

Everything was fine except the entertainment was not working for half of the flight.

I learned that seating towards the end of plane that a line forms for the restroom and people use your chair as a hand railing, bumping your seat consistently. I was seated in the aisle. I think that next time if I am towards the back row I would want to sit in the middle or window seat.

United sent me a mileage plus number last year but that number is invalid so I can’t use it to check into flights or collect mileage. There is human to speak about the problem, only computers who keep asking me if I am using the correct email. It’s so frustrating and I cannot resolve it.

It was delayed instead of departing at 9:20pm, we departed at 11pm… putting us in Columbus after 2am! It was awful. Had I known about the delay, I could have spent some time in the United Lounge… I was starving because I started my journey in Budapest… so I was exhausted and hungry. Plus I had to make new arrangements to be picked up at the airport in Columbus, instead of midnight it was 2:30 am after getting luggage and out of airport. Not feasible. I would have just stayed in Chicago for the night and gotten a morning flight.

Not a great experience. We paid for the upgrade for premium economy seats and seated ourselves in very comfortable seats. Someone came along with the same seat on their boarding pass. The aircraft had been changed and as a result we were booted out and sent further back to small uncomfortable seats. After complaining we were moved to emergency row seats, which gave us more leg room but the seats don’t recline. For people in our 70’s we found having to sit upright from California to NJ very uncomfortable. Not sure why they chose to move senior citizens instead of the two people that were allowed to take the more comfortable seats. Not happy.

I liked the choice of lemon ginger tea. I think stewardesses can be more considerate of older people needs.

It was great, I’m very grateful for the pilots and crew flight attendants for everything.

Everything was great. Only thing that could’ve made it better was buy on board options for hot food, but the snacks were decent. The flight attendants were great. I had no complaints. I was able to make it to my destination safely

Overall it was good. I missed my connection but I was put on another flight.

The attendant were friendly. I suggest you have a medical attendant on board every flight so that in case someone is sick , he/she will help them.

The woman gate agent in Phoenix was none too sympathetic about my check-in process as I am relatively new with using apps. I almost did not get on because she said I did not check-in. I thought I had via Kayak where I purchased a very expensive ticket. Lesson learned but to be told I may not get on as a matter of factly was difficult to hear.

My JetBlue experience was nice. The flights ran on time, the aircraft was clean and comfortable, and the flight attendants were attentive. My only issue, which is isolated to the low-cost (budget) option at JetBlue, is that the check in process makes the user feel that they have to buy their seats. The seats offered for purchase are upgrades from the budget seats you get (which are essentially the last seats remaining). The interface should not make it feel like you must purchase a seat.

The plane was late to leave.. Internet was lousy. TV was not working. when we arrived, We stayed on the plane for a long time before we got to the gate. It took us a long time to retrieve our luggage because they didn’t know what carousel to send them to. It was a bad experience.

I especially liked the lead crew officer. His boarding and safety announcements were made with a bit of novelty and humor. The flight also left the gate 10 minutes early and we landed about 20 minutes early… It was a delightful flight…

There were mutliple delays. There was inconsistent, delayed, and poor communication regarding the delays.

Spend hours delayed with no food, water anything sitting on the aieplane with no ability to eat or use the restroom. My entire experience was the absolute worst. I will never fly jet Blue again.

It would have been nice if they had offered more than one set of snacks

Seats were not too comfortable; it was impossible to locate the underseat power outlet.

You get what you pay for with JetBlue. Every little thing costs more, you are nickel and dimed until the end. Entertainment doesn’t function. Flight attendants do the bare minimum.

The check in and boarding process was a bit of a cluster. Two people at the counter to check in, three random lines that nobody knew which was for what, and people kept getting shuffled from one line to another for no apparent reason because then they’d get shuffled back and end up getting out further back in the line than they were originally. I only had to hand my already checked bag over and it took 45 minutes. I was never assigned a seat so when I tried to board I was pulled out of line again while someone had to try to manually assign me a seat. During the flight I got up to go to the bathroom, and there was an attendant in the aisle offering pillows etc and it was a 30 min wait unbuckled standing by the bathrooms because she said I couldn’t go past her. First and last time flying jet blue to be honest.

Communication since no reason or explanation was given for 3 hrs delay

Delayed flight, so I switched fights to SFO to Phoenix , Phoenix to DSM. Excellent service through American Airlines

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

The flight had a delay that made me being in a real rush to take the second flight. The delay was almost for 2 hours. They moved us from gate to gate in 4 times. Once I arrived to Philadelphia, I got to run thorough all the airport, as the train was already closed by that time. So I got sick with asthma for all the running I had to do. And I was the last one to board, when it was almost closed. So irresponsable with the people

Flight was delayed and after being in the airport for like seven hours, it was canceled.

Overall fine, but the delay was annoying and the reasons for the delay were not communicated. The crew on board were phenomenal!

Flight delays numerous times. Everytime we would get close to boarding it would be delayed again. Strung along the entire time.

