$49 Find Cheap Flights from Wisconsin to Massachusetts

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Low season

January

High season

July

Cheapest flight

$49
Best time to beat the crowds with an average 13% drop in price.
Most popular time to fly with an average 2% increase in price.
Flight from Chicago O'Hare Airport to Boston

FAQs for booking flights from Wisconsin to Massachusetts

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

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

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

    Prices will differ depending on the departure airport, but generally, the cheapest airport to fly to in Massachusetts is Boston Logan Intl Airport (BOS), with an average flight price of $183.

  • What is the cheapest day to fly to Massachusetts?

    Based on KAYAK data, the cheapest day to fly to Massachusetts is Tuesday where round-trip tickets can be as cheap as $313. On the other hand, the most expensive day to fly is Sunday, where round-trip prices are $448 on average.

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

    The cheapest time of day to fly to Massachusetts is generally at night, when round-trip flights cost $278 on average. Morning departures are around 15% more expensive than evening flights, on average. The most expensive time of day to fly to Massachusetts is generally in the morning, which is peak travel time and where the average cost of a ticket is $365.

  • What is the cheapest flight to Massachusetts?

    The cheapest ticket to Massachusetts from Wisconsin found in the last 72 hours was to Boston, at $113 round-trip. The most popular route is Milwaukee (MKE) to Boston (BOS) and the cheapest round-trip airline ticket found on this route in the last 72 hours was $113.

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

    The cheapest month for flights from Wisconsin to Massachusetts is April, when tickets cost $276 (return) on average. On the other hand, the most expensive months are March and December, when the average cost of round-trip tickets is $374 and $369 respectively.

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

    To get a below average price on the flight from Wisconsin to Massachusetts, you should book around 2 weeks before departure. For the absolute cheapest price, our data suggests you should book 22 weeks before departure.

  • How long is the flight to Massachusetts?

    An average nonstop flight from Wisconsin to Massachusetts takes 5h 48m, covering a distance of 915 miles. The shortest route is Chicago O'Hare Intl Airport (ORD) to Albany (ALB) with an average flight time of 1h 57m.

  • What are the most popular destinations in Massachusetts?

    Based on KAYAK flight searches, the most popular destination is Boston (74% of total searches to Massachusetts). The next most popular destinations are Hartford (15%) and Albany (9%). Searches for flights to Nantucket (1%), to West Tisbury (1%) and to Worcester (0%) are also popular.

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Top 5 airlines serving from Wisconsin to Massachusetts

Need help choosing which airline to fly with from Wisconsin 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.
8.0
SouthwestOverall score based on 4274 reviews
8.0Comfort
8.6Crew
8.2Boarding
7.6Entertainment
7.1Food
Airline reviews

Boarding process, crew were good. But the seats were so uncomfortable that was all I could focus on. I literally had to sit forward so that all 3 of us could fit in row. I will try to avoid Southwest in the future for any flights over 60 minutes.

6.0 GoodCarolynn, Mar 2025KOA - SMF
Read more Southwest reviews

Boarding process, crew were good. But the seats were so uncomfortable that was all I could focus on. I literally had to sit forward so that all 3 of us could fit in row. I will try to avoid Southwest in the future for any flights over 60 minutes.

1.5 hour delay, poor service, no compassion from the crew. Terrible experience

Great flight, 47 passengers on a 180 seat plane. Stewardess was pleasant and cheerful.

Short flight with plenty of open seats. Drinks and snacks were still provided even on such a short flight. <1 hr

I liked the crew member who gave flight instructions on "in case of a problem:. The seats are so small that only a young teenager could sit in middle seat.

Great experience flying Southwest. The crew was really kind and helpful, and very friendly with our toddler.

Very good. Sad to learn Southwest is going start to charge for bags

Our flight was diverted from being a non-stop to getting within 150 miles and requiring another plane. We heard 4 or 5 different versions from SW as to why we had to stop, then wait for a replacement plane. Five hour delay, weather did not come up as a single excuse.... communication was not clear and well explained. No one really took charge!

My flight to Chicago left and landed early. My return flight left two minutes late and arrived 2 minutes late. My seat selections were ideal! There were no snacks going to Chicago and no snacks on the return trip. There are no charging outlets on board.

WiFi on the flight was not working. Thus, entertainment options were limited.

A little bumpy ride . No food was being provided due the the turbulence. That was ok it was a short flight to my standards.

Simply outstanding. Their new lounge for Delta One customers is a cut above the rest.

The Dekta Rep that checked us in was great. She's very personable, pleasant, and can tell she enjoys her job.

The plane was old with small storage areas that had problems closing/latching and not enough storage for everyone, and worn, damaged seats. Service was great but feel a little unsafe on such well used planes.

Terrible and im avoiding them in the future. My initial flight was delayed causing me to rebook my flight and when speaking with the representative to rebook I explained this is the second time my flights were delayed and they did nothing to help me. I wasn't booked to comfort plus or given a voucher or anything. I was almost late for my meeting that I needed to attend on Monday because of the games delta played delaying my flights even more and putting me in the very back of the plane next to an extremely intoxicated passenger

Flights on time. .Ride was as comfortable as can be expected in steerage. Luggage arrived at destination. Attendants were fairly friendly.

