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Madison

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Madison Flights as Low as $102

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

Breeze Airways
Fri, Aug 29 - Mon, Sep 1
RDU
Raleigh - Durham Intl.
HVN
Tweed - New Haven Regional
$102 Roundtrip, found 21 hours ago
$102
Roundtrip
found 21 hours ago
Select Breeze Airways flight, departing Fri, Aug 29 from Raleigh - Durham Intl. to Tweed - New Haven Regional, returning Mon, Sep 1, priced at $102 found 21 hours ago
Breeze Airways
Fri, Aug 29 - Mon, Sep 1
RDU
Raleigh - Durham Intl.
HVN
Tweed - New Haven Regional
$107 Roundtrip, found 21 hours ago
$107
Roundtrip
found 21 hours ago
Select Breeze Airways flight, departing Fri, Aug 29 from Raleigh - Durham Intl. to Tweed - New Haven Regional, returning Mon, Sep 1, priced at $107 found 21 hours ago
Breeze Airways
Fri, Aug 29 - Mon, Sep 1
RDU
Raleigh - Durham Intl.
HVN
Tweed - New Haven Regional
$112 Roundtrip, found 21 hours ago
$112
Roundtrip
found 21 hours ago
Select Breeze Airways flight, departing Fri, Aug 29 from Raleigh - Durham Intl. to Tweed - New Haven Regional, returning Mon, Sep 1, priced at $112 found 21 hours ago
Breeze Airways
Wed, Aug 13 - Sat, Aug 16
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$135 Roundtrip, found 22 hours ago
$135
Roundtrip
found 22 hours ago
Select Breeze Airways flight, departing Wed, Aug 13 from Orlando Intl. to Tweed - New Haven Regional, returning Sat, Aug 16, priced at $135 found 22 hours ago
Breeze Airways
Wed, Aug 13 - Sat, Aug 16
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$138 Roundtrip, found 22 hours ago
$138
Roundtrip
found 22 hours ago
Select Breeze Airways flight, departing Wed, Aug 13 from Orlando Intl. to Tweed - New Haven Regional, returning Sat, Aug 16, priced at $138 found 22 hours ago
Breeze Airways
Wed, Aug 13 - Sat, Aug 16
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$140 Roundtrip, found 22 hours ago
$140
Roundtrip
found 22 hours ago
Select Breeze Airways flight, departing Wed, Aug 13 from Orlando Intl. to Tweed - New Haven Regional, returning Sat, Aug 16, priced at $140 found 22 hours ago
Breeze Airways
Wed, Aug 13 - Sat, Aug 16
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$145 Roundtrip, found 6 days ago
$145
Roundtrip
found 6 days ago
Select Breeze Airways flight, departing Wed, Aug 13 from Orlando Intl. to Tweed - New Haven Regional, returning Sat, Aug 16, priced at $145 found 6 days ago
Breeze Airways
Wed, Aug 13 - Sat, Aug 16
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$145 Roundtrip, found 2 days ago
$145
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Wed, Aug 13 from Orlando Intl. to Tweed - New Haven Regional, returning Sat, Aug 16, priced at $145 found 2 days ago
Breeze Airways
Wed, Aug 13 - Sat, Aug 16
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$148 Roundtrip, found 2 days ago
$148
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Wed, Aug 13 from Orlando Intl. to Tweed - New Haven Regional, returning Sat, Aug 16, priced at $148 found 2 days ago
Breeze Airways
Wed, Aug 13 - Sat, Aug 16
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$150 Roundtrip, found 6 days ago
$150
Roundtrip
found 6 days ago
Select Breeze Airways flight, departing Wed, Aug 13 from Orlando Intl. to Tweed - New Haven Regional, returning Sat, Aug 16, priced at $150 found 6 days ago
Breeze Airways
Wed, Aug 13 - Sat, Aug 16
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$150 Roundtrip, found 2 days ago
$150
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Wed, Aug 13 from Orlando Intl. to Tweed - New Haven Regional, returning Sat, Aug 16, priced at $150 found 2 days ago
Breeze Airways
Wed, Aug 13 - Sat, Aug 16
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$155 Roundtrip, found 2 days ago
$155
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Wed, Aug 13 from Orlando Intl. to Tweed - New Haven Regional, returning Sat, Aug 16, priced at $155 found 2 days ago
Breeze Airways
Wed, Aug 13 - Sat, Aug 16
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$158 Roundtrip, found 2 days ago
$158
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Wed, Aug 13 from Orlando Intl. to Tweed - New Haven Regional, returning Sat, Aug 16, priced at $158 found 2 days ago
Breeze Airways
Thu, Aug 7 - Thu, Aug 14
TPA
Tampa Intl.
HVN
Tweed - New Haven Regional
$164 Roundtrip, found 2 days ago
$164
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Thu, Aug 7 from Tampa Intl. to Tweed - New Haven Regional, returning Thu, Aug 14, priced at $164 found 2 days ago
Breeze Airways
Thu, Aug 7 - Thu, Aug 14
TPA
Tampa Intl.
HVN
Tweed - New Haven Regional
$166 Roundtrip, found 2 days ago
$166
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Thu, Aug 7 from Tampa Intl. to Tweed - New Haven Regional, returning Thu, Aug 14, priced at $166 found 2 days ago
Breeze Airways
Thu, Aug 7 - Thu, Aug 14
TPA
Tampa Intl.
HVN
Tweed - New Haven Regional
$169 Roundtrip, found 2 days ago
$169
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Thu, Aug 7 from Tampa Intl. to Tweed - New Haven Regional, returning Thu, Aug 14, priced at $169 found 2 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 $102, 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 $102 right now, why wait?

