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Cheap flights from Madison to Portland

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      Travelers and cabin class, 1 Adult, Economy

      Compare Madison to Portland flight deals

      Find the cheapest month or even day of the year to fly to Portland

      Book the best Portland fare with no extra fees

      Flight deals from Madison to Portland

      Looking for a cheap last-minute deal or the best round-trip flight from Madison Airport to Portland Airport? If you want to travel next month, round-trip fares start from $305. Find the lowest prices on one-way and round-trip tickets right here.
      Portland.$290 per passenger.Departing Sat, Sep 26, returning Wed, Sep 30.Round-trip flight with United.Outbound indirect flight with United, departing from Madison on Sat, Sep 26, arriving in Portland.Inbound indirect flight with United, departing from Portland on Wed, Sep 30, arriving in Madison.Price includes taxes and charges.From $290, select.
      Portland.$291 per passenger.Departing Tue, Sep 29, returning Tue, Oct 6.Round-trip flight with United.Outbound indirect flight with United, departing from Madison on Tue, Sep 29, arriving in Portland.Inbound indirect flight with United, departing from Portland on Tue, Oct 6, arriving in Madison.Price includes taxes and charges.From $291, select.
      Portland.$304 per passenger.Departing Fri, Oct 16, returning Tue, Oct 20.Round-trip flight with United.Outbound indirect flight with United, departing from Madison on Fri, Oct 16, arriving in Portland.Inbound indirect flight with United, departing from Portland on Tue, Oct 20, arriving in Madison.Price includes taxes and charges.From $304, select.
      Portland.$305 per passenger.Departing Thu, Aug 13, returning Wed, Aug 19.Round-trip flight with United.Outbound indirect flight with United, departing from Madison on Thu, Aug 13, arriving in Portland.Inbound indirect flight with United, departing from Portland on Wed, Aug 19, arriving in Madison.Price includes taxes and charges.From $305, select.
      Portland.$319 per passenger.Departing Thu, Nov 5, returning Sun, Nov 8.Round-trip flight with Delta.Outbound indirect flight with Delta, departing from Madison on Thu, Nov 5, arriving in Portland.Inbound indirect flight with Delta, departing from Portland on Sun, Nov 8, arriving in Madison.Price includes taxes and charges.From $319, select.
      Portland.$365 per passenger.Departing Tue, Mar 16, returning Sat, Mar 20.Round-trip flight with United.Outbound indirect flight with United, departing from Madison on Tue, Mar 16, arriving in Portland.Inbound indirect flight with United, departing from Portland on Sat, Mar 20, arriving in Madison.Price includes taxes and charges.From $365, select.
      Portland.$369 per passenger.Departing Wed, Dec 30, returning Mon, Jan 4.Round-trip flight with Delta.Outbound indirect flight with Delta, departing from Madison on Wed, Dec 30, arriving in Portland.Inbound indirect flight with Delta, departing from Portland on Mon, Jan 4, arriving in Madison.Price includes taxes and charges.From $369, select.
      Portland.$409 per passenger.Departing Fri, Jul 31, returning Thu, Aug 6.Round-trip flight with United.Outbound indirect flight with United, departing from Madison on Fri, Jul 31, arriving in Portland.Inbound indirect flight with United, departing from Portland on Thu, Aug 6, arriving in Madison.Price includes taxes and charges.From $409, select.
      Portland.$492 per passenger.Departing Sun, Jan 24, returning Fri, Jan 29.Round-trip flight with Breeze Airways.Outbound indirect flight with Breeze Airways, departing from Madison on Sun, Jan 24, arriving in Portland.Inbound indirect flight with Breeze Airways, departing from Portland on Fri, Jan 29, arriving in Madison.Price includes taxes and charges.From $492, select.
      Portland.$498 per passenger.Departing Mon, Jul 27, returning Fri, Jul 31.Round-trip flight with Breeze Airways and jetBlue.Outbound indirect flight with Breeze Airways, departing from Madison on Mon, Jul 27, arriving in Portland.Inbound indirect flight with jetBlue, departing from Portland on Fri, Jul 31, arriving in Madison.Price includes taxes and charges.From $498, select.

      Find the cheapest month to fly from Madison to Portland

      We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Madison to Portland flights are currently cheapest in September.
      Jul
      from $498
      Aug
      from $305
      Sep
      from $290
      Oct
      from $304
      Nov
      from $319
      Dec
      Find prices
      Jan
      from $492
      Feb
      Find prices
      Mar
      from $365
      Apr
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      May
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      Jun
      Find prices

      Madison to Portland: Alternative routes

      Compare routes from Madison to Portland below. You may find an airport to fly into that's cheaper, faster, or easier than Portland.

