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Madison

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Madison Flights as Low as $243

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

JetBlue Airways
Tue, Sep 1 - Tue, Sep 22
RSW
Southwest Florida Intl.
PWM
Portland Intl. Jetport
$243 Roundtrip, found 21 hours ago
$243
Roundtrip
found 21 hours ago
Select JetBlue Airways flight, departing Tue, Sep 1 from Southwest Florida Intl. to Portland Intl. Jetport, returning Tue, Sep 22, priced at $243 found 21 hours ago
Delta
Tue, Sep 1 - Sat, Sep 19
RSW
Southwest Florida Intl.
PWM
Portland Intl. Jetport
$257 Roundtrip, found 21 hours ago
$257
Roundtrip
found 21 hours ago
Select Delta flight, departing Tue, Sep 1 from Southwest Florida Intl. to Portland Intl. Jetport, returning Sat, Sep 19, priced at $257 found 21 hours ago
Delta
Wed, Sep 16 - Sat, Sep 19
RSW
Southwest Florida Intl.
PWM
Portland Intl. Jetport
$271 Roundtrip, found 21 hours ago
$271
Roundtrip
found 21 hours ago
Select Delta flight, departing Wed, Sep 16 from Southwest Florida Intl. to Portland Intl. Jetport, returning Sat, Sep 19, priced at $271 found 21 hours ago
Delta
Thu, Sep 17 - Sat, Sep 19
RSW
Southwest Florida Intl.
PWM
Portland Intl. Jetport
$276 Roundtrip, found 21 hours ago
$276
Roundtrip
found 21 hours ago
Select Delta flight, departing Thu, Sep 17 from Southwest Florida Intl. to Portland Intl. Jetport, returning Sat, Sep 19, priced at $276 found 21 hours ago
Delta
Thu, Sep 17 - Tue, Oct 6
RSW
Southwest Florida Intl.
PWM
Portland Intl. Jetport
$282 Roundtrip, found 21 hours ago
$282
Roundtrip
found 21 hours ago
Select Delta flight, departing Thu, Sep 17 from Southwest Florida Intl. to Portland Intl. Jetport, returning Tue, Oct 6, priced at $282 found 21 hours ago
Delta
Tue, Sep 8 - Thu, Oct 1
RSW
Southwest Florida Intl.
PWM
Portland Intl. Jetport
$291 Roundtrip, found 21 hours ago
$291
Roundtrip
found 21 hours ago
Select Delta flight, departing Tue, Sep 8 from Southwest Florida Intl. to Portland Intl. Jetport, returning Thu, Oct 1, priced at $291 found 21 hours ago
JetBlue Airways
Wed, Sep 2 - Fri, Sep 18
RSW
Southwest Florida Intl.
PWM
Portland Intl. Jetport
$295 Roundtrip, found 21 hours ago
$295
Roundtrip
found 21 hours ago
Select JetBlue Airways flight, departing Wed, Sep 2 from Southwest Florida Intl. to Portland Intl. Jetport, returning Fri, Sep 18, priced at $295 found 21 hours ago
Delta
Wed, Sep 16 - Wed, Oct 7
RSW
Southwest Florida Intl.
PWM
Portland Intl. Jetport
$305 Roundtrip, found 21 hours ago
$305
Roundtrip
found 21 hours ago
Select Delta flight, departing Wed, Sep 16 from Southwest Florida Intl. to Portland Intl. Jetport, returning Wed, Oct 7, priced at $305 found 21 hours ago
JetBlue Airways
Wed, Sep 16 - Mon, Sep 28
RSW
Southwest Florida Intl.
PWM
Portland Intl. Jetport
$309 Roundtrip, found 21 hours ago
$309
Roundtrip
found 21 hours ago
Select JetBlue Airways flight, departing Wed, Sep 16 from Southwest Florida Intl. to Portland Intl. Jetport, returning Mon, Sep 28, priced at $309 found 21 hours ago
Delta
Thu, Sep 17 - Wed, Oct 7
RSW
Southwest Florida Intl.
PWM
Portland Intl. Jetport
$310 Roundtrip, found 21 hours ago
$310
Roundtrip
found 21 hours ago
Select Delta flight, departing Thu, Sep 17 from Southwest Florida Intl. to Portland Intl. Jetport, returning Wed, Oct 7, priced at $310 found 21 hours ago
JetBlue Airways
Sat, Jul 25 - Fri, Jul 31
PHX
Sky Harbor Intl.
PWM
Portland Intl. Jetport
$321 Roundtrip, found 4 hours ago
$321
Roundtrip
found 4 hours ago
Select JetBlue Airways flight, departing Sat, Jul 25 from Sky Harbor Intl. to Portland Intl. Jetport, returning Fri, Jul 31, priced at $321 found 4 hours ago
American Airlines
Tue, Jun 30 - Tue, Jul 21
CID
Eastern Iowa
PWM
Portland Intl. Jetport
$389 Roundtrip, found 1 day ago
$389
Roundtrip
found 1 day ago
Select American Airlines flight, departing Tue, Jun 30 from Eastern Iowa to Portland Intl. Jetport, returning Tue, Jul 21, priced at $389 found 1 day ago
Breeze Airways
Sun, Oct 4 - Tue, Oct 20
RSW
Southwest Florida Intl.
PWM
Portland Intl. Jetport
$391 Roundtrip, found 21 hours ago
$391
Roundtrip
found 21 hours ago
Select Breeze Airways flight, departing Sun, Oct 4 from Southwest Florida Intl. to Portland Intl. Jetport, returning Tue, Oct 20, priced at $391 found 21 hours ago
American Airlines
Sun, Jun 21 - Wed, Aug 12
GRB
Austin Straubel Intl.
PWM
Portland Intl. Jetport
$422 Roundtrip, found 21 hours ago
$422
Roundtrip
found 21 hours ago
Select American Airlines flight, departing Sun, Jun 21 from Austin Straubel Intl. to Portland Intl. Jetport, returning Wed, Aug 12, priced at $422 found 21 hours ago
United
Tue, Jun 30 - Tue, Jul 21
CID
Eastern Iowa
PWM
Portland Intl. Jetport
$436 Roundtrip, found 1 day ago
$436
Roundtrip
found 1 day ago
Select United flight, departing Tue, Jun 30 from Eastern Iowa to Portland Intl. Jetport, returning Tue, Jul 21, priced at $436 found 1 day ago
American Airlines
Tue, Aug 4 - Tue, Aug 11
PHX
Sky Harbor Intl.
MHT
Manchester-Boston Regional
$517 Roundtrip, found 18 hours ago
$517
Roundtrip
found 18 hours ago
Select American Airlines flight, departing Tue, Aug 4 from Sky Harbor Intl. to Manchester-Boston Regional, returning Tue, Aug 11, priced at $517 found 18 hours 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 September, 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 $243, 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 $243 right now, why wait?