Madison Flight Information
Destination airport
Tweed - New Haven Regional
Destination airport IATA code
HVN
Roundtrip price
$101

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! (303 reviews)
"The staff here is amazing along with the rooms and the property. This is a very nice and quiet place to stay with the family and they always seem to have some type of entertainment for the guests. Close to town and other points of interest. Only thing missing is a pool, but other than that this is ..."

Reviewed on Jul 12, 2025

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Madison Beach Hotel
Motel 6 New Haven - Branford, CT

Motel 6 New Haven - Branford, CT

2 out of 5
320 E Main St, Branford, CT
Stay at this motel in Branford. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. ...
6.8/10 (1,023 reviews)
"It was good."

Reviewed on Jul 28, 2025

Get rates
Motel 6 New Haven - Branford, CT
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! (1,695 reviews)
"Right in the middle of downtown"

Reviewed on Jul 29, 2025

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New Haven 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! (827 reviews)
"The staff was very nice and accommodating. Parking on site was very easy and nice, though the cost seemed a little high. The hotel is walkable distance to a lot of the things we wanted to do / see and the restaurants we wanted to eat at."

Reviewed on Jul 26, 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! (1,239 reviews)
"Large clean property located in a convenient area"

Reviewed on Jul 30, 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! (1,018 reviews)
"The hotel was nice. But the surrounding area outside of the hotel was a little sketchy."

Reviewed on Jul 26, 2025

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Omni New Haven Hotel at Yale
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! (544 reviews)
"Every room comes with an ocean view, steps down to the beach. Activities at night. Band at the ocean on certain nights. Will be back every year! Help with bags and getting to room by golf cart."

Reviewed on Jul 22, 2025

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Sound View Greenport
Saybrook Point Resort & Marina

Saybrook Point Resort & Marina

3.5 out of 5
2 Bridge St, Old Saybrook, CT
Stay at this 3.5-star spa hotel in Old Saybrook. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the restaurant and the helpful staff in ...
9.4/10 Exceptional! (1,012 reviews)
"Service was exemplary and the resort is tremendous"

Reviewed on Jul 29, 2025

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Saybrook Point Resort & Marina
See all 1,921 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.