$52 Find Cheap Flights from Massachusetts to Wisconsin

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Low seasonJanuary
High seasonJuly
Cheapest flight$52
Best time to beat the crowds with an average 2% drop in price.
Most popular time to fly and prices are also 2% 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 $208.

  • 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 $299. On the other hand, the most expensive day to fly is Sunday, where round-trip prices are $388 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 1% cheaper 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 $346 (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 21 weeks before departure.

  • How long is the flight to Wisconsin?

    An average nonstop flight from Massachusetts to Wisconsin takes 6h 38m, 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 (70% of total searches to Wisconsin). The next most popular destinations are Minneapolis (18%) and Milwaukee (7%). Searches for flights to Madison (3%), to Appleton (1%) and to Green Bay (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 4259 reviews
7.0Food
8.2Boarding
7.6Entertainment
8.0Comfort
8.6Crew
Airline reviews

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.

4.0 OkayTraci, Jun 2025OAK - SEA
Read more Southwest reviews

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

First time traveling on Southwest since bag fees were implemented. Usual good service. Just more expensive now.

Everything was on time. I was disappointed by the front section female, African American flight attendant. I did not see her name tag or would have identified by name not race. As passengers moved to the bathroom early in flight, she would say with a disdainful tone “I have to say the seat belt light is on” then go back to her book. Better trained flight attendants say something like be careful the seat belt light is on.

Cluster mess boarding. Can't wait for SWA reserved seating. Internet didn't seem to work on the plane.

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!

Easy boarding with an extremely kind attendant. Seats were spacious and we had 3 seats for 2 people so we could stretch out. Comfortable air flow and very attentive and hospital attendants. Bathrooms and food were the only negative. Bathrooms were so small you could hardly get in and close the door. I don’t think an obese person would fit or a person with a movement disability. Food was the trending food for flights, nonexistent. We spent $40 getting sandwich and snack at airport for our 6 hour flught.

At first, we were on the runway for about an hour, literally. The Captain did explain that the Control Tower just had a change shift (sounds like an unrealistic excuse) and then that we had to change a runway. A regular economy seat is made for 12 yo twiggy. I understand Delta wants to push for an upgrade, but after sitting in a Comfort seat and in First class. I would say First class is not worthy of my money. The landing was delayed because of the weather in NYC, I don't hold that against Delta, of course. The Captain did alert us to that upon takeoff in Vegas and again as we reached NY.

No one fussed at me about my pap machine as a 3rd pice on the plane. Boarding was pleasant and smooth. The boarding agent in Anchorage was a fun character- he could be in a movie. :~) The on-board crew were downright pleasant. No militant attitudes on Delta. Like all planes these days the seats are too narrow for standard Americans and at 5’2” there is barely enough leg room. I don’t know how tall people fold themselves into the seats. But that’s nothing specific to Delta

My husband upgraded our seats and I don't know if it was due to the type of planet was or if they didn't upgrade our seats. We were supposed to be in I believe comfort seats and they were just as tight as any other seat- no leg room and we are very tall people but at least it wasn't extremely cold. My husband did put in a complaint about our seating because he paid extra and if we would have known that the space and the tightness would have been the same, we just would have gotten the emergency row emergency row seats that we normally get. We love Delta but both our flights coming home we're not good. Oh I forgot to mention that on our flight to Hawaii our luggage wheels got broke and we had to purse new luggage on vacation then we never had this problem so we didn't know protocol and reported it after we got home only for them to tell is we only had 24hrs to report the damage. Not sure what was going on with Delta this vacation trip.

My flight was extremely cold. I had a jacket and a cover was left in each seat. The cover was extremely thin and I have a disability, fibromyalgia and arthrithis and AC air is the worst. I closed my vent and my husbands vent and it still was frigid. I asked the attendant if I could get another cover and she quickly almost dismissively and totally unconcerned stating, (I quote) (one per chair) and walked off so quickly that I didn't get a chance to explain to her that I literally have adisability. I didnt want to make a seen so I set on that flight for over 5 hours in pain, joints locking up and extremely uncomfortable. When my fibromyalgia flares up my joints not only ache but they will lock up also and it takes me days to get back to my regular self even though I take medication for it. I felt like it would not have hurt anyone at all for her to just give me an extra cover because I'm sure they have all types of medical issues in people that fly every day.

After all the weather issues at least they got me to my destination the next day

My flight was canceled after being rescheduled for four days canceling my trip. Kayak and everyone affiliated with it I.e the airlines, and just fly have been excruciating to deal with. My trip to visit family had to be canceled as there was no way to make it. I am furious at all of you.

They delayed our flight because of bad weather in NY which was completely understandable. Then they cancelled our flight and a later flight that evening. The earliest we could fly was the next morning. We ended up buying last minute tickets on another airline and made it home slightly delayed but safely that evening. Delta kept saying it was weather related but if that was the case how did we make it back on another airline? The weather in NY was cloudy but not bad.

