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Madison

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Madison Flights as Low as $100

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

Frontier Airlines
Sat, Aug 16 - Sat, Aug 23
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$100 Roundtrip, found 6 days ago
$100
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Sat, Aug 16 from Orlando Intl. to Portland Intl. Jetport, returning Sat, Aug 23, priced at $100 found 6 days ago
JetBlue Airways
Sun, Oct 12 - Thu, Oct 16
JFK
John F. Kennedy Intl.
PWM
Portland Intl. Jetport
$117 Roundtrip, found 3 days ago
$117
Roundtrip
found 3 days ago
Select JetBlue Airways flight, departing Sun, Oct 12 from John F. Kennedy Intl. to Portland Intl. Jetport, returning Thu, Oct 16, priced at $117 found 3 days ago
Delta
Sun, Aug 17 - Thu, Aug 21
JFK
John F. Kennedy Intl.
PWM
Portland Intl. Jetport
$119 Roundtrip, found 1 day ago
$119
Roundtrip
found 1 day ago
Select Delta flight, departing Sun, Aug 17 from John F. Kennedy Intl. to Portland Intl. Jetport, returning Thu, Aug 21, priced at $119 found 1 day ago
Delta
Tue, Aug 19 - Fri, Aug 22
JFK
John F. Kennedy Intl.
PWM
Portland Intl. Jetport
$119 Roundtrip, found 1 day ago
$119
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Aug 19 from John F. Kennedy Intl. to Portland Intl. Jetport, returning Fri, Aug 22, priced at $119 found 1 day ago
JetBlue Airways
Mon, Oct 13 - Thu, Oct 16
JFK
John F. Kennedy Intl.
PWM
Portland Intl. Jetport
$127 Roundtrip, found 3 days ago
$127
Roundtrip
found 3 days ago
Select JetBlue Airways flight, departing Mon, Oct 13 from John F. Kennedy Intl. to Portland Intl. Jetport, returning Thu, Oct 16, priced at $127 found 3 days ago
JetBlue Airways
Sun, Oct 12 - Sun, Oct 19
JFK
John F. Kennedy Intl.
PWM
Portland Intl. Jetport
$137 Roundtrip, found 3 days ago
$137
Roundtrip
found 3 days ago
Select JetBlue Airways flight, departing Sun, Oct 12 from John F. Kennedy Intl. to Portland Intl. Jetport, returning Sun, Oct 19, priced at $137 found 3 days ago
JetBlue Airways
Sun, Aug 17 - Tue, Aug 19
JFK
John F. Kennedy Intl.
PWM
Portland Intl. Jetport
$139 Roundtrip, found 1 day ago
$139
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Sun, Aug 17 from John F. Kennedy Intl. to Portland Intl. Jetport, returning Tue, Aug 19, priced at $139 found 1 day ago
Breeze Airways
Sat, Sep 6 - Fri, Sep 12
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$143 Roundtrip, found 6 hours ago
$143
Roundtrip
found 6 hours ago
Select Breeze Airways flight, departing Sat, Sep 6 from Orlando Intl. to Portland Intl. Jetport, returning Fri, Sep 12, priced at $143 found 6 hours ago
Breeze Airways
Wed, Aug 27 - Sat, Aug 30
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$147 Roundtrip, found 5 days ago
$147
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Wed, Aug 27 from Orlando Intl. to Portland Intl. Jetport, returning Sat, Aug 30, priced at $147 found 5 days ago
JetBlue Airways
Thu, Nov 6 - Sat, Nov 8
MCO
Orlando Intl.
MHT
Manchester-Boston Regional
$155 Roundtrip, found 11 hours ago
$155
Roundtrip
found 11 hours ago
Select JetBlue Airways flight, departing Thu, Nov 6 from Orlando Intl. to Manchester-Boston Regional, returning Sat, Nov 8, priced at $155 found 11 hours ago
American Airlines
Tue, Sep 16 - Tue, Sep 30
MCO
Orlando Intl.
MHT
Manchester-Boston Regional
$189 Roundtrip, found 4 days ago
$189
Roundtrip
found 4 days ago
Select American Airlines flight, departing Tue, Sep 16 from Orlando Intl. to Manchester-Boston Regional, returning Tue, Sep 30, priced at $189 found 4 days ago
United
Wed, Aug 13 - Sat, Aug 23
MCO
Orlando Intl.
MHT
Manchester-Boston Regional
$209 Roundtrip, found 4 days ago
$209
Roundtrip
found 4 days ago
Select United flight, departing Wed, Aug 13 from Orlando Intl. to Manchester-Boston Regional, returning Sat, Aug 23, priced at $209 found 4 days ago
Delta
Wed, Dec 3 - Sat, Dec 6
FLL
Fort Lauderdale - Hollywood Intl.
PWM
Portland Intl. Jetport
$217 Roundtrip, found 4 days ago
$217
Roundtrip
found 4 days ago
Select Delta flight, departing Wed, Dec 3 from Fort Lauderdale - Hollywood Intl. to Portland Intl. Jetport, returning Sat, Dec 6, priced at $217 found 4 days ago
American Airlines
Fri, Sep 5 - Tue, Sep 9
FLL
Fort Lauderdale - Hollywood Intl.
MHT
Manchester-Boston Regional
$227 Roundtrip, found 1 day ago
$227
Roundtrip
found 1 day ago
Select American Airlines flight, departing Fri, Sep 5 from Fort Lauderdale - Hollywood Intl. to Manchester-Boston Regional, returning Tue, Sep 9, priced at $227 found 1 day ago
Delta
Tue, Sep 30 - Tue, Oct 7
IAH
George Bush Intercontinental
PWM
Portland Intl. Jetport
$257 Roundtrip, found 4 days ago
$257
Roundtrip
found 4 days ago
Select Delta flight, departing Tue, Sep 30 from George Bush Intercontinental to Portland Intl. Jetport, returning Tue, Oct 7, priced at $257 found 4 days ago
American Airlines
Tue, Oct 14 - Tue, Oct 21
IAH
George Bush Intercontinental
MHT
Manchester-Boston Regional
$359 Roundtrip, found 1 hour ago
$359
Roundtrip
found 1 hour ago
Select American Airlines flight, departing Tue, Oct 14 from George Bush Intercontinental to Manchester-Boston Regional, returning Tue, Oct 21, priced at $359 found 1 hour 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 August, 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 16 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 $100, 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 $100 right now, why wait?

