Search Cheap Flights to
Madison

Photo by Shannon Willitts

Search 400 airlines and 321,000 hotels worldwide.

Stop Planning & Start Exploring

FREE 24 hour cancellation on most flights

Madison Flights as Low as $102

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
$102 Roundtrip, found 3 hours ago
$102
Roundtrip
found 3 hours ago
Select Breeze Airways flight, departing Thu, Aug 14 from Norfolk Intl. to Tweed - New Haven Regional, returning Sun, Aug 17, priced at $102 found 3 hours ago
Breeze Airways
Thu, Aug 14 - Sun, Aug 17
ORF
Norfolk Intl.
HVN
Tweed - New Haven Regional
$107 Roundtrip, found 2 days ago
$107
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Thu, Aug 14 from Norfolk Intl. to Tweed - New Haven Regional, returning Sun, Aug 17, priced at $107 found 2 days ago
Breeze Airways
Thu, Aug 14 - Sun, Aug 17
ORF
Norfolk Intl.
HVN
Tweed - New Haven Regional
$112 Roundtrip, found 5 days ago
$112
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Thu, Aug 14 from Norfolk Intl. to Tweed - New Haven Regional, returning Sun, Aug 17, priced at $112 found 5 days ago
Breeze Airways
Thu, Aug 14 - Sun, Aug 17
ORF
Norfolk Intl.
HVN
Tweed - New Haven Regional
$117 Roundtrip, found 5 days ago
$117
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Thu, Aug 14 from Norfolk Intl. to Tweed - New Haven Regional, returning Sun, Aug 17, priced at $117 found 5 days ago
Breeze Airways
Thu, Aug 14 - Sun, Aug 17
ORF
Norfolk Intl.
HVN
Tweed - New Haven Regional
$122 Roundtrip, found 5 days ago
$122
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Thu, Aug 14 from Norfolk Intl. to Tweed - New Haven Regional, returning Sun, Aug 17, priced at $122 found 5 days ago
Breeze Airways
Wed, Aug 13 - Sat, Aug 16
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$122 Roundtrip, just found
$122
Roundtrip
just found
Select Breeze Airways flight, departing Wed, Aug 13 from Orlando Intl. to Tweed - New Haven Regional, returning Sat, Aug 16, priced at $122 just found
Breeze Airways
Mon, Aug 4 - Mon, Aug 11
TPA
Tampa Intl.
HVN
Tweed - New Haven Regional
$124 Roundtrip, found 2 days ago
$124
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Mon, Aug 4 from Tampa Intl. to Tweed - New Haven Regional, returning Mon, Aug 11, priced at $124 found 2 days ago
Breeze Airways
Mon, Aug 4 - Mon, Aug 11
TPA
Tampa Intl.
HVN
Tweed - New Haven Regional
$125 Roundtrip, found 16 hours ago
$125
Roundtrip
found 16 hours ago
Select Breeze Airways flight, departing Mon, Aug 4 from Tampa Intl. to Tweed - New Haven Regional, returning Mon, Aug 11, priced at $125 found 16 hours ago
Breeze Airways
Wed, Aug 13 - Sat, Aug 16
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$127 Roundtrip, just found
$127
Roundtrip
just found
Select Breeze Airways flight, departing Wed, Aug 13 from Orlando Intl. to Tweed - New Haven Regional, returning Sat, Aug 16, priced at $127 just found
Breeze Airways
Mon, Aug 4 - Mon, Aug 11
TPA
Tampa Intl.
HVN
Tweed - New Haven Regional
$128 Roundtrip, found 16 hours ago
$128
Roundtrip
found 16 hours ago
Select Breeze Airways flight, departing Mon, Aug 4 from Tampa Intl. to Tweed - New Haven Regional, returning Mon, Aug 11, priced at $128 found 16 hours ago
Breeze Airways
Sun, Aug 10 - Wed, Aug 13
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$130 Roundtrip, found 11 hours ago
$130
Roundtrip
found 11 hours ago
Select Breeze Airways flight, departing Sun, Aug 10 from Orlando Intl. to Tweed - New Haven Regional, returning Wed, Aug 13, priced at $130 found 11 hours ago
Breeze Airways
Mon, Aug 4 - Mon, Aug 11
TPA
Tampa Intl.
HVN
Tweed - New Haven Regional
$130 Roundtrip, found 16 hours ago
$130
Roundtrip
found 16 hours ago
Select Breeze Airways flight, departing Mon, Aug 4 from Tampa Intl. to Tweed - New Haven Regional, returning Mon, Aug 11, priced at $130 found 16 hours ago
Breeze Airways
Wed, Aug 13 - Sat, Aug 16
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$132 Roundtrip, just found
$132
Roundtrip
just found
Select Breeze Airways flight, departing Wed, Aug 13 from Orlando Intl. to Tweed - New Haven Regional, returning Sat, Aug 16, priced at $132 just found
Breeze Airways
Mon, Aug 4 - Mon, Aug 11
TPA
Tampa Intl.
HVN
Tweed - New Haven Regional
$134 Roundtrip, found 2 days ago
$134
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Mon, Aug 4 from Tampa Intl. to Tweed - New Haven Regional, returning Mon, Aug 11, priced at $134 found 2 days ago
Breeze Airways
Sun, Aug 10 - Wed, Aug 13
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$135 Roundtrip, found 11 hours ago
$135
Roundtrip
found 11 hours ago
Select Breeze Airways flight, departing Sun, Aug 10 from Orlando Intl. to Tweed - New Haven Regional, returning Wed, Aug 13, priced at $135 found 11 hours ago
Breeze Airways
Mon, Aug 4 - Mon, Aug 11
TPA
Tampa Intl.
HVN
Tweed - New Haven Regional
$135 Roundtrip, found 16 hours ago
$135
Roundtrip
found 16 hours ago
Select Breeze Airways flight, departing Mon, Aug 4 from Tampa Intl. to Tweed - New Haven Regional, returning Mon, Aug 11, priced at $135 found 16 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 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! (301 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

