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Chesapeake

$229+ Cheap flights from Greensboro (GSO) to Chesapeake, VA

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 7/23. Fares are subject to change and may not be available on all flights or dates of travel.
GSO — RIC
Jul 30 — Aug 61
Thu 7/30
Thu 8/6
1 adult, Economy
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Cheap flight deals from Greensboro to Chesapeake

Cheapest flights from Greensboro to Chesapeake
Explore the most affordable flight options available from Greensboro to Chesapeake. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 30, 2026.

This American Airlines deal was found by Cheapflights users on 6/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/237:50 pm
GSO
-
ORF
1 stop3h 55m
American Airlines
Mon 7/278:20 pm
ORF
-
GSO
1 stop3h 37m
American Airlines
Deal found 6/28$279
This American Airlines deal was found by Cheapflights users on 6/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/46:29 am
GSO
-
ORF
1 stop3h 21m
American Airlines
Tue 9/87:23 pm
ORF
-
GSO
1 stop3h 28m
American Airlines
Deal found 6/27$285
This American Airlines deal was found by Cheapflights users on 6/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/176:20 am
GSO
-
ORF
1 stop3h 14m
American Airlines
Sun 9/201:42 pm
ORF
-
GSO
1 stop4h 14m
American Airlines
Deal found 6/30$294
This American Airlines deal was found by Cheapflights users on 6/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/146:39 pm
GSO
-
ORF
1 stop5h 02m
American Airlines
Sat 7/188:20 pm
ORF
-
GSO
1 stop3h 37m
American Airlines
Deal found 6/28$309
This United Airlines deal was found by Cheapflights users on 6/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/146:00 am
GSO
-
ORF
1 stop3h 41m
United Airlines
Wed 11/187:15 pm
ORF
-
GSO
1 stop4h 37m
United Airlines
Deal found 6/25$331
This American Airlines deal was found by Cheapflights users on 6/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/262:46 pm
GSO
-
ORF
1 stop4h 47m
American Airlines
Sun 6/288:18 pm
ORF
-
GSO
1 stop3h 40m
American Airlines
Deal found 6/26$349
This American Airlines deal was found by Cheapflights users on 6/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/57:50 pm
GSO
-
ORF
1 stop3h 55m
American Airlines
Sun 7/125:01 am
ORF
-
GSO
1 stop3h 29m
American Airlines
Deal found 6/28$379
This United Airlines deal was found by Cheapflights users on 6/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/146:15 am
GSO
-
ORF
1 stop3h 24m
United Airlines
Sat 7/185:39 pm
ORF
-
GSO
1 stop6h 03m
United Airlines
Deal found 6/29$398
This United Airlines deal was found by Cheapflights users on 6/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/26:15 am
GSO
-
ORF
1 stop3h 24m
United Airlines
Sat 7/410:48 am
ORF
-
GSO
1 stop6h 09m
United Airlines
Deal found 6/25$399
This United Airlines deal was found by Cheapflights users on 6/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/16:15 am
GSO
-
ORF
1 stop3h 24m
United Airlines
Sun 7/1210:45 am
ORF
-
GSO
1 stop3h 35m
United Airlines
Deal found 6/28$410
This Kiwi.com deal was found by Cheapflights users on 6/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/209:50 pm
GSO
-
ORF
2 stops13h 25m
Multiple Airlines
Thu 7/239:34 pm
ORF
-
GSO
1 stop18h 28m
Multiple Airlines
Deal found 6/27$427

Find flight deals from Greensboro to Chesapeake

Keep the following information in mind while searching for Greensboro to Chesapeake flight deals. Data was last updated June 30, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$279
(American Airlines)

One-way from

$229
(American Airlines)

Popular in

June

Cheapest in

February

Average price

$531
Provider with most accurate pricing for Greensboro/H. Point-Norfolk flight deals.
Search Deals
Provider most trusted by Cheapflights users for Greensboro/H. Point-Norfolk flights.
Search Deals
From Greensboro/H. Point to Chesapeake
Search Deals
One-way flight from Greensboro/H. Point to Chesapeake
Search Deals
Highest demand for flights based on searches. 19% potential increase in price ($73 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 7% potential price decrease ($22 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in June 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Greensboro to Chesapeake that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated June 30, 2026.
Use the filters below to find and compare flights from Greensboro to Chesapeake that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

