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Cheap flights from Madison to Boston from $100

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Madison to Boston departing on 8/31. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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0 bags

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Find the cheapest flights from Madison to Boston

Cheap round-trip flights

Delta Logo
5:26 pm - 11:59 pmMSN-BOS
5h 33m1 stop
Delta Logo
10:30 am - 2:27 pmBOS-MSN
4h 57m1 stop
$251Delta
Find Deal
Sat, Sep 13 - Tue, Sep 16
American Airlines Logo
2:48 pm - 10:09 pmMSN-BOS
6h 21m1 stop
American Airlines Logo
4:50 pm - 10:57 pmBOS-MSN
7h 07m1 stop
$255American Airlines
Find Deal
Wed, Sep 24 - Mon, Sep 29
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
Tue, Sep 9 - Tue, Sep 16
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
Thu, Sep 4 - Sun, Sep 7
American Airlines Logo
7:56 am - 4:04 pmMSN-BOS
7h 08m1 stop
American Airlines Logo
11:00 am - 4:04 pmBOS-MSN
6h 04m1 stop
$260American Airlines
Find Deal
Tue, Sep 2 - Thu, Sep 4
American Airlines Logo
5:08 pm - 10:54 pmMSN-BOS
4h 46m1 stop
American Airlines Logo
3:57 pm - 9:51 pmBOS-MSN
6h 54m1 stop
$264American Airlines
Find Deal
Mon, Aug 18 - Mon, Aug 25
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
$269United Airlines
Find Deal
Thu, Sep 4 - Mon, Sep 8
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
Fri, Nov 21 - Mon, Nov 24
American Airlines Logo
6:44 pm - 11:59 pmMSN-BOS
4h 15m1 stop
American Airlines Logo
5:02 pm - 11:03 pmBOS-MSN
7h 01m1 stop
$289American Airlines
Find Deal
Sat, Aug 23 - Mon, Aug 25
United Airlines Logo
8:15 am - 4:28 pmMSN-BOS
7h 13m2 stops
United Airlines Logo
7:45 am - 1:49 pmBOS-MSN
7h 04m1 stop
$326United Airlines
Find Deal
Wed, Sep 3 - Sat, Sep 6

Delta flights from Madison to Boston

Our best Delta deals on Madison to Boston flight tickets
Delta
Sep 13
MSN5:26 pmMadison Truax Field
5h 33m
1 stop
BOS11:59 pmBoston Logan Intl
Sep 16
BOS10:30 amBoston Logan Intl
4h 57m
1 stop
MSN2:27 pmMadison Truax Field
$251
Find similar
Delta
Sep 4
MSN6:00 amMadison Truax Field
6h 20m
1 stop
BOS1:20 pmBoston Logan Intl
Sep 7
BOS5:34 amBoston Logan Intl
5h 33m
1 stop
MSN10:07 amMadison Truax Field
$259
Find similar
Delta
Aug 7
MSN6:00 amMadison Truax Field
6h 20m
1 stop
BOS1:20 pmBoston Logan Intl
Aug 12
BOS7:10 amBoston Logan Intl
5h 10m
1 stop
MSN11:20 amMadison Truax Field
$269
Find similar

United Airlines flights from Madison to Boston

Our best United Airlines deals on Madison to Boston flight tickets
United Airlines
Sep 9
MSN8:15 amMadison Truax Field
7h 13m
2 stops
BOS4:28 pmBoston Logan Intl
Sep 16
BOS6:10 amBoston Logan Intl
4h 38m
1 stop
MSN9:48 amMadison Truax Field
$256
Find similar
United Airlines
Sep 4
MSN6:30 amMadison Truax Field
6h 43m
2 stops
BOS2:13 pmBoston Logan Intl
Sep 8
BOS6:10 amBoston Logan Intl
4h 35m
1 stop
MSN9:45 amMadison Truax Field
$269
Find similar
United Airlines
Sep 3
MSN8:15 amMadison Truax Field
7h 13m
2 stops
BOS4:28 pmBoston Logan Intl
Sep 6
BOS7:45 amBoston Logan Intl
7h 04m
1 stop
MSN1:49 pmMadison Truax Field
$326
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Madison to Boston 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, momondo users made 832,500 searches. Data last updated August 2, 2025.
Use the filters below to find and compare flights from Madison to Boston that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

