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Madison

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Madison Flights as Low as $386

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

American Airlines
Sat, Sep 27 - Thu, Oct 2
BOS
Logan Intl.
SHD
Shenandoah Valley Regional
$386 Roundtrip, found 2 days ago
$386
Roundtrip
found 2 days ago
Select American Airlines flight, departing Sat, Sep 27 from Logan Intl. to Shenandoah Valley Regional, returning Thu, Oct 2, priced at $386 found 2 days ago
American Airlines
Sat, Sep 27 - Thu, Oct 2
BOS
Logan Intl.
SHD
Shenandoah Valley Regional
$387 Roundtrip, found 6 days ago
$387
Roundtrip
found 6 days ago
Select American Airlines flight, departing Sat, Sep 27 from Logan Intl. to Shenandoah Valley Regional, returning Thu, Oct 2, priced at $387 found 6 days ago
American Airlines
Tue, Sep 23 - Sat, Sep 27
BOS
Logan Intl.
SHD
Shenandoah Valley Regional
$397 Roundtrip, found 6 days ago
$397
Roundtrip
found 6 days ago
Select American Airlines flight, departing Tue, Sep 23 from Logan Intl. to Shenandoah Valley Regional, returning Sat, Sep 27, priced at $397 found 6 days ago
American Airlines
Tue, Sep 23 - Sat, Sep 27
BOS
Logan Intl.
SHD
Shenandoah Valley Regional
$398 Roundtrip, found 8 hours ago
$398
Roundtrip
found 8 hours ago
Select American Airlines flight, departing Tue, Sep 23 from Logan Intl. to Shenandoah Valley Regional, returning Sat, Sep 27, priced at $398 found 8 hours ago
United
Tue, Sep 23 - Thu, Oct 2
BOS
Logan Intl.
SHD
Shenandoah Valley Regional
$401 Roundtrip, found 5 days ago
$401
Roundtrip
found 5 days ago
Select United flight, departing Tue, Sep 23 from Logan Intl. to Shenandoah Valley Regional, returning Thu, Oct 2, priced at $401 found 5 days ago
United
Tue, Sep 23 - Wed, Sep 24
BOS
Logan Intl.
SHD
Shenandoah Valley Regional
$406 Roundtrip, found 6 days ago
$406
Roundtrip
found 6 days ago
Select United flight, departing Tue, Sep 23 from Logan Intl. to Shenandoah Valley Regional, returning Wed, Sep 24, priced at $406 found 6 days ago
American Airlines
Tue, Sep 23 - Sat, Sep 27
BOS
Logan Intl.
SHD
Shenandoah Valley Regional
$408 Roundtrip, found 8 hours ago
$408
Roundtrip
found 8 hours ago
Select American Airlines flight, departing Tue, Sep 23 from Logan Intl. to Shenandoah Valley Regional, returning Sat, Sep 27, priced at $408 found 8 hours ago
American Airlines
Sat, Sep 27 - Sat, Oct 4
BOS
Logan Intl.
SHD
Shenandoah Valley Regional
$408 Roundtrip, found 20 hours ago
$408
Roundtrip
found 20 hours ago
Select American Airlines flight, departing Sat, Sep 27 from Logan Intl. to Shenandoah Valley Regional, returning Sat, Oct 4, priced at $408 found 20 hours ago
American Airlines
Tue, Sep 23 - Wed, Sep 24
BOS
Logan Intl.
SHD
Shenandoah Valley Regional
$409 Roundtrip, found 6 days ago
$409
Roundtrip
found 6 days ago
Select American Airlines flight, departing Tue, Sep 23 from Logan Intl. to Shenandoah Valley Regional, returning Wed, Sep 24, priced at $409 found 6 days ago
United
Tue, Sep 23 - Sat, Sep 27
BOS
Logan Intl.
SHD
Shenandoah Valley Regional
$412 Roundtrip, found 6 days ago
$412
Roundtrip
found 6 days ago
Select United flight, departing Tue, Sep 23 from Logan Intl. to Shenandoah Valley Regional, returning Sat, Sep 27, priced at $412 found 6 days ago
United
Tue, Sep 23 - Sat, Sep 27
BOS
Logan Intl.
SHD
Shenandoah Valley Regional
$413 Roundtrip, found 8 hours ago
$413
Roundtrip
found 8 hours ago
Select United flight, departing Tue, Sep 23 from Logan Intl. to Shenandoah Valley Regional, returning Sat, Sep 27, priced at $413 found 8 hours ago
American Airlines
Sat, Sep 27 - Thu, Oct 2
BOS
Logan Intl.
SHD
Shenandoah Valley Regional
$418 Roundtrip, found 5 days ago
$418
Roundtrip
found 5 days ago
Select American Airlines flight, departing Sat, Sep 27 from Logan Intl. to Shenandoah Valley Regional, returning Thu, Oct 2, priced at $418 found 5 days ago
American Airlines
Tue, Sep 23 - Sat, Sep 27
BOS
Logan Intl.
SHD
Shenandoah Valley Regional
$422 Roundtrip, found 6 days ago
$422
Roundtrip
found 6 days ago
Select American Airlines flight, departing Tue, Sep 23 from Logan Intl. to Shenandoah Valley Regional, returning Sat, Sep 27, priced at $422 found 6 days ago
United
Tue, Sep 23 - Sat, Sep 27
BOS
Logan Intl.
SHD
Shenandoah Valley Regional
$423 Roundtrip, found 3 days ago
$423
Roundtrip
found 3 days ago
Select United flight, departing Tue, Sep 23 from Logan Intl. to Shenandoah Valley Regional, returning Sat, Sep 27, priced at $423 found 3 days ago
United
Tue, Sep 23 - Thu, Oct 2
BOS
Logan Intl.
SHD
Shenandoah Valley Regional
$424 Roundtrip, found 5 days ago
$424
Roundtrip
found 5 days ago
Select United flight, departing Tue, Sep 23 from Logan Intl. to Shenandoah Valley Regional, returning Thu, Oct 2, priced at $424 found 5 days ago
American Airlines
Sun, Jul 20 - Sat, Jul 26
OMA
Eppley Field
SHD
Shenandoah Valley Regional
$684 Roundtrip, found 1 day ago
$684
Roundtrip
found 1 day ago
Select American Airlines flight, departing Sun, Jul 20 from Eppley Field to Shenandoah Valley Regional, returning Sat, Jul 26, priced at $684 found 1 day 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 $386, 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 $386 right now, why wait?

