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Madison

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Madison Flights as Low as $631

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

American Airlines
Mon, Nov 2 - Fri, Nov 13
CHO
Charlottesville-Albemarle
SHD
Shenandoah Valley Regional
$631 Roundtrip, found 11 hours ago
$631
Roundtrip
found 11 hours ago
Select American Airlines flight, departing Mon, Nov 2 from Charlottesville-Albemarle to Shenandoah Valley Regional, returning Fri, Nov 13, priced at $631 found 11 hours ago
American Airlines
Sun, Nov 1 - Fri, Nov 13
CHO
Charlottesville-Albemarle
SHD
Shenandoah Valley Regional
$651 Roundtrip, found 11 hours ago
$651
Roundtrip
found 11 hours ago
Select American Airlines flight, departing Sun, Nov 1 from Charlottesville-Albemarle to Shenandoah Valley Regional, returning Fri, Nov 13, priced at $651 found 11 hours ago
American Airlines
Sat, Oct 31 - Fri, Nov 13
CHO
Charlottesville-Albemarle
SHD
Shenandoah Valley Regional
$722 Roundtrip, found 11 hours ago
$722
Roundtrip
found 11 hours ago
Select American Airlines flight, departing Sat, Oct 31 from Charlottesville-Albemarle to Shenandoah Valley Regional, returning Fri, Nov 13, priced at $722 found 11 hours ago
American Airlines
Fri, Oct 23 - Fri, Nov 6
CHO
Charlottesville-Albemarle
SHD
Shenandoah Valley Regional
$749 Roundtrip, found 11 hours ago
$749
Roundtrip
found 11 hours ago
Select American Airlines flight, departing Fri, Oct 23 from Charlottesville-Albemarle to Shenandoah Valley Regional, returning Fri, Nov 6, priced at $749 found 11 hours ago
American Airlines
Fri, Oct 30 - Fri, Nov 13
CHO
Charlottesville-Albemarle
SHD
Shenandoah Valley Regional
$759 Roundtrip, found 11 hours ago
$759
Roundtrip
found 11 hours ago
Select American Airlines flight, departing Fri, Oct 30 from Charlottesville-Albemarle to Shenandoah Valley Regional, returning Fri, Nov 13, priced at $759 found 11 hours ago
American Airlines
Wed, Oct 28 - Sat, Nov 14
CHO
Charlottesville-Albemarle
SHD
Shenandoah Valley Regional
$792 Roundtrip, found 11 hours ago
$792
Roundtrip
found 11 hours ago
Select American Airlines flight, departing Wed, Oct 28 from Charlottesville-Albemarle to Shenandoah Valley Regional, returning Sat, Nov 14, priced at $792 found 11 hours ago
American Airlines
Sat, Oct 17 - Sat, Oct 31
CHO
Charlottesville-Albemarle
SHD
Shenandoah Valley Regional
$802 Roundtrip, found 11 hours ago
$802
Roundtrip
found 11 hours ago
Select American Airlines flight, departing Sat, Oct 17 from Charlottesville-Albemarle to Shenandoah Valley Regional, returning Sat, Oct 31, priced at $802 found 11 hours ago
American Airlines
Wed, Oct 14 - Sat, Oct 31
CHO
Charlottesville-Albemarle
SHD
Shenandoah Valley Regional
$803 Roundtrip, found 11 hours ago
$803
Roundtrip
found 11 hours ago
Select American Airlines flight, departing Wed, Oct 14 from Charlottesville-Albemarle to Shenandoah Valley Regional, returning Sat, Oct 31, priced at $803 found 11 hours ago
American Airlines
Sat, Oct 17 - Fri, Oct 30
CHO
Charlottesville-Albemarle
SHD
Shenandoah Valley Regional
$812 Roundtrip, found 11 hours ago
$812
Roundtrip
found 11 hours ago
Select American Airlines flight, departing Sat, Oct 17 from Charlottesville-Albemarle to Shenandoah Valley Regional, returning Fri, Oct 30, priced at $812 found 11 hours ago
American Airlines
Wed, Sep 16 - Tue, Oct 6
CHO
Charlottesville-Albemarle
SHD
Shenandoah Valley Regional
$814 Roundtrip, found 11 hours ago
$814
Roundtrip
found 11 hours ago
Select American Airlines flight, departing Wed, Sep 16 from Charlottesville-Albemarle to Shenandoah Valley Regional, returning Tue, Oct 6, priced at $814 found 11 hours ago
American Airlines
Wed, Sep 16 - Wed, Sep 23
CHO
Charlottesville-Albemarle
SHD
Shenandoah Valley Regional
$824 Roundtrip, found 11 hours ago
$824
Roundtrip
found 11 hours ago
Select American Airlines flight, departing Wed, Sep 16 from Charlottesville-Albemarle to Shenandoah Valley Regional, returning Wed, Sep 23, priced at $824 found 11 hours ago
American Airlines
Fri, Oct 16 - Sat, Oct 31
CHO
Charlottesville-Albemarle
SHD
Shenandoah Valley Regional
$829 Roundtrip, found 11 hours ago
$829
Roundtrip
found 11 hours ago
Select American Airlines flight, departing Fri, Oct 16 from Charlottesville-Albemarle to Shenandoah Valley Regional, returning Sat, Oct 31, priced at $829 found 11 hours ago
American Airlines
Tue, Sep 15 - Tue, Oct 6
CHO
Charlottesville-Albemarle
SHD
Shenandoah Valley Regional
$836 Roundtrip, found 11 hours ago
$836
Roundtrip
found 11 hours ago
Select American Airlines flight, departing Tue, Sep 15 from Charlottesville-Albemarle to Shenandoah Valley Regional, returning Tue, Oct 6, priced at $836 found 11 hours ago
American Airlines
Fri, Oct 16 - Fri, Oct 30
CHO
Charlottesville-Albemarle
SHD
Shenandoah Valley Regional
$839 Roundtrip, found 11 hours ago
$839
Roundtrip
found 11 hours ago
Select American Airlines flight, departing Fri, Oct 16 from Charlottesville-Albemarle to Shenandoah Valley Regional, returning Fri, Oct 30, priced at $839 found 11 hours ago
American Airlines
Thu, Oct 15 - Sat, Oct 31
CHO
Charlottesville-Albemarle
SHD
Shenandoah Valley Regional
$841 Roundtrip, found 11 hours ago
$841
Roundtrip
found 11 hours ago
Select American Airlines flight, departing Thu, Oct 15 from Charlottesville-Albemarle to Shenandoah Valley Regional, returning Sat, Oct 31, priced at $841 found 11 hours ago
American Airlines
Sat, Sep 5 - Sat, Sep 19
CHO
Charlottesville-Albemarle
SHD
Shenandoah Valley Regional
$842 Roundtrip, found 11 hours ago
$842
Roundtrip
found 11 hours ago
Select American Airlines flight, departing Sat, Sep 5 from Charlottesville-Albemarle to Shenandoah Valley Regional, returning Sat, Sep 19, priced at $842 found 11 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 CHO 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 November, 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 Charlottesville-Albemarle 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 $631, 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 $631 right now, why wait?

