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$41 Cheap Flights to Madison, CT

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Popular airlines to Madison

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How much is the cheapest flight to Madison?

Prices were available within the past 7 days and start at $41 for one-way flights and $85 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Breeze Airways
Breeze Airways
Breeze Airways
Breeze Airways
Avelo Airlines

What you need to know for your flight to Madison

Flights to Madison at a glance

Traveling to Madison is easy, thanks to budget airlines providing a range of travel options. Explore different flight schedules and journey times to select the best direct flight that aligns with your budget and itinerary while you discover the city's renowned attractions and neighborhoods.

  • Major airport near Madison: Tweed - New Haven Regional Airport (HVN)
  • Flights per week: 180+ flights arriving at Madison airport
  • Number of airlines that fly to Madison: around 2 carriers

Popular airport near Madison

Madison is a charming city ideal for outdoor enthusiasts and adventure seekers. Visitors are drawn to its vibrant culture, romantic ambiance, and scenic landscapes. The area is conveniently served by a major airport, making it easy for travelers to reach this delightful destination in Connecticut.

  • Tweed - New Haven Regional Airport (HVN): Situated in New Haven County, Connecticut, approximately 17 miles from Madison, this airport provides both domestic and international flights, linking to about 25 cities in the U.S. and 1 overseas destination. Breeze and Avelo Airlines are among the key carriers operating here.

Top routes to Madison

  • Orlando (MCO) to Madison (HVN), with one-way fares starting at around $40
  • Raleigh (RDU) to Madison (HVN), with one-way fares starting at around $35
  • West Palm Beach (PBI) to Madison (HVN), with one-way flights starting at around $40
  • Charleston (CHS) to Madison (HVN), with one-way flights starting at around $30
  • Tampa (TPA) to Madison (HVN), with one-way tickets available from around $50

Cheapest routes to Madison

  • Baltimore (BWI) to Madison (HVN), with affordable one-way prices from around $30
  • Norfolk (ORF) to Madison (HVN), with affordable one-way prices from around $30
  • Charleston (CHS) to Madison (HVN), with low-cost one-way tickets from around $30
  • Richmond (RIC) to Madison (HVN), with budget one-way fares from around $35
  • Raleigh (RDU) to Madison (HVN), with low one-way fares from around $35

*Flight times and fares vary by season and availability and are based on one-way routes

Top airlines with flights to Madison

  • Breeze: Operating flights to Tweed - New Haven Regional Airport (HVN), Breeze handles about 54% of arrivals in Madison. Expect an average one-way ticket price of roughly $90.
  • Avelo Airlines: Also flying to Tweed - New Haven Regional Airport (HVN), Avelo Airlines accounts for nearly 46% of arrivals to Madison. The typical one-way fare is around $100.

Best time to fly to Madison

The most popular months for travelers to fly to Madison are March, April, and June, when peak temperatures in Madison can reach up to 66.4°F in June. If you prefer quieter travel, consider September, the least busy and relatively cheaper time to visit with fewer crowds and temperatures around 66.2°F. For better deals, August usually offers the lowest average one-way fare around $85, roughly 15% cheaper than the yearly average. Looking for additional cheaper months to fly? October, September, and May offer average one-way fares of around $89, making them good options for flexible travelers.

calendar iconMonthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinesscrowd level iconDemandprice iconAverage one-way Fare
January31.3°F (-0.4°C)Light RainMostly SunnyAverage$95
February32.4°F (0.2°C)Light RainMostly SunnyAverage$119
March38.5°F (3.6°C)Light RainMostly SunnyHigh$115
April48.2°F (9.0°C)Light RainMostly SunnyHigh$123
May57.9°F (14.4°C)Light RainMostly SunnyAverage$90
June66.4°F (19.1°C)Light RainMostly SunnyHigh$99
July73.8°F (23.2°C)Light RainMostly SunnyAverage$92
August72.7°F (22.6°C)Light RainMostly SunnyAverage$85
September66.2°F (19.0°C)Light RainMostly SunnyLow$89
October56.5°F (13.6°C)Light RainMostly SunnyAverage$88
November45.5°F (7.5°C)Light RainMostly SunnyLow$119
December37.8°F (3.2°C)Light RainMostly SunnyLow$104

*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.

