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Madison

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Madison Flights as Low as $165

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

Breeze Airways
Thu, Aug 14 - Sun, Aug 17
ORF
Norfolk Intl.
HVN
Tweed - New Haven Regional
$165 Roundtrip, found 4 days ago
$165
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Thu, Aug 14 from Norfolk Intl. to Tweed - New Haven Regional, returning Sun, Aug 17, priced at $165 found 4 days ago
Breeze Airways
Thu, Aug 14 - Sun, Aug 17
ORF
Norfolk Intl.
HVN
Tweed - New Haven Regional
$170 Roundtrip, found 4 days ago
$170
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Thu, Aug 14 from Norfolk Intl. to Tweed - New Haven Regional, returning Sun, Aug 17, priced at $170 found 4 days ago
Breeze Airways
Thu, Aug 14 - Sun, Aug 17
ORF
Norfolk Intl.
HVN
Tweed - New Haven Regional
$175 Roundtrip, found 4 days ago
$175
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Thu, Aug 14 from Norfolk Intl. to Tweed - New Haven Regional, returning Sun, Aug 17, priced at $175 found 4 days ago
Breeze Airways
Thu, Aug 14 - Sun, Aug 17
ORF
Norfolk Intl.
HVN
Tweed - New Haven Regional
$190 Roundtrip, found 1 day ago
$190
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Thu, Aug 14 from Norfolk Intl. to Tweed - New Haven Regional, returning Sun, Aug 17, priced at $190 found 1 day ago
Breeze Airways
Thu, Aug 14 - Sun, Aug 17
ORF
Norfolk Intl.
HVN
Tweed - New Haven Regional
$195 Roundtrip, found 1 day ago
$195
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Thu, Aug 14 from Norfolk Intl. to Tweed - New Haven Regional, returning Sun, Aug 17, priced at $195 found 1 day ago
Breeze Airways
Thu, Aug 14 - Sun, Aug 17
ORF
Norfolk Intl.
HVN
Tweed - New Haven Regional
$200 Roundtrip, found 1 day ago
$200
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Thu, Aug 14 from Norfolk Intl. to Tweed - New Haven Regional, returning Sun, Aug 17, priced at $200 found 1 day ago
Breeze Airways
Thu, Aug 14 - Sun, Aug 17
ORF
Norfolk Intl.
HVN
Tweed - New Haven Regional
$234 Roundtrip, found 6 days ago
$234
Roundtrip
found 6 days ago
Select Breeze Airways flight, departing Thu, Aug 14 from Norfolk Intl. to Tweed - New Haven Regional, returning Sun, Aug 17, priced at $234 found 6 days ago
Breeze Airways
Thu, Aug 14 - Sun, Aug 17
ORF
Norfolk Intl.
HVN
Tweed - New Haven Regional
$239 Roundtrip, found 6 days ago
$239
Roundtrip
found 6 days ago
Select Breeze Airways flight, departing Thu, Aug 14 from Norfolk Intl. to Tweed - New Haven Regional, returning Sun, Aug 17, priced at $239 found 6 days ago
Breeze Airways
Thu, Aug 14 - Sun, Aug 17
ORF
Norfolk Intl.
HVN
Tweed - New Haven Regional
$244 Roundtrip, found 6 days ago
$244
Roundtrip
found 6 days ago
Select Breeze Airways flight, departing Thu, Aug 14 from Norfolk Intl. to Tweed - New Haven Regional, returning Sun, Aug 17, priced at $244 found 6 days ago
Breeze Airways
Tue, Oct 28 - Thu, Oct 30
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$251 Roundtrip, found 3 days ago
$251
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Tue, Oct 28 from Orlando Intl. to Tweed - New Haven Regional, returning Thu, Oct 30, priced at $251 found 3 days ago
Breeze Airways
Thu, Aug 14 - Sun, Aug 17
ORF
Norfolk Intl.
HVN
Tweed - New Haven Regional
$275 Roundtrip, found 4 days ago
$275
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Thu, Aug 14 from Norfolk Intl. to Tweed - New Haven Regional, returning Sun, Aug 17, priced at $275 found 4 days ago
Breeze Airways
Thu, Aug 14 - Sun, Aug 17
ORF
Norfolk Intl.
HVN
Tweed - New Haven Regional
$280 Roundtrip, found 4 days ago
$280
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Thu, Aug 14 from Norfolk Intl. to Tweed - New Haven Regional, returning Sun, Aug 17, priced at $280 found 4 days ago
Breeze Airways
Thu, Aug 14 - Sun, Aug 17
ORF
Norfolk Intl.
HVN
Tweed - New Haven Regional
$286 Roundtrip, found 4 days ago
$286
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Thu, Aug 14 from Norfolk Intl. to Tweed - New Haven Regional, returning Sun, Aug 17, priced at $286 found 4 days ago
Breeze Airways
Fri, Aug 15 - Mon, Aug 18
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$313 Roundtrip, found 3 days ago
$313
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Fri, Aug 15 from Orlando Intl. to Tweed - New Haven Regional, returning Mon, Aug 18, priced at $313 found 3 days ago
Breeze Airways
Sat, Aug 16 - Mon, Aug 18
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$326 Roundtrip, found 3 days ago
$326
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Sat, Aug 16 from Orlando Intl. to Tweed - New Haven Regional, returning Mon, Aug 18, priced at $326 found 3 days ago
Breeze Airways
Wed, Oct 29 - Thu, Oct 30
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$340 Roundtrip, found 3 days ago
$340
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Wed, Oct 29 from Orlando Intl. to Tweed - New Haven Regional, returning Thu, Oct 30, priced at $340 found 3 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 BDR 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 Tweed - New Haven 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 $165, 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 $165 right now, why wait?

