HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Madison

$100+ Cheap flights from Massachusetts to Madison (MSN)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 5/10. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — MSN
Mar 15 — Mar 221
Sun 3/15
Sun 3/22
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Massachusetts to Madison with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap flight deals from Massachusetts to Madison

Cheapest flights from Massachusetts to Madison
Explore the most affordable flight options available from Massachusetts to Madison. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 13, 2026.

This Delta deal was found by Cheapflights users on 2/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/126:00 am
BDL
-
MSN
1 stop5h 31m
Delta
Sat 3/146:28 pm
MSN
-
BDL
1 stop3h 44m
Delta
Deal found 2/13$269
This Delta deal was found by Cheapflights users on 2/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/261:54 pm
BOS
-
MSN
Nonstop2h 53m
Delta
Wed 9/24:25 pm
MSN
-
BOS
Nonstop2h 34m
Delta
Deal found 2/13$273
This United Airlines deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/86:00 am
BDL
-
MSN
2 stops9h 00m
United Airlines
Sat 7/112:35 pm
MSN
-
BDL
1 stop6h 17m
United Airlines
Deal found 2/11$274
This Delta deal was found by Cheapflights users on 2/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/181:54 pm
BOS
-
MSN
Nonstop2h 53m
Delta
Mon 6/224:25 pm
MSN
-
BOS
Nonstop2h 34m
Delta
Deal found 2/12$279
This United Airlines deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/2510:05 am
BDL
-
MSN
1 stop5h 52m
United Airlines
Sat 2/286:30 am
MSN
-
BDL
1 stop6h 40m
United Airlines
Deal found 2/10$279
This Delta deal was found by Cheapflights users on 2/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/295:30 am
BOS
-
MSN
1 stop4h 16m
Delta
Tue 8/114:25 pm
MSN
-
BOS
Nonstop2h 34m
Delta
Deal found 2/13$283
This United Airlines deal was found by Cheapflights users on 2/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/116:00 am
BOS
-
MSN
1 stop5h 12m
United Airlines
Tue 3/176:30 am
MSN
-
BOS
2 stops7h 46m
United Airlines
Deal found 2/13$284
This United Airlines deal was found by Cheapflights users on 2/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/119:20 am
BOS
-
MSN
1 stop6h 38m
United Airlines
Tue 3/246:30 am
MSN
-
BOS
1 stop5h 19m
United Airlines
Deal found 2/13$286
This Kiwi.com deal was found by Cheapflights users on 2/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/37:00 am
BOS
-
MSN
1 stop11h 25m
Multiple Airlines
Mon 6/86:50 pm
MSN
-
BOS
1 stop14h 57m
Multiple Airlines
Deal found 2/13$288
This Delta deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/271:54 pm
BOS
-
MSN
Nonstop2h 53m
Delta
Thu 9/34:25 pm
MSN
-
BOS
Nonstop2h 34m
Delta
Deal found 2/10$289
This Delta deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/252:30 pm
ALB
-
MSN
1 stop5h 43m
Delta
Sun 3/15:38 am
MSN
-
ALB
1 stop5h 17m
Delta
Deal found 2/10$289
This United Airlines deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/1112:10 pm
BOS
-
MSN
1 stop5h 59m
United Airlines
Wed 3/186:30 am
MSN
-
BOS
2 stops7h 01m
United Airlines
Deal found 2/10$291

Find flight deals from Massachusetts to Madison

Keep the following information in mind while searching for Massachusetts to Madison flight deals. Data was last updated February 13, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$269
(American Airlines)

One-way from

$100
(Kiwi.com)

Popular in

April

Cheapest in

January

Average price

$404

Good one-way deal

$919 or less
Provider with most accurate pricing for Boston Logan Intl-Madison Truax Field flight deals.
Search Deals
Provider most trusted by Cheapflights users for Boston Logan Intl-Madison Truax Field flights.
Search Deals
From Massachusetts to Madison Truax Field
Search Deals
One-way flight from Massachusetts to Madison Truax Field
Search Deals
Highest demand for flights based on searches. 13% potential increase in price ($56 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($8 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2026
Search Deals
Price to beat on a one-way flight from Massachusetts to Madison Truax Field.
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Massachusetts to Madison that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated February 13, 2026.
Use the filters below to find and compare flights from Massachusetts to Madison that are best for you.

