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Madison

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Madison Flights as Low as $180

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

Bargain Flight
Tue, May 5 - Wed, May 27
SYR
Hancock Intl.
CHO
Charlottesville-Albemarle
$180 Roundtrip, found 3 days ago
$180
Roundtrip
found 3 days ago
Select Bargain Flight flight, departing Tue, May 5 from Hancock Intl. to Charlottesville-Albemarle, returning Wed, May 27, priced at $180 found 3 days ago
Delta
Tue, May 5 - Wed, May 27
SYR
Hancock Intl.
CHO
Charlottesville-Albemarle
$187 Roundtrip, found 3 days ago
$187
Roundtrip
found 3 days ago
Select Delta flight, departing Tue, May 5 from Hancock Intl. to Charlottesville-Albemarle, returning Wed, May 27, priced at $187 found 3 days ago
Delta
Tue, May 5 - Tue, May 19
SYR
Hancock Intl.
CHO
Charlottesville-Albemarle
$199 Roundtrip, found 1 day ago
$199
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, May 5 from Hancock Intl. to Charlottesville-Albemarle, returning Tue, May 19, priced at $199 found 1 day ago
Delta
Mon, May 4 - Tue, May 19
SYR
Hancock Intl.
CHO
Charlottesville-Albemarle
$211 Roundtrip, found 1 day ago
$211
Roundtrip
found 1 day ago
Select Delta flight, departing Mon, May 4 from Hancock Intl. to Charlottesville-Albemarle, returning Tue, May 19, priced at $211 found 1 day ago
United
Wed, Mar 11 - Tue, Mar 17
ORD
O'Hare Intl.
CHO
Charlottesville-Albemarle
$212 Roundtrip, found 17 hours ago
$212
Roundtrip
found 17 hours ago
Select United flight, departing Wed, Mar 11 from O'Hare Intl. to Charlottesville-Albemarle, returning Tue, Mar 17, priced at $212 found 17 hours ago
United
Wed, Mar 11 - Tue, Mar 17
ORD
O'Hare Intl.
CHO
Charlottesville-Albemarle
$222 Roundtrip, found 17 hours ago
$222
Roundtrip
found 17 hours ago
Select United flight, departing Wed, Mar 11 from O'Hare Intl. to Charlottesville-Albemarle, returning Tue, Mar 17, priced at $222 found 17 hours ago
Delta
Tue, Apr 28 - Tue, May 19
SYR
Hancock Intl.
CHO
Charlottesville-Albemarle
$223 Roundtrip, found 7 hours ago
$223
Roundtrip
found 7 hours ago
Select Delta flight, departing Tue, Apr 28 from Hancock Intl. to Charlottesville-Albemarle, returning Tue, May 19, priced at $223 found 7 hours ago
American Airlines
Wed, Mar 11 - Tue, Mar 17
ORD
O'Hare Intl.
CHO
Charlottesville-Albemarle
$232 Roundtrip, found 17 hours ago
$232
Roundtrip
found 17 hours ago
Select American Airlines flight, departing Wed, Mar 11 from O'Hare Intl. to Charlottesville-Albemarle, returning Tue, Mar 17, priced at $232 found 17 hours ago
Delta
Tue, Mar 10 - Tue, Mar 17
ORD
O'Hare Intl.
CHO
Charlottesville-Albemarle
$234 Roundtrip, found 4 days ago
$234
Roundtrip
found 4 days ago
Select Delta flight, departing Tue, Mar 10 from O'Hare Intl. to Charlottesville-Albemarle, returning Tue, Mar 17, priced at $234 found 4 days ago
United
Tue, May 5 - Wed, May 27
SYR
Hancock Intl.
CHO
Charlottesville-Albemarle
$236 Roundtrip, found 3 days ago
$236
Roundtrip
found 3 days ago
Select United flight, departing Tue, May 5 from Hancock Intl. to Charlottesville-Albemarle, returning Wed, May 27, priced at $236 found 3 days ago
United
Wed, Mar 11 - Tue, Mar 17
ORD
O'Hare Intl.
CHO
Charlottesville-Albemarle
$240 Roundtrip, found 17 hours ago
$240
Roundtrip
found 17 hours ago
Select United flight, departing Wed, Mar 11 from O'Hare Intl. to Charlottesville-Albemarle, returning Tue, Mar 17, priced at $240 found 17 hours ago
United
Wed, May 13 - Thu, May 28
SYR
Hancock Intl.
CHO
Charlottesville-Albemarle
$241 Roundtrip, found 20 hours ago
$241
Roundtrip
found 20 hours ago
Select United flight, departing Wed, May 13 from Hancock Intl. to Charlottesville-Albemarle, returning Thu, May 28, priced at $241 found 20 hours ago
United
Tue, May 5 - Tue, May 19
SYR
Hancock Intl.
CHO
Charlottesville-Albemarle
$245 Roundtrip, found 1 day ago
$245
Roundtrip
found 1 day ago
Select United flight, departing Tue, May 5 from Hancock Intl. to Charlottesville-Albemarle, returning Tue, May 19, priced at $245 found 1 day ago
American Airlines
Wed, Mar 11 - Tue, Mar 17
ORD
O'Hare Intl.
CHO
Charlottesville-Albemarle
$247 Roundtrip, found 17 hours ago
$247
Roundtrip
found 17 hours ago
Select American Airlines flight, departing Wed, Mar 11 from O'Hare Intl. to Charlottesville-Albemarle, returning Tue, Mar 17, priced at $247 found 17 hours ago
Delta
Sun, Jan 25 - Sun, Feb 1
DAL
Love Field
CHO
Charlottesville-Albemarle
$354 Roundtrip, found 6 days ago
$354
Roundtrip
found 6 days ago
Select Delta flight, departing Sun, Jan 25 from Love Field to Charlottesville-Albemarle, returning Sun, Feb 1, priced at $354 found 6 days ago
American Airlines
Wed, May 6 - Wed, May 27
SYR
Hancock Intl.
SHD
Shenandoah Valley Regional
$432 Roundtrip, found 1 hour ago
$432
Roundtrip
found 1 hour ago
Select American Airlines flight, departing Wed, May 6 from Hancock Intl. to Shenandoah Valley Regional, returning Wed, May 27, priced at $432 found 1 hour 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 May, 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 15 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 $180, 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 $180 right now, why wait?

