$50 Find Cheap Flights from Wisconsin to Massachusetts

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Wisconsin to Massachusetts departing on 1/14. 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.
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Good to know

Low season

January

High season

July

Cheapest flight

$50
Best time to beat the crowds with an average 24% drop in price.
Most popular time to fly and prices are also 24% lower on average.
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 to Massachusetts from 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 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 to Massachusetts with an airline and back to Wisconsin 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 to Massachusetts from Wisconsin up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

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.
8.1
SouthwestOverall score based on 4821 reviews
8.1Comfort
8.7Crew
7.2Food
8.2Boarding
7.7Entertainment
Airline reviews

I recently flew Southwest from San Jose to Honolulu. I was very impressed with the flight crew, especially the flight attendant in charge of the front of the plane. She came through the aisle at least five times for drinks and water, and two times for snacks. I have not seen such service since I flew first class. Also, for the first time, they gave us the correct baggage claim number, and the luggage came out quickly. I can't wait for Southwest to have assigned seating! I absolutely hate the Cattle Call boarding procedure and the mad dash to get seats and overhead bins. However, the boarding was efficient.

10.0 ExcellentWilliam Drew, Dec 2024SJC - HNL
Read more Southwest reviews

I recently flew Southwest from San Jose to Honolulu. I was very impressed with the flight crew, especially the flight attendant in charge of the front of the plane. She came through the aisle at least five times for drinks and water, and two times for snacks. I have not seen such service since I flew first class. Also, for the first time, they gave us the correct baggage claim number, and the luggage came out quickly. I can't wait for Southwest to have assigned seating! I absolutely hate the Cattle Call boarding procedure and the mad dash to get seats and overhead bins. However, the boarding was efficient.

Crew was great flight was great baggage claim was a failure. It took over 1 hour for bags to arrive. Poor communication poor effort when I spoke to the supervisor about the delay

Much better than the.last. flight on SW on Thanksgiving day

Fine, but how to board on SW versus othrr airlines, is just lame. Goood staff though and all was solid otherwise.

The movies using Southwest WiFi kept pausing and I had to restart multiple times.

It went well. Plane wasn't full. Will be great when assigned seating is in place

Everything was great except the food. The pretzels are really crappy.

For the first time in a long time we had a flawless experience with Southwest. Both flights were early and no mechanical errors at all. We were shocked and pleasantly surprised 😮.

It was fine. For some reason the flight was much longer than usual. It may have been explained, but I had noise cancelling earbuds on and missed a couple of announcements. The crew was fine, but there was a flight attendant who kept telling dumb jokes, occasionally one I found distasteful. This was my second time with him, but luckily it was a late flight so he didn't do as many. But I heard all of today's jokes twice, which was two times too many. Good takeout and landing.

One of the crew performed a hilarious skit to accompany the standard instructions. Passengers enjoyed it so much they applauded at the end!

I was with one of the last zones to board. It was kind of annoying to finally get called to board and my whole section was already on the plane. Clearly they boarded with previous zones. So by the time I got on board, there were no spaces for my luggage above my head. I had to put my luggage 4+ rows behind me, which meant that I had to wait even longer to get off the plane, since I had to wait for those rows to clear the aisle before I could retrieve my luggage and exit the plane. This also held up the plane cleaners, as they couldn't service my row until I cleared it, so they were all standing there waiting for me, while I'm standing there waiting for the other passengers to clear the aisle. Anyways, I wasn't in a rush this time, so I just waited, but I could see that being a problem in the future. Now, I could have checked my luggage, of course, but coincidentally, a friend of mine on the same flight got their luggage damaged (wheel completely knocked off) and was told by the Baggage Attendant in the airport that Delta doesn't "cover wheel damage" on luggage. This was disappointing to hear. I'm glad I didn't check mine through. If it were my luggage, I'd be highly frustrated to hear that. It makes me not want to check my luggage in the future.

I think they can provide the better food/snack option for the 4 hours flight. Drinks are fine.

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?

Typically I give delta excellent reviews. Our flight was delayed 2hrs, I was one of the fortunate ones who were able to get to my connecting flight. Also, annoying that on the connecting flight boarding personnel make me put away a small bag into my carryon. It small enough to put in back pocket seat, why hold me and the line up to just push it into my carryon.

Everything was great. Great service, excellent communication, and early arrival

Delta flight attendants poorly managed the boarding process and overhead storage. My bag was checked last minute and no claim ticket was provided. My bag is now lost. Complete incompetence by all flight crew involved.

