$67 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 2/4. 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, 0 bags

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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Flight Deals

Cheap Flights from Boston to Wisconsin

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Milwaukee
Milwaukee1 stop$189
Madison
Madison1 stop$279
Appleton
Appleton1 stop$280
Green Bay
Green Bay1 stop$269
Wausau
Wausau1 stop$279
La Crosse
La Crosse1 stop$454
Duluth
Duluth1 stop$300
Chicago
Chicago1 stop$132
Milwaukee
Milwaukee1 stop$189
Madison
Madison1 stop$279
Appleton
Appleton1 stop$280
Green Bay
Green Bay1 stop$269
Wausau
Wausau1 stop$279
La Crosse
La Crosse1 stop$454
Duluth
Duluth1 stop$300
Chicago
Chicago1 stop$132

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

Sun, Mar 1 - Mon, Mar 2
Frontier Logo
6:00 am - 10:51 am
BOS
-
ORD
29h 51m
1 stop
Frontier Logo
4:42 pm - 1:13 am
ORD
-
BOS
7h 31m
1 stop
$132Frontier
Fri, Feb 6 - Mon, Feb 9
JetBlue Logo
3:35 pm - 5:43 pm
BOS
-
ORD
3h 08mnonstop
JetBlue Logo
7:40 am - 11:05 am
ORD
-
BOS
2h 25mnonstop
$133JetBlue
Sun, Feb 22 - Sat, Feb 28
Delta Logo
7:15 am - 9:28 am
BOS
-
ORD
3h 13mnonstop
Delta Logo
7:05 am - 10:37 am
ORD
-
BOS
2h 32mnonstop
$136Delta
Wed, Feb 11 - Sun, Feb 15
Delta Logo
4:10 pm - 6:19 pm
BOS
-
ORD
3h 09mnonstop
Delta Logo
7:05 am - 10:37 am
ORD
-
BOS
2h 32mnonstop
$137Delta
Tue, Feb 10 - Sat, Feb 14
American Airlines Logo
2:43 pm - 6:25 pm
BOS
-
MKE
4h 42m
1 stop
American Airlines Logo
6:04 am - 2:14 pm
MKE
-
BOS
7h 10m
1 stop
$217American Airlines
Sat, Feb 21 - Tue, Feb 24
American Airlines Logo
5:54 pm - 10:57 pm
BOS
-
MKE
6h 03m
1 stop
American Airlines Logo
12:10 pm - 6:00 pm
MKE
-
BOS
4h 50m
1 stop
$227American Airlines
Tue, Mar 10 - Wed, Mar 11
Southwest Logo
5:25 pm - 10:05 pm
BOS
-
MKE
5h 40m
1 stop
Southwest Logo
5:50 am - 2:35 pm
MKE
-
BOS
7h 45m
2 stops
$232Southwest
Tue, Mar 10 - Wed, Mar 11
Southwest Logo
3:15 pm - 11:05 pm
BOS
-
MKE
8h 50m
2 stops
Southwest Logo
5:50 am - 2:35 pm
MKE
-
BOS
7h 45m
2 stops
$237Southwest
Wed, Feb 11 - Sun, Feb 15
United Airlines Logo
4:16 pm - 9:31 pm
BOS
-
GRB
6h 15m
1 stop
United Airlines Logo
3:05 pm - 9:48 pm
GRB
-
BOS
5h 43m
1 stop
$279United Airlines
Wed, Mar 18 - Tue, Mar 24
United Airlines Logo
7:16 am - 11:38 am
BOS
-
MSN
5h 22m
1 stop
United Airlines Logo
6:30 am - 12:49 pm
MSN
-
BOS
5h 19m
1 stop
$279United Airlines
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.

What is the cheapest Boston to Wisconsin flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest ticket to Wisconsin from Boston found in the last 72 hours was to Milwaukee, at $153 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 $153.

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.

No, with an average price for the route of $345, prices are generally cheapest when you fly direct.

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 September, when tickets cost $239 (return) on average. On the other hand, the most expensive months are November and December, when the average cost of round-trip tickets is $472 and $395 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 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 44% 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$67
Best time to beat the crowds with an average 16% drop in price.
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 $289 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 in the morning, which is peak travel time and where the average cost of a ticket is $343.

