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Madison

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Madison Flights as Low as $127

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

Breeze Airways
Wed, Aug 6 - Wed, Aug 13
MCO
Orlando Intl.
MHT
Manchester-Boston Regional
$127 Roundtrip, found 4 hours ago
$127
Roundtrip
found 4 hours ago
Select Breeze Airways flight, departing Wed, Aug 6 from Orlando Intl. to Manchester-Boston Regional, returning Wed, Aug 13, priced at $127 found 4 hours ago
Breeze Airways
Wed, Aug 6 - Wed, Aug 13
MCO
Orlando Intl.
MHT
Manchester-Boston Regional
$132 Roundtrip, found 4 hours ago
$132
Roundtrip
found 4 hours ago
Select Breeze Airways flight, departing Wed, Aug 6 from Orlando Intl. to Manchester-Boston Regional, returning Wed, Aug 13, priced at $132 found 4 hours ago
Breeze Airways
Wed, Aug 6 - Wed, Aug 13
MCO
Orlando Intl.
MHT
Manchester-Boston Regional
$137 Roundtrip, found 4 hours ago
$137
Roundtrip
found 4 hours ago
Select Breeze Airways flight, departing Wed, Aug 6 from Orlando Intl. to Manchester-Boston Regional, returning Wed, Aug 13, priced at $137 found 4 hours ago
Breeze Airways
Wed, Aug 13 - Sat, Aug 23
MCO
Orlando Intl.
MHT
Manchester-Boston Regional
$149 Roundtrip, found 5 hours ago
$149
Roundtrip
found 5 hours ago
Select Breeze Airways flight, departing Wed, Aug 13 from Orlando Intl. to Manchester-Boston Regional, returning Sat, Aug 23, priced at $149 found 5 hours ago
Frontier Airlines
Sat, Aug 16 - Sat, Aug 23
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$151 Roundtrip, found 9 hours ago
$151
Roundtrip
found 9 hours ago
Select Frontier Airlines flight, departing Sat, Aug 16 from Orlando Intl. to Portland Intl. Jetport, returning Sat, Aug 23, priced at $151 found 9 hours ago
Breeze Airways
Wed, Aug 6 - Wed, Aug 20
MCO
Orlando Intl.
MHT
Manchester-Boston Regional
$154 Roundtrip, found 14 hours ago
$154
Roundtrip
found 14 hours ago
Select Breeze Airways flight, departing Wed, Aug 6 from Orlando Intl. to Manchester-Boston Regional, returning Wed, Aug 20, priced at $154 found 14 hours ago
Bargain Flight
Tue, Sep 30 - Wed, Oct 1
DCA
Ronald Reagan Washington National
PWM
Portland Intl. Jetport
$172 Roundtrip, found 4 hours ago
$172
Roundtrip
found 4 hours ago
Select Bargain Flight flight, departing Tue, Sep 30 from Ronald Reagan Washington National to Portland Intl. Jetport, returning Wed, Oct 1, priced at $172 found 4 hours ago
JetBlue Airways
Tue, Oct 28 - Mon, Nov 3
MCO
Orlando Intl.
MHT
Manchester-Boston Regional
$172 Roundtrip, found 18 hours ago
$172
Roundtrip
found 18 hours ago
Select JetBlue Airways flight, departing Tue, Oct 28 from Orlando Intl. to Manchester-Boston Regional, returning Mon, Nov 3, priced at $172 found 18 hours ago
American Airlines
Tue, Sep 30 - Wed, Oct 1
DCA
Ronald Reagan Washington National
PWM
Portland Intl. Jetport
$177 Roundtrip, found 4 hours ago
$177
Roundtrip
found 4 hours ago
Select American Airlines flight, departing Tue, Sep 30 from Ronald Reagan Washington National to Portland Intl. Jetport, returning Wed, Oct 1, priced at $177 found 4 hours ago
Breeze Airways
Sat, Sep 20 - Fri, Sep 26
TPA
Tampa Intl.
PWM
Portland Intl. Jetport
$181 Roundtrip, found 6 days ago
$181
Roundtrip
found 6 days ago
Select Breeze Airways flight, departing Sat, Sep 20 from Tampa Intl. to Portland Intl. Jetport, returning Fri, Sep 26, priced at $181 found 6 days ago
American Airlines
Sun, Nov 23 - Thu, Nov 27
DCA
Ronald Reagan Washington National
MHT
Manchester-Boston Regional
$189 Roundtrip, found 20 hours ago
$189
Roundtrip
found 20 hours ago
Select American Airlines flight, departing Sun, Nov 23 from Ronald Reagan Washington National to Manchester-Boston Regional, returning Thu, Nov 27, priced at $189 found 20 hours ago
Delta
Tue, Sep 30 - Wed, Oct 1
DCA
Ronald Reagan Washington National
PWM
Portland Intl. Jetport
$197 Roundtrip, found 4 hours ago
$197
Roundtrip
found 4 hours ago
Select Delta flight, departing Tue, Sep 30 from Ronald Reagan Washington National to Portland Intl. Jetport, returning Wed, Oct 1, priced at $197 found 4 hours ago
American Airlines
Sat, Oct 4 - Thu, Oct 9
CLT
Charlotte-Douglas Intl.
MHT
Manchester-Boston Regional
$205 Roundtrip, found 22 hours ago
$205
Roundtrip
found 22 hours ago
Select American Airlines flight, departing Sat, Oct 4 from Charlotte-Douglas Intl. to Manchester-Boston Regional, returning Thu, Oct 9, priced at $205 found 22 hours ago
American Airlines
Tue, Aug 12 - Sun, Aug 17
TPA
Tampa Intl.
MHT
Manchester-Boston Regional
$248 Roundtrip, found 16 hours ago
$248
Roundtrip
found 16 hours ago
Select American Airlines flight, departing Tue, Aug 12 from Tampa Intl. to Manchester-Boston Regional, returning Sun, Aug 17, priced at $248 found 16 hours ago
JetBlue Airways
Wed, Sep 10 - Tue, Sep 16
TPA
Tampa Intl.
LEB
Lebanon Municipal
$365 Roundtrip, just found
$365
Roundtrip
just found
Select JetBlue Airways flight, departing Wed, Sep 10 from Tampa Intl. to Lebanon Municipal, returning Tue, Sep 16, priced at $365 just found
JetBlue Airways
Thu, Sep 4 - Fri, Sep 12
DCA
Ronald Reagan Washington National
LEB
Lebanon Municipal
$375 Roundtrip, just found
$375
Roundtrip
just found
Select JetBlue Airways flight, departing Thu, Sep 4 from Ronald Reagan Washington National to Lebanon Municipal, returning Fri, Sep 12, priced at $375 just found

