Cheap Flights To Madison 2026

Madison Flights as Low as $300

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.

Breeze Airways
Mon, Sep 21 - Fri, Sep 25
CVG
Cincinnati - Northern Kentucky Intl.
PWM
Portland Intl. Jetport
$300
Roundtrip
found 6 days ago
Select Breeze Airways flight, departing Mon, Sep 21 from Cincinnati - Northern Kentucky Intl. to Portland Intl. Jetport, returning Fri, Sep 25, priced at $300 found 6 days ago
Breeze Airways
Mon, Sep 21 - Mon, Sep 28
CVG
Cincinnati - Northern Kentucky Intl.
PWM
Portland Intl. Jetport
$320
Roundtrip
found 6 days ago
Select Breeze Airways flight, departing Mon, Sep 21 from Cincinnati - Northern Kentucky Intl. to Portland Intl. Jetport, returning Mon, Sep 28, priced at $320 found 6 days ago
Delta
Fri, Sep 25 - Tue, Sep 29
CVG
Cincinnati - Northern Kentucky Intl.
PWM
Portland Intl. Jetport
$378
Roundtrip
found 6 days ago
Select Delta flight, departing Fri, Sep 25 from Cincinnati - Northern Kentucky Intl. to Portland Intl. Jetport, returning Tue, Sep 29, priced at $378 found 6 days ago
American Airlines
Delta
Tue, Sep 22 - Fri, Sep 25
CVG
Cincinnati - Northern Kentucky Intl.
PWM
Portland Intl. Jetport
$391
Roundtrip
found 6 days ago
Select Delta flight, departing Tue, Sep 22 from Cincinnati - Northern Kentucky Intl. to Portland Intl. Jetport, returning Fri, Sep 25, priced at $391 found 6 days ago
American Airlines
American Airlines
American Airlines
Delta
Sun, Sep 20 - Tue, Sep 29
CVG
Cincinnati - Northern Kentucky Intl.
PWM
Portland Intl. Jetport
$435
Roundtrip
found 6 days ago
Select Delta flight, departing Sun, Sep 20 from Cincinnati - Northern Kentucky Intl. to Portland Intl. Jetport, returning Tue, Sep 29, priced at $435 found 6 days ago
Southwest Airlines
United
Sat, Sep 19 - Mon, Sep 28
CVG
Cincinnati - Northern Kentucky Intl.
PWM
Portland Intl. Jetport
$445
Roundtrip
found 6 days ago
Select United flight, departing Sat, Sep 19 from Cincinnati - Northern Kentucky Intl. to Portland Intl. Jetport, returning Mon, Sep 28, priced at $445 found 6 days ago
American Airlines
Sun, Oct 4 - Sat, Oct 10
CVG
Cincinnati - Northern Kentucky Intl.
MHT
Manchester-Boston Regional
$448
Roundtrip
found 1 day ago
Select American Airlines flight, departing Sun, Oct 4 from Cincinnati - Northern Kentucky Intl. to Manchester-Boston Regional, returning Sat, Oct 10, priced at $448 found 1 day ago
American Airlines
American Airlines
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.