$53 Find Cheap Flights from Wisconsin to Massachusetts

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Low season

January

High season

July

Cheapest flight

$53
Best time to beat the crowds with an average 12% drop in price.
Most popular time to fly with an average 1% 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 $218.

  • 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 $103 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 $103.

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

    The cheapest month for flights from Wisconsin to Massachusetts is September, when tickets cost $286 (return) on average. On the other hand, the most expensive months are March and December, when the average cost of round-trip tickets is $371 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 16 weeks before departure.

  • How long is the flight to Massachusetts?

    An average nonstop flight from Wisconsin to Massachusetts takes 6h 32m, 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 2h 01m.

  • What are the most popular destinations in Massachusetts?

    Based on KAYAK flight searches, the most popular destination is Boston (73% of total searches to Massachusetts). The next most popular destinations are Hartford (16%) and Albany (8%). Searches for flights to Nantucket (2%), to West Tisbury (1%) and to Worcester (0%) are also popular.

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.
8.0
SouthwestOverall score based on 4287 reviews
7.6Entertainment
8.0Comfort
8.6Crew
8.2Boarding
7.1Food
Airline reviews

I’ve always loved Southwest. No issues at all. I was flying standby and the gate agent was extremely friendly and helpful. Boarding was smooth and I was able to get a window seat in the emergency exit row. Crew was fantastic! They were very professional and accommodating. We had to divert from our destination due to weather but the flight crew kept everyone at ease and informed us of all pertinent information. Excellent flight

8.0 ExcellentJonathan, Apr 2025AUS - MSY
Read more Southwest reviews

I’ve always loved Southwest. No issues at all. I was flying standby and the gate agent was extremely friendly and helpful. Boarding was smooth and I was able to get a window seat in the emergency exit row. Crew was fantastic! They were very professional and accommodating. We had to divert from our destination due to weather but the flight crew kept everyone at ease and informed us of all pertinent information. Excellent flight

The price of the tickets isn't matching the flight experience. No matter how long the flight is, you're only getting pretzels. The flight attendants looked unkept and over it.

Plz don't take away free bags and free seating

The seats were a bit cramped and worn, but otherwise okay.

I would have liked to arrive on time - not 5 hours late!

After a 3 hour layover in Denver my flight was delayed over 5 hours! No explanation; no assistance; no offer to provide compensation; no one at Southwest was willing to offer any assistance. 8 hours in the Denver airport - ridiculous!

It was a perfect flight in all aspects! Both legs!

Only one drink pass through the cabin for a 4 hour flight. Quite rough and bumpy landing.

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

This had nothing to do with Delta… The flights were on time and flawless. The service was excellent. We purchased seats in (aisle/middle) comfort plus since this was a cross country flight. Unfortunately, the woman seated at the window was 300+ pounds and, as might be expected, covered up about a third of the middle seat also. there was absolutely nothing that Delta could have done about that… I just don’t know what the answer should be. If you purchase a seat, you should should be able to use the entire seat and not just the portion that someone else is not sitting/oozing in. Disappointing…there should be something that could be done….I'm just not sure what solution could be.

Delayed take-off. Very small plane so very scary with lots of bumps during the flight. Would never fly Delta on short flights in small 80 seaters plane again! Felt relieved when landed.

Delta is a cut above the others in customer service.

The worst part was I was NOT allowed in the lounge even though I was holding a first class ticket and have a premium American Express card. I have flown Business or First Class with many airlines. Delta is the ONLY one who does not extend this courtesy to anyone except people who hold the very expensive American Express card. As a result, I won’t fly Delta if I have any other choice.

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.

Multiple delays and not straight answer from the United team

Stewardess spilled orange juice on my clothes/seat no help no apology just threw napkins at me to clean the mess up. Not Happy.

Smooth flight. Boarding was chaotic. Could not hear the gate agent over the intercom. People were lined up in the wrong lines. Groups one and two were told to board through line one and group 3 through line 2. All very confusing. Once in the air, the flight was smooth. There was no entertainment option on this aircraft, even though it was a larger aircraft.

The plane pushed back from the gate on time. However, it stopped on the ramp, and we waited for over 20 minutes before the aircraft pulled back to the gate. Apparently, something of importance had to be removed from the aircraft by the gate agent. I found this to be odd. The delay was not significant, but I felt that whatever was on the aircraft that had to be taken off, should’ve been done before we pushed back from the gate.

Electric plugs didn't work. Entertainment system wasn't working

The design of the light switch on the arm rest is ridiculous.

Smooth boarding process. Early departure, smooth flight, early arrival. The entertainment package has very good recent movie options. The flight crew were friendly and professional.

leg space better than expected. two washrooms for one plane isn't enough.

The gate attendant let me walk right by her with a bag too big for the overhead compartment

I just got back from a trip with 3 flights each way. The flights were good and we were happy with out experience. There was one steward on our first flight that was harsh and grump with passengers. It did not leave a good impression. All of the other flight crews were great on the other five flights.

Great flight. Departed early, arrived early. However they were out of meals for sale. Also, we arrived early and the gate was not available so we sat on the taxiway for quite a while (not JetBlue’s fault).

Cancelled flight with no specific instructions to get a boarding pass for another flight. The whole flight of people were in line for an hour because there was only 1 person to help at the desk. This was unusual for JetBlue.

It was too hot in the cabin. The AC did not help.