Madison Flight Information
Destination airport
Charlottesville-Albemarle
Destination airport IATA code
CHO
Roundtrip price
$179

Last Minute Hotel Deals in Madison

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! (1,206 reviews)
We have been We have been coming for 4 years now, and each year, our room has been more amazing. We were in a very spacious condo this time in an area where we were one of the only ones there, which was fantastic. The room was spotless and looked like it had just been renovated. There were a couple ...

Reviewed on Jan 20, 2026

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Massanutten Resort
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! (2,709 reviews)
Wonderful staff

Reviewed on Jan 19, 2026

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English Inn of Charlottesville
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! (1,132 reviews)
The room was great and very clean. Breakfast was very good. And the staff were friendly and helpful.

Reviewed on Jan 20, 2026

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Country Inn & Suites by Radisson, Charlottesville-UVA, VA
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 ...
9.4/10 Exceptional! (421 reviews)
Easy check in, warm lobby. Super clean room.

Reviewed on Jan 2, 2026

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Kimpton The Forum Hotel by IHG
Postcard Cabins Shenandoah, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Shenandoah, Outdoor Collection by Marriott Bonvoy

2 out of 5
2010 Madison Rd Stanardsville VA
Stay at this cabin in Stanardsville. Enjoy free parking, patios, and climate control. Popular attractions Green Hills Golf Course and Greene County Library are ...
9.4/10 Exceptional! (64 reviews)
This was a beautiful cabin. I wasn't exactly sure what to expect but it was everything and more. We had brought a lot of supplies but it turns out we didnt really need much considering they provided all basic necessities. Showers had hot water. Everything was very clean. Easy check in and out. Very ...

Reviewed on Jan 16, 2026

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Postcard Cabins Shenandoah, Outdoor Collection by Marriott Bonvoy
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, free parking, and breakfast (surcharge). Our guests praise the helpful staff ...
8.2/10 Very Good! (1,000 reviews)
The room was very clean. The only wrong was the bed was not very comfortable.

Reviewed on Jan 6, 2026

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DoubleTree by Hilton Hotel Charlottesville
Extended Stay America Premier Suites - Charlottesville

Extended Stay America Premier Suites - Charlottesville

2.5 out of 5
3400 Berkmar Drive Charlottesville VA
Stay at this hotel in Charlottesville. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Downtown Mall and Monticello are located ...
8.8/10 Excellent! (398 reviews)
the first room had a leaking toliet

Reviewed on Jan 15, 2026

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Extended Stay America Premier Suites - Charlottesville
Comfort Inn & Suites Charlottesville Hollymead Town Center

Comfort Inn & Suites Charlottesville Hollymead Town Center

2.5 out of 5
1615 Timberwood Blvd 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 ...
8.8/10 Excellent! (699 reviews)
Room was clean, roomy and comfortable beds and pillows! Comfort in never disappoints.

Reviewed on Jan 17, 2026

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Comfort Inn & Suites Charlottesville Hollymead Town Center
See all 1,756 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.