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South Boston

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South Boston Flights as Low as $58

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

Frontier Airlines
Thu, Aug 6 - Mon, Aug 10
MCO
Orlando Intl.
RDU
Raleigh - Durham Intl.
$58 Roundtrip, found 1 day ago
$58
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Thu, Aug 6 from Orlando Intl. to Raleigh - Durham Intl., returning Mon, Aug 10, priced at $58 found 1 day ago
Frontier Airlines
Tue, Aug 11 - Tue, Aug 11
MCO
Orlando Intl.
RDU
Raleigh - Durham Intl.
$68 Roundtrip, found 1 day ago
$68
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Tue, Aug 11 from Orlando Intl. to Raleigh - Durham Intl., returning Tue, Aug 11, priced at $68 found 1 day ago
Frontier Airlines
Thu, Aug 6 - Mon, Aug 10
MCO
Orlando Intl.
RDU
Raleigh - Durham Intl.
$76 Roundtrip, found 1 day ago
$76
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Thu, Aug 6 from Orlando Intl. to Raleigh - Durham Intl., returning Mon, Aug 10, priced at $76 found 1 day ago
Frontier Airlines
Tue, Aug 11 - Fri, Aug 21
MCO
Orlando Intl.
RDU
Raleigh - Durham Intl.
$78 Roundtrip, found 1 day ago
$78
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Tue, Aug 11 from Orlando Intl. to Raleigh - Durham Intl., returning Fri, Aug 21, priced at $78 found 1 day ago
Breeze Airways
Thu, Aug 6 - Mon, Aug 10
MCO
Orlando Intl.
RDU
Raleigh - Durham Intl.
$94 Roundtrip, found 1 day ago
$94
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Thu, Aug 6 from Orlando Intl. to Raleigh - Durham Intl., returning Mon, Aug 10, priced at $94 found 1 day ago
Frontier Airlines
Thu, Oct 29 - Mon, Nov 16
DFW
Dallas-Fort Worth Intl.
RDU
Raleigh - Durham Intl.
$152 Roundtrip, found 2 hours ago
$152
Roundtrip
found 2 hours ago
Select Frontier Airlines flight, departing Thu, Oct 29 from Dallas-Fort Worth Intl. to Raleigh - Durham Intl., returning Mon, Nov 16, priced at $152 found 2 hours ago
American Airlines
Tue, Sep 1 - Sat, Sep 5
ORD
O'Hare Intl.
RDU
Raleigh - Durham Intl.
$212 Roundtrip, found 4 days ago
$212
Roundtrip
found 4 days ago
Select American Airlines flight, departing Tue, Sep 1 from O'Hare Intl. to Raleigh - Durham Intl., returning Sat, Sep 5, priced at $212 found 4 days ago
United
Tue, Sep 1 - Sat, Sep 5
ORD
O'Hare Intl.
RDU
Raleigh - Durham Intl.
$212 Roundtrip, found 4 days ago
$212
Roundtrip
found 4 days ago
Select United flight, departing Tue, Sep 1 from O'Hare Intl. to Raleigh - Durham Intl., returning Sat, Sep 5, priced at $212 found 4 days ago
Frontier Airlines
Wed, Sep 2 - Tue, Sep 15
IND
Indianapolis Intl.
RDU
Raleigh - Durham Intl.
$215 Roundtrip, found 5 days ago
$215
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Wed, Sep 2 from Indianapolis Intl. to Raleigh - Durham Intl., returning Tue, Sep 15, priced at $215 found 5 days ago
Delta
Thu, Aug 6 - Mon, Aug 10
MCO
Orlando Intl.
RDU
Raleigh - Durham Intl.
$220 Roundtrip, found 1 day ago
$220
Roundtrip
found 1 day ago
Select Delta flight, departing Thu, Aug 6 from Orlando Intl. to Raleigh - Durham Intl., returning Mon, Aug 10, priced at $220 found 1 day ago
Bargain Flight
Tue, Aug 11 - Wed, Aug 12
MKE
General Mitchell Intl.
RDU
Raleigh - Durham Intl.
$236 Roundtrip, found 2 hours ago
$236
Roundtrip
found 2 hours ago
Select Bargain Flight flight, departing Tue, Aug 11 from General Mitchell Intl. to Raleigh - Durham Intl., returning Wed, Aug 12, priced at $236 found 2 hours ago
Delta
Sat, Aug 8 - Thu, Aug 13
DAL
Love Field
RDU
Raleigh - Durham Intl.
$267 Roundtrip, found 2 days ago
$267
Roundtrip
found 2 days ago
Select Delta flight, departing Sat, Aug 8 from Love Field to Raleigh - Durham Intl., returning Thu, Aug 13, priced at $267 found 2 days ago
United
Wed, Aug 12 - Mon, Aug 31
ORD
O'Hare Intl.
ROA
Roanoke Regional
$269 Roundtrip, found 2 hours ago
$269
Roundtrip
found 2 hours ago
Select United flight, departing Wed, Aug 12 from O'Hare Intl. to Roanoke Regional, returning Mon, Aug 31, priced at $269 found 2 hours ago
JetBlue Airways
Mon, Sep 28 - Wed, Oct 14
DFW
Dallas-Fort Worth Intl.
RDU
Raleigh - Durham Intl.
$323 Roundtrip, found 17 hours ago
$323
Roundtrip
found 17 hours ago
Select JetBlue Airways flight, departing Mon, Sep 28 from Dallas-Fort Worth Intl. to Raleigh - Durham Intl., returning Wed, Oct 14, priced at $323 found 17 hours ago
Delta
Tue, Aug 11 - Sat, Aug 15
DAL
Love Field
ROA
Roanoke Regional
$439 Roundtrip, found 2 hours ago
$439
Roundtrip
found 2 hours ago
Select Delta flight, departing Tue, Aug 11 from Love Field to Roanoke Regional, returning Sat, Aug 15, priced at $439 found 2 hours ago
American Airlines
Sun, Aug 9 - Mon, Aug 17
DFW
Dallas-Fort Worth Intl.
ROA
Roanoke Regional
$477 Roundtrip, found 2 hours ago
$477
Roundtrip
found 2 hours ago
Select American Airlines flight, departing Sun, Aug 9 from Dallas-Fort Worth Intl. to Roanoke Regional, returning Mon, Aug 17, priced at $477 found 2 hours ago