Get rates
Madison Beach Hotel
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! (1,662 reviews)
"Excellent location to walk all over the city maximizing your time to do different things."

Reviewed on Jul 21, 2025

Get rates
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! (817 reviews)
"Awesome stay"

Reviewed on Jul 19, 2025

Get rates
Cambria Hotel New Haven University Area
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 (1,006 reviews)
"Quick and easy check in, room was clean and looked newly renovated. I was traveling with my pup, and they were very friendly and welcoming both her and i. Would absolutely stay again."

Reviewed on Jul 16, 2025

Get rates
Motel 6 New Haven - Branford, CT
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! (1,210 reviews)
"Recently renovated it appears and looking very good, much better than the last time I stayed here a few years ago."

Reviewed on Jul 19, 2025

Get rates
Best Western Executive Hotel Of New Haven - West Haven
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! (1,002 reviews)
Summer fun
"I always enjoy stopping at the Saybrook Inn and Spa. The front desk gentleman were very nice and welcomed me back. We arrived almost at restaurant closing time and our server was accommodating and kind. The hotel is pet friendly and the breakfast wait staff were great. Look forward to our next ..."

Reviewed on Jul 18, 2025

Get rates
Saybrook Point Resort & Marina
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 free parking. Our guests praise the breakfast and the helpful ...
5.8/10 (1,038 reviews)
Pleasant stay
"Very grateful for my time here"

Reviewed on Jul 18, 2025

Get rates
La Quinta Inn & Suites by Wyndham New Haven
The Blake Hotel

The Blake Hotel

4 out of 5
9 High Street, New Haven, CT
Stay at this 4-star business-friendly hotel in New Haven. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the bar and the helpful staff ...
9.4/10 Exceptional! (1,009 reviews)
Modern, clean, super friendly
"Really enjoyable stay at The Blake. Staff were super friendly, hotel is clean, modern, well designed. The rooms are really spacious and the beds/pillows extremely comfortable. To finish it off, the sun was shining, the rooftop bar/restaurant was very much appreciated, serving very good food and drink. ..."

Reviewed on Jul 19, 2025

Get rates
The Blake Hotel
See all 1,937 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.