$229 Cheap Flights from Madison (MSN) to Boston (BOS)

Madison (MSN) to Boston (BOS) at a glance

Travel from Madison (MSN) to Boston (BOS) with a selection of airlines offering convenient routes on this domestic short-haul journey. Discover options for nonstop flights to Boston as you compare itineraries from full-service carriers that align with your budget and schedule. Whether you're eager to explore Boston's iconic attractions or its charming neighborhoods, find essential information for flights from Dane County Regional Airport to Logan International Airport.

• Fastest flight duration: around 2h 30m non-stop
• Route distance: roughly 900 miles (1,450 km)
• Flights per week: around 15+ flights with multiple daily departures on average
• Typical fares (one-way): economy tickets often range from $125–$435, depending on seasonality and how far ahead you book

Flights from Dane County Regional Airport (MSN) to Logan International Airport (BOS)

Recent traveler bookings reveal the top airlines flying from Madison to Boston, featuring both non-stop and one-stop flights. Common layover options include O'Hare International Airport (ORD) with a layover of about 1 hour and 15 minutes, Philadelphia International Airport (PHL) also around 1 hour and 15 minutes, and LaGuardia Airport (LGA) for approximately 1 hour and 15 minutes. This variety allows you to mix and match factors like price, total travel time, and cabin class to find the ideal itinerary.

• American Airlines: This full-service airline provides both non-stop and one-stop flights, with one-way prices usually falling between $125 and $390. It represents around 53% of the departures for this route, featuring a typical one-stop flight duration of 3 hours and 45 minutes, leading to an overall travel time of about 5 hours.
• United: Another full-service option, United offers one-stop flights with one-way fares generally ranging from $125 to $475. Approximately 25% of the departures on this route are operated by United, with an in-flight time of 3 hours and 45 minutes, resulting in a total travel duration of around 5 hours, including layover time.
• Delta: A full-service carrier, Delta provides both non-stop and one-stop services, with one-way fares typically between $125 and $490. It accounts for roughly 22% of the departures on this route, featuring a standard one-stop journey time of 3 hours and 45 minutes, leading to an overall travel time close to 5 hours.

Travelers flying from Madison to Boston can opt for an upgrade, with Delta providing both first class and premium economy service, while American Airlines offers first class seating.

Best time to fly from Madison (MSN) to Boston (BOS)

The most popular months for travelers flying from Madison to Boston are March, August, and October, when peak temperatures in Boston reach up to 72.7°F in August. If you prefer quieter travel, consider December, the least busy and relatively cheaper time to visit with fewer crowds and temperatures around 36.3°F. For better deals, September usually offers the lowest average one-way fare around $199. Flight availability peaks in August, with approximately 24 flights per week, making it easier to find convenient departure times. January has the fewest flights, with approximately 12 flights per week.

• Cheapest time to fly: September usually offers good deals with average one-way fare around $199, roughly 15% cheaper than the yearly average.
• More budget-friendly months to fly: August and June typically offer average one-way fares of around $214.
• Most flight options: August has the highest number of flights from Madison to Boston, with approximately 24 flights per week, giving you more flexibility in scheduling your trip.

*Average one-way fare is based on Expedia flight booking data from January 2025 to April 2026 for the specified route and travel class and may change depending on availability, dates, and demand.

Alternative route from Madison (MSN) to Boston (BOS)

• Appleton to Boston (ATW-BOS): Appleton International Airport (ATW) is located approximately 88 miles from Dane County Regional Airport (MSN). One-way economy ticket prices on this route generally fall between $125 and $410, influenced by the season and how far in advance you book. Travelers can choose from both one-stop and multi-stop flights, with common layover spots at O'Hare International Airport (ORD) and Detroit Metropolitan Wayne County Airport (DTW). Major airlines on this route include American Airlines and Delta, with first-class service also offered.

How to find the best prices for flights from Madison (MSN) to Boston (BOS)

Getting some of the best deals on flights from Madison to Boston is all about timing and flexibility. Here are some key tips to help you save:

1. Best times to book and fly: cheaper fares are usually found when booking 2-8 weeks in advance, which aligns with when most travelers make their reservations. Departures in the afternoon (12pm-6pm) often offer lower prices, while morning flights (5am-12pm) are the most popular. Additionally, flying on Wednesday generally provides cheaper options, even though Thursday is the preferred travel day for many.
2. Set up price alerts: stay updated on price changes by using Expedia's Price Tracker. Receive alerts when fares drop for your selected route.
3. Bundle and save: bundle your flight and hotel to save on Expedia, or unlock a hotel deal after booking your flight.*
4. Compare flight options: use Expedia's search tool to compare airlines, routes, direct vs. non-direct flights, and flight times. You can also sort by price to find the most affordable options.
5. Stay flexible with dates: being open to different travel days can sometimes help you find better prices on flights and hotels.
6. Think about luggage: nowadays, it's important to check the airline's baggage policies to find the best value. That may be paying for an additional carry-on bag or booking a ticket with checked luggage included. Either way, double-check your allowance before confirming your booking to avoid excess baggage fees at the airport.

*Members only. Savings vary and are not available on all bundles. Select hotels.

Arriving at Logan International Airport from Dane County Regional Airport

Boston welcomes travelers from Madison with a range of transport options based on price, convenience, and proximity. Here's how to reach Boston efficiently:

• Hotel transfer: Transfers offer a convenient way to reach your hotel in Boston, with private rides that can be arranged in advance.
• Car rental: Renting a car from Logan International Airport is a great option if you plan to explore and sightsee beyond the city. Browse cheap car rentals at Logan International Airport on Expedia.
• Taxi/ride-hailing: Taxis and ride-hailing services may be available from designated pickup areas outside the terminal, check locally on arrival.
• Public transportation: From Logan International Airport, travelers will find key transport links within a short distance. Airport Station, a metro station, is about 0.9 miles away by car, while Chelsea Station, a train station, is located approximately 2.8 miles from the airport. Additionally, Boston Seaport, a seaport, is about 3.1 miles away by car.

Madison to Boston Flights

The cheapest times to fly from Madison to Boston

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Madison to Boston are during the month of November. You can find some of the cheapest flights from Madison to Boston with Expedia's search tool and vast selection of airlines.

The best time to book a flight from Madison to Boston

Sunday is one of the best days to book for cheap flights from Madison to Boston: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

How to find cheap round-trip tickets from Madison to Boston

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Madison to Boston in 2026. You can also book with separate airlines for your outbound and return journeys, from $229 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Madison to Boston flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

You could also save big by booking one of Expedia's vacation packages. Bundling together your Madison to Boston airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

*Terms apply.

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.