MadisonBoston

MSN - BOS

MSNBOS

Madison Truax Field

Sat 9/13

5:26 pm-11:59 pm

1 stop5h 33m

Boston Logan Intl

Tue 9/16

10:30 am-2:27 pm

1 stop4h 57m

$251

MadisonBoston

MSN - BOS

MSNBOS

Madison Truax Field

Wed 9/24

2:48 pm-10:09 pm

1 stop6h 21m

Boston Logan Intl

Mon 9/29

4:50 pm-10:57 pm

1 stop7h 07m

$255

MadisonBoston

MSN - BOS

MSNBOS

Madison Truax Field

Tue 9/9

8:15 am-4:28 pm

2 stops7h 13m

Boston Logan Intl

Tue 9/16

6:10 am-9:48 am

1 stop4h 38m

$256

MadisonBoston

MSN - BOS

MSNBOS

Madison Truax Field

Thu 9/4

6:00 am-1:20 pm

1 stop6h 20m

Boston Logan Intl

Sun 9/7

5:34 am-10:07 am

1 stop5h 33m

$259

MadisonBoston

MSN - BOS

MSNBOS

Madison Truax Field

Tue 9/2

7:56 am-4:04 pm

1 stop7h 08m

Boston Logan Intl

Thu 9/4

11:00 am-4:04 pm

1 stop6h 04m

$260

MadisonBoston

MSN - BOS

MSNBOS

Madison Truax Field

Mon 8/18

5:08 pm-10:54 pm

1 stop4h 46m

Boston Logan Intl

Mon 8/25

3:57 pm-9:51 pm

1 stop6h 54m

$264

MadisonBoston

MSN - BOS

MSNBOS

Madison Truax Field

Thu 9/4

6:30 am-2:13 pm

2 stops6h 43m

Boston Logan Intl

Mon 9/8

6:10 am-9:45 am

1 stop4h 35m

$269

MadisonBoston

MSN - BOS

MSNBOS

Madison Truax Field

Fri 11/21

4:00 pm-10:19 pm

1 stop5h 19m

Boston Logan Intl

Mon 11/24

7:00 am-12:44 pm

1 stop6h 44m

$274

MadisonBoston

MSN - BOS

MSNBOS

Madison Truax Field

Sat 8/23

6:44 pm-11:59 pm

1 stop4h 15m

Boston Logan Intl

Mon 8/25

5:02 pm-11:03 pm

1 stop7h 01m

$289

MadisonBoston

MSN - BOS

MSNBOS

Madison Truax Field

Wed 9/3

8:15 am-4:28 pm

2 stops7h 13m

Boston Logan Intl

Sat 9/6

7:45 am-1:49 pm

1 stop7h 04m

$326

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Boston from

How to get the cheapest flight ticket from Madison to Boston

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest month to fly to Boston?

In general, August is the cheapest month to fly from Madison to Boston. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $336. If you aren’t able to travel during the month of August, then book flights to Boston from Madison during September instead. Flights to Boston in September, while not as cheap as those in August, still average around $348.

What is the cheapest day to depart on your flight to Boston?

The cheapest day to depart from Madison to Boston is on a Wednesday when prices can be found for as low as $376. Be sure to avoid booking your departure on a Thursday as prices are generally higher than usual. According to our data, the average ticket price to Boston on Thursday is $587.

What is the cheapest time of day to depart on your flight to Boston?

According to our data, the cheapest time of day to fly to Boston is in the afternoon. momondo users have found flights departing from Madison to Boston in the afternoon for as low as $376. Keep in mind that these prices may fluctuate based on what airline you choose and the time of year you plan to travel. In the morning is when there is more demand to fly to Boston, so prices are often more expensive at around $516 per ticket.