Madison Flight Information
Destination airport
Shenandoah Valley Regional
Destination airport IATA code
SHD
Roundtrip price
$631

Last Minute Hotel Deals in Madison

English Inn of Charlottesville

English Inn of Charlottesville

3 out of 5
2000 Morton Drive Charlottesville VA
Book a stay at this business-friendly hotel in Charlottesville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool ...
9.2/10 Wonderful! (3,029 reviews)
"The room was clean but the door would stick...you had to give the door a shove to get it open. The shower had a shower curtain compared to shower doors. The shower curtain didn't have enough weight to weigh it down so the shower curtain would provide gaps and in turn, the floor would get wet There ..."

Reviewed on Aug 18, 2026

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English Inn of Charlottesville
Massanutten Resort

Massanutten Resort

2.5 out of 5
1822 Resort Dr McGaheysville VA
Book a stay at this spa hotel in McGaheysville. Enjoy free WiFi, free parking, and 2 indoor pools. Our guests praise the helpful staff and the clean rooms in ...
8/10 Very Good! (1,495 reviews)
"Solo incluye las piscinas del local no incluye water park las cuales son la mayoría de las fotos en la publicación todo es un poco caro en los alrededores pero muy bonito todo"

Reviewed on Aug 17, 2026

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Massanutten Resort
Country Inn & Suites by Radisson, Charlottesville-UVA, VA

Country Inn & Suites by Radisson, Charlottesville-UVA, VA

3 out of 5
1600 Emmet Street Charlottesville VA
Book a stay at this business-friendly hotel in Charlottesville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
9.2/10 Wonderful! (1,225 reviews)
"Look this because of the waffle maker and the golden waffles. Stayed for two nights and they were out of the waffle mix for both days. I thought the road was clean until I started moving the bed looking around if I had left anything and found living and dead bugs behind my bed. Contacted the property ..."

Reviewed on Aug 18, 2026

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Country Inn & Suites by Radisson, Charlottesville-UVA, VA
Mimslyn Inn Historic Hotels Of America

Mimslyn Inn Historic Hotels Of America

3 out of 5
401 W Main St Luray VA
Book a stay at this spa hotel in Luray. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the breakfast and the restaurant in our reviews. ...
9/10 Wonderful! (1,027 reviews)
"Staff in the restaurants and the Sunday brunch were amazing. Glad we stayed for the long weekend."

Reviewed on Aug 17, 2026

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Mimslyn Inn Historic Hotels Of America
Skyland

Skyland

2 out of 5
Skyline Dr Mile 41.7 & 42.5 Luray VA
Stay at this hotel in Luray. Enjoy free parking, breakfast (surcharge), and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in ...
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Skyland
Big Meadows Lodge

Big Meadows Lodge

3 out of 5
Mile 51.2 Skyline Drive Luray VA
Stay at this hotel in Luray. Enjoy free parking, breakfast (surcharge), and daily housekeeping. Our guests praise the helpful staff in our reviews. Popular attractions ...
7.8/10 Good! (900 reviews)
"The rooms were clean and they were able to switch out our room to our liking"

Reviewed on Aug 17, 2026

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Big Meadows Lodge
Kimpton The Forum Hotel by IHG

Kimpton The Forum Hotel by IHG

4 out of 5
540 Massie Road Charlottesville VA
Book a stay at this business-friendly hotel in Charlottesville. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful ...
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Kimpton The Forum Hotel by IHG
DoubleTree by Hilton Hotel Charlottesville

DoubleTree by Hilton Hotel Charlottesville

4 out of 5
990 Hilton Heights Rd Charlottesville VA
Book a stay at this business-friendly hotel in Charlottesville. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful ...
8.4/10 Very Good! (1,006 reviews)
"clean room"

Reviewed on Aug 18, 2026

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DoubleTree by Hilton Hotel Charlottesville
See all 1,761 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.