Madison Flight Information
Destination airport
Portland Intl. Jetport
Destination airport IATA code
PWM
Roundtrip price
$242

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! (199 reviews)
"Dustin at front desk was very nice. Room was quite clean and looked nice. No complaints at all."

Reviewed on Jun 7, 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! (1,084 reviews)
"My room shower wasn't clean. There was dirt left behind and a used face cloth not mine. Air Conditioner was making a loud clunk noice whenever it went on, wasn't able to sleep. The pools were a nice temperature but dirty could use a good cleaning and vacuum. When I was telling the front desk about ..."

Reviewed on Jun 7, 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! (1,003 reviews)
"The staff was very accommodating and so so sweet! We have two children with delicate needs and I could not have been more impressed! From the moment that we walked in. We were greeted with such tacked and a beautiful introduction. The rooms were great. We booked two so that three of us stayed in ..."

Reviewed on Jun 4, 2026

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Hampton Inn & Suites North Conway
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 ...
8.8/10 Excellent! (1,252 reviews)
"Charm and a friendly staff."

Reviewed on Jun 8, 2026

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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 ...
8.6/10 Excellent! (1,006 reviews)
"Greeting at check in was very pleasant. Immaculate grounds. Best bargain on the web for a king room. Very nice breakfast too."

Reviewed on Jun 8, 2026

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Swiss Chalets Village Inn
Golden Gables Inn Dazzler Select by Wyndham

Golden Gables Inn Dazzler Select by Wyndham

2.5 out of 5
1814 White Mountain Hwy North Conway NH
Stay at this motel in North Conway. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms in our reviews. ...
9/10 Wonderful! (1,005 reviews)
"Stayed at the location many times over the last several years. Never a bad experience so I will keep coming back."

Reviewed on Jun 5, 2026

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Golden Gables Inn Dazzler Select by Wyndham
The Lodge At Jackson Village

The Lodge At Jackson Village

2.5 out of 5
153 Route 16 Jackson NH
Book a stay at this beach hotel in Jackson. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. ...
9/10 Wonderful! (1,009 reviews)
"We got a room facing front. A street view. Next time I will request a room facing the back. It's a view of the river and a very beautiful backyard with balconies"

Reviewed on Jun 7, 2026

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The Lodge At Jackson Village
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! (595 reviews)
"Very comfortable, well appointed. Close to restaurants & Mt Washington."

Reviewed on Jun 6, 2026

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Cambria Hotel North Conway
See all 2,478 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.