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Madison

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Madison Flights as Low as $179

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Breeze Airways
Wed, May 27 - Sat, May 30
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$179 Roundtrip, found 2 days ago
$179
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Wed, May 27 from Orlando Intl. to Portland Intl. Jetport, returning Sat, May 30, priced at $179 found 2 days ago
Breeze Airways
Wed, May 27 - Sat, May 30
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$182 Roundtrip, found 2 days ago
$182
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Wed, May 27 from Orlando Intl. to Portland Intl. Jetport, returning Sat, May 30, priced at $182 found 2 days ago
Breeze Airways
Sun, Aug 2 - Thu, Aug 13
RDU
Raleigh - Durham Intl.
MHT
Manchester-Boston Regional
$183 Roundtrip, found 3 days ago
$183
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Sun, Aug 2 from Raleigh - Durham Intl. to Manchester-Boston Regional, returning Thu, Aug 13, priced at $183 found 3 days ago
Breeze Airways
Fri, May 29 - Sat, May 30
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$187 Roundtrip, found 1 day ago
$187
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Fri, May 29 from Orlando Intl. to Portland Intl. Jetport, returning Sat, May 30, priced at $187 found 1 day ago
Breeze Airways
Wed, May 27 - Sat, May 30
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$189 Roundtrip, found 2 days ago
$189
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Wed, May 27 from Orlando Intl. to Portland Intl. Jetport, returning Sat, May 30, priced at $189 found 2 days ago
Breeze Airways
Wed, Aug 19 - Tue, Aug 25
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$190 Roundtrip, found 2 days ago
$190
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Wed, Aug 19 from Orlando Intl. to Portland Intl. Jetport, returning Tue, Aug 25, priced at $190 found 2 days ago
Breeze Airways
Fri, May 29 - Wed, Jun 3
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$192 Roundtrip, found 3 days ago
$192
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Fri, May 29 from Orlando Intl. to Portland Intl. Jetport, returning Wed, Jun 3, priced at $192 found 3 days ago
Breeze Airways
Sun, Aug 2 - Thu, Aug 13
RDU
Raleigh - Durham Intl.
MHT
Manchester-Boston Regional
$193 Roundtrip, found 3 days ago
$193
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Sun, Aug 2 from Raleigh - Durham Intl. to Manchester-Boston Regional, returning Thu, Aug 13, priced at $193 found 3 days ago
Bargain Flight
Tue, Aug 18 - Sat, Aug 22
RDU
Raleigh - Durham Intl.
PWM
Portland Intl. Jetport
$204 Roundtrip, found 5 days ago
$204
Roundtrip
found 5 days ago
Select Bargain Flight flight, departing Tue, Aug 18 from Raleigh - Durham Intl. to Portland Intl. Jetport, returning Sat, Aug 22, priced at $204 found 5 days ago
American Airlines
Tue, Aug 18 - Sat, Aug 22
RDU
Raleigh - Durham Intl.
PWM
Portland Intl. Jetport
$213 Roundtrip, found 5 days ago
$213
Roundtrip
found 5 days ago
Select American Airlines flight, departing Tue, Aug 18 from Raleigh - Durham Intl. to Portland Intl. Jetport, returning Sat, Aug 22, priced at $213 found 5 days ago
Breeze Airways
Thu, Sep 3 - Thu, Sep 17
MCO
Orlando Intl.
MHT
Manchester-Boston Regional
$215 Roundtrip, found 2 hours ago
$215
Roundtrip
found 2 hours ago
Select Breeze Airways flight, departing Thu, Sep 3 from Orlando Intl. to Manchester-Boston Regional, returning Thu, Sep 17, priced at $215 found 2 hours ago
Delta
Wed, Aug 19 - Tue, Aug 25
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$217 Roundtrip, found 2 days ago
$217
Roundtrip
found 2 days ago
Select Delta flight, departing Wed, Aug 19 from Orlando Intl. to Portland Intl. Jetport, returning Tue, Aug 25, priced at $217 found 2 days ago
Bargain Flight
Wed, May 20 - Wed, May 27
GRR
Gerald R. Ford Intl.
PWM
Portland Intl. Jetport
$241 Roundtrip, found 5 days ago
$241
Roundtrip
found 5 days ago
Select Bargain Flight flight, departing Wed, May 20 from Gerald R. Ford Intl. to Portland Intl. Jetport, returning Wed, May 27, priced at $241 found 5 days ago
JetBlue Airways
Sat, Jun 13 - Sun, Jun 14
MCO
Orlando Intl.
MHT
Manchester-Boston Regional
$247 Roundtrip, found 1 day ago
$247
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Sat, Jun 13 from Orlando Intl. to Manchester-Boston Regional, returning Sun, Jun 14, priced at $247 found 1 day ago
Bargain Flight
Wed, May 27 - Wed, Jun 3
CLT
Charlotte-Douglas Intl.
PWM
Portland Intl. Jetport
$270 Roundtrip, found 1 day ago
$270
Roundtrip
found 1 day ago
Select Bargain Flight flight, departing Wed, May 27 from Charlotte-Douglas Intl. to Portland Intl. Jetport, returning Wed, Jun 3, priced at $270 found 1 day ago
Bargain Flight
Tue, May 5 - Thu, May 7
CLT
Charlotte-Douglas Intl.
MHT
Manchester-Boston Regional
$318 Roundtrip, found 5 days ago
$318
Roundtrip
found 5 days ago
Select Bargain Flight flight, departing Tue, May 5 from Charlotte-Douglas Intl. to Manchester-Boston Regional, returning Thu, May 7, priced at $318 found 5 days ago

Cheap Flights to Madison

Fall in love at first flight with your vacation to Madison by saving a ton of cash on your last-minute cheap flight. There’s no more scouring the internet for a good deal—book your flight to Madison on Hotwire, and you’ll be up, up, and on a getaway in no time.