Fly from

Massachusetts

Fly to

Madison

Route

Depart

Return

Price

HartfordMadison

BDL - MSN

BDLMSN

Hartford Bradley Intl

Wed 7/8

6:23 pm-11:57 pm

1 stop6h 34m

Madison Truax Field

Sat 7/11

2:35 pm-9:52 pm

1 stop6h 17m

$269

HartfordMadison

BDL - MSN

BDLMSN

Hartford Bradley Intl

Thu 3/12

6:00 am-10:31 am

1 stop5h 31m

Madison Truax Field

Sat 3/14

6:28 pm-11:12 pm

1 stop3h 44m

$269

HartfordMadison

BDL - MSN

BDLMSN

Hartford Bradley Intl

Sat 3/14

4:58 pm-10:32 pm

1 stop6h 34m

Madison Truax Field

Tue 3/17

6:30 am-2:15 pm

1 stop6h 45m

$269

BostonMadison

BOS - MSN

BOSMSN

Boston Logan Intl

Thu 6/18

1:54 pm-3:47 pm

Nonstop2h 53m

Madison Truax Field

Mon 6/22

4:25 pm-7:59 pm

Nonstop2h 34m

$279

HartfordMadison

BDL - MSN

BDLMSN

Hartford Bradley Intl

Sat 3/14

5:50 pm-10:34 pm

1 stop5h 44m

Madison Truax Field

Thu 3/19

6:00 am-1:57 pm

1 stop6h 57m

$279

HartfordMadison

BDL - MSN

BDLMSN

Hartford Bradley Intl

Wed 4/22

6:00 am-10:32 am

1 stop5h 32m

Madison Truax Field

Sun 4/26

6:30 pm-11:56 pm

1 stop4h 26m

$279

BostonMadison

BOS - MSN

BOSMSN

Boston Logan Intl

Wed 7/29

5:30 am-8:46 am

1 stop4h 16m

Madison Truax Field

Tue 8/11

4:25 pm-7:59 pm

Nonstop2h 34m

$283

BostonMadison

BOS - MSN

BOSMSN

Boston Logan Intl

Wed 7/29

5:30 am-8:46 am

1 stop4h 16m

Madison Truax Field

Sat 8/8

4:25 pm-7:59 pm

Nonstop2h 34m

$283

BostonMadison

BOS - MSN

BOSMSN

Boston Logan Intl

Wed 3/11

11:02 am-2:58 pm

1 stop4h 56m

Madison Truax Field

Tue 3/24

6:30 am-3:16 pm

2 stops7h 46m

$284

AlbanyMadison

ALB - MSN

ALBMSN

Albany Intl

Wed 2/25

2:30 pm-7:13 pm

1 stop5h 43m

Madison Truax Field

Sun 3/1

5:38 am-11:55 am

1 stop5h 17m

$289

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/10

Showing 1-10 of 41 results
1
2
3
...
5

Best time to book a flight from Massachusetts to Madison

Have a flexible travel schedule? Discover the best time to fly to Madison from Massachusetts with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Massachusetts to Madison

What is the cheapest month to book a flight from Massachusetts to Madison?

Currently, September is the cheapest month in which you can book a flight from Massachusetts to Madison (average of $98). Flying from Massachusetts to Madison in December is currently the most expensive (average of $254). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from MA to MSN?

Find hourly flight availability from Massachusetts to Madison. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated February 13, 2026.

It’s typically best to fly out from Massachusetts to Madison at noon. Doing so could potentially save you 63% on the flight price compared to flying in the evening, which is usually more expensive.

Related info for your journey

Find useful and relevant information for your journey from Massachusetts to Madison. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to Madison from Massachusetts?

    Most people fly into Madison Truax Field (MSN) if they book a flight to Madison from Massachusetts. Truax Field is conveniently located just 5.4 mi from Madison’s city center.

  • How long is the flight from Massachusetts to Madison?

