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Madison

$126+ Cheap flights from Boston to Madison (BOS - 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 11/19. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — MSN
nov. 29 — dic. 61
sáb. 11/29
sáb. 12/6
1 adult, Economy
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Cheap flight deals from Boston to Madison

Discover tips and strategies to find the most affordable flight options for your journey from Boston (BOS) to Madison (MSN). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated octubre 30, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$255
(United Airlines)

One-way from

$126
(United Airlines)

Popular in

January

Cheapest in

August

Average price

$392

Good one-way deal

$919 or less
Provider with most accurate pricing for Boston Logan Intl-Madison Truax Field flight deals.
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Provider most trusted by Cheapflights users for Boston Logan Intl-Madison Truax Field flights.
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From Boston Logan Intl to Madison Truax Field
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One-way flight from Boston Logan Intl to Madison Truax Field
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Highest demand for flights based on searches. 18% potential increase in price ($100 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($14 potential savings vs. average RT price).
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Average for round-trip flights in October 2025
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Price to beat on a one-way flight from Boston Logan Intl to Madison Truax Field.
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Find flight deals from Boston to Madison

Cheapest flights from Boston to Madison
Explore the most affordable flight options available from Boston to Madison. Find the lowest fares from popular airlines and budget airlines, with prices last updated on octubre 30, 2025.

This United Airlines deal was found by Cheapflights users on 10/30. 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.
sáb. 11/227:50 amBOS - MSN
1 stop4h 53mUnited Airlines
vie. 11/286:30 amMSN - BOS
1 stop5h 14mUnited Airlines
Deal found 10/30$259
This American Airlines deal was found by Cheapflights users on 10/29. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 11/215:25 amBOS - MSN
1 stop6h 15mAmerican Airlines
lun. 11/248:00 amMSN - BOS
1 stop6h 57mAmerican Airlines
Deal found 10/29$284
This American Airlines deal was found by Cheapflights users on 10/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 11/135:25 amBOS - MSN
1 stop6h 15mAmerican Airlines
dom. 11/165:00 amMSN - BOS
1 stop5h 33mAmerican Airlines
Deal found 10/30$307
This Delta deal was found by Cheapflights users on 10/28. 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.
jue. 11/135:50 amBOS - MSN
1 stop7h 53mDelta
dom. 11/166:00 amMSN - BOS
1 stop6h 54mDelta
Deal found 10/28$309
This United Airlines deal was found by Cheapflights users on 10/30. 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.
sáb. 11/152:21 pmBOS - MSN
2 stops7h 14mUnited Airlines
dom. 11/166:30 amMSN - BOS
1 stop5h 14mUnited Airlines
Deal found 10/30$314
This United Airlines deal was found by Cheapflights users on 10/29. 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.
vie. 11/213:09 pmBOS - MSN
1 stop5h 12mUnited Airlines
lun. 11/246:30 amMSN - BOS
2 stops6h 59mUnited Airlines
Deal found 10/29$328
This United Airlines deal was found by Cheapflights users on 10/29. 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.
mié. 11/264:29 pmBOS - MSN
1 stop7h 16mUnited Airlines
lun. 12/12:48 pmMSN - BOS
1 stop6h 01mUnited Airlines
Deal found 10/29$329
This United Airlines deal was found by Cheapflights users on 10/29. 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.
vie. 12/510:30 amBOS - MSN
2 stops11h 17mUnited Airlines
lun. 12/82:48 pmMSN - BOS
1 stop5h 57mUnited Airlines
Deal found 10/29$334
This United Airlines deal was found by Cheapflights users on 10/30. 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.
jue. 11/1310:25 amBOS - MSN
2 stops9h 56mUnited Airlines
dom. 11/166:50 pmMSN - BOS
1 stop4h 55mUnited Airlines
Deal found 10/30$336
This United Airlines deal was found by Cheapflights users on 10/30. 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.
vie. 11/1410:40 amBOS - MSN
1 stop5h 14mUnited Airlines
mar. 11/186:30 amMSN - BOS
2 stops7h 52mUnited Airlines
Deal found 10/30$338

Cheapflights Fare Finder

 
Customize your flight search to find flights from Boston 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 octubre 30, 2025.
Use the filters below to find and compare flights from Boston to Madison that are best for you.

