$55 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 8/20. 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.
1 adult
1 adult, Economy

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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Cheap Flights from Boston to Wisconsin

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Milwaukee
Milwaukeenonstop$157
Madison
Madison1 stop$198
Appleton
Appleton1 stop$249
Green Bay
Green Bay1 stop$249
Wausau
Wausau1 stop$329
La Crosse
La Crosse1 stop$412
Chicago
Chicagononstop$117
Minneapolis
Minneapolisnonstop$175
Duluth
Duluth1 stop$248
Milwaukee
Milwaukeenonstop$157
Madison
Madison1 stop$198
Appleton
Appleton1 stop$249
Green Bay
Green Bay1 stop$249
Wausau
Wausau1 stop$329
La Crosse
La Crosse1 stop$412
Chicago
Chicagononstop$117
Minneapolis
Minneapolisnonstop$175
Duluth
Duluth1 stop$248

Book Cheap Boston to Wisconsin Plane Tickets

 
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.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Boston to Wisconsin

Tue, Sep 2 - Thu, Sep 4
United Airlines Logo
9:43 am - 11:33 amBOS-ORD
2h 50mnonstop
United Airlines Logo
6:30 am - 9:56 amORD-BOS
2h 26mnonstop
$117United Airlines
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Wed, Aug 20 - Tue, Aug 26
Spirit Airlines Logo
6:05 am - 7:07 pmBOS-ORD
14h 02m1 stop
Spirit Airlines Logo
8:12 pm - 11:18 amORD-BOS
14h 06m1 stop
$121Spirit Airlines
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Sat, Sep 6 - Wed, Sep 10
JetBlue Logo
7:00 am - 8:56 amBOS-ORD
2h 56mnonstop
JetBlue Logo
9:51 am - 1:20 pmORD-BOS
2h 29mnonstop
$129JetBlue
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Sat, Sep 13 - Sat, Sep 20
American Airlines Logo
5:00 am - 6:51 amBOS-ORD
2h 51mnonstop
American Airlines Logo
5:36 pm - 9:00 pmORD-BOS
2h 24mnonstop
$136American Airlines
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Tue, Aug 19 - Mon, Aug 25
Delta Logo
7:55 pm - 9:54 pmBOS-ORD
2h 59mnonstop
Delta Logo
7:00 am - 10:29 amORD-BOS
2h 29mnonstop
$137Delta
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Thu, Sep 4 - Sun, Sep 7
Southwest Logo
7:30 am - 12:45 pmBOS-ORD
6h 15m1 stop
Southwest Logo
1:50 pm - 8:35 pmORD-BOS
5h 45m1 stop
$146Southwest
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Tue, Aug 19 - Wed, Aug 27
Delta Logo
7:55 pm - 9:54 pmBOS-ORD
2h 59mnonstop
Delta Logo
7:00 am - 10:29 amORD-BOS
2h 29mnonstop
$147Delta
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Thu, Aug 21 - Mon, Aug 25
Southwest Logo
6:40 am - 2:05 pmBOS-ORD
8h 25m1 stop
Southwest Logo
1:50 pm - 10:15 pmORD-BOS
7h 25m1 stop
$156Southwest
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Sat, Aug 30 - Sat, Sep 6
JetBlue Logo
3:15 pm - 4:43 pmBOS-MKE
2h 28mnonstop
JetBlue Logo
4:38 pm - 8:17 pmMKE-BOS
2h 39mnonstop
$157JetBlue
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Tue, Aug 12 - Wed, Aug 20
American Airlines Logo
8:35 am - 10:30 amBOS-ORD
2h 55mnonstop
American Airlines Logo
6:15 am - 9:43 amORD-BOS
2h 28mnonstop
$177American Airlines
Find Deal
Booking Insights

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.

How much is a round-trip flight from Boston to Wisconsin?

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 $117 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 $117.

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 2 stops layover the cheapest option at $532 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 $286 (return) on average. On the other hand, the most expensive months are December and November, when the average cost of round-trip tickets is $420 and $400 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 Sunday is the most expensive. Flying from Wisconsin back to Boston, the best deals are generally found on Saturday, 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, which saves you about 42% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 26 weeks before departure.


Good to know

Low seasonJanuary
Cheapest flight$55
Best time to beat the crowds with an average 4% drop in price.
Most popular time to fly and prices are also 13% 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 $288 on average. Morning departures are around 5% more expensive 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 $133 one-way - $218 round-trip

Reviews of the 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 4241 reviews
8.1Boarding
7.0Food
7.5Entertainment
8.0Comfort
8.6Crew
Airline reviews

southwest just starting charging for luggage. hadnt realized it until it was too late. now out $70 when i couldve bought a carry on if i wouldve known. free bags was one of the only reasons i chose southwest over another airline (the other being no assigned seats, which is apparently also being changed). stupid business decision. wont be flying southwest anymore.