    For as low as $269, United Airlines can have you in Madison from Massachusetts in 5h 31m. The distance between Massachusetts and Madison is about 849 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What are the cheapest airlines to fly from Massachusetts to Madison one-way?

    For one-way options, check prices for American Airlines. According to our data, you can fly for as low as $125. Users have also found prices from $129 and $138 on Delta and United Airlines, respectively.

  • What are the most popular routes from Massachusetts to Madison?

    Most travelers choose Boston Logan Intl - Madison Truax Field, Hartford Bradley Intl - Madison Truax Field or Albany Intl - Madison Truax Field when deciding on the best route from Massachusetts to Madison.

  • What are the cheapest flights from Massachusetts to Madison?

    Looking at all options, your cheapest flight can be booked for $919. While the most popular route (Boston Logan Intl - Madison Truax Field) can be booked for $279 on average, our data indicates $1,566 when flying from Massachusetts to Madison.

  • Can I find deals for flights from Massachusetts to Madison that include hotel bookings?

    Yes. In addition to deals on Massachusetts to Madison flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Massachusetts to Madison?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Massachusetts to Madison.

  • Can I find deals for business class flights from Massachusetts to Madison?

    Yes. Cheapflights offers flight deals from Massachusetts to Madison by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Massachusetts to Madison?

    Currently, September is the cheapest month in which you can book a flight from Massachusetts to Madison (average of $98). Flying from Massachusetts to Madison in December is currently the most expensive (average of $254). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Madison?

Book flights to Madison if you plan to visit one of these locations
Portage
Middleton
Baraboo
Fitchburg

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Massachusetts to Madison

See prices for flight routes from nearby airports that may be better suited for you.
Dallas/Fort Worth to O'Hare Intl flights
John F Kennedy Intl to O'Hare Intl flights
Newark to O'Hare Intl flights
Los Angeles to O'Hare Intl flights
LaGuardia to O'Hare Intl flights
Baltimore to O'Hare Intl flights
Dulles Intl to O'Hare Intl flights
San Francisco to O'Hare Intl flights
Reagan-National to O'Hare Intl flights
Boston to O'Hare Intl flights
Denver to O'Hare Intl flights
Seattle to O'Hare Intl flights
Philadelphia to O'Hare Intl flights
Atlanta to O'Hare Intl flights
Sky Harbor Intl to O'Hare Intl flights
Ontario to O'Hare Intl flights
Sky Harbor Intl to Minneapolis flights
Raleigh to O'Hare Intl flights
Santa Ana to O'Hare Intl flights
Minneapolis to O'Hare Intl flights
Charlotte to O'Hare Intl flights
Austin to O'Hare Intl flights
George Bush Intcntl to O'Hare Intl flights
Dallas/Fort Worth to Minneapolis flights
Love Field to O'Hare Intl flights
Fort Lauderdale to O'Hare Intl flights
Atlanta to Minneapolis flights
Newark to Minneapolis flights
Hobby to O'Hare Intl flights
LaGuardia to Minneapolis flights
San Diego to O'Hare Intl flights
Miami to O'Hare Intl flights
Salt Lake City to O'Hare Intl flights
John F Kennedy Intl to Minneapolis flights
Seattle to Minneapolis flights
Los Angeles to Minneapolis flights
Tampa to O'Hare Intl flights
Boston to Minneapolis flights
San Francisco to Minneapolis flights
Orlando to O'Hare Intl flights
Denver to Minneapolis flights
San Jose to O'Hare Intl flights
Portland to O'Hare Intl flights
Cleveland to O'Hare Intl flights
O'Hare Intl to Minneapolis flights
Dulles Intl to Minneapolis flights
Detroit to O'Hare Intl flights
Hartford to O'Hare Intl flights
Baltimore to Minneapolis flights
Sacramento to O'Hare Intl flights

Top 3 airlines flying from Massachusetts to Madison

Discover the top 3 airlines that operate flights from Massachusetts to Madison. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated February 13, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$250Average$387FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$254Average$363FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$258Average$387FlexibilityNo cancel feeOn-time69%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.