Cheap Flights To Madison 2026

Madison Flights as Low as $287

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.

JetBlue Airways
JetBlue Airways
Breeze Airways
Breeze Airways
Breeze Airways
JetBlue Airways
Delta
Wed, Oct 21 - Fri, Oct 30
GSP
Greenville-Spartanburg Intl.
PWM
Portland Intl. Jetport
$358
Roundtrip
found 19 hours ago
Select Delta flight, departing Wed, Oct 21 from Greenville-Spartanburg Intl. to Portland Intl. Jetport, returning Fri, Oct 30, priced at $358 found 19 hours ago
JetBlue Airways
Delta
Tue, Oct 6 - Thu, Oct 8
GSP
Greenville-Spartanburg Intl.
PWM
Portland Intl. Jetport
$365
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Oct 6 from Greenville-Spartanburg Intl. to Portland Intl. Jetport, returning Thu, Oct 8, priced at $365 found 1 day ago
Delta
Fri, Oct 16 - Fri, Oct 30
GSP
Greenville-Spartanburg Intl.
PWM
Portland Intl. Jetport
$371
Roundtrip
found 19 hours ago
Select Delta flight, departing Fri, Oct 16 from Greenville-Spartanburg Intl. to Portland Intl. Jetport, returning Fri, Oct 30, priced at $371 found 19 hours ago
JetBlue Airways
Tue, Aug 25 - Mon, Aug 31
ATL
Hartsfield-Jackson Atlanta Intl.
PWM
Portland Intl. Jetport
$373
Roundtrip
found 21 hours ago
Select JetBlue Airways flight, departing Tue, Aug 25 from Hartsfield-Jackson Atlanta Intl. to Portland Intl. Jetport, returning Mon, Aug 31, priced at $373 found 21 hours ago
American Airlines
JetBlue Airways
United
Sun, Oct 11 - Sat, Oct 17
GSP
Greenville-Spartanburg Intl.
PWM
Portland Intl. Jetport
$404
Roundtrip
found 19 hours ago
Select United flight, departing Sun, Oct 11 from Greenville-Spartanburg Intl. to Portland Intl. Jetport, returning Sat, Oct 17, priced at $404 found 19 hours ago
Southwest Airlines
American Airlines

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.