Madison Flight Information
Destination airport
Charlottesville-Albemarle
Destination airport IATA code
CHO
Roundtrip price
$258

Last Minute Hotel Deals in Madison

English Inn of Charlottesville
English Inn of Charlottesville
3 out of 5
2000 Morton Drive, Charlottesville, VA
Stay at this 3-star business-friendly hotel in Charlottesville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool ...
9/10 Wonderful! (2,312 reviews)
Great!
"Everything was wonderful. It exceeded my expectations. 2 negatives...the pillows are too fluffy and there was no soap for the shower. Other than that, it was great, and will definitely stay again, since I have to be in that area alot."

Reviewed on Jul 11, 2025

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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! (822 reviews)
"Amazing"

Reviewed on Jul 10, 2025

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Massanutten Resort
DoubleTree by Hilton Hotel Charlottesville
DoubleTree by Hilton Hotel Charlottesville
4 out of 5
990 Hilton Heights Rd, Charlottesville, VA
Stay at this 4-star business-friendly hotel in Charlottesville. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff ...
7.8/10 Good! (1,003 reviews)
"Overall it was nice"

Reviewed on Jul 11, 2025

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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 ...
9.4/10 Exceptional! (109 reviews)
"I was surprised that the kitchenware was not in the room when I checked in, but am pleased with the innkeeper addressing eco-friendly concerns by providing the Kitchenware of choice at check in. If the hotel leaves the Kitchenware in the room, the hotel has to fully wash the dishes and utensils between ..."

Reviewed on Jul 11, 2025

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Extended Stay America Premier Suites - Charlottesville
Skyland
Skyland
2 out of 5
Skyline Dr Mile 41.7 & 42.5, Luray, VA
Book a stay at this eco-certified hotel in Luray. Enjoy free parking, breakfast (surcharge), and a 24-hour front desk. Our guests praise the helpful staff and ...
8.4/10 Very Good! (1,012 reviews)
"Very helpful and friendly staff"

Reviewed on Jul 9, 2025

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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 3-star hotel in Luray. Enjoy free parking, breakfast (surcharge), and daily housekeeping. Our guests praise the helpful staff in our reviews. Popular ...
7.6/10 Good! (678 reviews)
"Very pleasant experience and good was excellent"

Reviewed on Jul 9, 2025

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Big Meadows Lodge
Days Inn by Wyndham Charlottesville/University Area
Days Inn by Wyndham Charlottesville/University Area
2 out of 5
1610 Emmet St N, Charlottesville, VA
Book a stay at this business-friendly motel in Charlottesville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the ...
7.8/10 Good! (1,011 reviews)
"Very clean, if utilitarian hotel. I’d stay there again."

Reviewed on Jul 12, 2025

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Days Inn by Wyndham Charlottesville/University Area
Kimpton The Forum Hotel by IHG
Kimpton The Forum Hotel by IHG
4 out of 5
540 Massie Road, Charlottesville, VA
Stay at this 4-star 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! (349 reviews)
"We have stayed here before and really love the amenities the decor, the architecture and most of all the friendly staff especially Catherine, Taylor, and Cortney. The food is really delicious."

Reviewed on Jul 6, 2025

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Kimpton The Forum Hotel by IHG
See all 1,708 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.