Madison Flight Information
Destination airport
Tweed - New Haven Regional
Destination airport IATA code
HVN
Roundtrip price
$164

Last Minute Hotel Deals in Madison

Madison Beach Hotel

Madison Beach Hotel

4 out of 5
94 West Wharf Road, Madison, CT
Stay at this 4-star beach hotel in Madison. Enjoy free WiFi, a full-service spa, and a private beach. Our guests praise the helpful staff and the property condition ...
9.4/10 Exceptional! (308 reviews)
"Had a wonderful time. GREAT"

Reviewed on Aug 8, 2025

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Madison Beach Hotel
Cambria Hotel New Haven University Area

Cambria Hotel New Haven University Area

3 out of 5
20 Dwight Street, New Haven, CT
Stay at this 3-star business-friendly hotel in New Haven. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the helpful staff and ...
8.6/10 Excellent! (848 reviews)
Excellent stay
"We had a great stay. The entire venue and room was very clean and the bed was comfortable. The check in and check out process was efficient. We would definitely stay again."

Reviewed on Aug 11, 2025

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Cambria Hotel New Haven University Area
Best Western Executive Hotel Of New Haven - West Haven

Best Western Executive Hotel Of New Haven - West Haven

2.5 out of 5
490 Saw Mill Rd, West Haven, CT
Book a stay at this business-friendly hotel in West Haven. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
7.8/10 Good! (1,265 reviews)
"Good place"

Reviewed on Aug 9, 2025

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Best Western Executive Hotel Of New Haven - West Haven
Omni New Haven Hotel at Yale

Omni New Haven Hotel at Yale

4 out of 5
155 Temple St, New Haven, CT
Stay at this 4-star business-friendly hotel in New Haven. Enjoy 2 restaurants, breakfast (surcharge), and room service. Our guests praise the helpful staff and ...
8.2/10 Very Good! (1,006 reviews)
"Great hotel near Yale with friendly staff"

Reviewed on Aug 10, 2025

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Omni New Haven Hotel at Yale
New Haven Hotel

New Haven Hotel

3.5 out of 5
229 George Street, New Haven, CT
Stay at this 3.5-star business-friendly hotel in New Haven. Enjoy free WiFi, a fitness center, and parking (surcharge). Our guests praise the helpful staff and ...
8.8/10 Excellent! (1,707 reviews)
It was a wonderful hotel
"We booked Airbnb and it was the New Haven Hotel. So Just like a hotel, no extra fees that I could see. Good area for walking to the Yale campus. Coffee maker in the room. Thanks for wonderful front desk service!"

Reviewed on Aug 11, 2025

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New Haven Hotel
La Quinta Inn & Suites by Wyndham New Haven

La Quinta Inn & Suites by Wyndham New Haven

3 out of 5
400 Sargent Dr, New Haven, CT
Stay at this 3-star business-friendly hotel in New Haven. Enjoy free breakfast, free WiFi, and parking (surcharge). Our guests praise the breakfast and the helpful ...
5.8/10 (1,095 reviews)
"Everything is fine. Only issue I had is the elevators were out and I was on the 7th floor. I thought I was going to pass out going up."

Reviewed on Aug 11, 2025

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La Quinta Inn & Suites by Wyndham New Haven
Clarion Inn

Clarion Inn

3 out of 5
201 Washington Avenue, North Haven, CT
Book a stay at this business-friendly hotel in North Haven. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
7.4/10 Good! (1,006 reviews)
Other residents let you down
"The entrance lobby was bright and welcoming, and the young lady on reception (8/4/25) was pleasant and welcoming. The room was nice and clean although walls are paper thin and air con is quite loud but the swimming pool needs some attention. The sign says shower before entering, but the shower didn't ..."

Reviewed on Aug 12, 2025

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Clarion Inn
Sound View Greenport

Sound View Greenport

4 out of 5
58775 County Rd 48, Greenport, NY
Stay at this 4-star beach hotel in Greenport. Enjoy free breakfast, free WiFi, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular ...
8.4/10 Very Good! (558 reviews)
Perfect get away
"This place is a real joy so much energy and lots to do. They are not overly fancy but worth the ride."

Reviewed on Aug 12, 2025

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Sound View Greenport
See all 1,913 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.