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 $120 one-way - $209 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 4268 reviews
7.5Entertainment
8.6Crew
8.0Comfort
7.0Food
8.1Boarding
Airline reviews

All good except once again bags took an hour at Midway Airport Happens all the time. Ridiculous

10.0 ExcellentAnonymous, Jan 2026
PHX - MDW
Read more Southwest reviews

All good except once again bags took an hour at Midway Airport Happens all the time. Ridiculous

Everything went smoothly and we even arrived a little bit early.

Great vacation. Can't wait till next year for another one.

Great flight but super high price. Glad it was a business trip and not personal

On time. Friendly staff. Took to long to pre bord all the specialty groups. Cramped small plane

The seats were comfortable, and the boarding process was pretty smooth.

3 hour delay. Had to change plans and was still delayed.

The staff was very friendly, professional, and courteous. The overall flight was a great experience.

The crew canceled the complementary snack and drink in anticipation of turbulence that never materialized. I was counting on the drink (water) to take the the doses of medication - prescribed for my heart condition - that were due during the flight. Since no snack or meal was served on this flight, I cannot rate the food quality. Otherwise, this flight was excellent.

Departure was delayed more than 1/2 hour while we waited for luggage (only) transfer from another flight/plane. Once approved for takeoff, the flight was excellent.

It was last minute due to weather - considering - it was amazing! Good smiles, friendly staff and they were making sure we knew what was going on when and where.

delta last minute gave me a boarding pass for a different flight with no confirmation that they were changing it

The service from the flight attendants were of supreme quality. They greeted and treated everyone with a wide smile. This is totally absent nowadays. Kudos to them!!!!

Excellent flight and got us around tough weather. Only issue was seat TV did not work and crew tried to reboot.

Very large passenger too space from my own seat. Arm board couldn’t be lowered because of his size. It wads very uncomfortable trip, as the flight was full couldn’t move anywhere having back pain because of the position in which I was the entire flight.

was sitting in the jet bridge for 10 minutes in -20 degree weather waiting for my bag

Outdated equipment in disrepair, wifi inoperable. Broken seats, taped air vents, generally poor condition, the 717 showed its age and lack of upkeep.

My flight out of Baton Rouge to Atlanta was delayed by a half hour. This got us into Atlanta airport 30 minutes late. I ran through the airport to get to my connecting flight. As I approached the boarding gate, I saw the boarding door was still open and a passenger was being checked in. But when I got to the gate, the boarding agent told me they had already given away my seat and there were no empty seats on that flight. So I had to take a later flight. That has never happened to me before. Very frustrating.

Connection through Atlanta was difficult. Mechanical issue on plane caused a two hour delay. New gate was a mile away.

No WiFi. Comfort plus should have alcohol provided, crew only offered water or tea. Who the heck wants tea?

In overall it was a good experience, the only down point was that the entertainment screen was working properly.

HORRIBLE, my initial flight was cancelled, they made me pay $200 extra dollars and that got cancelled as well! After 6 cancellations I decided to get a refund because I needed to get home to my babies. Out of $1000+ dollars they offered me only $40 in refund! Totally unacceptable! The flight that they cancelled I was able to fly it on another airline. I had to spend $400 on one way tickets just to get home! I’m still getting the runaround.

First class ticket gets you a choice of chips or nuts. . Just like economy Southwest. Also no screen in the seats. This is first class???!

Seated dude next to me even though lots of empty rows. But main thing was we sat on the tarmac after landing for 30 minutes because of, in the words of the dude who sat next to me, “operational incompetence”. We got changing directions about where to pick up gate checked bags. Pilot and flight attendant were awesome though.

It was a pretty standard flight... until the almost hour and a half spent on the taxi way. I get that the weather has been poor but the delay had nothing to do with the weather and more to do with a plane with several issues tying up the gate. I get that that happens from time to time but this has been EVERY flight I've been on for the past 5 years and I fly 3 to 5 times a year. This isn't just United... it's American, it's Delta. It's an issue with the entire industry. I work for UPS and packages on a cargo plane get better service than people do these days. Anymore I HATE flying.