Fly from

Boston

Fly to

Madison

Route

Depart

Return

Price

BostonMadison

BOS - MSN

BOSMSN

Boston Logan Intl

sáb. 11/22

7:50 am-11:43 am

1 stop4h 53m

Madison Truax Field

vie. 11/28

6:30 am-12:44 pm

1 stop5h 14m

$259

BostonMadison

BOS - MSN

BOSMSN

Boston Logan Intl

vie. 12/5

8:05 am-12:42 pm

1 stop5h 37m

Madison Truax Field

lun. 12/8

1:22 pm-7:40 pm

1 stop5h 18m

$259

BostonMadison

BOS - MSN

BOSMSN

Boston Logan Intl

lun. 12/15

5:22 pm-9:48 pm

1 stop5h 26m

Madison Truax Field

lun. 1/19

3:09 pm-11:30 pm

1 stop7h 21m

$259

BostonMadison

BOS - MSN

BOSMSN

Boston Logan Intl

vie. 2/20

9:45 am-2:07 pm

1 stop5h 22m

Madison Truax Field

mié. 2/25

3:58 pm-11:57 pm

2 stops6h 59m

$260

BostonMadison

BOS - MSN

BOSMSN

Boston Logan Intl

vie. 11/21

5:25 am-10:40 am

1 stop6h 15m

Madison Truax Field

lun. 11/24

8:00 am-3:57 pm

1 stop6h 57m

$284

BostonMadison

BOS - MSN

BOSMSN

Boston Logan Intl

jue. 11/13

5:25 am-10:40 am

1 stop6h 15m

Madison Truax Field

dom. 11/16

5:00 am-11:33 am

1 stop5h 33m

$307

BostonMadison

BOS - MSN

BOSMSN

Boston Logan Intl

vie. 11/14

1:42 pm-7:42 pm

1 stop7h 00m

Madison Truax Field

dom. 11/16

5:00 am-11:33 am

1 stop5h 33m

$307

BostonMadison

BOS - MSN

BOSMSN

Boston Logan Intl

jue. 11/13

5:50 am-12:43 pm

1 stop7h 53m

Madison Truax Field

dom. 11/16

6:00 am-1:54 pm

1 stop6h 54m

$309

BostonMadison

BOS - MSN

BOSMSN

Boston Logan Intl

vie. 11/14

5:50 am-10:11 am

1 stop5h 21m

Madison Truax Field

lun. 11/17

1:24 pm-7:43 pm

1 stop5h 19m

$309

BostonMadison

BOS - MSN

BOSMSN

Boston Logan Intl

mié. 11/19

4:15 pm-8:35 pm

1 stop5h 20m

$126

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/29

Showing 1-10 of 19 results
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Compare providers for flights from Boston to Madison

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Boston to Madison in October.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Boston-Madison flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Boston-Madison flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Boston-Madison flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Boston-Madison flights, Cheapflights users trust eDreams the most. eDreams has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Boston-Madison flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Boston to Madison

Have a flexible travel schedule? Discover the best time to fly to Madison from Boston 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 Boston to Madison

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

Use this chart to determine the optimal time to book a round-trip flight from Boston to Madison. Price data was last updated on October 24, 2025.

The price you pay for your flight from Boston to Madison may vary depending on when you book. For the best chance of a lower fare, look to book 90 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

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

Currently, September is the cheapest month in which you can book a flight from Boston to Madison (average of $98). Flying from Boston to Madison in December is currently the most expensive (average of $267). 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 BOS to MSN?

Find hourly flight availability from Boston 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 octubre 30, 2025.

A simple way to save on the total cost of your ticket is to fly from Boston to Madison in the morning. If you’re flexible enough to do this you can expect to save up to 61% on your trip compared to booking a flight in the evening.

Reviews of airlines servicing Madison

Get insights into the airlines that provide service to Madison. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Madison. Reviews last updated octubre 30, 2025.
Read through reviews of airlines operating flights from Boston to Madison, such as Delta, United Airlines, and American Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Delta
7.9
Good
7,998 reviews

Overall

7.9

Entertainment

7.9

Boarding

8.2

Food

7.3

Crew

8.5

Comfort

7.9

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
Delta
7.9
Good
7,998 reviews
Delta
7.9
Good
7,998 reviews

Overall

7.9

Entertainment

7.9

Boarding

8.2

Food

7.3

Crew

8.5

Comfort

7.9

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
United Airlines
7.4
Good
8,998 reviews
Delta
7.9
Good
7,998 reviews

Overall

7.9

Entertainment

7.9

Boarding

8.2

Food

7.3

Crew

8.5

Comfort

7.9

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
American Airlines
7.2
Good
11,035 reviews
Delta
7.9
Good
7,998 reviews

Overall

7.9

Entertainment

7.9

Boarding

8.2

Food

7.3

Crew

8.5

Comfort

7.9

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.

Related info for your journey

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

  • How long is the flight from Boston to Madison?

    Airlines like United Airlines, Delta, and American Airlines fly from Boston to Madison in about 5h 22m. The time it takes to get you to your destination can typically vary by up to 15m. The distance from Boston to Madison is about 929 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the cheapest airlines flying from Boston to Madison round-trip?

    According to our current data, Delta ($250), American Airlines ($254), and United Airlines ($306) offers the cheapest pricing from Boston to Madison. Delta is priced at 43% lower than the current average price of a flight leaving 3 months from now.

  • What are the most reliable airlines from Boston to Madison?

    Looking for the most reliable airlines to get you to your destination on time? Our data shows these are most likely to get you from Boston to Madison on time: American Airlines (0%), KLM (0%), Envoy Air (0%).

  • What are the cheapest flights from Boston to Madison?

    On average you can expect to pay $1,566 for a flight from Boston to Madison. The cheapest flight overall is $919 while the most popular route, (Boston Logan Intl - Madison Truax Field) is currently priced at $251.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Boston 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 Boston to Madison?

    Currently, September is the cheapest month in which you can book a flight from Boston to Madison (average of $98). Flying from Boston to Madison in December is currently the most expensive (average of $267). 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

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Alternative routes for Boston to Madison

See prices for flight routes from nearby airports that may be better suited for you.
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Top 3 airlines flying from Boston to Madison

Discover the top 3 airlines that operate flights from Boston 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 octubre 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$250Average$499FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$254Average$376FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$306Average$457FlexibilityNo cancel feeOn-time69%

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