      Portland

      4km from central Portland
      ClosestCheapest
      from $290
      Search flights

      Portsmouth

      79km from central Portland
      from $555
      Search flights

      Augusta

      82km from central Portland
      from $716
      Search flights

      Madison to Portland: Flight information

      The things to know before you go.
      Cheapest flight found$290
      Cheapest month to flySeptember

      Finding cheap flights from Madison to Portland: Frequently asked questions

      The best price we found for a round-trip flight from Madison to Portland is $290. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.
      Currently, there are no airlines that fly direct from Madison to Portland. But we found flights with one or more stops from $290.
      There are no flights flying from Madison to Portland, as of July 2026.
      The cheapest month to fly from Madison to Portland is usually September.
      After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Madison Airport to Portland Airport on Saturday, September 26, 2026.
      No airlines currently offer direct flights between Madison Airport and Portland Airport. Most routes have one or more stops.
      We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to Portland but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.

      We crunched all the numbers in our flight calendar, and it looks like the cheapest time to book a flight to Portland is around 40 days in advance, so don’t leave your flight to the last minute.

      Currently, United offers the cheapest flight tickets to Portland.

      Traveling from Madison Airport (MSN) to Portland Airport (PWM): what you need to know

      • To ensure you get on your MSN to PWM flight, leave plenty of time to check in and find your gate. Arriving two hours ahead of international departures and an hour before domestic flights is the standard rule.

      • During popular months like August, it's best to get to the airport earlier. Arrive two hours before domestic departures and four hours ahead for an international flight whenever you're flying during peak periods in general.

      • Think about adding a stopover when booking your ticket from Madison Airport to Portland Airport. Simply deselect 'Direct flights only' to break up your trip, or even explore someplace new along the way. Here are some options between MSN and PWM:

        • Chicago O'Hare International Airport

        • Detroit Wayne County Airport

        • Washington Ronald Reagan Airport

      How to find the cheapest flights from Madison Airport (MSN) to Portland Airport (PWM)

      • $218 is currently the best price for a one-way Madison Airport to Portland Airport flight. Return flights start at $290. These fares can change based on availability.

      • Don't leave everything to the last moment. You're more likely to get cheap tickets from MSN to PWM if you book in advance. Airlines often have some fantastic early bird deals.

      • The 'Whole month' search tool shows you the cheapest flights from Madison Airport to Portland Airport across every month. It's a great way to find a bargain if your travel dates aren't set in stone.

      • Save time searching for cheap flights from MSN to PWM by setting up a Price Alert. You'll receive an email or notification on the app when a new discounted fare appears.

      • Discover the perfect flight for you with the help of the filters. To see the 'Best,' 'Cheapest' or 'Fastest' flights from Madison Airport to Portland Airport, use the 'Sort by' tool. You can also filter results by airline, departure and arrival times, and journey duration.

      Handy information about Madison Airport (MSN)

      • The address for MSN is 4000 International Lane.

      • When it comes to the on-time performance of Madison Airport, 75% of flights arrive within the expected timeframe.

      • Central Madison to Madison Airport is approximately 13 kilometers. Depending on traffic, it'll take you about 20 minutes to get there if you're ride-sharing, catching a cab or driving.

      • Expect a trip time of roughly 40 minutes on public transport.

      • Taking an early flight from Madison Airport to Portland Airport? Avoid the stress of rushing to the terminal (and catch some extra z's) by picking one of these hotels close to MSN:

      Arriving at Portland Airport (PWM)

      Getting from Portland Airport (PWM) to central Portland

      • The street address for PWM is 1001 Westbrook Street.

      • Portland Airport is approximately 8 kilometers from the center of Portland. The drive time takes about 15 minutes.

      • If you're taking public transport, expect a journey time of about 30 minutes.

      When to fly to Portland Airport (PWM)

      • Visit Portland during the high season if you want a bustling atmosphere, but keep in mind prices are typically higher. Alternatively, plan your flights from Madison Airport to Portland Airport in the low season for a slower pace and better deals.

      • When reserving your flight from Madison Airport to Portland Airport, consider the type of weather you enjoy. July is the warmest month in Portland, with temperatures ranging from 14ºC (57ºF) to 25ºC (77ºF).

      • Search for cheap tickets from MSN to PWM in January if you like traveling in cooler conditions. Temperatures are at their lowest around then, ranging between -10ºC (14ºF) and 3ºC (37ºF) on average.

      Explore more of the United States

      • You've seen Portland, now it's time to explore more of the United States. Travel about 451 kilometers south-west to New York to check off its top attractions. From Central Park to Statue of Liberty and Metropolitan Museum of Art, your itinerary will be busy.

      • If you're ready to explore another corner of the United States, head for Boston, about 161 kilometers south-west of Portland. Museum of Fine Arts Boston, Freedom Trail and USS Constitution Museum are key highlights.

      Plan the rest of your trip from Madison to Portland

      Prices shown on this page are estimated lowest prices only. Found in the last 12 days.