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Madison

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Madison Flights as Low as $234

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

American Airlines
Tue, Sep 29 - Sat, Oct 3
ORD
O'Hare Intl.
SHD
Shenandoah Valley Regional
$234 Roundtrip, found 20 hours ago
$234
Roundtrip
found 20 hours ago
Select American Airlines flight, departing Tue, Sep 29 from O'Hare Intl. to Shenandoah Valley Regional, returning Sat, Oct 3, priced at $234 found 20 hours ago
American Airlines
Thu, Sep 17 - Sat, Sep 19
JFK
John F. Kennedy Intl.
CHO
Charlottesville-Albemarle
$259 Roundtrip, found 20 hours ago
$259
Roundtrip
found 20 hours ago
Select American Airlines flight, departing Thu, Sep 17 from John F. Kennedy Intl. to Charlottesville-Albemarle, returning Sat, Sep 19, priced at $259 found 20 hours ago
American Airlines
Tue, Sep 29 - Sat, Oct 3
ORD
O'Hare Intl.
SHD
Shenandoah Valley Regional
$284 Roundtrip, found 20 hours ago
$284
Roundtrip
found 20 hours ago
Select American Airlines flight, departing Tue, Sep 29 from O'Hare Intl. to Shenandoah Valley Regional, returning Sat, Oct 3, priced at $284 found 20 hours ago
United
Fri, Jul 17 - Sun, Jul 19
ORD
O'Hare Intl.
CHO
Charlottesville-Albemarle
$286 Roundtrip, found 1 day ago
$286
Roundtrip
found 1 day ago
Select United flight, departing Fri, Jul 17 from O'Hare Intl. to Charlottesville-Albemarle, returning Sun, Jul 19, priced at $286 found 1 day ago
Delta
Wed, Aug 12 - Tue, Aug 18
ORD
O'Hare Intl.
CHO
Charlottesville-Albemarle
$289 Roundtrip, found 2 days ago
$289
Roundtrip
found 2 days ago
Select Delta flight, departing Wed, Aug 12 from O'Hare Intl. to Charlottesville-Albemarle, returning Tue, Aug 18, priced at $289 found 2 days ago
United
Tue, Aug 25 - Wed, Sep 2
IAH
George Bush Intercontinental
CHO
Charlottesville-Albemarle
$291 Roundtrip, found 11 hours ago
$291
Roundtrip
found 11 hours ago
Select United flight, departing Tue, Aug 25 from George Bush Intercontinental to Charlottesville-Albemarle, returning Wed, Sep 2, priced at $291 found 11 hours ago
Delta
Mon, Jul 13 - Tue, Jul 21
PBI
Palm Beach Intl.
CHO
Charlottesville-Albemarle
$293 Roundtrip, found 4 days ago
$293
Roundtrip
found 4 days ago
Select Delta flight, departing Mon, Jul 13 from Palm Beach Intl. to Charlottesville-Albemarle, returning Tue, Jul 21, priced at $293 found 4 days ago
American Airlines
Tue, Aug 11 - Mon, Aug 17
ORD
O'Hare Intl.
CHO
Charlottesville-Albemarle
$296 Roundtrip, found 2 days ago
$296
Roundtrip
found 2 days ago
Select American Airlines flight, departing Tue, Aug 11 from O'Hare Intl. to Charlottesville-Albemarle, returning Mon, Aug 17, priced at $296 found 2 days ago
American Airlines
Thu, Sep 17 - Sat, Sep 19
JFK
John F. Kennedy Intl.
CHO
Charlottesville-Albemarle
$301 Roundtrip, found 20 hours ago
$301
Roundtrip
found 20 hours ago
Select American Airlines flight, departing Thu, Sep 17 from John F. Kennedy Intl. to Charlottesville-Albemarle, returning Sat, Sep 19, priced at $301 found 20 hours ago
United
Tue, Aug 11 - Mon, Aug 17
ORD
O'Hare Intl.
CHO
Charlottesville-Albemarle
$302 Roundtrip, found 2 days ago
$302
Roundtrip
found 2 days ago
Select United flight, departing Tue, Aug 11 from O'Hare Intl. to Charlottesville-Albemarle, returning Mon, Aug 17, priced at $302 found 2 days ago
Delta
Wed, Aug 12 - Sat, Aug 15
ORD
O'Hare Intl.
CHO
Charlottesville-Albemarle
$309 Roundtrip, found 2 days ago
$309
Roundtrip
found 2 days ago
Select Delta flight, departing Wed, Aug 12 from O'Hare Intl. to Charlottesville-Albemarle, returning Sat, Aug 15, priced at $309 found 2 days ago
United
Tue, Aug 11 - Mon, Aug 17
ORD
O'Hare Intl.
CHO
Charlottesville-Albemarle
$312 Roundtrip, found 2 days ago
$312
Roundtrip
found 2 days ago
Select United flight, departing Tue, Aug 11 from O'Hare Intl. to Charlottesville-Albemarle, returning Mon, Aug 17, priced at $312 found 2 days ago
Delta
Mon, Jul 13 - Mon, Jul 20
PBI
Palm Beach Intl.
CHO
Charlottesville-Albemarle
$316 Roundtrip, found 4 days ago
$316
Roundtrip
found 4 days ago
Select Delta flight, departing Mon, Jul 13 from Palm Beach Intl. to Charlottesville-Albemarle, returning Mon, Jul 20, priced at $316 found 4 days ago
United
Tue, Aug 25 - Wed, Sep 2
IAH
George Bush Intercontinental
CHO
Charlottesville-Albemarle
$318 Roundtrip, found 11 hours ago
$318
Roundtrip
found 11 hours ago
Select United flight, departing Tue, Aug 25 from George Bush Intercontinental to Charlottesville-Albemarle, returning Wed, Sep 2, priced at $318 found 11 hours ago
United
Tue, Aug 11 - Mon, Aug 17
ORD
O'Hare Intl.
CHO
Charlottesville-Albemarle
$322 Roundtrip, found 2 days ago
$322
Roundtrip
found 2 days ago
Select United flight, departing Tue, Aug 11 from O'Hare Intl. to Charlottesville-Albemarle, returning Mon, Aug 17, priced at $322 found 2 days ago
American Airlines
Thu, Jul 16 - Sun, Jul 19
PBI
Palm Beach Intl.
SHD
Shenandoah Valley Regional
$566 Roundtrip, found 4 days ago
$566
Roundtrip
found 4 days ago
Select American Airlines flight, departing Thu, Jul 16 from Palm Beach Intl. to Shenandoah Valley Regional, returning Sun, Jul 19, priced at $566 found 4 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 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 September, 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 $234, 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 $234 right now, why wait?

