BOS - MSN

$160 Find Cheap Flights from Boston to Madison

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 Madison departing on 1/18. 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 Madison

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Boston to Madison, 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 Madison, as well as popular online travel agencies
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

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Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Everything you should know

Cheapest round-trip
$251
Overall average: $588
United Airlines
Wed 1/21Sat 1/24
BOS - MSN • 1 stop
Cheapest one-way
$160
Typical prices: $164-$261
American Airlines
Sun 1/18
BOS - MSN • 1 stop
Video guide: How to find cheap flights to Madison
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Top airlines
United Airlines
Cheapest • from $256 (round-trip)
Delta
Best reviews • 7.9 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
When to book
4 weeks
in advance
Our data shows that travelers who book at least 4 weeks in advance save around 46% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
August
Cheapest • 30% price drop
June
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
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KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Madison!
Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Boston to Madison (BOS-MSN)

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

Wed, Jan 21 - Sat, Jan 24
United Airlines Logo
12:45 pm - 5:47 pm
BOS
-
MSN
6h 02m1 stop
United Airlines Logo
6:00 am - 1:20 pm
MSN
-
BOS
6h 20m1 stop
$251United Airlines
Wed, Jan 21 - Sat, Jan 24
United Airlines Logo
12:45 pm - 4:50 pm
BOS
-
MSN
5h 05m1 stop
United Airlines Logo
3:49 pm - 11:49 pm
MSN
-
BOS
7h 00m2 stops
$256United Airlines
Thu, Jan 22 - Sun, Jan 25
American Airlines Logo
11:00 am - 3:27 pm
BOS
-
MSN
5h 27m1 stop
American Airlines Logo
10:50 am - 5:05 pm
MSN
-
BOS
5h 15m1 stop
$279American Airlines
Thu, Feb 12 - Sun, Feb 15
American Airlines Logo
9:00 am - 3:30 pm
BOS
-
MSN
7h 30m1 stop
American Airlines Logo
2:55 pm - 10:51 pm
MSN
-
BOS
6h 56m1 stop
$299American Airlines
Tue, Dec 30 - Thu, Jan 1
American Airlines Logo
2:14 pm - 7:45 pm
BOS
-
MSN
6h 31m1 stop
American Airlines Logo
6:18 pm - 11:51 pm
MSN
-
BOS
4h 33m1 stop
$317American Airlines
Fri, Feb 6 - Mon, Feb 9
United Airlines Logo
10:30 am - 2:52 pm
BOS
-
MSN
5h 22m1 stop
United Airlines Logo
6:30 am - 12:46 pm
MSN
-
BOS
5h 16m1 stop
$349United Airlines
Fri, Feb 6 - Mon, Feb 9
United Airlines Logo
2:20 pm - 9:05 pm
BOS
-
MSN
7h 45m2 stops
United Airlines Logo
6:30 am - 12:46 pm
MSN
-
BOS
5h 16m1 stop
$354United Airlines
Thu, Jan 22 - Sun, Jan 25
United Airlines Logo
6:00 am - 2:52 pm
BOS
-
MSN
9h 52m2 stops
United Airlines Logo
3:48 pm - 11:49 pm
MSN
-
BOS
7h 01m2 stops
$359United Airlines
Fri, Feb 6 - Mon, Feb 9
United Airlines Logo
10:30 am - 7:07 pm
BOS
-
MSN
9h 37m2 stops
United Airlines Logo
2:56 pm - 11:49 pm
MSN
-
BOS
7h 53m2 stops
$373United Airlines
Thu, May 21 - Sun, May 24
American Airlines Logo
9:11 am - 12:41 pm
BOS
-
MSN
4h 30m1 stop
American Airlines Logo
6:16 am - 11:31 am
MSN
-
BOS
4h 15m1 stop
$393American Airlines
Booking Insights

KAYAK's insights & trends for Boston to Madison flights

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

Find cheap flights to Madison
Find cheap flights to Madison

Planning a trip from Boston to Madison? 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 Boston to Madison?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Boston to Madison, 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 Madison is August, where tickets cost $298 (return) on average. On the other hand, the most expensive months are January and March, where the average cost of round-trip tickets is $588 and $515 respectively.

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

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 $352 on average.

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

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 Madison, 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 Madison, you should book around 4 weeks before departure, which saves you about 46% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 17 weeks before departure.

Good to know

Low seasonJanuary
Cheapest flight$160
Best time to beat the crowds but there is an average 38% increase in price.
Most popular time to fly and prices are also 18% lower on average.
Flight from Boston to Madison

When to book flights from Boston to Madison

Are your dates flexible? Find out the best times to travel from Boston to Madison 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 Boston to Madison

  • What is the cheapest flight from Boston to Madison?

    In the last 3 days, the lowest price for a flight from Boston to Madison was $160 for a one-way ticket and $251 for a round-trip.

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

    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 Boston to Madison?

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

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

    The Airbus A319 is the aircraft model that flies most regularly on the Boston to Madison flight route.

  • Which airline alliances offer flights from Boston to Madison?

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

  • What is the most popular layover when flying to Madison from Boston?

    Chicago is the most popular layover city among KAYAK users traveling from Boston to Madison.