Great staff. Wifi is terrible. Signing up for skylines is a painstaking process. Had to call customer service just to get my flight itinerary and confirmation sent to me. Consistent delays. A well staffed company that is run so poorly. Upper management needs to be renewed.

The WiFi didn't seem as fast as it normally is

Thank you for not flipping the plane on the run way. You guys get a 5 star rating for the flight!!!

The crew was wonderful and attentive. The seats near exit row were restrictive. Offer healthy snacks please

The gate was too far away for the connecting flight

Compared with other carriers business class for an overnight was not worth the extra expense.

Generally good. The aisles have gotten narrower which can slow down boarding. Flight crew was great! Healthier complimentary snacks would be appreciated. Due to earthquake in San Francisco we had to circle in air space for a bit but then had a smooth landing. I laud the flight crew for their patience ;)

Easy to board. Flight was super crowded though so I didn't sleep well on that cross country red-eye flight. The aisles seem ot have gotten narrower and the seat smaller whn luggage and people are getting bigger so it would be AWESOME to have more space and breathing room in general ;)

We boarded but then sat there waiting on some missed connection people to get on so we sat for about 15 minutes for that. Then we sat again because the passenger manifest was wrong and they had to figure it out before we could leave. That took about another 20 minutes or so. The crew was working hard to figure it out so it’s not their fault. It ended up being a system glitch where someone was upgraded to first class while another person was also in the same seat and it just created a mess that took a little while to figure out. They literally went to every person on the plane asking their names to see who was sitting in the wrong seat. I also hate the entertainment that must be watched on your phone or tablet. Just give us setback screens. It’s so much better. Almost every Delta flight has this now and it is so nice to have them. The crew did a great job. I have no complaints from them. They were very hard working, even with the mishap and a disgruntled passenger.

Overall poor for me I paid extra for seats with leg room and my regional flights exit row seats have less leg room then the others that's money that could have been saved and on my final flight home the flights air was not operating it was unbearably hot in the cabin I will be contacting United and filing a DOT complaint

My priority checked bag was not loaded on the flight. I had to sit in baggage claim in Las Vegas for 2 1/2 hours waiting for the next flight. All baggage staff were very helpful, tracking showed it as scanned for loading. Nobody told me why it wasn't on my flight.

My flight was scheduled for about 6:05 departure. There were 11 gate changes from 4-7pm and the flight was 3 hours delayed due to operational issues. The plane taxied around the airport for about half an hour before stopping to be de-iced. It would have been nice if we were alerted of the plan to de-ice prior to the 30 minute drive around the airport. The flight attendant was friendly, which was the only redeeming thing about this flight. As a former flight attendant for United, I was extremely disappointed.

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

Had a short delay once we boarded the aircraft in Chicago, but it was fixed in no time flat then we were on our way. The pilot was able to make up the time lost and we landed 5 minute later then schedualed . Great service

Except for the 28 minute delay leaving and the earlier reschedule to a later takeoff time the flight was good.

Loved the leg room and tvs screens on the seats and free WiFi. Wish the price was lower and could save by rebooking

It took 1-1/2 hours to get our luggage after we landed. That to me is unacceptable

The flight was delayed for 4 hours. Once onboard the crew was wonderful.

Overall was excellent. Will definitely us JetBlue in the future.

Love the mosaic program, being able to move to an extra space seat for free is awesome

I rate it is good we had a 4-hour travel delay at one point but JetBlue gave out food vouchers and travel points credits for another flight so they try to make up for it

Smooth boarding and friendly crew. Unfortunately as soon as we boarded the unit that provides air circulation failed. The pilot informed us and requested maintenance technicians to check it out. The plane became uncomfortably warm without any fresh air coming in. Plus the repair delayed our departure. I am glad the maintenance crew were able to fix the problem. I also was without use of my tv monitor for the first 1/3rd of the trip.

Communication with the customer and stay is important. Staff off with a minor inconvenience but it worked out of course. Also this was a very old Mint Class plane. They snuck this one in on us. The updated aircraft are much better.

The flight itself was fine, but the boarding process was extremely frustrating. There is no one scanning boarding passes - passengers just scan themselves and enter the jetway. By the time my husband and I got on the plane and were halfway to our seats they determined there were too many bags on the plane and everything at that point needed to be checked. This created a lot of unnecessary chaos. They should have alerted people before getting on the plane that they would need to start checking bags instead of waiting until people were already on the plane.

Wonderful crew and early arrival to our destination. It was so nice to have free wifi access and movies too. Thank you!

Very friendly and efficient and smooth boarding. We were even way early arriving at my destination. Thank you.

The trip was very smooth and they provided great customer service

The plane was late and then sat on the runway for almost 45 minutes before taking off.

Wonderful as usual except for other guests that were unruly and not kept in check by the Crew.

