$53 Find Cheap Flights from Boston to Wisconsin

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Boston to Wisconsin departing on 10/16. 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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KAYAK searches hundreds of travel sites at once for deals on flights to Wisconsin

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Boston to Wisconsin, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Boston to Wisconsin, as well as popular online travel agencies
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Flights Deals

Best Wisconsin Flight Deals from Boston

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours

Milwaukee
Milwaukeenonstop$177
Madison
Madison1 stop$259
Appleton
Appleton1 stop$271
Green Bay
Green Bay1 stop$271
Wausau
Wausau1 stop$412
La Crosse
La Crosse1 stop$434
Chicago
Chicagononstop$113
Minneapolis
Minneapolisnonstop$155
Milwaukee
Milwaukeenonstop$177
Madison
Madison1 stop$259
Appleton
Appleton1 stop$271
Green Bay
Green Bay1 stop$271
Wausau
Wausau1 stop$412
La Crosse
La Crosse1 stop$434
Chicago
Chicagononstop$113
Minneapolis
Minneapolisnonstop$155

Cheap Flights from Boston to Wisconsin

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Boston to Wisconsin that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.

Recent round-trip flight deals from Boston to Wisconsin

Recommended round-trip deals departing in the coming months from the most popular airlines that fly from Boston to Wisconsin.
Discover the best prices for you by selecting your travel dates on KAYAK.
Spirit Airlines Logo
8:00 am - 9:53 amBOS-ORD
2h 53mnonstop
Spirit Airlines Logo
3:29 pm - 12:39 amORD-BOS
8h 10m1 stop
$113Spirit Airlines
Find Deal
Thu, Oct 23 - Tue, Oct 28
JetBlue Logo
6:00 am - 7:55 amBOS-ORD
2h 55mnonstop
JetBlue Logo
8:40 am - 12:04 pmORD-BOS
2h 24mnonstop
$117JetBlue
Find Deal
Thu, Jun 12 - Mon, Jun 16
American Airlines Logo
2:08 pm - 4:03 pmBOS-ORD
2h 55mnonstop
American Airlines Logo
8:40 pm - 12:20 amORD-BOS
2h 40mnonstop
$118American Airlines
Find Deal
Sat, Jun 7 - Tue, Jun 10
United Airlines Logo
6:59 pm - 11:37 pmBOS-ORD
5h 38m1 stop
United Airlines Logo
7:30 am - 10:57 amORD-BOS
2h 27mnonstop
$123United Airlines
Find Deal
Tue, Jul 1 - Tue, Jul 8
United Airlines Logo
7:45 am - 9:43 amBOS-ORD
2h 58mnonstop
United Airlines Logo
7:54 pm - 11:21 pmORD-BOS
2h 27mnonstop
$134United Airlines
Find Deal
Sun, May 25 - Wed, May 28
Southwest Logo
6:45 am - 3:00 pmBOS-ORD
9h 15m1 stop
Southwest Logo
4:00 pm - 11:55 pmORD-BOS
6h 55m1 stop
$136Southwest
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Sat, Jun 7 - Wed, Jun 11
Delta Logo
8:20 pm - 10:14 pmBOS-ORD
2h 54mnonstop
Delta Logo
7:00 am - 10:25 amORD-BOS
2h 25mnonstop
$137Delta
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Tue, May 27 - Sat, May 31
Delta Logo
5:10 pm - 7:14 pmBOS-ORD
3h 04mnonstop
Delta Logo
7:00 am - 10:25 amORD-BOS
2h 25mnonstop
$138Delta
Find Deal
Sun, May 25 - Sat, May 31
American Airlines Logo
6:35 am - 8:31 amBOS-ORD
2h 56mnonstop
American Airlines Logo
3:20 pm - 6:43 pmORD-BOS
2h 23mnonstop
$141American Airlines
Find Deal
Wed, May 21 - Wed, May 28
Southwest Logo
5:00 am - 12:45 pmBOS-ORD
8h 45m1 stop
Southwest Logo
1:50 pm - 8:35 pmORD-BOS
5h 45m1 stop
$142Southwest
Find Deal
Tue, Jul 1 - Fri, Jul 4
Useful Info

KAYAK's insights & trends for Boston to Wisconsin flights

Get data-powered insights and trends into flights from Boston to Wisconsin to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest Boston to Wisconsin flight route?

The cheapest price for flight routes found by users searching on KAYAK in the last 2 weeks for round-trip flights from Boston to Wisconsin.

The cheapest ticket to Wisconsin from Boston found in the last 72 hours was to Milwaukee, at $103 round-trip. The most popular route is from Boston (BOS) to Milwaukee (MKE), and the cheapest round-trip airline ticket found on this route in the last 72 hours was $103.

Can I save money by flying with a layover from Boston to Wisconsin?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 1 stop layover the cheapest option at $429 on average.

What is the cheapest month to fly from Boston to Wisconsin?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Boston to Wisconsin, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Boston to Wisconsin is August, when tickets cost $291 (return) on average. On the other hand, the most expensive months are December and November, when the average cost of round-trip tickets is $426 and $397 respectively.

What’s the cheapest day of the week to fly from Boston to Wisconsin?

The average price of all round-trip flights from Boston to Wisconsin clicked on KAYAK for each day over the last 12 months.

For Boston to Wisconsin, Wednesday is the cheapest day to fly on average and Monday is the most expensive. Flying from Wisconsin back to Boston, the best deals are generally found on Tuesday, with Sunday being the most expensive.

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

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Boston to Wisconsin, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Boston to Wisconsin, you should book around 4 weeks before departure. For the absolute cheapest price, our data suggests you should book 23 weeks before departure.


Good to know

Low seasonJanuary
High seasonMay
Cheapest flight$53
Best time to beat the crowds with an average 5% drop in price.
Most popular time to fly and prices are also 5% lower on average.
Flight from Boston to Chicago O'Hare Airport

FAQs - booking Wisconsin flights

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

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Boston 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 Boston 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 Boston 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 Boston 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 Boston to Wisconsin up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • 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 $298 on average. Morning departures are around 7% 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.

Top tips for finding cheap flights to Wisconsin

  • Looking for a cheap flight? 25% of our users found tickets from Boston to the following destinations at these prices or less: Chicago $106 one-way - $211 round-trip

Top 5 airlines serving from Boston to Wisconsin

 
See real verified KAYAK customer reviews for airlines flying from Boston to Wisconsin. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Boston 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 4294 reviews
7.1Food
7.6Entertainment
8.6Crew
8.0Comfort
8.2Boarding
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.

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.

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 from start to finish. All staff members were amazing!

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.

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.

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

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.

Everything you need to know for your flight from Boston to Wisconsin

Information on your arrival and departure airports

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