Inexpensive, got an exit row aisle aeat with no middle passenger, bought a great breakfast sandwich, flight comfortable & arrived ahead of schedule.

Customer service at the gate in the flight was exceptional. On time. Aircraft and seat was decent. Thanks Delta. 💗

It was terrible, if they ran flights on time it would make a big difference.

Great flight. On-time, comfortable, clean aircraft, and offered snacks pre-flight to plan for a potentially turbulent route. I wish there was Wi-Fi an all Delta Aircrafts but for a short flight this is not much of a problem.

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.

The best flight I’ve had in a while. The plane was like 25% capacity, if that. Smoothest boarding and deplaning process I’ve ever experienced. Wish all flights were this smooth.

I paid for the service of having the right to choose my seat and it was not like that, they put me where they wanted and I explained to one of the staff that they were before boarding and they were very rude. I am traveling with the family and they put us in separate seats.

Everything was great except for some reason crew and ground crew could not figure out how to deal with an electric wheelchair and it delayed us 20-30mins. Was pretty frustrating for passengers and the captain.

Great! I love Jet Blue. My favorite airline! Very efficient, clean and timely.

We were told that our flight would be delayed for 90+ minutes because of weather, so we went to get something to eat only to have them randomly start boarding 15 minutes after the announcement, with no warning.

We arrived early and finally made it to our gate almost an hour after.

The reason I don’t fly United. No in seat entertainment for a long flight and inconsistent WiFi and entertainment available from my device.

We were delayed 3x and because I didn’t purchase my tickets directly from United Airlines I was told I Have to take care of it myself so I called Underpricer and they helped me but before I changed my flights I took the risk of sticking by what my tickets were and was lucky to have gotten on the original all flight with only 15 mins before take off. not sure if I will do this again

The planes are so dirty! Food crumbs and finger print smudges, Dust over the vents and carpet stains. It’s disgusting.

Everything good until we waited for jet bridge at SFO. Then pilot gets on speaker & said it won’t reach plane- too short, need to go to different gate. Then 5 min later, adjusted plane/jetbridge & all ok?!?

David went above and beyond to make our flight the best that it could be

Was a pain having to leave the plane and reboard but glad the plane was fixed

How badly can you screw up baggage claim? We were told to go to baggage claim too for our bags from this flight. Another flights bags were there. They finished up. More bags from a different flight arrived. Our bags did not Finally the baggage claim belt stopped working and and are flight was still listed on the arrivals for that baggage claim 2. And then nothing It turns out that they had been delivered not only the United baggage claim but far away on a Delta baggage claim No I never told us. It was only the people looking around who had been on the flight But I’m sure there was plenty of time for the employees to raffle through the bags and steal whatever they wanted

The bag drop personal were not helpful. There was no food on the flight. Boeing aircraft, lousy as always. Everything else was fine.

We had to wait almost an hour for the wheelchair porter to be ready to pick up my mother. And when she arrived in Newark airport the porter was not there and she started walking with her cane and her poor mobility. When the Newark porter found her they didn't want to transfer her bags to the wheelchair for her.

Other than being delayed 5.5 hours and having to get a hotel because I missed my connecting flight, it was an okay flight. No in-flight Wi-Fi or entertainment.

Flight areas delayed 3 hours , train in the airport didn’t work

Flight attendant walked away once they landed and we were forced to wait another hour after an already 3hr delay.

No overhead space so all carryons were checked. No internet.

The flight was on time and everything went very smoothly.

A thousand choices for movies and nothing to watch. I avoid 'R' rated shows and others with violence and sexual content, which results in a handful of flicks to view and I have them already.

I think I paid for an extra legroom seat and to be honest, there was not a lot of space available for my not very long legs. The flight was totally full and the staff did everything possible to meet the needs of all passengers. My only concern was for the size and spacing of my seat.

Two issues. The plane was old and dirty. The armrest looked like an old car that had the vinyl rubbed off. The Seats in these aircraft are about as hard and uncomfortable. I want to tour Italy for a month and I want to buy a one-way ticket to Thailand but I will not sit in the seats these planes have. It is seriously stupid how hard they are.

The meals were mediocre and the alcohol selection was poor. I enjoyed the selection of movies and other entertainment.

