$53 Find Cheap Flights from Wisconsin to Massachusetts

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Low seasonJanuary
High seasonJuly
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 $219.

  • 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 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 2h 01m.

  • What are the most popular destinations in Massachusetts?

    Based on KAYAK flight searches, the most popular destination is Boston (71% of total searches to Massachusetts). The next most popular destinations are Hartford (16%) and Albany (10%). Searches for flights to Nantucket (2%), to West Tisbury (1%) and to Worcester (0%) are also popular.

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 4294 reviews
8.2Boarding
7.1Food
8.0Comfort
7.6Entertainment
8.6Crew
Airline reviews

It is southwest seat was ok. Not the most comfortable seat

8.0 ExcellentJohn, Apr 2025PVD - FLL
Read more Southwest reviews

It is southwest seat was ok. Not the most comfortable seat

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.

Delta is my preferred airline. I've traveled with them for years. On time in most cases, good communication, easy to use app. Most planes are pretty nice. I was on a CRJ 700/900 however, which was pretty badly aged inside and needed a refresh. No infotainment, unreliable wifi, best to download before boarding or bring a book. Food choices are really just snacks on this flight, nice variety but about what you'd expect. Great staff and prompt in departure and early arrival too. Overall quite satisfied.

Crew was friendly Love the entertainment in the seat head rest.

Delta flight was on time, seats were comfortable, and crew was nice.

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.

A bit rush for transit. Food and entertainment are not available

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

Excellent. Although they used to greet me as a mosaic member and provide a free drink, early boarding helps me to keep coming back to JetBlue.

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

Several delays. Next flight was worse. Did not arrive home until 2am PT

Very helpful ground crew after an earlier flight delay and being rebooked on a different flight.

Everything about the flight was lovely…We left early, arrived early, cabin crew were efficient and helpful. Flight was easy and most pleasant.

First world problems, but still… We were seated in first class and asked for a cocktail on a very short, 50 minute flight. After our drink order was taken, a half hour went by, and we noticed that every other person in the small plane had been served except for us. We got up to ask about it, the drinks finally came, then were taken away three minutes later since the flight was so short. Really strange situation, on the other hand, we were in Utah.

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.

Book cheap flights from Wisconsin to Massachusetts

Recent round-trip flight deals

6/4Wed
1 stopSpirit Airlines
13h 13mORD-BOS
6/11Wed
1 stopSpirit Airlines
8h 15mBOS-ORD
$109
6/20Fri
nonstopJetBlue
2h 36mORD-BOS
6/23Mon
nonstopJetBlue
2h 55mBOS-ORD
$117
6/6Fri
nonstopAmerican Airlines
2h 40mORD-BOS
6/11Wed
nonstopAmerican Airlines
2h 55mBOS-ORD
$118
6/3Tue
nonstopUnited Airlines
2h 27mORD-BOS
8/12Tue
1 stopUnited Airlines
5h 38mBOS-ORD
$123
5/28Wed
nonstopUnited Airlines
2h 27mORD-BOS
5/29Thu
nonstopUnited Airlines
2h 58mBOS-ORD
$134
5/31Sat
nonstopDelta
2h 25mORD-BOS
6/4Wed
nonstopDelta
2h 54mBOS-ORD
$137
5/28Wed
1 stopSouthwest
4h 20mORD-BOS
5/30Fri
1 stopSouthwest
8h 45mBOS-ORD
$142
6/8Sun
nonstopAmerican Airlines
2h 22mORD-BOS
6/12Thu
nonstopAmerican Airlines
2h 54mBOS-ORD
$149
7/4Fri
nonstopDelta
2h 31mORD-BOS
7/11Fri
nonstopDelta
2h 58mBOS-ORD
$158
6/27Fri
1 stopSouthwest
7h 55mORD-BOS
7/2Wed
1 stopSouthwest
8h 45mBOS-ORD
$197

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Recent one-way flight deals

10/16Thu
nonstopSpirit Airlines
2h 26mORD-BOS
$53
9/16Tue
1 stopSpirit Airlines
7h 20mORD-BOS
$58
6/4Wed
nonstopJetBlue
2h 29mORD-BOS
$59
8/2Sat
nonstopDelta
2h 32mORD-BOS
$69
5/19Mon
nonstopUnited Airlines
2h 25mORD-BOS
$76
7/1Tue
nonstopJetBlue
2h 24mORD-BOS
$77
5/29Thu
nonstopAmerican Airlines
2h 07mORD-BDL
$79
5/27Tue
nonstopUnited Airlines
2h 27mORD-BOS
$83
5/21Wed
nonstopAmerican Airlines
2h 24mORD-BOS
$89
6/15Sun
1 stopDelta
3h 57mORD-BDL
$99

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Last minute flights from Wisconsin to Massachusetts

Last minute flight, train and bus deals

5/5Mon
nonstopUnited Airlines
2h 25mORD-BOS
5/8Thu
nonstopUnited Airlines
2h 57mBOS-ORD
$117
5/5Mon
nonstopDelta
2h 26mORD-BOS
5/10Sat
nonstopDelta
3h 04mBOS-ORD
$137
5/5Mon
nonstopJetBlue
2h 29mORD-BOS
5/8Thu
nonstopJetBlue
3h 00mBOS-ORD
$148
5/5Mon
nonstopAmerican Airlines
2h 24mORD-BOS
5/9Fri
multi-stopAmerican Airlines
4h 45mBOS-ORD
$207
5/5Mon
multi-stopJetBlue
7h 29mORD-BOS
5/8Thu
nonstopJetBlue
3h 00mBOS-ORD
$210
5/5Mon
nonstopSpirit Airlines
2h 21mORD-BOS
5/9Fri
multi-stopSpirit Airlines
6h 55mBOS-ORD
$218
5/5Mon
nonstopSpirit Airlines
2h 24mORD-BOS
5/8Thu
multi-stopSpirit Airlines
4h 24mBOS-ORD
$226
5/3Sat
nonstopAmerican Airlines
2h 23mORD-BOS
5/7Wed
nonstopAmerican Airlines
2h 56mBOS-ORD
$254
5/3Sat
multi-stopSouthwest
4h 15mORD-BOS
5/7Wed
multi-stopSouthwest
6h 45mBOS-ORD
$272
5/2Fri
multi-stopSouthwest
7h 05mORD-BOS
5/6Tue
multi-stopSouthwest
5h 20mBOS-ORD
$292

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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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