GreensboroNorfolk

GSO - ORF

GSOORF

Greensboro/H. Point

Tue 7/14

6:39 pm-11:41 pm

1 stop5h 02m

Norfolk

Sat 7/18

8:20 pm-11:57 pm

1 stop3h 37m

$309

GreensboroNorfolk

GSO - ORF

GSOORF

Greensboro/H. Point

Sat 11/14

6:00 am-9:41 am

1 stop3h 41m

Norfolk

Wed 11/18

7:15 pm-11:52 pm

1 stop4h 37m

$331

GreensboroNorfolk

GSO - ORF

GSOORF

Greensboro/H. Point

Wed 11/4

6:00 am-9:41 am

1 stop3h 41m

Norfolk

Sat 11/7

7:15 pm-11:52 pm

1 stop4h 37m

$331
Quickest round-trip

GreensboroNorfolk

GSO - ORF

GSOORF

Greensboro/H. Point

Sat 7/11

6:15 am-9:34 am

1 stop3h 19m

Norfolk

Wed 7/15

10:45 am-2:20 pm

1 stop3h 35m

$379

GreensboroNorfolk

GSO - ORF

GSOORF

Greensboro/H. Point

Tue 7/14

6:15 am-9:39 am

1 stop3h 24m

Norfolk

Sat 7/18

5:39 pm-11:42 pm

1 stop6h 03m

$398

GreensboroNorfolk

GSO - ORF

GSOORF

Greensboro/H. Point

Thu 7/23

3:15 pm-11:44 pm

2 stops8h 29m

Norfolk

Mon 7/27

5:44 pm-11:42 pm

1 stop5h 58m

$520

GreensboroNorfolk

GSO - ORF

GSOORF

Greensboro/H. Point

Thu 9/17

6:00 am-9:53 am

1 stop3h 53m

Norfolk

Sun 9/20

6:15 am-7:48 pm

2 stops13h 33m

$533

GreensboroNorfolk

GSO - ORF

GSOORF

Greensboro/H. Point

Wed 7/15

2:33 pm-11:44 pm

2 stops9h 11m

Norfolk

Sun 7/19

10:45 am-2:20 pm

1 stop3h 35m

$543
Cheapest one-way
Quickest one-way

GreensboroNorfolk

GSO - ORF

GSOORF

Greensboro/H. Point

Sat 7/25

5:16 am-8:24 am

1 stop3h 08m

$229

GreensboroNorfolk

GSO - ORF

GSOORF

Greensboro/H. Point

Thu 7/30

7:50 pm-11:45 pm

1 stop3h 55m

$229

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/29

Showing 1-10 of 12 resultsSorted by cheapest first
1
2

Best time to book a flight from Greensboro to Chesapeake

Have a flexible travel schedule? Discover the best time to fly to Chesapeake from Greensboro with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Greensboro to Chesapeake
No data available for this route at this time. Please check back soon.

Reviews of airlines servicing Chesapeake

Get insights into the airlines that provide service to Chesapeake. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chesapeake. Reviews last updated June 30, 2026.
Peruse reviews from past customers who have flown with American Airlines from Greensboro to Chesapeake to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
American Airlines
7.1
Good
11,762 reviews

Crew

7.9

Comfort

7.2

Food

6.4

Overall

7.1

Entertainment

6.8

Boarding

7.5

Reviews

1 / 20
2.0
Mediocre

Susie,Jan 2026

CLT - TPA

This flight was delayed 3 or 4 times. We had boarded the plane, sat on plane for a good 30 minutes, then we had to board the aircraft, walk to a different gate, wait and then board another aircraft. We arrived in Tampa 4 hours later than the original booking. I feel there should have been some sort of compensation especially for the advantage members.
American Airlines
7.1
Good
11,762 reviews
American Airlines
7.1
Good
11,762 reviews

Crew

7.9

Comfort

7.2

Food

6.4

Overall

7.1

Entertainment

6.8

Boarding

7.5

Reviews

1 / 20
2.0
Mediocre

Susie,Jan 2026

CLT - TPA

This flight was delayed 3 or 4 times. We had boarded the plane, sat on plane for a good 30 minutes, then we had to board the aircraft, walk to a different gate, wait and then board another aircraft. We arrived in Tampa 4 hours later than the original booking. I feel there should have been some sort of compensation especially for the advantage members.

Related info for your journey

Find useful and relevant information for your journey from Greensboro to Chesapeake. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Greensboro to Chesapeake?

    Located just 8.4 mi from the city center, Greensboro/H. Point is the airport most travelers will use when flying to Chesapeake from Greensboro. Booking flights from Greensboro/H. Point (GSO) to Chesapeake should be relatively easy as there are 0 daily outbound flights to Chesapeake from 1 airline.

  • How long is the flight from Greensboro to Chesapeake?

    There are many flights that can get you from Greensboro to Chesapeake in 3h 41m. Fly via American Airlines or United Airlines to get the fastest option. The distance from Greensboro to Chesapeake is about 214 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • Can I find deals for flights from Greensboro to Chesapeake that include hotel bookings?

    Yes. In addition to deals on Greensboro to Chesapeake flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Greensboro to Chesapeake?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Greensboro to Chesapeake.

  • Can I find deals for business class flights from Greensboro to Chesapeake?

    Yes. Cheapflights offers flight deals from Greensboro to Chesapeake by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

See more FAQs

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Top airline flying from Greensboro to Chesapeake

Discover the top airline that operate flights from Greensboro to Chesapeake. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated June 30, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$218Average$278FlexibilityNo cancel feeOn-time71%

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