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Madison

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Madison Flights as Low as $206

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

Breeze Airways
Fri, Dec 4 - Sun, Dec 6
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$206 Roundtrip, found 22 hours ago
$206
Roundtrip
found 22 hours ago
Select Breeze Airways flight, departing Fri, Dec 4 from Orlando Intl. to Tweed - New Haven Regional, returning Sun, Dec 6, priced at $206 found 22 hours ago
Breeze Airways
Thu, Dec 3 - Thu, Dec 3
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$207 Roundtrip, found 3 days ago
$207
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Thu, Dec 3 from Orlando Intl. to Tweed - New Haven Regional, returning Thu, Dec 3, priced at $207 found 3 days ago
Breeze Airways
Fri, Dec 4 - Sun, Dec 6
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$211 Roundtrip, found 22 hours ago
$211
Roundtrip
found 22 hours ago
Select Breeze Airways flight, departing Fri, Dec 4 from Orlando Intl. to Tweed - New Haven Regional, returning Sun, Dec 6, priced at $211 found 22 hours ago
Breeze Airways
Fri, Dec 4 - Sun, Dec 6
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$216 Roundtrip, found 22 hours ago
$216
Roundtrip
found 22 hours ago
Select Breeze Airways flight, departing Fri, Dec 4 from Orlando Intl. to Tweed - New Haven Regional, returning Sun, Dec 6, priced at $216 found 22 hours ago
Breeze Airways
Fri, Dec 4 - Sun, Dec 6
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$222 Roundtrip, found 22 hours ago
$222
Roundtrip
found 22 hours ago
Select Breeze Airways flight, departing Fri, Dec 4 from Orlando Intl. to Tweed - New Haven Regional, returning Sun, Dec 6, priced at $222 found 22 hours ago
Breeze Airways
Fri, Dec 4 - Sun, Dec 6
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$227 Roundtrip, found 22 hours ago
$227
Roundtrip
found 22 hours ago
Select Breeze Airways flight, departing Fri, Dec 4 from Orlando Intl. to Tweed - New Haven Regional, returning Sun, Dec 6, priced at $227 found 22 hours ago
Breeze Airways
Fri, Dec 4 - Sun, Dec 6
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$232 Roundtrip, found 22 hours ago
$232
Roundtrip
found 22 hours ago
Select Breeze Airways flight, departing Fri, Dec 4 from Orlando Intl. to Tweed - New Haven Regional, returning Sun, Dec 6, priced at $232 found 22 hours ago
Breeze Airways
Fri, Oct 16 - Mon, Oct 19
FLL
Fort Lauderdale - Hollywood Intl.
HVN
Tweed - New Haven Regional
$235 Roundtrip, found 3 hours ago
$235
Roundtrip
found 3 hours ago
Select Breeze Airways flight, departing Fri, Oct 16 from Fort Lauderdale - Hollywood Intl. to Tweed - New Haven Regional, returning Mon, Oct 19, priced at $235 found 3 hours ago
Avelo Airlines
Fri, Nov 6 - Sun, Nov 8
ATL
Hartsfield-Jackson Atlanta Intl.
HVN
Tweed - New Haven Regional
$236 Roundtrip, found 4 hours ago
$236
Roundtrip
found 4 hours ago
Select Avelo Airlines flight, departing Fri, Nov 6 from Hartsfield-Jackson Atlanta Intl. to Tweed - New Haven Regional, returning Sun, Nov 8, priced at $236 found 4 hours ago
Breeze Airways
Fri, Oct 16 - Mon, Oct 19
FLL
Fort Lauderdale - Hollywood Intl.
HVN
Tweed - New Haven Regional
$240 Roundtrip, found 3 hours ago
$240
Roundtrip
found 3 hours ago
Select Breeze Airways flight, departing Fri, Oct 16 from Fort Lauderdale - Hollywood Intl. to Tweed - New Haven Regional, returning Mon, Oct 19, priced at $240 found 3 hours ago
Breeze Airways
Thu, Oct 22 - Sun, Nov 8
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$242 Roundtrip, found 22 hours ago
$242
Roundtrip
found 22 hours ago
Select Breeze Airways flight, departing Thu, Oct 22 from Orlando Intl. to Tweed - New Haven Regional, returning Sun, Nov 8, priced at $242 found 22 hours ago
Breeze Airways
Fri, Oct 16 - Mon, Oct 19
FLL
Fort Lauderdale - Hollywood Intl.
HVN
Tweed - New Haven Regional
$245 Roundtrip, found 3 hours ago
$245
Roundtrip
found 3 hours ago
Select Breeze Airways flight, departing Fri, Oct 16 from Fort Lauderdale - Hollywood Intl. to Tweed - New Haven Regional, returning Mon, Oct 19, priced at $245 found 3 hours ago
Breeze Airways
Thu, Oct 22 - Sun, Nov 8
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$247 Roundtrip, found 22 hours ago
$247
Roundtrip
found 22 hours ago
Select Breeze Airways flight, departing Thu, Oct 22 from Orlando Intl. to Tweed - New Haven Regional, returning Sun, Nov 8, priced at $247 found 22 hours ago
Breeze Airways
Thu, Oct 22 - Sun, Nov 8
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$252 Roundtrip, found 22 hours ago
$252
Roundtrip
found 22 hours ago
Select Breeze Airways flight, departing Thu, Oct 22 from Orlando Intl. to Tweed - New Haven Regional, returning Sun, Nov 8, priced at $252 found 22 hours ago
Avelo Airlines
Sat, Dec 19 - Mon, Dec 21
ATL
Hartsfield-Jackson Atlanta Intl.
HVN
Tweed - New Haven Regional
$255 Roundtrip, found 4 hours ago
$255
Roundtrip
found 4 hours ago
Select Avelo Airlines flight, departing Sat, Dec 19 from Hartsfield-Jackson Atlanta Intl. to Tweed - New Haven Regional, returning Mon, Dec 21, priced at $255 found 4 hours ago
Avelo Airlines
Fri, Oct 23 - Sun, Oct 25
ATL
Hartsfield-Jackson Atlanta Intl.
HVN
Tweed - New Haven Regional
$258 Roundtrip, just found
$258
Roundtrip
just found
Select Avelo Airlines flight, departing Fri, Oct 23 from Hartsfield-Jackson Atlanta Intl. to Tweed - New Haven Regional, returning Sun, Oct 25, priced at $258 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 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 December, 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 $206, 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 $206 right now, why wait?

