Cheap Flights To Madison 2026

Madison Flights as Low as $369

These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Thu, Dec 31 - Tue, Jan 12
PNS
Pensacola Intl.
PWM
Portland Intl. Jetport
$369
Roundtrip
found 16 hours ago
Select Delta flight, departing Thu, Dec 31 from Pensacola Intl. to Portland Intl. Jetport, returning Tue, Jan 12, priced at $369 found 16 hours ago
Delta
Thu, Dec 31 - Mon, Jan 11
PNS
Pensacola Intl.
PWM
Portland Intl. Jetport
$374
Roundtrip
found 16 hours ago
Select Delta flight, departing Thu, Dec 31 from Pensacola Intl. to Portland Intl. Jetport, returning Mon, Jan 11, priced at $374 found 16 hours ago
Delta
Mon, Dec 21 - Wed, Jan 6
PNS
Pensacola Intl.
PWM
Portland Intl. Jetport
$394
Roundtrip
found 16 hours ago
Select Delta flight, departing Mon, Dec 21 from Pensacola Intl. to Portland Intl. Jetport, returning Wed, Jan 6, priced at $394 found 16 hours ago
Delta
Tue, Nov 17 - Tue, Dec 1
PNS
Pensacola Intl.
PWM
Portland Intl. Jetport
$399
Roundtrip
found 16 hours ago
Select Delta flight, departing Tue, Nov 17 from Pensacola Intl. to Portland Intl. Jetport, returning Tue, Dec 1, priced at $399 found 16 hours ago
Delta
Tue, Nov 17 - Sun, Dec 6
PNS
Pensacola Intl.
PWM
Portland Intl. Jetport
$406
Roundtrip
found 16 hours ago
Select Delta flight, departing Tue, Nov 17 from Pensacola Intl. to Portland Intl. Jetport, returning Sun, Dec 6, priced at $406 found 16 hours ago
Delta
Sat, Dec 5 - Fri, Dec 18
PNS
Pensacola Intl.
PWM
Portland Intl. Jetport
$409
Roundtrip
found 16 hours ago
Select Delta flight, departing Sat, Dec 5 from Pensacola Intl. to Portland Intl. Jetport, returning Fri, Dec 18, priced at $409 found 16 hours ago
Delta
Thu, Dec 31 - Sun, Jan 17
PNS
Pensacola Intl.
PWM
Portland Intl. Jetport
$411
Roundtrip
found 16 hours ago
Select Delta flight, departing Thu, Dec 31 from Pensacola Intl. to Portland Intl. Jetport, returning Sun, Jan 17, priced at $411 found 16 hours ago
Delta
Sat, Dec 5 - Sat, Dec 19
PNS
Pensacola Intl.
PWM
Portland Intl. Jetport
$419
Roundtrip
found 16 hours ago
Select Delta flight, departing Sat, Dec 5 from Pensacola Intl. to Portland Intl. Jetport, returning Sat, Dec 19, priced at $419 found 16 hours ago
Breeze Airways
Breeze Airways
Delta
Mon, Dec 21 - Sun, Jan 10
PNS
Pensacola Intl.
PWM
Portland Intl. Jetport
$431
Roundtrip
found 16 hours ago
Select Delta flight, departing Mon, Dec 21 from Pensacola Intl. to Portland Intl. Jetport, returning Sun, Jan 10, priced at $431 found 16 hours ago
American Airlines
United
Tue, Nov 24 - Tue, Dec 8
PNS
Pensacola Intl.
PWM
Portland Intl. Jetport
$520
Roundtrip
found 16 hours ago
Select United flight, departing Tue, Nov 24 from Pensacola Intl. to Portland Intl. Jetport, returning Tue, Dec 8, priced at $520 found 16 hours ago
Southwest Airlines
Delta
Sun, Nov 1 - Tue, Nov 17
VPS
Northwest Florida Regional
PWM
Portland Intl. Jetport
$674
Roundtrip
found 16 hours ago
Select Delta flight, departing Sun, Nov 1 from Northwest Florida Regional to Portland Intl. Jetport, returning Tue, Nov 17, priced at $674 found 16 hours ago
Delta
Sun, Nov 1 - Mon, Nov 16
ECP
Northwest Florida Beaches Intl.
PWM
Portland Intl. Jetport
$703
Roundtrip
found 16 hours ago
Select Delta flight, departing Sun, Nov 1 from Northwest Florida Beaches Intl. to Portland Intl. Jetport, returning Mon, Nov 16, priced at $703 found 16 hours ago

Madison Flights

No matter how much you fight the travel bug, sometimes there's only one solution—to hop on the next plane to Madison. AARP Travel Center Powered by Expedia® is here to help you cure that bug with great deals on flights and activities. AARP Travel features their members-only discount with the best rates from Expedia, giving members the best price in travel, guaranteed. AARP members pay no booking fees on flights, and often receive exclusive rates on car rentals and hotels.

Once you've got your trip scheduled, we'll show you a full list of deals for your route. Don't forget to look at flights to alternative airports nearby, which can help you score a lower airfare rate.

Airport Transportation

Once you've got your flight scheduled to Madison with AARP Travel, you may want to book a rental car so you can get around on your own. You can book Madison car rentals under our cars tab and hop into the car as soon as you step outside. If you would prefer public transportation, check out the Metropolitan Transit System bus, or if there's trolleys or Amtrak stations nearby.

Things to Do in Madison

If you aren't sure where to start, we can help you with that too. Not to worry—there's so many things to do in this city. Madison has so much to do, and we can help you get started.

If you're looking for some fun activities to do in Madison, make sure you look at our "Things to Do in Madison" page for excursions and activities for the whole family.

Book Your Hotel in Madison

Madison has accommodation options in the area, make sure you check out our hotel listings tab for some great recommendations from past visitors. Remember that you will get the best price out there when you book with us.

Book Your Madison Trip Today

Whether you are heading out on a business trip, exploring a place you have never been before or are bringing the family on the annual holiday, we have the perfect getaway waiting for you. There is no better time than now to start booking that next trip. Book one of our flights today.