The flight was initially delayed, then cancelled. American Airlines says the cancellation was weather related, though the actual weather was not bad in both Washington and Providence and between. There were very few cancellations that day. In fact, AA2120 from Washington, DC to Boston flew with a minor delay at about the same time. So, the weather somehow affected only this particular flight AA5230. The next available flight was the following morning. The American Airlines refused to reimburse accommodation (hotel at DCA)

I have long legs, my foot was out in the aisle and when a flight attendant came walking by and I didn't notice, instead of saying "excuse me" or anything like that, she kicked my foot. Extremely rude

One bottle of water and a package of cookies for comfort plus. We had to literally beg a flight attendant for an extra bottle of water later in the flight due to feeling dehydrated.

Fine. On time, cabin service was fine, bag arrived. All good. Flying into DCA so did not collide with any helicopters, which is also good. Horrid incident that could have and should have been prevented.

Cabin was roomy enough to easily slide my carry on under the seat in front of me!

Book cheap flights from Wisconsin to Massachusetts

Recent round-trip flight deals

4/14Mon
nonstopUnited Airlines
2h 28mORD-BOS
4/16Wed
nonstopUnited Airlines
2h 57mBOS-ORD
$97
4/13Sun
nonstopUnited Airlines
2h 28mORD-BOS
5/8Thu
nonstopUnited Airlines
2h 57mBOS-ORD
$107
5/10Sat
nonstopAmerican Airlines
2h 32mORD-BOS
5/10Sat
nonstopAmerican Airlines
2h 58mBOS-ORD
$113
5/7Wed
nonstopJetBlue
2h 28mORD-BOS
5/12Mon
nonstopJetBlue
3h 00mBOS-ORD
$117
5/13Tue
nonstopAmerican Airlines
2h 22mORD-BOS
5/17Sat
nonstopAmerican Airlines
3h 01mBOS-ORD
$118
5/13Tue
1 stopJetBlue
5h 56mORD-BOS
5/13Tue
nonstopJetBlue
3h 06mBOS-ORD
$121
5/6Tue
1 stopSouthwest
5h 05mORD-BOS
5/8Thu
1 stopSouthwest
7h 20mBOS-ORD
$136
5/31Sat
1 stopSouthwest
8h 55mORD-BOS
6/3Tue
1 stopSouthwest
6h 45mBOS-ORD
$142
7/5Sat
nonstopDelta
2h 30mORD-BOS
7/10Thu
nonstopDelta
3h 00mBOS-ORD
$177
7/5Sat
nonstopDelta
2h 29mORD-BOS
7/5Sat
nonstopDelta
3h 01mBOS-ORD
$179

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Recent one-way flight deals

4/11Fri
nonstopUnited Airlines
2h 28mORD-BOS
$49
5/13Tue
1 stopSpirit Airlines
8h 39mORD-BOS
$58
5/7Wed
nonstopJetBlue
2h 28mORD-BOS
$59
7/2Wed
1 stopSouthwest
5h 15mORD-BOS
$68
5/6Tue
1 stopJetBlue
4h 27mORD-BOS
$69
6/27Fri
1 stopSouthwest
7h 50mORD-BOS
$74
5/12Mon
nonstopDelta
2h 25mORD-BOS
$99
6/3Tue
1 stopDelta
4h 24mORD-ACK
$103
5/17Sat
nonstopAmerican Airlines
2h 32mORD-BOS
$109
6/3Tue
nonstopAmerican Airlines
2h 07mORD-ALB
$113

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Last minute flights from Wisconsin to Massachusetts

Last minute flight, train and bus deals

4/8Tue
multi-stopSpirit Airlines
10h 52mORD-BOS
4/10Thu
multi-stopSpirit Airlines
11h 25mBOS-ORD
$145
4/8Tue
multi-stopSpirit Airlines
10h 52mORD-BOS
4/11Fri
multi-stopSpirit Airlines
11h 25mBOS-ORD
$151
4/8Tue
nonstopJetBlue
2h 29mORD-BOS
4/12Sat
nonstopJetBlue
3h 05mBOS-ORD
$233
4/8Tue
nonstopUnited Airlines
2h 32mORD-BOS
4/9Wed
nonstopUnited Airlines
2h 57mBOS-ORD
$243
4/5Sat
nonstopAmerican Airlines
2h 24mORD-BOS
4/9Wed
nonstopAmerican Airlines
3h 08mBOS-ORD
$244
4/8Tue
nonstopJetBlue
2h 29mORD-BOS
4/13Sun
nonstopJetBlue
3h 05mBOS-ORD
$248
4/8Tue
multi-stopUnited Airlines
4h 30mORD-BOS
4/9Wed
nonstopUnited Airlines
2h 57mBOS-ORD
$253
4/6Sun
multi-stopAmerican Airlines
5h 54mORD-BOS
4/9Wed
nonstopAmerican Airlines
3h 08mBOS-ORD
$278
4/8Tue
multi-stopDelta
6h 57mORD-BOS
4/12Sat
nonstopDelta
3h 02mBOS-ORD
$314
4/5Sat
multi-stopDelta
4h 06mMSN-BDL
4/7Mon
multi-stopDelta
4h 17mBDL-MSN
$339

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Everything you need to know for your flight to Massachusetts

Cabin class types available on flights to Wisconsin

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

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