Madison Flight Information
Destination airport
Tweed - New Haven Regional
Destination airport IATA code
HVN
Roundtrip price
$206

Last Minute Hotel Deals in Madison

Madison Beach Hotel

Madison Beach Hotel

4 out of 5
94 West Wharf Road Madison CT
Book a stay at this 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 ...
Get rates
Madison Beach Hotel
New Haven Hotel

New Haven Hotel

3.5 out of 5
229 George Street New Haven CT
Book a stay at this business-friendly hotel in New Haven. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the helpful staff and ...
9.2/10 Wonderful! (2,358 reviews)
"The rooms were small and you could tell they hadn’t been updated in a very long time. Parking was tight and across the street and they charged you extra for it convenient location, but that was about it."

Reviewed on Sep 28, 2026

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New Haven Hotel
Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

2 out of 5
1430 Boston Post Rd Old Saybrook CT
Stay at this hotel in Old Saybrook. Enjoy free WiFi, free parking, and a picnic area. Our guests praise the helpful staff and the clean rooms in our reviews. ...
8/10 Very Good! (1,015 reviews)
"It is an older property that is very well maintained - the staff could not be more friendly and accommodating. This is coastal CT and hotel prices can be extremely high and there are plenty of options at those price-points - it is nice to find the rare property where “older”, can be clean and comfortable ..."

Reviewed on Sep 28, 2026

Get rates
Pier Blue Inn Old Saybrook - Essex
Holiday Inn Express Southington by IHG

Holiday Inn Express Southington by IHG

2.5 out of 5
120 Laning St Southington CT
Book a stay at this business-friendly hotel in Southington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Get rates
Holiday Inn Express Southington by IHG
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. ...
7.4/10 Good! (1,029 reviews)
"Didn’t have my reservation at check in. Showed confirmation and they seemed annoyed.Took too long to resolve and person was rude. Also did not get King Bed which I had confirmed."

Reviewed on Sep 28, 2026

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Motel 6 New Haven - Branford, CT
Hampton Inn & Suites New Haven - South - West Haven

Hampton Inn & Suites New Haven - South - West Haven

2.5 out of 5
510 Saw Mill Rd West Haven CT
Book a stay at this business-friendly hotel in West Haven. Enjoy free breakfast, free WiFi, and a fitness center. Our guests praise the breakfast and the helpful ...
8.4/10 Very Good! (1,007 reviews)
"Room was clean. Receptionist didn't seem happy to see us but was helpful. No wash clothes or glasses in bathroom. Bulb blown out in one lamp. Couldn't adjust clock. Direct TV in room is AWFUL! Hate the duvet on the bed (too hot). Breakfast was minimal. We expected more considering the price and the ..."

Reviewed on Sep 28, 2026

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Hampton Inn & Suites New Haven - South - West Haven
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 ...
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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
Book a stay at this business-friendly hotel in New Haven. Enjoy breakfast (surcharge), room service, and a 24-hour fitness center. Our guests praise the helpful ...
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Omni New Haven Hotel at Yale
See all 1,985 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.