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

    The two airlines most popular with KAYAK users for flights from Boston to Madison are Delta and United Airlines. With an average price for the route of $410 and an overall rating of 7.9, Delta is the most popular choice. United Airlines is also a great choice for the route, with an average price of $399 and an overall rating of 7.4.

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

    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 Madison.

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

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

    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 Madison with an airline and back to Boston with another airline. Booking your flights between Boston and MSN 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 Boston to Madison?

    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 Madison from Boston 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 Boston to Madison

  • Looking for a cheap flight? 25% of our users found flights on this route for $919 or less one-way.

Reviews of the top 3 airlines serving from Boston to Madison

 
See real verified KAYAK customer reviews for airlines flying from Boston to Madison. 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 Madison? 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.
7.9
DeltaOverall score based on 8007 reviews
8.5Crew
7.9Comfort
7.9Entertainment
7.3Food
8.1Boarding
Airline reviews

Original flight was cancelled and when i was rebooked by the airline, they couldn't seat me in the same type of seat as I had originally booked (went from window/aisle to middle/middle and one was a bulkhead seat, and other wasn't in the same class)

6.0 GoodJeff, Dec 2025
JFK - MIA
Read more Delta reviews

Original flight was cancelled and when i was rebooked by the airline, they couldn't seat me in the same type of seat as I had originally booked (went from window/aisle to middle/middle and one was a bulkhead seat, and other wasn't in the same class)

Lady Pilot was perfect in every way wheels up to wheels down communication, professionalism, excellent on time departure and on time arrival, excellent communication! Fantastic job with Superb attitude!!

The food is terrible. The staff is wonderful. Comfort is good.

Left on time, a bit delayed due to headwinds most of the trip.

I fly Delta all the time, have Platinum Medallion status. But this route seems to have major problems with delays and seems to never leave on time! Have only taken it twice in the last two weeks, and each time it had delays of more than 1 hour... very disappointed!!!!

Good seats in Main cabin, excellent service and excellent landing

My flight was cancelled with no explanation after I had already cleared security. I was given 4 options to rebook, only one being non-stop like I had paid for. I grabbed it. It was 4 plus hours later and then took off even later. Biggest complaint is that I booked early and had an aisle seat. They gave me a "window" seat in front of the exit row, so the seat did not decline. I weigh all of 103 #s and it was tight for me! For what I paid, I feel I was kind of ripped off. I think they should have given me the empty comfort seat for the inconvenience. There was no apology nor any explanation as to why the flight was cancelled. My guess is it benefitted Delta in some way.

Very smooth, on-time, and pleasantly uneventful flight. The team at the gate and on board were professional and genuinely courteous. The pilot kept us well updated throughout, and both takeoff and landing were steady and enjoyable without any drama. Just a good, solid flight. Thank you! 💗

Staff was exceptional! Everyone was kind, professional and friendly making the trip very pleasant. Thank you!

No lunch on a x-country flight scheduled for 10:50 am departure, arrived 5+ hrs later. That requires a black box label before you pay for the tickets. Worst, when I checked in online, it's specifically said that lunch was served on his flight for economy Plus passengers.

It was nice to have gotten up upgraded to first class with a meal on a three hour flight

United have really come back. Airport and boarding process is clear and good, app and information also very good

Flight was delayed 8 times. We were sitting at the airport for 14 hours. We got 2 hours of sleep (if that) on what was not meant to be a red-eye.

After a delay at the gate, C3, at Ohare on Sunday, I left my Blk ski coat on the bench at the gate, lost! Please review my lob claim, thx.

Very bad! They kept delaying my flight and wouldn’t do anything about it

They brought an empty plane to the gate. Then a flight delay was announced for maintenance and waiting on a part. I was then put on a flight to San Francisco instead with a connecting flight to my final destination. Arrived at my final destination 2 hours late.

The only downside was my cell phone charger wouldn’t work in the charging port but everyone else’s would work in them all. My cell phone cable works fine in my hotel room in Frankfurt.

Flight team stood out for perzonal attention, kindness at bright cheery attitudes at 8am. Very helpful.

Ot was overall fine. Left on time and had basic snacks. Weather was finicky but that’s not the airlines fault.

Very thoughtful flight attendant offered me water immediately since I had run to make my connection.

The boarding was as always, the crew tried their best but not enough. The food was a disaster I had dietary restrictions that were half met because the company did not loaded the food for the flight. The entertainment screen was fine but content was not and also they removed the free messaging option from the flight and they charged 30 dollars for that crappy bandwidth. This flight is not worth the cost and the company is going down on quality.

Awful. They won’t help me with anything. I booked on American but they abdicated to Iberia. The ticket was overpriced. Everything negative

it was fine, decent flight... dont get food besides cookies or pretzels so not sure why you ask about food. same for entertainment..

I got sick nothing contagious but distressing and the care I received by Kayla? Keighly the flight attendant will be memorable for ever. Thank You

I got sick nothing contagious but distressing enough and the care I received on the flight was astounding.

Waaay too small plane. They also need to up the size of the overhead bins. I would love to keep me 3k with of camera equipment in my hard case baggahe instead of it being thrown into the belly of the plane

Attendants were pleasant and the flight was smooth and relaxed.

A little late at the start but all worked out well.

It was fine. No drinks nor snacks offered though. I thought that was unusual.

I liked the humor of the captain and crew on the flight from Flagstaff to Dallas. They were humorous.

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

Information on your arrival and departure airports