Because once the wheels are down in Madison, the good times start rolling. So buckle up, you’re in for a fun ride.

Frequently Asked Questions About flights to Madison

Don’t waste your time on endless searches for cheap airline tickets oneway or roundtrip. We’ll have you on your way to Madison with a tiny bag of pretzels in your hand before you can say “tray tables in the upright position”—and for a ticket price that works for your vacay budget.

So all you have to worry about is where you’re headed after the PWM airport.

What is the cheapest month to fly to Madison?

Airline ticket prices fluctuate all the time, depending on the day of the week or the month of the year. The cheapest round trip flights to Madison are in May, but when you book your flight on Hotwire, savings are always in season.

How many airlines fly to Madison?

Variety is the spice of life, even when it comes to booking your next trip. Want options for airlines? You’ll find 12 to choose from for your flight to Madison.

What airport is best to fly into Madison?

When you’re planning your trip to Madison, convenience is the name of the game. Luckily, Madison Eastern Slopes Regional Airport is nearby so you can deplane and get going on checking off everything on your Madison must-do list.

How much are flights to Madison?

Got very cheap flights on your vacation itinerary? When you book your airline tickets to Madison on Hotwire, you may just get what’s on your getaway wish list. With tickets as low as $179, you’ll have leftover cash for at least a magazine and a bottle of water at the airport book store.

How to get cheap flights to Madison?

The trick to saving a stack of cash on your flight to Madison? Snatch up that Hotwire flight deal when you see a killer rate because it could be gone in a flash. And with flights as low as $179 right now, why wait?

Madison Flight Information
Destination airport
Portland Intl. Jetport
Destination airport IATA code
PWM
Roundtrip price
$178

Last Minute Hotel Deals in Madison

Purity Spring Resort

Purity Spring Resort

2 out of 5
1251 Eaton Rd Madison NH
Book a stay at this ski hotel in Madison. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the helpful staff in our reviews. Popular attractions ...
8.8/10 Excellent! (196 reviews)
A wonderful oasis. Skiing, skating, swimming, restaurant and tavern, cross country ski trails, snowshoe trails and exercise room/hot tub all a minutes walk away in a picturesque valley setting.

Reviewed on Mar 13, 2026

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Purity Spring Resort
North Conway Grand Hotel

North Conway Grand Hotel

4 out of 5
72 Common Court North Conway NH
Book a stay at this family-friendly hotel in North Conway. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the pool and the helpful ...
8.4/10 Very Good! (1,047 reviews)
Loved the hot tub in the room

Reviewed on Apr 26, 2026

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North Conway Grand Hotel
Hampton Inn & Suites North Conway

Hampton Inn & Suites North Conway

2.5 out of 5
1788 White Mountain Hwy North Conway NH
Book a stay at this ski hotel in North Conway. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. ...
8.6/10 Excellent! (1,009 reviews)
If you want sleep stay somewhere else. You can hear everything from every room around you, everyone going up and down the hall late at night and early in the morning. My toddler was woken up multiple times from the room upstairs. The breakfast was okay. Room wasn’t the cleanest. There was an old ...

Reviewed on Apr 27, 2026

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Hampton Inn & Suites North Conway
Comfort Inn & Suites North Conway

Comfort Inn & Suites North Conway

3 out of 5
2001 White Mountain Hwy North Conway NH
Book a stay at this business-friendly hotel in North Conway. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
9.4/10 Exceptional! (1,005 reviews)
Excelente e todos los servicios y atenciones

Reviewed on Apr 26, 2026

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Comfort Inn & Suites North Conway
Swiss Chalets Village Inn

Swiss Chalets Village Inn

2 out of 5
457 Intervale Resort Loop Intervale NH
Book a stay at this golf hotel in Intervale. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our ...
8.6/10 Excellent! (1,002 reviews)
We are so happy with our stay here. This is honestly the best lodging we have seen in the White Mountains. The exterior architecture property is absolutely stunning, we are grateful to be here! Great photo opportunities with family! We have a small baby and the staff has been very accommodating to ...

Reviewed on Apr 24, 2026

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Swiss Chalets Village Inn
Cambria Hotel North Conway

Cambria Hotel North Conway

3 out of 5
1858 White Mountain Highway North Conway NH
Book a stay at this business-friendly hotel in North Conway. Enjoy free WiFi, free parking, and breakfast (surcharge). Popular attractions M&D Playhouse and ...
9/10 Wonderful! (562 reviews)
Modern, clean and beautiful place to stay

Reviewed on Apr 27, 2026

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Cambria Hotel North Conway
The Green Granite North Conway, an Ascend Collection Hotel

The Green Granite North Conway, an Ascend Collection Hotel

2.5 out of 5
1515 White Mountain Hwy North Conway NH
Book a stay at this family-friendly hotel in North Conway. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in ...
6.6/10 (1,228 reviews)
Everything was perfect clean room staff amazing parking easy

Reviewed on Apr 19, 2026

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The Green Granite North Conway, an Ascend Collection Hotel
Fairfield Inn & Suites By Marriott North Conway

Fairfield Inn & Suites By Marriott North Conway

3 out of 5
165 Skimobile Road North Conway NH
Book a stay at this ski hotel in North Conway. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our ...
9.4/10 Exceptional! (578 reviews)
Yes very nice and convenient touch will definitely book again on our return.

Reviewed on Apr 26, 2026

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Fairfield Inn & Suites By Marriott North Conway
See all 2,575 properties in Madison
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.