How to save money on a flight to Madison

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

  1. 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.
  2. Set up price alerts—as an Expedia member you can use Price Tracking to receive notifications when flight prices change.
  3. Bundle and save—book a flight and unlock a hotel deal on Expedia*, or explore our Madison hotel and flight deals.
  4. 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 baggage allowance before confirming your booking to avoid excess baggage fees at the airport.
  5. Earn miles—you can earn airline miles when you book your Madison flight with Expedia. Just select your frequent flyer program and enter your program number when confirming your booking.

*For members. Select hotels.

Arriving in Madison

Madison welcomes travelers through its range of transport options based on price, convenience, and proximity. Here's how to reach Madison efficiently:

  • Public transportation: From Tweed - New Haven Regional Airport, New Haven Seaport, a seaport, is located about 1.3 miles away by car, while New Haven State Street Station, a train station, is situated approximately 3.5 miles away by car, providing convenient access to both sea and rail travel.
  • Hotel transfer: Transfers offer a convenient way to reach your hotel in Madison, with options including free hotel shuttles and private rides, which can be arranged in advance.
  • Car rental: Renting a car in Madison is a good option if you plan to explore and sightsee beyond the city. Browse cheap car rentals in Madison on Expedia.
  • Taxi/ride-hailing: Taxis and ride-hailing services may be available from designated pickup areas outside the terminal, check locally on arrival.

Where to stay around Madison

  • Chester: Chester is located 9 miles away from Madison and is an ideal destination for travelers seeking outdoor adventures and romantic escapes. This charming city boasts beautiful scenery and a variety of recreational options. Key attractions include the breathtaking Gillette Castle State Park, perfect for hiking and enjoying nature, and the Essex Steam Train, which offers a cultural glimpse into the region’s history. Nearby, visitors can explore the picturesque lake and beach, making Chester a delightful stop for those looking to soak in the outdoors and scenic beauty.
  • Essex: Essex is located 13 miles drive away from Madison, offering a perfect blend of outdoor activities and romantic settings. This quaint city features a lovely golf course, expansive recreational areas, and a welcoming resort atmosphere. Visitors can take in stunning views at the nearby beach and marina, while attractions like the Essex Steam Train and Gillette Castle State Park provide enriching cultural experiences. Goose Island is another highlight, ideal for beach lovers eager to explore the serene coastal environment of Essex.
  • North Branford: North Branford is located 10 miles away from Madison and is a vibrant city well-suited for those interested in outdoor sports and cultural experiences. With various educational venues and music concerts to enjoy, travelers will find plenty to keep them engaged. Highlights include the historic Yale University, which showcases academic excellence, and Bill Miller’s Castle, perfect for romantic outings. The Stony Creek - Thimble Islands Historic District also offers a glimpse into the area’s rich history, making North Branford a fascinating place to explore.

Tips for short-haul flights to Madison

For quick getaways, efficiency is key. Here is how to make your short-haul journey smoother:

  • Pack light and skip checked bags—with budget airlines, traveling with just a carry-on is often more cost-effective. Maximize your packing space by using mini toiletries, wearing your bulkiest clothing, and planning versatile outfits. This approach also helps you avoid the hassle of waiting at baggage claim upon arrival.
  • Bring your own entertainment—many short-haul flights may not provide in-flight entertainment. To keep yourself occupied, download TV shows, movies, music, or podcasts ahead of time, and consider bringing a book. Remember to fully charge your devices before you board.
  • Arrive at the airport in plenty of time—for short or domestic flights, it’s advisable to arrive at least 1.5 to 2 hours before your departure time, taking traffic and security lines into account.
  • Bring your own snacks and water—pack some snacks and a refillable water bottle to stay hydrated and save money while at the airport.

Tips for long-haul flights to Madison

Flying long-haul sometimes requires extra planning to ensure a comfortable journey:

  • Select your seat in advance—for longer flights, choosing your seat is essential for comfort. Full-service airlines often allow free seat selection once online check-in opens, which typically occurs 24–48 hours before your flight. Some airlines may permit seat selection even earlier.
  • Arrive at the airport in plenty of time—make sure to arrive at the airport at least 3 hours before departure for international flights to accommodate check-in, security, and immigration procedures.
  • Relax at the airport—if you have some extra time, take a moment to explore the shops, grab a coffee, or unwind at the gate or in a departure lounge if you have access. Airport Wi-Fi is generally free and available.
  • Adjust to the new time zone mid-flight—begin aligning your body clock by changing your watch and adjusting your sleep schedule to reflect your destination's time zone. Aim to sleep or stay awake during the flight according to the local time of your arrival to help minimize jet lag.