I chatted with the captain before the flight, and similarly during the welcome announcement, he warned of a turbulent flight that may impact the in-flight service. However, once at altitude, he announced that the weather changed and he immediately turned off the seatbelt sign. But it appeared the cabin crew had already decided to take off this flight. They remained seated and then just chatted in the galley. The flight was fully catered, but only first class received service.

Book cheap flights from Wisconsin to Massachusetts

Recent round-trip flight deals

1/14Tue
1 stopFrontier
8h 30mORD-BOS
1/15Wed
1 stopFrontier
6h 47mBOS-ORD
$100
1/14Tue
1 stopFrontier
8h 30mORD-BOS
1/15Wed
1 stopFrontier
6h 47mBOS-ORD
$101
1/9Thu
nonstopJetBlue
2h 18mORD-BOS
1/14Tue
nonstopJetBlue
3h 02mBOS-ORD
$157
1/9Thu
nonstopAmerican Airlines
2h 33mORD-BOS
1/13Mon
nonstopAmerican Airlines
3h 08mBOS-ORD
$158
1/24Fri
1 stopJetBlue
6h 13mORD-BOS
2/1Sat
nonstopJetBlue
3h 07mBOS-ORD
$166
1/6Mon
nonstopDelta
2h 33mORD-BOS
1/9Thu
nonstopDelta
3h 10mBOS-ORD
$178
2/15Sat
nonstopAmerican Airlines
2h 17mORD-BOS
2/18Tue
nonstopAmerican Airlines
3h 04mBOS-ORD
$183
1/4Sat
nonstopDelta
2h 28mORD-BOS
1/8Wed
nonstopDelta
3h 10mBOS-ORD
$202
2/24Mon
1 stopUnited Airlines
4h 45mORD-BOS
2/26Wed
nonstopUnited Airlines
3h 02mBOS-ORD
$222
1/2Thu
nonstopUnited Airlines
2h 24mORD-BOS
1/6Mon
nonstopUnited Airlines
2h 58mBOS-ORD
$223

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Recent one-way flight deals

1/14Tue
1 stopFrontier
8h 30mORD-BOS
$50
1/7Tue
1 stopFrontier
8h 30mORD-BOS
$51
1/21Tue
nonstopAmerican Airlines
2h 27mORD-BOS
$78
1/12Sun
nonstopJetBlue
2h 18mORD-BOS
$79
1/11Sat
1 stopUnited Airlines
5h 55mORD-BOS
$88
4/4Fri
nonstopJetBlue
2h 30mORD-BOS
$89
1/6Mon
nonstopDelta
2h 37mORD-BOS
$100
3/17Mon
nonstopDelta
2h 29mORD-BOS
$119
1/19Sun
1 stopUnited Airlines
5h 07mORD-BOS
$123
3/19Wed
1 stopAmerican Airlines
5h 00mORD-BOS
$128

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Last minute flights from Wisconsin to Massachusetts

Last minute flight, train and bus deals

12/25Wed
nonstopAmerican Airlines
2h 21mORD-BOS
1/1Wed
nonstopAmerican Airlines
3h 04mBOS-ORD
$209
12/22Sun
multi-stopFrontier
8h 19mORD-BOS
1/14Tue
multi-stopFrontier
8h 34mBOS-ORD
$214
12/25Wed
nonstopUnited Airlines
2h 24mORD-BOS
12/31Tue
nonstopUnited Airlines
3h 03mBOS-ORD
$235
12/25Wed
nonstopUnited Airlines
2h 24mORD-BOS
12/31Tue
multi-stopUnited Airlines
4h 43mBOS-ORD
$244
12/25Wed
nonstopDelta
2h 28mORD-BOS
12/31Tue
multi-stopDelta
5h 20mBOS-ORD
$254
12/24Tue
nonstopJetBlue
2h 29mORD-BOS
1/14Tue
nonstopJetBlue
3h 07mBOS-ORD
$282
12/25Wed
nonstopDelta
2h 28mORD-BOS
12/31Tue
nonstopDelta
3h 03mBOS-ORD
$293
12/25Wed
nonstopJetBlue
2h 21mORD-BOS
12/31Tue
nonstopJetBlue
3h 00mBOS-ORD
$297
12/25Wed
multi-stopSouthwest
9h 45mORD-BOS
12/29Sun
multi-stopSouthwest
15h 25mBOS-ORD
$351
12/25Wed
multi-stopSouthwest
7h 50mORD-BOS
12/29Sun
multi-stopSouthwest
15h 25mBOS-ORD
$356

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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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