Cheap Flights to South Boston

Fall in love at first flight with your vacation to South Boston 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 South Boston on Hotwire, and you’ll be up, up, and on a getaway in no time.

Because once the wheels are down in South Boston, the good times start rolling. So buckle up, you’re in for a fun ride.

Frequently Asked Questions About flights to South Boston

Don’t waste your time on endless searches for cheap airline tickets oneway or roundtrip. We’ll have you on your way to South Boston 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 ROA airport.

What is the cheapest month to fly to South Boston?

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 South Boston are in August, but when you book your flight on Hotwire, savings are always in season.

How many airlines fly to South Boston?

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 South Boston.

What airport is best to fly into South Boston?

When you’re planning your trip to South Boston, convenience is the name of the game. Luckily, South Boston Danville Regional Airport is nearby so you can deplane and get going on checking off everything on your South Boston must-do list.

How much are flights to South Boston?

Got very cheap flights on your vacation itinerary? When you book your airline tickets to South Boston on Hotwire, you may just get what’s on your getaway wish list. With tickets as low as $58, 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 South Boston?

The trick to saving a stack of cash on your flight to South Boston? 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 $58 right now, why wait?

South Boston Flight Information
Destination airport
Raleigh - Durham Intl.
Destination airport IATA code
RDU
Roundtrip price
$152

Last Minute Hotel Deals in South Boston

The Berry Hill Resort & Conference Center

The Berry Hill Resort & Conference Center

4 out of 5
3105 River Road South Boston VA
Book a stay at this spa hotel in South Boston. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the property condition ...
9.2/10 Wonderful! (751 reviews)
"This is the perfect place to stay in the South Boston area."