Frequently asked questions

What month is the cheapest to fly to Madison?
Schedule your trip for September if you want to land a deal on your fare. It's the cheapest month to fly to Madison. If possible, avoid traveling during busy periods such as public holidays or major events.
Which US cities have the cheapest flights to Madison?
Score cheap flights to Madison from Washington, Chicago and Orlando. These cities typically offer the lowest fares to this destination. But bear in mind that stopovers, seasonality and demand will also influence rates, so remain flexible and book when you spot a bargain.
Which US cities fly direct to Madison?
There are 32 US cities that you can fly to Madison nonstop from. Explore the options by selecting the "Direct flights only" box on Expedia and find the best departure point for your trip. Here are some of the leading cities to take off from:
  • Washington
  • Chicago
  • Orlando
  • Atlanta
  • Charlotte
How to find a cheap flight to Madison?
Book early to maximize your chances of getting cheap flights to Madison. Also, consider traveling during off-season months like January and February. If you fly on a Thursday, you can save 16% on average compared to departing on a Sunday.* Save time checking every day and set up a price alert on the Expedia app. We'll send you a notification when fares change.*Best day of the week to book, depart and ideal booking window recommendations based on average round-trip ticket prices for January through August 2023, sourced from Airline Reporting Corporation's (ARC) global airline sales database. Percentages noted are averages.
How to get a cheap last-minute flight to Madison?
While booking in advance is usually the best way to save cash, don't worry if your Madison getaway is last minute. You can still find cheap flights to Madison, especially if your plans have a little leeway. Try switching up your travel dates, looking at different ticket types or jetting out of an alternative airport.
How far in advance should I book a flight to Madison?
To snap up some of the best deals on domestic journeys, book your flight to Madison 28 days ahead of your travel dates. For international flights, book between two and four months in advance. This increases your chances of locking in the departure dates and times you want.**Best day of the week to book, depart and ideal booking window recommendations based on average round-trip ticket prices for January through August 2023, sourced from Airline Reporting Corporation's (ARC) global airline sales database. Percentages noted are averages.
Which day of the week is the cheapest day to buy a plane ticket to Madison?
You'll save an average of 8% if you purchase tickets on a Sunday rather than Fridays, which tend to be the most expensive day to book.* When it comes to scoring a cheap flight to Madison, timing makes a difference.*Best day of the week to book, depart and ideal booking window recommendations based on average round-trip ticket prices for January through August 2023, sourced from Airline Reporting Corporation's (ARC) global airline sales database. Percentages noted are averages.
Which airlines fly to Madison?
A total of 10 airlines connect 34 airports around the world to Madison. Here are a few of the most popular airlines to Madison, where Bradley Intl. Airport (BDL) is the major gateway:
  • Delta Air Lines
  • American Airlines
  • United Airlines
  • JetBlue Airways
Where do you fly into Madison?
Madison's main point of arrival is Tweed - New Haven Regional Airport (HVN). If you're looking for more nearby options when flying to Madison, consider Hartford, CT (HFD-Hartford - Brainard), Bradley Intl. Airport (BDL) or MacArthur Airport (ISP). You can also opt to fly to Madison through New London, CT (GON-Groton - New London).
How far is the airport from central Madison?
You'll be around 17 mi west of the center of Madison after touching down at Tweed - New Haven Regional Airport (HVN).
Can I save money by booking a Madison trip package?
Bundle your hotel and flight and you could save hundreds of dollars. Better yet, you can add extras like activities and car rentals to your Madison flight and hotel package deal. With Expedia, it's a breeze to look after all your Madison travel arrangements in one place.
Can I change or cancel my flight to Madison?
It's often possible to change or cancel your flight to Madison. Many airlines let you cancel your flights for free within 24 hours of making your booking. However, some flights are non-refundable, and airlines may offer you a credit toward a future trip instead of a direct refund. To find affordable flights to Madison with flexible change policies, check the "Changes included" or "No cancel fee" filters when you search. Want more information? Head to our Customer Service Portal.