From Atlanta to Savannah - flight connection was way to short (we weren't even late landing ) and flight was already boarding when we landed - we were told we were the last on board and so we had to gate check our bags. Once we got on the plane, there were at least seven open bag spots so that was unnecessary delay. There should be better communication between the gate agent and the crew.

Crew was excellent. Comfort seats not as nice as other kinds of planes.

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.

Overall a very poor experience - booked premium economy tickets but due to last minute flight delays , all my itinery went for a toss and had to fly economy class with no access to lounge or any compensation by united airlines to make up for the flight delays . i had expected better experience than that from united.

Boarded plane and then delayed 1.5 hours while on the plane

Survey sent before we actually left. Delay after delay. Now a crew problem.

I love flying with United. Unfortunately, I flew on an older plane with minimal upgraded technology (no Bluetooth functionality or handy charging ports). Otherwise, the flight was great and even arrived early.

They changed my seats after I checked in and I was stressed from the time I saw that information until just before boarding, when the gate attendant fixed it, but it shouldn't have happened. And if it couldn't be prevented, then the people on the phone I spoke with should have done something to help, which they did not, nor did they offer me compensation, just meaningless apologies.

Horrific. They missed my connecting flight to San Diego. I didn’t get there until Monday at 9am when I had a mandatory court settlement conference scheduled at 6am since we had parties on the east coast. This caused many issues. All because United apparently forgot to hold the doors open until my flight landed that only had a 10 minute delay. This was the last flight to Southern California. So I couldn’t even rent a car to finish the trip. United cannot be trusted when traveling on specific days and times since weather didn’t have anything to do with the delays.

My flight was delayed a very short period of time but they did not hold my connecting flight to San Diego, also through United. So they closed the doors before we got off our plane. They would only have to help the door open for another five to ten minutes. So I missed a court deadline for a manditory mediation settlement conference for my client. I had to get an associate to be there in person and be on the phone with him relaying what he needs to do the entire time. The court was very upset with me and so was my client. United cannot be trusted.

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

Flight was delayed several 3 hours - no reason was given and no communication what so ever.

No overhead baggage room even though I was seated in row 2. Consequently had to check in my carry on bag. Baggage carousel was jammed. Took 45 min to get my bag.

Excellent from start to finish. All staff members were amazing!

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.

Amazing food, great staff, with one noticable detail missing ...but no seat entertainment in any of aircraft ...I am not a fan

AA re-routed flight from HNL to LAX due to delay. My group of 3 with reserved seats in row 9 was broken up, with one assigned to a middle seat, another in the last row of the plane. Not happy. No explanation to the delay. No apologies. No compensation. Would have been nice to be offered an Admiral Club admission or a voucher for the extra 3 hours of layover in LAX. Could not hear the boarding gate announcements in LAX. Adjacent gate was boarding at the same time. Loud speakers were competing against each other. Barely made my boarding group.

Boarding gate in Honolulu was staffed with a great clerk with a soothing voice despite the flight delay of over an hour. Flight attendants in the plane were all grumpy, not pleasant looking bunch. Their sour attitude showed throughout the flight. Inly able to get a select few movies started. Most of the movie links in the “free entertainment” did not work.

Above and beyond effort from this crew in a tough situation. So helpful and understanding. Thank you!

The flight delay in Dallas created a domino effect that impacted all connecting flights, leading to an increase in the number of connections. As a result, I missed my flight from Casablanca to Marrakech due to the tight turnaround when landing in Casablanca. CMN Airport was understaffed; only one employee was available to assist passengers while others just stood by and watched. It was an extremely frustrating situation. Many passengers were crying and banging their hands on the counter while talking to customer service representative Allabough. Unfortunately, Allabough couldn’t change my flight in the system. At the same time, I was on the phone with an American Airlines customer service representative named Solomon, who said he couldn’t make the change either. So, I decided to take an ONYA Voyages train from Casablanca to Marrakech to reach my destination on Friday, June 26. It turned out to be an unpredictable trip.

The flight was fine and the crew awesome. The problem is ORD and AA. Computers went down, ORD fell apart and a 40 min flight turned into a 3 hour trip. Guess the answer is to not try and fly to ORD after noon. But, as I said, crew was awesome and did everything they could to lesson the flight time.

Almost a 6 hour flight and the only food option is a cheese plate… and chips. Also how is it there are no options for texting on American. I’ll be going back to delta and united.

This flight never occurred because AA couldn’t get their act together.

