MSN - BOS

$100 Find Cheap Flights from Madison to Boston

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Madison to Boston departing on 8/31. 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 Boston

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Madison to Boston, 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 Madison to Boston, as well as popular online travel agencies
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Cheap Flights from Madison to Boston (MSN-BOS)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Madison to Boston 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 Madison to Boston

Sat, Sep 13 - Tue, Sep 16
Delta Logo
5:26 pm - 11:59 pmMSN-BOS
5h 33m1 stop
Delta Logo
4:00 pm - 9:23 pmBOS-MSN
6h 23m1 stop
$251Delta
Find Deal
Tue, Oct 28 - Sun, Nov 2
Delta Logo
12:30 pm - 6:28 pmMSN-BOS
4h 58m1 stop
Delta Logo
5:45 am - 10:18 amBOS-MSN
5h 33m1 stop
$255Delta
Find Deal
Tue, Sep 9 - Tue, Sep 16
United Airlines Logo
8:15 am - 4:28 pmMSN-BOS
7h 13m2 stops
United Airlines Logo
6:10 am - 9:48 amBOS-MSN
4h 38m1 stop
$256United Airlines
Find Deal
Thu, Sep 4 - Sun, Sep 7
Delta Logo
6:00 am - 1:20 pmMSN-BOS
6h 20m1 stop
Delta Logo
5:34 am - 10:07 amBOS-MSN
5h 33m1 stop
$259Delta
Find Deal
Tue, Sep 2 - Thu, Sep 4
American Airlines Logo
6:19 am - 1:30 pmMSN-BOS
6h 11m1 stop
American Airlines Logo
9:17 am - 2:18 pmBOS-MSN
6h 01m1 stop
$260American Airlines
Find Deal
Fri, Sep 5 - Mon, Sep 8
United Airlines Logo
3:58 pm - 11:57 pmMSN-BOS
6h 59m2 stops
United Airlines Logo
6:10 am - 9:45 amBOS-MSN
4h 35m1 stop
$264United Airlines
Find Deal
Sun, Sep 14 - Thu, Sep 18
American Airlines Logo
6:00 am - 11:51 amMSN-BOS
4h 51m1 stop
American Airlines Logo
5:00 am - 9:59 amBOS-MSN
5h 59m1 stop
$269American Airlines
Find Deal
Thu, Sep 4 - Sun, Sep 7
United Airlines Logo
6:30 am - 2:13 pmMSN-BOS
6h 43m2 stops
United Airlines Logo
6:10 am - 9:45 amBOS-MSN
4h 35m1 stop
$271United Airlines
Find Deal
Fri, Nov 21 - Mon, Nov 24
American Airlines Logo
4:00 pm - 10:19 pmMSN-BOS
5h 19m1 stop
American Airlines Logo
7:00 am - 12:44 pmBOS-MSN
6h 44m1 stop
$274American Airlines
Find Deal
Thu, Oct 2 - Sun, Oct 5
American Airlines Logo
6:00 am - 12:22 pmMSN-BOS
5h 22m1 stop
American Airlines Logo
5:00 am - 9:59 amBOS-MSN
5h 59m1 stop
$289American Airlines
Find Deal
Booking Insights

KAYAK's insights & trends for Madison to Boston flights

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

Find cheap flights to Boston
Find cheap flights to Boston

Planning a trip from Madison to Boston? KAYAK’s data-powered insights will help you find cheap flights. Learn the best time to fly, how early to book your ticket, and other tips to secure great prices.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Madison to Boston, 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 Madison to Boston is August, where tickets cost $336 (return) on average. On the other hand, the most expensive months are February and November, where the average cost of round-trip tickets is $578 and $521 respectively.

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

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Madison to Boston, 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 Madison to Boston, you should book around 6 weeks before departure, which saves you about 31% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 18 weeks before departure.

Good to know

Low seasonJanuary
Cheapest flight$100
Best time to beat the crowds but there is an average 4% increase in price.
Most popular time to fly and prices are also 24% lower on average.
Flight from Madison to Boston

When to book flights from Madison to Boston

Are your dates flexible? Find out the best times to travel from Madison to Boston based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking flights from Madison to Boston

  • Where can I park at MSN?

    The Economy Lot at MSN is the ideal place for long-term parking, since it's price is nearly half that of the most expensive parking. All parking spots at MSN are first come, first served, so beware. If a third party claims to be selling reserved spaces at the airport, they are not. The MSN Parking page on their website displays real-time information about how many spots are available in all the different parking locations.

  • Does MSN provide any facilities for nursing mothers?

    Yes. MSN has three different Mother’s Rooms in the terminals. There is one on the first floor labeled “Family Lounge,” and two on the second floor, one by Gate 8 and one by Gate 5. Each mother's lounge has a table, comfy leather chair, electrical outlet, baby changing table, and a sink.

  • Does BOS have animal relief facilities?

    Yes. If you're a traveling with a service animal or four-legged friend that needs to go potty or get a drink of water as soon as you land at BOS, you can take advantage of the animal relief stations located at Gates B29, C20, and E7.

  • Does Boston Logan have a USO?