*Flight schedules are subject to change.

*Available to One Key members.

Book with confidence

Tips to find the cheapest flights to Madison

The cheapest day to fly

Get started finding a cheap flight to Madison on Expedia by either choosing a deal on this page or entering into the search bar your travel dates, origin airport, and whether you want roundtrip or one-way airfare. You can filter for flexibility, number of stops, airline, and departure/arrival times to find the best flight for you.

The cheapest month to fly

September is the cheapest month to fly to Madison. This coincides with the low season when fewer people travel. Whichever month you travel in, though, be sure to book at least a month in advance if you want to score cheap tickets to Madison. ARC's data shows that domestic flights booked 28 days or more before departure are typically 24% cheaper than those booked last minute.

The most affordable time to book a flight

Typically, a Sunday can be the cheapest time to book a flight to Madison, according to ARC’s data. On average, you could save between 6% and 13% by booking on a Sunday instead of a Friday, which is the most expensive day to make a reservation.

The cheapest round-trip tickets to Madison

The lowest price for round-trip flights to Madison in 2026 starts from from $85, while one-way tickets start from from $41. Expedia's effective search tool is one of the best ways to find a budget airfare. Simply enter your dates, and within seconds, it'll show you a vast selection of the cheapest flights to Madison. If you have a preferred departure time or airline, you can use the handy filters to customize your search.

The cheapest airlines flying to Madison

Breeze Airways, Avelo Airlines are just some of the airlines that can typically offer cheap tickets to Madison. You can find their most affordable flights by using the “airline” search filter and then sorting prices from low to high. As a trusted partner of the world's leading airlines, Expedia offers you some of the best airfare deals to Madison and countless more destinations worldwide.

The most affordable airports to fly into

To view the cheapest airports to fly into for Madison, simply order your search results from lowest to highest price. Expedia's search tool compares flight prices for all airports close to your destination, so you don't have to manually search them one by one to find the cheapest flight to Madison. If you have a preferred place to fly into, take advantage of the “arrival airport” filter to narrow down your search on Expedia.

Save with a package

With Expedia's amazing package deals, you could save hundreds of dollars by booking your Madison plane tickets together with your accommodations, car rental, or activities. Just select the search wizard's “package” option to view some of the cheapest deals. Look out for the green savings label to see how much you're saving.

Date flexibility for the cheapest flights to Madison

If you can be flexible with your travel dates, it's a good idea to broaden your search by comparing prices on different days. This will open up more options, meaning you could uncover a less expensive flight to Madison.

Stopover savings

The cheapest tickets to Madison are sometimes those with a stopover. Book one of these flights, and you'll change planes at an airport en route to Madison. While the overall travel time might be longer than a non-stop flight, you may decide it's worth it for the money saved.

Get Expedia's Price Drop Protection

Price Drop Protection means that if your flight gets cheaper after booking, you'll be credited the difference*. This gives you peace of mind that you're getting one of the cheapest flights to Madison for your chosen departure. Expedia's Price Drop Protection is available for a small fee but is free to One Key Gold and Platinum tier members.

*Terms apply.

Use our Price Tracking feature

Expedia's Price Tracking feature is another great tool that removes the guesswork from finding cheap flights to Madison. Simply download the free Expedia app to your smart device and activate Madison flight price alerts for your travel dates. There's even a price predictor tool that uses historical data to indicate the best time to book, giving you peace of mind that you'll nab the lowest prices.

Book with Expedia

As well as Price Drop Protection and Price Tracking, Expedia's close partnership with a vast selection of the world's leading airlines means you're sure to find cheap flights to Madison. Plus, the One Key rewards program lets you earn real cash rewards on most bookings that you can use to save money on future trips. Best of all, it's free to join, and members often unlock exclusive discounts, too.

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

Tips to find the cheapest flights to Madison

Travel information

Destination airport
Tweed - New Haven Regional
Destination airport IATA code
HVN
Destination city name
New Haven
Roundtrip price
$85

Trending flights to Madison

Prices were available within the past 7 days and start at $41 for one-way flights and $85 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Avelo Airlines

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