2.0 MediocreAnonymous, Jul 2025AUS - RDU
Read more Southwest reviews

southwest just starting charging for luggage. hadnt realized it until it was too late. now out $70 when i couldve bought a carry on if i wouldve known. free bags was one of the only reasons i chose southwest over another airline (the other being no assigned seats, which is apparently also being changed). stupid business decision. wont be flying southwest anymore.

The quality of Southwest Airlines continues to degrade each time I fly with them. If it were not for the free luggage, I would probably choose another airline. Their prices are a little bit competitive, but way too high for the quality of the service. Southwest is not unique in this way. Domestic flight in the United States of America has continued to be a lower and lower quality product. Very sad when you compare the quality of domestic airlines to that of many international airlines around the world.

Very smooth checking in our luggage with a super pleasant SW agent. I enjoyed a fun entertaining movie.

WiFi did not work. For as outrageous as these flights cost, when they’re advertised with certain services/ features they should be in working order

Worst experience I had on Southwest. Still better than most, but the seating was barely tolerable.

The Southwest employees (all two of them) were very nice and cheerful despite the fact the line to self-check a bag (simply drop it off) was hundreds of people long. Thank God I arrived early to the airport because I stood in this line for at least an hour. Once on the flight that had been delayed by an hour, we had no Wi-Fi and thus no entertainment. Finally, I hope the investor strong arm tactics against Southwest pay off in a short-term windfall to your C-Suite because the rest of you are screwed. I have been a faithful Southwest customer for 15 years due to everything you just got rid of. I'm flying to Idaho and Washington in October, both places I used to simply book with Southwest without a second thought now with Frontier (Washington) and United (Idaho) because they offer everything the "new" Southwest does but cheaper and at better times, destinations, etc. This really makes me sad...

It was okay. The plane was delayed from earlier in the day, but they kept updating the departure time, sometimes later, sometimes earlier. That was stressful. Once we finally got on and took off, it was fine. I was supposed to have a connection in Chicago to Los Angeles, and the time for so late I was rebooked to arrive in LA 3 hours late. The departure time to Chicago later became early enough to have taken my original connection and arrive earlier but that wasn't an option.

It was one and half hour late... Not sure if any other experience matters.

Delayed flight. Nicest crew member was a SW pilot flying seated next to me who kindly move to seat the final passenger. Flight extra delayed. My cup of refreshment of ginger ale was so packed with ice it was literally 2 sips.

For my birthday trip this was my second time ever flying, this trip was the best.

Delayed and took off even later than the scheduled delay time

For a 69 year old with health problems I had the worse experience, no wheelchair when I entered a lady told me to sit and wait while a gentleman told me I had to walk to the Delta station, which I did. I had a carry on and a bag, and I was traveling with my service dog, which was on his carrier and the lady charged me for my carry on luggage, beside all the waiting cause of the delay, I had to walk to get my luggage cause no wheelchair showed up, I am so disappointed. I will get in touch with the company. I got home at 3:00 am, not good for my health situation.

Only issue was with seating. The economy fare we purchased did say there was no guarantee the three people in our party would be seated together, and we were not. At the gate, the agent told us more specifically, the fare we purchased meant we would be seated in middle seats only. This should just be made more obvious.

Great experience on Delta. Staff from baggage check to flight attendants were very courteous and professional. My only issue was a personal preference for pretzels instead of the chips and cookies that were offered.

There was no problems, just a little uncomfortable with seats that do not lay back a little

Always good but we must do something about people in rows ahead of you that don't put their seats back up when they are suppose to. And It's rough to not be able to even lean over to get something out of my purse.

Flight was delayed, 30+ bags had to be gate checked. Crew were very friendly!

Everything was good until we were boarding our connection flight in Atlanta, we were told to gate check our carry-on, but when we got inside the plane, there was plenty of room in the overhead.

Did not know my son and I had different seating arrangements. He was fine, but it was disappointing.

Flight was canceled, and no effort was made to help with rebooking, no hotel vouchers, no car transportation and minimal food voucher and most places for food were closed by the time the voucher was given. Waited for 3 hours for bags. Simply the worst travel experience I have ever had

Was on time until within 1 hour of flight-how does that happen? Staff very friendly.

Weather delay in Chicago?. No sense of urgency to make connection in Chicago for our connecting flight that wasn't delayed. Connection was missed.

Our flight was understandably diverted to a small regional airport in Laramie, Wyoming due to weather conditions, which I fully recognize and appreciate. However, the low rating stems from the experience that followed: passengers remained on board for over an hour without the option to deplane and stretch, despite the aircraft being stationary. Although the pilot opened the cabin door, only he was permitted to exit. Meanwhile, passengers grew increasingly uncomfortable as warm summer air entered the cabin through the open door, and being in the second row meant we were impacted immediately. While the flight attendants made efforts to keep everyone at ease, I believe allowing passengers to deplane briefly, given the extended delay, would have significantly improved the overall experience.

I never flew. Flight was canceled. DIA worst airport in the country. Avoid at all costs.