Madison Flight Information
Destination airport
Portland Intl. Jetport
Destination airport IATA code
PWM
Roundtrip price
$171

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 ...
8.6/10 Excellent! (155 reviews)
"We had 8 adults and 3 young kids staying together and the house was wonderful. Every staff member was accommodating and welcoming. The rooms were perfect and quiet. We especially loved the canoes and kayaks and being close to Purity Pond. We want to come back again and stay longer to experience the ..."

Reviewed on Aug 3, 2025

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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
Stay at this 4-star family-friendly hotel in North Conway. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the pool and the helpful ...
8.2/10 Very Good! (1,004 reviews)
"Like"

Reviewed on Aug 1, 2025

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North Conway Grand Hotel
Green Granite Inn, Ascend Hotel Collection

Green Granite Inn, Ascend Hotel Collection

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 ...
6.8/10 (1,219 reviews)
"Vending machines and ice need fixing"

Reviewed on Jul 29, 2025

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Green Granite Inn, Ascend Hotel Collection
North Conway Mountain Inn

North Conway Mountain Inn

2.5 out of 5
2114 White Mountain Highway, North Conway, NH
Book a stay at this golf motel in North Conway. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the helpful staff and the clean rooms ...
8.6/10 Excellent! (1,082 reviews)
"The beds and environment were like comfortable and cozy. They also had this awesome Dick Tracy statue in the lobby."

Reviewed on Aug 1, 2025

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North Conway Mountain Inn
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 ...
8.4/10 Very Good! (1,007 reviews)
"My husband and I stayed there 2 nights with our 6 year old granddaughter. It’s a great little motel. Nice pool and grounds. My only complaint is that there is no grab bar in bathroom in tub area. The tub is slippery and stepping out of tub is rather difficult. Yes, I’m 72, but I’m also a personal ..."

Reviewed on Aug 1, 2025

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Swiss Chalets Village Inn
The Aurora Inn & Cottages

The Aurora Inn & Cottages

2 out of 5
1477 U.S. 302, Bartlett, NH
Stay at this inn in Bartlett. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Attitash Mountain Resort and Bear Notch Ski Touring Center ...
9.4/10 Exceptional! (23 reviews)
"Great place to stay. We was hiking in and out. Everything was up to par."

Reviewed on Jul 29, 2025

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The Aurora Inn & Cottages
Cambria Hotel North Conway

Cambria Hotel North Conway

3 out of 5
1858 White Mountain Highway, North Conway, NH
Stay at this 3-star business-friendly hotel in North Conway. Enjoy free WiFi, free parking, and breakfast (surcharge). Popular attractions Settlers' Green Outlet ...
9/10 Wonderful! (326 reviews)
"Wonderful place. Clean. Easy access to all things North Conway"

Reviewed on Jul 25, 2025

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Cambria Hotel North Conway
School House Inn

School House Inn

2 out of 5
2152 White Mountain Highway, North Conway, NH
Stay at this hotel in North Conway. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the helpful staff and the clean rooms in our reviews. ...
8.8/10 Excellent! (1,001 reviews)
"Great location! Close to shopping and good dining. Clean and comfortable."

Reviewed on Aug 1, 2025

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School House Inn
See all 2,479 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.