PWM - MSN

$293 Find Cheap Flights from Portland to Madison - Compare and Save

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Everything you should know

Cheapest round-trip
$335
Typical prices: $328-$504
American Airlines
Sat 11/3Mon 11/12
PWM - MSN • 1 stop
Cheapest one-way
$293
Typical prices: $198-$298
Breeze Airways
Fri 11/30
PWM - MSN • 2 stops
Nonstop flights
Not available
There are currently no direct flights between Portland and Madison. You'll need to take a connecting flight to reach the destination.
Insights
Insights
When to travel
February
Cheapest • 28% price drop
October
Most popular
Good to know
+1
Good to know
+1
Top layover airports
Washington, D.C. Reagan-National (DCA)
Cheapest • Avg $360 (round-trip)
Detroit Metropolitan Wayne County (DTW)
Shortest trip • 5h 05m (one-way)
Insights
Insights
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Flight Deals

Cheap Flights from Portland to Madison (PWM-MSN)

 
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Portland to Madison

Tue, Nov 3 - Thu, Nov 12
American Airlines Logo
4:10 pm - 10:27 pmPWM  Portland-MSN Madison Truax Field
7h 17m1 stop Washington, D.C. Reagan-National
American Airlines Logo
5:00 am - 11:58 amMSN  Madison Truax Field-PWM Portland
5h 58m1 stop Chicago O'Hare Intl
$335American Airlines
Wed, Oct 28 - Sun, Nov 1
American Airlines Logo
5:45 pm - 12:12 amPWM  Portland-MSN Madison Truax Field
7h 27m1 stop Chicago O'Hare Intl
American Airlines Logo
6:02 am - 11:53 amMSN  Madison Truax Field-PWM Portland
4h 51m1 stop Chicago O'Hare Intl
$335American Airlines
Wed, Nov 4 - Thu, Nov 12
American Airlines Logo
11:07 am - 4:53 pmPWM  Portland-MSN Madison Truax Field
6h 46m1 stop Philadelphia
American Airlines Logo
6:02 am - 11:58 amMSN  Madison Truax Field-PWM Portland
4h 56m1 stop Chicago O'Hare Intl
$335American Airlines
Wed, Oct 28 - Sun, Nov 1
Delta Logo
1:52 pm - 11:03 pmPWM  Portland-MSN Madison Truax Field
10h 11m2 stops New York LaGuardia Atlanta Hartsfield-Jackson
Delta Logo
7:00 am - 11:57 amMSN  Madison Truax Field-PWM Portland
3h 57m1 stop Detroit Metropolitan Wayne County
$340Delta
Tue, Nov 3 - Thu, Nov 12
Delta Logo
1:52 pm - 11:03 pmPWM  Portland-MSN Madison Truax Field
10h 11m2 stops New York LaGuardia Atlanta Hartsfield-Jackson
Delta Logo
9:58 am - 4:10 pmMSN  Madison Truax Field-PWM Portland
5h 12m1 stop Detroit Metropolitan Wayne County
$340Delta
Mon, Dec 21 - Fri, Dec 25
Delta Logo
7:00 am - 1:03 pmPWM  Portland-MSN Madison Truax Field
7h 03m1 stop New York LaGuardia
Delta Logo
10:00 am - 5:30 pmMSN  Madison Truax Field-PWM Portland
6h 30m1 stop New York LaGuardia
$349Delta
Fri, Dec 25 - Fri, Jan 1
United Airlines Logo
4:28 pm - 9:41 pmPWM  Portland-MSN Madison Truax Field
6h 13m1 stop Chicago O'Hare Intl
United Airlines Logo
7:00 am - 7:03 pmMSN  Madison Truax Field-PWM Portland
11h 03m2 stops Chicago O'Hare Intl Washington, D.C. Dulles Intl
$371United Airlines
Wed, Oct 28 - Sun, Nov 1
United Airlines Logo
5:30 am - 11:54 amPWM  Portland-MSN Madison Truax Field
7h 24m2 stops Washington, D.C. Dulles Intl Chicago O'Hare Intl
United Airlines Logo
6:25 am - 2:27 pmMSN  Madison Truax Field-PWM Portland
7h 02m2 stops Chicago O'Hare Intl Washington, D.C. Dulles Intl
$387United Airlines
Fri, Dec 25 - Fri, Jan 1
United Airlines Logo
4:28 pm - 9:41 pmPWM  Portland-MSN Madison Truax Field
6h 13m1 stop Chicago O'Hare Intl
United Airlines Logo
7:00 am - 3:31 pmMSN  Madison Truax Field-PWM Portland
7h 31m1 stop Chicago O'Hare Intl
$390United Airlines
Wed, Oct 28 - Sun, Nov 1
Breeze Airways Logo
5:09 pm - 5:20 pmPWM  Portland-MSN Madison Truax Field
25h 11m2 stops Raleigh-Durham Orlando
Breeze Airways Logo
6:00 pm - 1:57 pmMSN  Madison Truax Field-PWM Portland
18h 57m3 stops Orlando Raleigh-Durham Columbus
$943Breeze Airways
Booking Insights

Price, demand and travel trends for Portland to Madison flights

Use KAYAK data on prices, travel dates, airlines and seasonal trends to compare options and book flights from Portland to Madison with more confidence.

