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Chesapeake

$239+ Cheap flights from Greensboro (GSO) to Chesapeake, VA

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 5/11. Fares are subject to change and may not be available on all flights or dates of travel.
GSO — RIC
May 2 — May 91
Sat 5/2
Sat 5/9
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 April 2, 2026.

This Kiwi.com deal was found by Cheapflights users on 3/31. 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 5/113:16 pm
GSO
-
ORF
2 stops43h 55m
Multiple Airlines
Sun 5/179:12 pm
ORF
-
GSO
1 stop18h 36m
Multiple Airlines
Deal found 3/31$239
This United Airlines deal was found by Cheapflights users on 3/31. 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 5/136:00 am
GSO
-
ORF
1 stop3h 31m
United Airlines
Sun 5/176:15 am
ORF
-
GSO
1 stop3h 31m
United Airlines
Deal found 3/31$280
This United Airlines deal was found by Cheapflights users on 3/29. 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.
Sat 4/256:00 am
GSO
-
ORF
1 stop6h 09m
United Airlines
Thu 4/306:00 am
ORF
-
GSO
1 stop3h 46m
United Airlines
Deal found 3/29$299
This United Airlines deal was found by Cheapflights users on 3/30. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/146:00 am
GSO
-
ORF
1 stop3h 31m
United Airlines
Sat 4/185:20 pm
ORF
-
GSO
1 stop4h 37m
United Airlines
Deal found 3/30$309
This United Airlines deal was found by Cheapflights users on 3/30. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/106:00 am
GSO
-
ORF
1 stop3h 31m
United Airlines
Mon 4/137:55 pm
ORF
-
GSO
1 stop3h 48m
United Airlines
Deal found 3/30$319
This Kiwi.com deal was found by Cheapflights users on 3/31. 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 5/113:16 pm
GSO
-
ORF
1 stop22h 14m
Multiple Airlines
Thu 5/147:44 pm
ORF
-
GSO
1 stop20h 04m
Multiple Airlines
Deal found 3/31$327
This United Airlines deal was found by Cheapflights users on 3/30. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/236:00 am
GSO
-
ORF
1 stop3h 34m
United Airlines
Wed 5/277:59 pm
ORF
-
GSO
1 stop3h 45m
United Airlines
Deal found 3/30$331
This American Airlines deal was found by Cheapflights users on 3/31. 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.
Wed 4/11:06 pm
GSO
-
ORF
1 stop5h 33m
American Airlines
Sat 4/116:13 pm
ORF
-
GSO
1 stop3h 48m
American Airlines
Deal found 3/31$347
This United Airlines deal was found by Cheapflights users on 4/1. 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.
Fri 4/106:00 am
GSO
-
ORF
1 stop3h 31m
United Airlines
Sun 4/127:55 pm
ORF
-
GSO
1 stop3h 48m
United Airlines
Deal found 4/1$349
This United Airlines deal was found by Cheapflights users on 3/31. 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.
Mon 5/115:39 pm
GSO
-
ORF
1 stop7h 20m
United Airlines
Tue 5/1910:37 am
ORF
-
GSO
1 stop3h 32m
United Airlines
Deal found 3/31$350
This American Airlines deal was found by Cheapflights users on 4/1. 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 4/26:00 am
GSO
-
ORF
1 stop4h 06m
American Airlines
Thu 4/96:00 am
ORF
-
GSO
1 stop3h 49m
American Airlines
Deal found 4/1$359

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 April 2, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$239
(Kiwi.com)

Popular in

March

Cheapest in

February

Average price

$248
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
Highest demand for flights based on searches. 0% potential increase in price ($2 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($10 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 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 April 2, 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

Sat 5/23

6:00 am-9:34 am

1 stop3h 34m

Norfolk

Mon 5/25

10:45 am-2:20 pm

1 stop3h 35m

$280
Quickest round-trip

GreensboroNorfolk

GSO - ORF

GSOORF

Greensboro/H. Point

Wed 5/13

6:00 am-9:31 am

1 stop3h 31m

Norfolk

Sun 5/17

6:15 am-9:46 am

1 stop3h 31m

$280

GreensboroNorfolk

GSO - ORF

GSOORF

Greensboro/H. Point

Sat 4/25

6:00 am-12:09 pm

1 stop6h 09m

Norfolk

Thu 4/30

6:00 am-9:46 am

1 stop3h 46m

$299

GreensboroNorfolk

GSO - ORF

GSOORF

Greensboro/H. Point

Sat 5/23

6:00 am-9:34 am

1 stop3h 34m

Norfolk

Wed 5/27

7:59 pm-11:44 pm

1 stop3h 45m

$331

GreensboroNorfolk

GSO - ORF

GSOORF

Greensboro/H. Point

Tue 5/12

6:15 am-2:24 pm

1 stop8h 09m

Norfolk

Mon 5/18

6:00 am-11:58 am

1 stop5h 58m

$350

GreensboroNorfolk

GSO - ORF

GSOORF

Greensboro/H. Point

Mon 5/11

5:40 pm-11:32 pm

1 stop5h 52m

Norfolk

Wed 5/20

7:46 pm-11:44 pm

1 stop3h 58m

$350
Cheapest one-way

GreensboroNorfolk

GSO - ORF

GSOORF

Greensboro/H. Point

Fri 4/10

3:16 pm-4:34 pm

2 stops25h 18m

$259
Quickest one-way

GreensboroNorfolk

GSO - ORF

GSOORF

Greensboro/H. Point

Fri 4/10

6:00 am-2:20 pm

2 stops8h 20m

$676

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/29

Sorted by cheapest first

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

What is the cheapest month to book a flight from Greensboro to Chesapeake?

Currently, September is the cheapest month in which you can book a flight from Greensboro to Chesapeake (average of $196). Flying from Greensboro to Chesapeake in November is currently the most expensive (average of $267). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

How much does it cost to fly round-trip from Greensboro to Chesapeake?

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 April 2, 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
11,550 reviews

Crew

8.0

Food

6.4

Comfort

7.2

Overall

7.1

Entertainment

6.9

Boarding

7.5

Reviews

1 / 20
4.0
Okay

Elizabeth,Mar 2026

ORD - MIA

Staff was rude and flight attendants 2 out of 3 looked like they had just been thru a hurricane.
American Airlines
7.1
Good
11,550 reviews
American Airlines
7.1
Good
11,550 reviews

Crew

8.0

Food

6.4

Comfort

7.2

Overall

7.1

Entertainment

6.9

Boarding

7.5

Reviews

1 / 20
4.0
Okay

Elizabeth,Mar 2026

ORD - MIA

Staff was rude and flight attendants 2 out of 3 looked like they had just been thru a hurricane.

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 34m. Fly via United Airlines to get the fastest option. The distance from Greensboro to Chesapeake is about 214 mi.

  • 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.

  • What is the cheapest month to book a flight from Greensboro to Chesapeake?

    Currently, September is the cheapest month in which you can book a flight from Greensboro to Chesapeake (average of $196). Flying from Greensboro to Chesapeake in November is currently the most expensive (average of $267). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

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See prices for flight routes from nearby airports that may be better suited for you.
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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 April 2, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$218Average$248FlexibilityNo cancel feeOn-time71%

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