    Yes. If you are an active duty member of the US military or family, and you would like to regroup and refresh before heading out into Boston, you can use the USO free of charge. This lounge is located landside in Terminal C on the lower level and it is open from 8 am to 9 pm on weekdays and 8 am to 8 pm on weekends. Some amenities of this USO include comfy seating, TV with DVDs and Xbox games, computers, a kitchen, personal care kits, and much more.

  • How many flights are there between Madison and Boston per day?

    Each day, there are between 1 and 2 nonstop flights that take off from Madison and land in Boston, with an average flight time of 2h 28m. The most common departure time is 4:00 pm and most flights take off in the afternoon. Each week, there are 4 flights. The most frequent day of departure is Thursday, when 50% of all weekly flights depart. The fewest flights depart on a Sunday.

  • What is the cheapest flight from Madison to Boston?

    In the last 3 days, the lowest price for a flight from Madison to Boston was $100 for a one-way ticket and $251 for a round-trip.

  • Do I need a passport to fly between Madison and Boston?

    Even though you are not required to have a passport, keep in mind that an official ID is needed to board the airplane.

  • Which airlines offer Wi-Fi service onboard planes from Madison to Boston?

    Delta, and American Airlines offer inflight Wi-Fi service on the Madison to Boston flight route.

  • Which aircraft models fly most regularly from Madison to Boston?

    The Embraer 175 is the aircraft model that flies most regularly on the Madison to Boston flight route.

  • Which airline alliances offer flights from Madison to Boston?

    oneworld, and SkyTeam are the airline alliances operating flights between Madison and Boston, with SkyTeam being the most commonly used for this route.

  • On which days can I fly direct from Madison to Boston?

    You can catch a nonstop flight from Madison to Boston on on Thursday, Friday, and Sunday.

  • Which is the best airline for flights from Madison to Boston, Delta or United Airlines?

    The two airlines most popular with KAYAK users for flights from Madison to Boston are Delta and United Airlines. With an average price for the route of $490 and an overall rating of 8.0, Delta is the most popular choice. United Airlines is also a great choice for the route, with an average price of $455 and an overall rating of 7.4.

  • How does KAYAK find such low prices on flights from Madison to Boston?

    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 Madison to Boston.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Boston from Madison 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 Madison to Boston?

    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 to Boston with an airline and back to Madison with another airline. Booking your flights between Madison and BOS can sometimes prove cheaper using this method.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Madison to Boston?

    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 to Boston from Madison up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

KAYAK’s top tips for finding a cheap flight from Madison to Boston

  • The Dane County Regional Airport (MSN), or Truax Field, serves the city of Madison, Wisconsin. The Boston Logan International Airport (BOS) is a hub for Delta Airlines and a focus city for JetBlue.
  • When you are planning your trip from Madison to Boston, it is unlikely that you will find a direct flight. However, Airlines such as Delta, American, and United fly from MSN to BOS with one stop, often in Charlotte, Chicago, or New York. American and United are among the airlines that offer two-stop flights between MSN and BOS, with stops often in Washington DC, Dallas, Pittsburgh, and other cities.
  • If you need to pick up a rental car at Boston Logan, when you land, make your way to the Arrivals curb. Here, you will look for the blue and white shuttle buses for the Rental Car Center (RCC), where all rental car agencies are housed at BOS. The RCC shuttle buses run about every 5 minutes.
  • Some accommodations that MSN has made for differently-abled travelers include include handicapped parking in the surface lot and the ramp, visual interpretation services, companion care restrooms, and TTY phones. If you need wheelchair assistance, make sure that you contact your airline before you arrive at MSN so that airport and airline staff are ready and waiting to assist you.
  • In order to get from the Boston Logan Airport into downtown Boston, you can “Take the T”, meaning MBTA Transit. This mode of transportation includes the Blue Line subway, the MBTA ferries, and the Silver Line rapid transit buses.

Prefer to fly direct from Madison to Boston?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Madison Truax Field to Boston Logan Intl.
Find which airlines fly direct from Madison Truax Field Airport to Boston Logan Intl Airport, which days they fly and book direct flights.

Direct departures

Madison Truax Field to Boston Logan Intl

Thursday

American Airlines, Delta

American Airlines, Delta

Friday

American Airlines

American Airlines

Sunday

Delta

Delta

See more direct flights

Direct returns

Boston Logan Intl to Madison Truax Field

Thursday

Delta, KLM

Delta, KLM

Friday

American Airlines

American Airlines

Sunday

American Airlines, Delta

American Airlines, Delta

See more direct flights

Reviews of the top 3 airlines serving from Madison to Boston

 
See real verified KAYAK customer reviews for airlines flying from Madison to Boston. 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 Madison to Boston? 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
DeltaOverall score based on 7981 reviews
7.9Comfort
8.2Boarding
8.5Crew
7.9Entertainment
7.3Food
Airline reviews

My experience on any Delta flight is always overshadowed by the time Delta removed me from a flight for no apparent reason.

2.0 MediocreGim, Jul 2025BGM - DTW
Read more Delta reviews

My experience on any Delta flight is always overshadowed by the time Delta removed me from a flight for no apparent reason.

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.

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

Terrible. Delayed 7 hours, and cancelled the flight, leaving me stranded and out of pocket $500 for an alternative last minute flight

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.

We had to turn around and head back to Manchester. Problem with a plane engine.

Flight was delayed. Staff at the gate effectively and proactively communicated about the delay.

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"

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