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

We missed our flight. The boarding pass had the wrong gate and by the time we received the text from Kayak, our flight was already gone. I’ll never use Kayak again and will go direct to the airlines in the future.

Boarding took forever, the plane was cramped and cold, and the seatbelt song came on constantly throughout the red eye flight with a loud pre-recorded message playing each time

Cabin felt crammed Snacks are lame But crew was super efficient getting us out on time despite delay

Took off on time and successfully avoided weather that looked to be a problem along the way

There were five broken seats on the plane. The crew was very rude in telling people they had to get off the plane and get a flight the next day. No call for volunteers, but telling people they had to get off. One woman was flying with her elderly mother and daughter and was told she had to leave or all three had to leave. Fortunately, a volunteer offered to stay. The situation was handled poorly.

The flight to Tokyo AA61 took off about two hours late, but then had to turn back. By that time the crew had to be replaced. Then they kept promising to take off in an hour, then in 3, then switch to the next day.

Any sort of gluten free snack option would be nice

They lost my luggage and it didn’t get delivered until the next day.

Would have thought that they would gas up plane before everyone got on board

3 hours late. Not even water offered on a 2.25 hour flight.

Book cheap flights from Wisconsin to Massachusetts

Recent round-trip flight deals

5/7Wed
nonstopUnited Airlines
2h 28mORD-BOS
5/27Tue
nonstopUnited Airlines
2h 58mBOS-ORD
$117
5/10Sat
nonstopAmerican Airlines
2h 22mORD-BOS
5/11Sun
nonstopAmerican Airlines
2h 56mBOS-ORD
$118
5/13Tue
1 stopSpirit Airlines
9h 48mORD-BOS
5/21Wed
1 stopSpirit Airlines
8h 15mBOS-ORD
$128
6/6Fri
1 stopSouthwest
7h 05mORD-BOS
6/10Tue
1 stopSouthwest
7h 05mBOS-ORD
$136
6/6Fri
1 stopSouthwest
7h 05mORD-BOS
6/9Mon
1 stopSouthwest
8h 15mBOS-ORD
$142
6/7Sat
1 stopSpirit Airlines
9h 48mORD-BOS
6/10Tue
1 stopSpirit Airlines
8h 15mBOS-ORD
$144
5/30Fri
nonstopJetBlue
2h 29mORD-BOS
6/2Mon
nonstopJetBlue
3h 00mBOS-ORD
$148
5/8Thu
nonstopJetBlue
2h 28mORD-BOS
5/13Tue
nonstopJetBlue
3h 00mBOS-ORD
$152
5/12Mon
nonstopDelta
2h 32mORD-BOS
5/19Mon
nonstopDelta
2h 54mBOS-ORD
$197
5/8Thu
nonstopDelta
2h 19mMKE-BOS
5/11Sun
nonstopDelta
2h 43mBOS-MKE
$197

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Recent one-way flight deals

10/16Thu
nonstopSpirit Airlines
2h 26mORD-BOS
$53
10/16Thu
nonstopSpirit Airlines
2h 26mORD-BOS
$55
5/21Wed
nonstopJetBlue
2h 29mORD-BOS
$59
5/20Tue
nonstopAmerican Airlines
2h 35mORD-BOS
$60
7/26Sat
nonstopUnited Airlines
2h 38mORD-BOS
$78
5/8Thu
nonstopUnited Airlines
2h 24mORD-BOS
$79
5/2Fri
nonstopAmerican Airlines
2h 20mORD-BOS
$89
5/25Sun
nonstopDelta
2h 25mORD-BOS
$90
5/10Sat
nonstopDelta
2h 29mORD-BOS
$99
5/10Sat
nonstopJetBlue
2h 17mMKE-BOS
$104

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Last minute flights from Wisconsin to Massachusetts

Last minute flight, train and bus deals

4/28Mon
multi-stopSouthwest
15h 10mORD-BOS
5/2Fri
multi-stopSouthwest
7h 20mBOS-ORD
$247
4/28Mon
multi-stopSpirit Airlines
24h 36mORD-BOS
5/1Thu
multi-stopSpirit Airlines
13h 05mBOS-ORD
$248
4/28Mon
nonstopUnited Airlines
2h 28mORD-BOS
4/29Tue
nonstopUnited Airlines
2h 57mBOS-ORD
$253
4/28Mon
nonstopAmerican Airlines
2h 31mORD-BOS
5/1Thu
nonstopAmerican Airlines
3h 08mBOS-ORD
$257
4/28Mon
multi-stopAmerican Airlines
4h 01mORD-BOS
5/3Sat
nonstopAmerican Airlines
2h 56mBOS-ORD
$263
4/24Thu
nonstopDelta
2h 26mORD-BOS
4/28Mon
nonstopDelta
3h 04mBOS-ORD
$288
4/25Fri
multi-stopDelta
5h 25mORD-BOS
4/28Mon
nonstopDelta
3h 04mBOS-ORD
$298
4/28Mon
nonstopJetBlue
2h 29mORD-BOS
4/29Tue
nonstopJetBlue
3h 12mBOS-ORD
$308
4/28Mon
nonstopUnited Airlines
2h 28mORD-BOS
5/3Sat
nonstopUnited Airlines
2h 57mBOS-ORD
$323
4/24Thu
nonstopJetBlue
2h 28mORD-BOS
5/2Fri
nonstopJetBlue
3h 05mBOS-ORD
$343

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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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