Reviewed on Jul 14, 2026

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The Berry Hill Resort & Conference Center
Fairfield Inn & Suites South Boston

Fairfield Inn & Suites South Boston

3 out of 5
1120 Bill Tuck Hwy South Boston VA
Book a stay at this business-friendly hotel in South Boston. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
8.8/10 Excellent! (419 reviews)
"The rooms need a refresh - certainly are clean, but in some portions, (bathroom) definitely moving toward dingy. Just clearly showing wear."

Reviewed on Jul 9, 2026

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Fairfield Inn & Suites South Boston
Clarion Pointe South Boston - Danville East

Clarion Pointe South Boston - Danville East

3.5 out of 5
1074 Bill Tuck Hwy South Boston VA
Book a stay at this business-friendly hotel in South Boston. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Riverdale Plaza and Constitution ...
7.2/10 Good! (328 reviews)
"Breakfast was very good and well kept. The front doors were not functioning properly. The side door had to be pulled closed. The room was nice. A good stay overall."

Reviewed on Jul 13, 2026

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Clarion Pointe South Boston - Danville East
Quality Inn South Boston - Danville East

Quality Inn South Boston - Danville East

2.5 out of 5
2001 Seymour Drive South Boston VA
Book a stay at this business-friendly hotel in South Boston. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
7.2/10 Good! (405 reviews)
"The staff were very helpful and friendly as was the manager. We especially liked the nice young lady who was cleaning in the breakfast area. She was so polite and helpful attempting to answer our questions. When she didn’t know right away she found out for us. No problems at all with our stay. Not ..."

Reviewed on Jun 27, 2026

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Quality Inn South Boston - Danville East
Super 8 by Wyndham South Boston VA

Super 8 by Wyndham South Boston VA

2 out of 5
1040 Bill Tuck Hwy South Boston VA
Stay at this motel in South Boston. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions ...
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Super 8 by Wyndham South Boston VA
Americas Best Value Inn & Suites South Boston

Americas Best Value Inn & Suites South Boston

2 out of 5
2050 Philpott Rd South Boston VA
Stay at this motel in South Boston. Enjoy free parking, a 24-hour front desk, and daily housekeeping. Popular attractions Riverdale Plaza and Tobacco Heritage ...
5.6/10 (372 reviews)
"Toilet was dirty and several light was broken"

Reviewed on Jul 6, 2026

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Americas Best Value Inn & Suites South Boston
Charles Bass House Bed & Breakfast

Charles Bass House Bed & Breakfast

2.5 out of 5
1505 North Main Street South Boston VA
Stay at this B&B in South Boston. Enjoy free breakfast, free parking, and a computer station. Popular attractions North Main Street Park and Penick Park are ...
9.8/10 Exceptional! (108 reviews)
"We had a wonderful experience at this property. A lovely older home with loads of charm. Located in the town’s historic district, it was easy to walk to a local restaurant for dinner. The owner provided clear and easy to understand instructions. It had everything we needed and would happily stay ..."

Reviewed on Apr 30, 2026

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Charles Bass House Bed & Breakfast
Riverside Inn and Suites Danville Virginia

Riverside Inn and Suites Danville Virginia

2.5 out of 5
2500 Riverside Dr Danville VA
Stay at this hotel in Danville. Enjoy free WiFi, free parking, and room service. Popular attractions Caesars Virginia Casino and Danville Mall are located ...
5.8/10 (35 reviews)
"There were burn marks and a smell in the first room that was supposed to be ours, which was a king room then we got downgraded to a queen room that had a bug in the shower and the water pressure was horrible. The room was just not clean at all."

Reviewed on Jul 8, 2026

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Riverside Inn and Suites Danville Virginia
See all 280 properties in South Boston
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.