How much is a round-trip flight from Portland to Madison?

Round-trip flights from Portland to Madison start at $335. Prices are typical for this route right now, with typical round-trip fares ranging from $328 to $504. The lowest price found in the past 5 days was $335 on American Airlines.

What's the cheapest day of the week to fly from Portland to Madison?

Tuesday is the cheapest day of the week to fly from Portland to Madison, it is 25% cheaper than the average day. Monday is the most expensive day with flight prices 22% higher than average. Based on deals found by KAYAK users in the last 12 months.

What is the cheapest month to fly from Portland to Madison?

•February is the cheapest month to fly from Portland to Madison at $278 round-trip.
•July ($586) and December ($583) are the most expensive months.
•The price difference between flying in the cheapest and most expensive months is 110% on average.
This is based on KAYAK aggregated and averaged internal data over the past 12 months.

Find deals

Key details for Portland to Madison flights

Low season

February

Cheapest flight

$293
Best time to beat the crowds with an average 28% drop in price.
Most popular time to fly and prices are also 4% lower on average.
Flight from Portland to Madison

When to book flights from Portland to Madison

Are your dates flexible? Find out the best times to travel from Portland to Madison based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price

Your Portland to Madison flight questions, answered

Find helpful route details based on KAYAK data, including flight times, airports, airlines and booking questions.

  • Which airports can I use when flying from Portland to Madison?

    Flights from Portland to Madison usually depart from Portland (PWM) and arrive at Madison Truax Field (MSN).

  • What cabin classes can I book on flights from Portland to Madison?

    Only Economy Class is available on flights from Portland to Madison.

  • Which airports do connecting flights from Portland to Madison pass through?

    One-stop flights from Portland to Madison most commonly connect through:

    • Chicago O'Hare Intl (ORD) - 59% of one-stop connections
    • Washington, D.C. Reagan-National (DCA) - 23% of one-stop connections
    • Detroit Metropolitan Wayne County (DTW) - 8% of one-stop connections
    • New York LaGuardia (LGA) - 4% of one-stop connections

    Chicago O'Hare Intl (ORD) handles the largest share of one-stop connections on this route.

  • Can I save money by using flexible dates for flights from Portland to Madison?

    Yes. Being flexible with your travel dates can save you up to 39% on the Portland to Madison route. Tuesday is the cheapest departure day at $290 round-trip on average, while Monday is the most expensive at $473, a difference of $183. KAYAK's flexible dates feature shows options up to 3 days before and after your selected dates, making it easier to compare nearby fares.

  • How long is a flight from Portland to Madison?

    A nonstop flight from Portland to Madison takes 0h 00m, covering 953 miles.

  • Do I need a passport to fly from Portland to Madison?

    No, a passport is not required for this domestic route, but you will need a real ID-compliant driver's license, a state ID, or another TSA-accepted form of identification.

  • Have flight prices from Portland to Madison changed much recently?

    Yes. Based on fares seen in the past 5 days, round-trip prices on this route showed a wide range, from about $335 to $1,438. That means the highest observed fare was about 4x higher than the lowest one.

  • How are flight prices from Portland to Madison looking right now?

    One-way fares from Portland to Madison are currently higher than usual. Average one-way flight prices are about $500, which is 97% above the typical average for this route.

  • How much time can I save by choosing a different layover airport from Portland to Madison?

    Flying via Detroit Metropolitan Wayne County (DTW) gives the shortest average 1-stop total travel time at 5h 05m, compared with 5h 28m via Washington, D.C. Reagan-National (DCA) and 5h 34m via Chicago O'Hare Intl (ORD).

  • What is the time difference between Portland and Madison?

    Madison is 1 hour behind Portland (Central Time vs Eastern Time). Plan for the time shift when scheduling connections or first-day activities.

  • What car rental options are available at Madison Truax Field Airport (MSN)?

    Madison Truax Field Airport (MSN) hosts 5 major car rental companies, with daily rates starting from around $31 for economy cars. Top options include:
    • Hertz
    • Alamo
    • Enterprise Rent-A-Car
    • Avis
    • Budget

  • How much should I expect to pay for a Portland to Madison flight?

    Round-trip flights from Portland to Madison range from $328 to $504, with an average of $385 over the past 12 months. Anything below $328 counts as a good deal.

Your guide to booking Portland to Madison flights

Get tips on when to book, when to fly and what to know before your trip.
  • If your dates can be flexible, aim for a Tuesday departure instead of Monday. On this route, Tuesday flights average $290 - about $183 less than Monday (39% savings) based on the last 12 months.
  • If you can choose when to travel, plan your Portland to Madison trip for February. Fares historically average $278 round-trip in that month - typically $308 less than the most expensive month, which is July (based on the last 12 months).
  • If you're arriving late at night and need somewhere to stay, check out these hotels close to Madison Truax Field Airport.
    - Doubletree by Hilton East Madison East
    - Best Western East Towne Suites
    - Holiday Inn Madison At The American Center By IHG

More options for your flight from Portland to Madison

Complete your trip to Madison with a hotel stay or car rental

Car rentals in Madison
Hotels in Madison
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