Madison Flight Information
Destination airport
Shenandoah Valley Regional
Destination airport IATA code
SHD
Roundtrip price
$233

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! (2,891 reviews)
"The English Inn has an old English feel. My room was clean and the bed was very comfortable. The breakfast was buffet was super each day I was there (4 days). From 4-6pm each day there is tea and fresh baked cookies. I took a day trip to Monticello (Thomas Jefferson's home) and enjoyed it immensely. ..."

Reviewed on Jun 14, 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! (1,370 reviews)
"It’s an old resort that looks good in pictures but not much is included with stay and rooms are very old. It was below my expectations"

Reviewed on Jun 14, 2026

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Massanutten Resort
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 ...
8.8/10 Excellent! (1,017 reviews)
"Staff was great. Loved Tamika,the bartender/waitress at the Taproom. Shenandoah is beautiful. Wonderful place for hikers."

Reviewed on Jun 13, 2026

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Skyland
Holiday Inn Charlottesville-Univ Area by IHG

Holiday Inn Charlottesville-Univ Area by IHG

3 out of 5
1901 Emmet St N Charlottesville VA
Book a stay at this business-friendly hotel in Charlottesville. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the helpful staff in our ...
8.2/10 Very Good! (1,003 reviews)
"Pleasant, friendly staff. Comfy beds."

Reviewed on Jun 6, 2026

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Holiday Inn Charlottesville-Univ Area by IHG
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! (1,012 reviews)
"Outstanding"

Reviewed on Jun 12, 2026

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Mimslyn Inn Historic Hotels Of America
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 ...
9/10 Wonderful! (1,166 reviews)
"I think this place is brand new!! It is absolutely fabulous!! Clean, fresh, new, new, new!! The room was great, the staff was amazing!! Plenty of parking!!! A great smoking patio out back is easy to access and pleanty of seating!!!"

Reviewed on Jun 15, 2026

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Country Inn & Suites by Radisson, Charlottesville-UVA, VA
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! (844 reviews)
"Nice spacious cabins with privacy and many trails to hike."

Reviewed on Jun 14, 2026

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Big Meadows Lodge
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! (1,001 reviews)
"Very nice hotel. Staff was nice. Room was fairly quiet though we had loud neighbors screaming at each other half the night-that wasn’t the hotels fault"

Reviewed on Jun 9, 2026

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DoubleTree by Hilton Hotel Charlottesville
See all 1,753 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.