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 15 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 $127, 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 $127 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! (153 reviews)
"Great"

Reviewed on Jul 6, 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! (1,002 reviews)
"We didn’t appreciate the young children who were jumping in and out of the hot tub where it clearly stated no one under 12 allowed. Also a family playing football in a crowded pool."

Reviewed on Jul 17, 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 (1,214 reviews)
Great hotel
"The rooms and food were great"

Reviewed on Jul 20, 2025

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Green Granite Inn, Ascend Hotel Collection
Grand Summit Hotel at Attitash

Grand Summit Hotel at Attitash

3 out of 5
104 Grand Summit Road, Bartlett, NH
Stay at this 3-star ski hotel in Bartlett. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms ...
8.4/10 Very Good! (1,006 reviews)
"Great hotel only place I stay when I go to North Conway"

Reviewed on Jul 21, 2025

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Grand Summit Hotel at Attitash
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! (316 reviews)
"I"

Reviewed on Jul 20, 2025

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Cambria Hotel 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 ...
8.4/10 Very Good! (1,007 reviews)
"Perfect little cottage like rooms. Room was clean. Beds not that comfy but not bad either. They have a fire pit for use, grills. The pool was a nice temp. Very clean on the outside and in general. Breakfast was basic. The kids liked the waffle maker. The room we had you had to slam the door to make ..."

Reviewed on Jul 13, 2025

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Swiss Chalets Village Inn
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! (1,098 reviews)
"Lovely staff and nice motel with a beautiful view"

Reviewed on Jul 19, 2025

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North Conway Mountain Inn
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. ...
8.4/10 Very Good! (1,006 reviews)
"This was a great find for our family! So affordable and kept our kids soo happy the whole trip!"

Reviewed on Jul 16, 2025

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Hampton Inn & Suites North Conway
See all 2,499 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.