After a two hour delay, my flight was CANCELLED! No pilot available. Such BS.

Overall very good, only complaint I have is the crew from CLT to SAT could have collected trash sooner.

The AA app really sucks ... Every flight & connecting flights were delayed over 30 mins. One connecting flight on American Eagle said it was delayed in its arrival ... when it was actually parked across from the gate for over 1 hr before they pulled it to the gate. Seats in the economy/ main cabin are packed together like sardines ... no leg room.

Initial flight was cancelled at the time of arrival to the airport, flight alternative requires switching from direct to flight with a layover, and the plane felt like it would split apart, it was so rattle-y.

Book cheap flights from Massachusetts to Wisconsin

Recent round-trip flight deals

8/30Sat
nonstopAmerican Airlines
2h 54mBOS-ORD
9/2Tue
nonstopAmerican Airlines
2h 34mORD-BOS
$117
8/6Wed
1 stopSpirit Airlines
13h 16mBOS-ORD
8/13Wed
1 stopSpirit Airlines
10h 39mORD-BOS
$125
9/3Wed
nonstopJetBlue
2h 56mBOS-ORD
9/8Mon
nonstopJetBlue
2h 28mORD-BOS
$129
8/13Wed
nonstopJetBlue
2h 55mBOS-ORD
8/15Fri
nonstopJetBlue
2h 35mORD-BOS
$137
8/28Thu
nonstopUnited Airlines
2h 43mBDL-ORD
9/2Tue
nonstopUnited Airlines
2h 25mORD-BDL
$137
8/30Sat
1 stopSouthwest
7h 30mBOS-ORD
8/31Sun
1 stopSouthwest
6h 20mORD-BOS
$146
8/20Wed
nonstopDelta
2h 55mBOS-ORD
9/2Tue
nonstopDelta
2h 30mORD-BOS
$147
8/12Tue
nonstopUnited Airlines
2h 48mBDL-ORD
8/26Tue
nonstopUnited Airlines
2h 18mORD-BDL
$147
8/30Sat
2 stopsSouthwest
11h 00mBOS-ORD
8/31Sun
1 stopSouthwest
6h 20mORD-BOS
$152
8/14Thu
nonstopDelta
2h 55mBOS-ORD
8/19Tue
nonstopDelta
2h 38mORD-BOS
$155

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Recent one-way flight deals

8/6Wed
1 stopSpirit Airlines
13h 16mBOS-ORD
$55
8/30Sat
nonstopUnited Airlines
2h 56mBOS-ORD
$59
7/24Thu
nonstopJetBlue
2h 55mBOS-ORD
$69
8/24Sun
nonstopAmerican Airlines
2h 40mBDL-ORD
$74
7/24Thu
1 stopSouthwest
5h 20mBOS-ORD
$78
10/1Wed
nonstopJetBlue
2h 28mBOS-MKE
$79
8/28Thu
1 stopSouthwest
6h 30mBDL-ORD
$79
8/14Thu
nonstopAmerican Airlines
2h 41mBDL-ORD
$84
8/5Tue
nonstopDelta
2h 58mBOS-ORD
$87
9/16Tue
nonstopDelta
2h 43mBOS-MKE
$94

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Last minute flights from Massachusetts to Wisconsin

Last minute flight, train and bus deals

7/22Tue
nonstopJetBlue
2h 55mBOS-ORD
7/30Wed
nonstopJetBlue
2h 24mORD-BOS
$137
7/22Tue
nonstopDelta
2h 58mBOS-ORD
8/20Wed
nonstopDelta
2h 32mORD-BOS
$147
7/22Tue
nonstopDelta
2h 58mBOS-ORD
8/20Wed
nonstopDelta
2h 29mORD-BOS
$155
7/22Tue
multi-stopSouthwest
8h 45mBOS-ORD
7/25Fri
multi-stopSouthwest
7h 05mORD-BOS
$162
7/22Tue
nonstopAmerican Airlines
2h 59mBOS-ORD
7/23Wed
nonstopAmerican Airlines
2h 23mORD-BOS
$177
7/22Tue
multi-stopUnited Airlines
6h 03mBOS-ORD
7/22Tue
nonstopUnited Airlines
2h 27mORD-BOS
$187
7/22Tue
nonstopAmerican Airlines
3h 01mBOS-ORD
7/29Tue
multi-stopAmerican Airlines
4h 14mORD-BOS
$200
7/22Tue
multi-stopSouthwest
8h 45mBOS-ORD
7/22Tue
multi-stopSouthwest
5h 15mORD-BOS
$202
7/22Tue
nonstopUnited Airlines
2h 51mBOS-ORD
7/31Thu
nonstopUnited Airlines
2h 27mORD-BOS
$207
7/22Tue
nonstopJetBlue
2h 55mBOS-ORD
8/1Fri
multi-stopJetBlue
4h 59mORD-BOS
$215

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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.

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