What is the cheapest Madison Truax Field to Boston Logan Intl flight route?

Fly from Madison Truax Field to Boston Logan Intl for the best Madison Truax Field - Boston Logan Intl flight prices

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

You are more likely to see cheaper flights to Boston from Madison when booking weeks ahead of your departure date. In general, you can expect to find flights to Boston for around $438 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Boston from Madison for as low as $306 on momondo.

What cabin class options are available on Madison Truax Field to Boston Logan Intl flights?

There are 1 cabin classes available to choose from on Madison Truax Field to Boston Logan Intl flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

How have Madison to Boston flight prices changed over time?

As of August 2025, prices for Madison to Boston flights are approximately 28% more expensive when compared to flights at the same time last year.

When to book flights from Madison to Boston

Are you open to changing your travel dates? Check out the ideal times to fly from Madison to Boston according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Madison to Boston (MSN to BOS) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Madison to Boston

Best Price Found

$100

Fastest flight time

2h 25m

Direct flights

Mon, Fri and Sat

Airports in Boston

1 airport
The best one-way flight to Boston from Madison in the past 72 hours is $100. The best round-trip flight deal from Madison to Boston found on momondo in the last 72 hours is $251.
The fastest flight from Madison to Boston takes 2h 25m
Direct flights go from Madison to Boston on Monday, Friday and Saturday. Airlines offering direct flights are: Delta and American Airlines.
There is 1 airport near Boston: Boston Logan Intl (BOS)
Search flight deals

  • How far is Madison Truax Field to Boston Logan Intl by plane?

    There are 929.9 mi between Madison Truax Field and Boston Logan Intl. Typically, this will take 2h 25m by plane in normal conditions.

  • When did momondo last update prices for flights from Madison Truax Field Airport to Boston Logan Intl Airport?

    Prices for flights from Madison Truax Field Airport to Boston Logan Intl Airport are refreshed on a daily basis.

  • How many operators does momondo search for flights from Madison Truax Field Airport to Boston Logan Intl Airport?

  • How old do you have to be to fly from Madison Truax Field Airport to Boston Logan Intl Airport?

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Madison Truax Field Airport to Boston Logan Intl Airport.

  • What documentation or ID do you need to fly to Boston Logan Intl Airport?

    The travel and health documents you'll need for your trip to Boston Logan Intl Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Boston Logan Intl Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Madison to Boston?

  • What is the most popular airline from Madison to Boston?

Best airlines flying from Madison to Boston

Compare and see reviews for airlines that fly from Madison to Boston with momondo
Airline
Rating
Free Cancellation
Price
American AirlinesPriceFrom $254Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
DeltaPriceFrom $255Free CancellationRating
8.0
7,983 reviews
Search Delta flights
United AirlinesPriceFrom $297Free CancellationRating
7.4
8,904 reviews
Search United Airlines flights

Traveling to a place near Boston?

Book flights to Boston if you plan to visit one of these locations
Hampton Beach
Salem
Ogunquit
Hampton
Old Orchard Beach
York Beach
Plymouth
Kennebunkport
Nashua
Cambridge
Narragansett
Laconia
Brockton
South Yarmouth
Gloucester
Concord
Everett
Wells
Falmouth
Middletown

Why use momondo?

Why should I use momondo to find a flight deal from Madison to Boston?

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Madison to Boston. Millions of users trust and use momondo every year so you are in good hands.

Can I find flights from Madison to Boston with flexible booking policies on momondo?

All flight searches from Madison to Boston on momondo can be filtered to show those which offer flexible booking policies.

How can momondo help me find flights from Madison to Boston?

momondo helps you find the best flight between Madison and Boston by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

I’m not ready to book a flight from Madison to Boston right now. Can momondo alert me if prices change?

Of course. momondo tracks the price of Madison to Boston flights. All you need is a valid email address and we will do the rest; it is that quick and easy.

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