I learned that seating towards the end of plane that a line forms for the restroom and people use your chair as a hand railing, bumping your seat consistently. I was seated in the aisle. I think that next time if I am towards the back row I would want to sit in the middle or window seat.

United sent me a mileage plus number last year but that number is invalid so I can’t use it to check into flights or collect mileage. There is human to speak about the problem, only computers who keep asking me if I am using the correct email. It’s so frustrating and I cannot resolve it.

It was delayed instead of departing at 9:20pm, we departed at 11pm… putting us in Columbus after 2am! It was awful. Had I known about the delay, I could have spent some time in the United Lounge… I was starving because I started my journey in Budapest… so I was exhausted and hungry. Plus I had to make new arrangements to be picked up at the airport in Columbus, instead of midnight it was 2:30 am after getting luggage and out of airport. Not feasible. I would have just stayed in Chicago for the night and gotten a morning flight.

Not a great experience. We paid for the upgrade for premium economy seats and seated ourselves in very comfortable seats. Someone came along with the same seat on their boarding pass. The aircraft had been changed and as a result we were booted out and sent further back to small uncomfortable seats. After complaining we were moved to emergency row seats, which gave us more leg room but the seats don’t recline. For people in our 70’s we found having to sit upright from California to NJ very uncomfortable. Not sure why they chose to move senior citizens instead of the two people that were allowed to take the more comfortable seats. Not happy.

I liked the choice of lemon ginger tea. I think stewardesses can be more considerate of older people needs.

It was great, I’m very grateful for the pilots and crew flight attendants for everything.

Worst flight experience ever flights canceled. JetBlue told us just did not even bother standing in line to come back in one and a half hours then without any information we had to go pick up all of our luggage and spend over $2000 in accommodation just to get home. JetBlue said that the next flight available for us to get home would be three days later. Absolutely absurd hasn’t offered to give us any compensation do not fly JetBlue horrible company. They said it was based on the weather and the weather is great in all locations that we would’ve been flying to total hoax. I think it’s a conspiracy theory.

The captain gave good announcements and the flight attendants were friendly. The WiFi was pretty good. The plane itself looked very old inside and the seats were very uncomfortable. The screens in the seat backs were the smallest I’ve ever seen. There were so many loud and obnoxious kids on this flight and the parents didn’t do much to try to quiet them down. Some had videos and games on tablets with higher than necessary volume going the whole time.

Too many long delays with JetBlue. Worst major airline that serves JFK but unfortunately I keep going back because of the prices.

My JetBlue experience was nice. The flights ran on time, the aircraft was clean and comfortable, and the flight attendants were attentive. My only issue, which is isolated to the low-cost (budget) option at JetBlue, is that the check in process makes the user feel that they have to buy their seats. The seats offered for purchase are upgrades from the budget seats you get (which are essentially the last seats remaining). The interface should not make it feel like you must purchase a seat.

The plane was late to leave.. Internet was lousy. TV was not working. when we arrived, We stayed on the plane for a long time before we got to the gate. It took us a long time to retrieve our luggage because they didn’t know what carousel to send them to. It was a bad experience.

I especially liked the lead crew officer. His boarding and safety announcements were made with a bit of novelty and humor. The flight also left the gate 10 minutes early and we landed about 20 minutes early… It was a delightful flight…

There were mutliple delays. There was inconsistent, delayed, and poor communication regarding the delays.

Spend hours delayed with no food, water anything sitting on the aieplane with no ability to eat or use the restroom. My entire experience was the absolute worst. I will never fly jet Blue again.

It would have been nice if they had offered more than one set of snacks

Seats were not too comfortable; it was impossible to locate the underseat power outlet.

Very poor delay in dfw was really bad n long

Our flight was 1.5 hours delayed. There was no weather for the inbound flight, so I don't understand why. This meant a VERY late arrival and only a quick nap before my morning flight.

Because of rescheduling, they had to put me on a flight that didn't go through Dallas

It was very difficult to stretch my knee out and I am very short. I also had a torn tendon in my knee which made it extra uncomfortable anyways. My husband is 6'2" and I can't imagine him flying in that plane.

3 hour weather delay followed by 1 hour (and counting) maintenance delay. UGH!

Couldn’t get the door on the plane to close leading to a nearly 2 hour delay. But, hey at least they didn’t cancel the flight.

Flight was cancelled 3 hrs AFTER etd. Thetefore Missed connection from JFK to New Zealand . No accommodation provided… This cost ne aporox 1000 USD in extra expenses and turned whst should have been a 24 hr trip ftom Boston - New Zealand into a VERY expensive , late 70+ hr nightmare … Complete nonsense!!!

After we'd boarded , they canceled the flight. The crew didn't even know , we just all received text messages. Then after they deplaned us , AA was just like "too bad, go F your self, we sure ain't gonna help you"

The flight got delayed 2.5 hrs due to a maintenance issue that cause a domino effect. American should have spare planes for when something like this happens.

Delayed flight, so I switched fights to SFO to Phoenix , Phoenix to DSM. Excellent service through American Airlines

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