Terrible. Cancelled my original flight. It made getting a boarding pass difficult. The AA employee (in a loud voice, so everyone around could hear) griped at me for not getting a boarding pass 24 hours before. I asked how I was supposed to do that when I had no idea what flight I was going to be on. She said (loudly), “Talk to AA customer service, not me!” I could certainly tell serving customers was not important to her. Our new flight was set to a completely different city. We had to change our rental car, and the price went way up. It took 2-1/2 hours to get checked in. By then our new flight had left. We ended up on stand by and had to split up the family to get to our destination. It cost us the whole first day of the trip. AA needs to employ people who actually care about doing a good job. I suppose those people are getting harder to find, but atleast try.

Book cheap flights from Massachusetts to Wisconsin

Recent round-trip flight deals

9/23Tue
1 stopSouthwest
7h 10mBOS-ORD
9/27Sat
1 stopSouthwest
5h 00mORD-BOS
$104
9/23Tue
2 stopsSouthwest
9h 50mBOS-ORD
9/27Sat
1 stopSouthwest
5h 00mORD-BOS
$109
7/23Wed
nonstopJetBlue
2h 55mBOS-ORD
7/30Wed
nonstopJetBlue
2h 24mORD-BOS
$137
8/19Tue
nonstopUnited Airlines
2h 43mBDL-ORD
8/26Tue
nonstopUnited Airlines
2h 32mORD-BDL
$137
10/15Wed
nonstopDelta
2h 52mBOS-ORD
11/1Sat
nonstopDelta
2h 34mORD-BOS
$145
7/29Tue
nonstopAmerican Airlines
2h 37mBDL-ORD
7/31Thu
nonstopAmerican Airlines
2h 28mORD-BDL
$157
9/2Tue
nonstopJetBlue
2h 28mBOS-MKE
9/13Sat
nonstopJetBlue
2h 21mMKE-BOS
$157
7/16Wed
nonstopUnited Airlines
2h 58mBOS-ORD
7/19Sat
nonstopUnited Airlines
2h 27mORD-BOS
$158
7/24Thu
nonstopAmerican Airlines
2h 58mBOS-ORD
7/27Sun
nonstopAmerican Airlines
2h 24mORD-BOS
$166
8/29Fri
nonstopDelta
2h 59mBOS-ORD
9/3Wed
nonstopDelta
2h 33mORD-BOS
$167

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Recent one-way flight deals

8/23Sat
1 stopSouthwest
7h 30mBOS-ORD
$52
7/29Tue
1 stopSpirit Airlines
13h 16mBOS-ORD
$55
9/28Sun
nonstopUnited Airlines
2h 43mBDL-ORD
$69
8/23Sat
nonstopUnited Airlines
2h 56mBOS-ORD
$69
10/1Wed
nonstopJetBlue
2h 28mBOS-MKE
$79
9/3Wed
nonstopDelta
2h 49mBOS-MKE
$89
7/21Mon
nonstopAmerican Airlines
2h 59mBOS-ORD
$97
9/5Fri
nonstopJetBlue
2h 28mBOS-MKE
$99
8/5Tue
1 stopDelta
6h 05mALB-ORD
$109
8/23Sat
nonstopAmerican Airlines
2h 36mALB-ORD
$113

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Last minute flights from Massachusetts to Wisconsin

Last minute flight, train and bus deals

7/11Fri
nonstopUnited Airlines
2h 58mBOS-ORD
7/18Fri
nonstopUnited Airlines
2h 27mORD-BOS
$137
7/11Fri
multi-stopSouthwest
5h 20mBOS-ORD
7/15Tue
multi-stopSouthwest
6h 55mORD-BOS
$157
7/11Fri
nonstopAmerican Airlines
2h 58mBOS-ORD
7/15Tue
nonstopAmerican Airlines
2h 30mORD-BOS
$177
7/11Fri
multi-stopAmerican Airlines
5h 22mBOS-ORD
7/18Fri
nonstopAmerican Airlines
2h 44mORD-BOS
$197
7/11Fri
multi-stopSpirit Airlines
13h 16mBOS-ORD
7/14Mon
multi-stopSpirit Airlines
13h 29mORD-BOS
$199
7/7Mon
multi-stopSpirit Airlines
6h 13mBOS-ORD
8/13Wed
multi-stopSpirit Airlines
10h 39mORD-BOS
$202
7/11Fri
nonstopDelta
2h 58mBOS-ORD
7/14Mon
nonstopDelta
2h 31mORD-BOS
$257
7/11Fri
nonstopDelta
3h 06mBOS-ORD
7/16Wed
nonstopDelta
2h 31mORD-BOS
$273
7/9Wed
nonstopJetBlue
2h 55mBOS-ORD
7/16Wed
nonstopJetBlue
2h 24mORD-BOS
$284
7/8Tue
nonstopJetBlue
2h 28mBOS-MKE
7/21Mon
nonstopJetBlue
2h 12mMKE-BOS
$382

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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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