Flight arrived 30 min early and bag was waiting at the baggage pickup. United Club HNL was one of the nicest in the system

Unfortunately weather delayed our flight waiting for our plane to arrive and due to a little snow time was needed to deice the plane so departure was very delayed and I missed the connecting flight

Very good. Because of the delays with my previous flight, I missed my connection, but I was able to book another flight through the United app easily.

I wish there were outlets to charge my iPhone. The crew was great; we had a female pilot who was great with explaining what was happening and delays,

The flight crew where really good. Better then the crew from BNE to SFO

Flight was canceled. I asked to be rerouted to OKC and then took an Uber.

AA did not allow to board a flight because my connecting flight from DFW had been canceled. I got on another flight to another city. No service on the plane and I did not use their entertainment system.

On time on a day with lots of weather cancellations on other flights. Thank you for getting me home during a winter storm!

Don't change gate multiple times make people run across the airport. Announce delays in a timely manner. Have maintenance crew ready. Don't delay and keep passengers on the plane for 3 hrs. on tarmac.

The plane was experiencing problems with the HVAC system, it was very cold in the front of the plane and very hot in the back.

The attendants were kind and helpful. A sugar-free drink would have been very welcome.

Pilot navigated severe weather/snow storm with skill. Described his intentions clearly

one crew said "he" didn't serve double alcohol drinks for travelers in exit rows. crew on prior flight did. Is this a AA rule, and the prior crew was being nice? Also, I think we deserve more than a 25% refund for losing first class seats when rescheduling a flight due to weather

It was a little concerning to hear the ground crew arguing with the flight crew over baggage space. Instead of taking them and checking them, they started checking for space in the first class cabin moving items around like the flight crew didn't know what they were doing. I was embarrassed for them.

2 hour delay due to equipment failure. No updates via the app and airport screens (which continued to show a departure time in the past). AA eventually switched planes and the new plane was not catered or cleaned correctly.

Terrible. They canceled our early morning flight after midnight on the day of and had no available flights to rebook my family on for the next 72 hours. Yet they still had other flights that were not cancelled from JFK so it couldn’t be based on the weather. It felt like they canceled the flight based on it not being profitable enough for them. I am not interested in traveling with the again. The absolute worse customer service and lack of accountability.

Horribly rude check in at airport, worst in 25 years of flying. All over a simple issue they could have googled to resolve.

First time flying with JetBlue and never again. I went to the counter to request meet and assist because I'm 74 and my wife is 79. I walk with a cane and my wife is handicapped and has her own wheel chair. I told the agent that my wife and luggage was at the entrance door. The ticketing agent said to me that they don't offer meet and assist. I need to bring them our luggage and then go back and get my wife in order to get my boarding pass. As I went back to get my luggage a Southwest agent along with a TSA agent recognized the situation and came over and took my wife and luggage to the JetBlue ticketing counter alongside the line and told the JetBlue agent to issue to take our luggage as soon as they could.

1) No pilot available for 1 hour 2) no room for most passengers careyon in overhead—-> stowed below 3) when we landed we had to wait 45 min. Before docking at gate as gate was not ready

It was good. I prefer JB over other airlines.I just wish we had headphones for the films, but other than that - good.

The ride share experience in JFK is terrible. After traveling on a flight, then you need to take a subway to the last stop to get an uber or lyft. Unacceptable. Bad job JetBlue for permitting JFK and Port Authority to do this to your passengers.

Checking In on JetBlue site was impossible. It hung up on REAL ID. Even my Global Entry did not help. Luckily, on Kayak site it was a breeze. Entire flight the temperature was COLD! Otherwise the crew was great!

The flight was two hours late due to a computer fault and resulting maintenance. Nothing was offered as compensation beyond bottles of water during the time we were deplaned and waiting in the terminal.

Very pleasant flight attendants. Gate crew rather loud chatting with each other.

Four plus hour flight delay in New York caused us to take off after 11:30pm. We didn’t arrive at our hotel until five hours after check in. Started the trip off feeling exhausted.

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

Information on your arrival and departure airports