Chesapeake

$52+ Cheap flights from Charleston (CHS) 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 5/7. Fares are subject to change and may not be available on all flights or dates of travel.
CHS — RIC
May 2 — May 91
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Cheap flight deals from Charleston to Chesapeake

Cheapest flights from Charleston to Chesapeake
Explore the most affordable flight options available from Charleston 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.
Tue 8/258:00 am
CHS
-
ORF
Nonstop1h 20m
Breeze Airways
Tue 9/11:59 pm
ORF
-
CHS
Nonstop1h 23m
Breeze Airways
Deal found 3/31$97
This Booking.com 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/73:57 pm
CHS
-
ORF
Nonstop1h 20m
Breeze Airways
Tue 5/121:59 pm
ORF
-
CHS
Nonstop1h 23m
Breeze Airways
Deal found 4/1$108
This Booking.com 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/304:05 pm
CHS
-
ORF
Nonstop1h 19m
Breeze Airways
Sun 5/311:05 pm
ORF
-
CHS
Nonstop1h 25m
Breeze Airways
Deal found 4/1$118
This Breeze Airways deal was found by Cheapflights users on 4/2. 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 Breeze Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/233:31 pm
CHS
-
ORF
Nonstop1h 19m
Breeze Airways
Sun 4/269:30 pm
ORF
-
CHS
Nonstop1h 25m
Breeze Airways
Deal found 4/2$123
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.
Sat 4/185:16 pm
CHS
-
ORF
1 stop4h 20m
Breeze Airways
Sun 4/199:30 pm
ORF
-
CHS
Nonstop1h 25m
Breeze Airways
Deal found 3/31$153
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.
Tue 8/258:00 am
CHS
-
ORF
Nonstop1h 20m
Multiple Airlines
Tue 9/112:21 pm
ORF
-
CHS
2 stops21h 17m
Multiple Airlines
Deal found 3/31$158
This Booking.com 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/174:34 pm
CHS
-
ORF
1 stop5h 11m
Breeze Airways
Sun 6/219:52 pm
ORF
-
CHS
Nonstop1h 23m
Breeze Airways
Deal found 4/1$172
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/3010:48 pm
CHS
-
ORF
1 stop18h 17m
Multiple Airlines
Sun 5/311:05 pm
ORF
-
CHS
Nonstop1h 25m
Multiple Airlines
Deal found 4/1$178
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/72:53 pm
CHS
-
ORF
1 stop5h 24m
Multiple Airlines
Tue 5/121:59 pm
ORF
-
CHS
Nonstop1h 23m
Multiple Airlines
Deal found 4/1$189
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/233:01 pm
CHS
-
ORF
1 stop22h 13m
Multiple Airlines
Sun 4/269:30 pm
ORF
-
CHS
Nonstop1h 25m
Multiple Airlines
Deal found 3/29$195

Find flight deals from Charleston to Chesapeake

Keep the following information in mind while searching for Charleston 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

$97
(Kiwi.com)

One-way from

$52
(Booking.com)

Popular in

February

Cheapest in

July

Average price

$235
Provider with most accurate pricing for Charleston-Norfolk flight deals.
Provider most trusted by Cheapflights users for Charleston-Norfolk flights.
From Charleston to Chesapeake
One-way flight from Charleston to Chesapeake
Highest demand for flights based on searches. 33% potential increase in price ($146 potential increase over avg. RT price).
Cheapest flight prices on average. 16% potential price decrease ($42 potential savings vs. average RT price).
Average for round-trip flights in April 2026

Cheapflights Fare Finder

 
Customize your flight search to find flights from Charleston 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 Charleston to Chesapeake that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

CharlestonNorfolk

CHS - ORF

CHSORF

Charleston

Sun 6/28

3:53 pm-5:13 pm

Nonstop1h 20m

Norfolk

Thu 7/2

9:52 pm-11:15 pm

Nonstop1h 23m

$232

CharlestonNorfolk

CHS - ORF

CHSORF

Charleston

Tue 6/30

4:04 pm-11:26 am

2 stops19h 22m

Norfolk

Thu 7/2

9:52 pm-11:15 pm

Nonstop1h 23m

$236

CharlestonNorfolk

CHS - ORF

CHSORF

Charleston

Thu 4/23

12:57 pm-10:26 pm

1 stop9h 29m

Norfolk

Sun 4/26

9:30 pm-10:55 pm

Nonstop1h 25m

$280

CharlestonNorfolk

CHS - ORF

CHSORF

Charleston

Wed 4/15

5:16 pm-9:36 pm

1 stop4h 20m

Norfolk

Tue 4/21

8:05 am-11:35 am

1 stop27h 30m

$311

CharlestonNorfolk

CHS - ORF

CHSORF

Charleston

Wed 4/15

12:05 pm-7:46 pm

2 stops31h 41m

Norfolk

Tue 4/21

8:05 am-11:35 am

1 stop27h 30m

$313

CharlestonNorfolk

CHS - ORF

CHSORF

Charleston

Sat 4/25

5:16 pm-9:36 pm

1 stop4h 20m

Norfolk

Sun 4/26

1:17 pm-8:19 pm

1 stop7h 02m

$323

CharlestonNorfolk

CHS - ORF

CHSORF

Charleston

Mon 6/29

6:43 pm-12:42 am

1 stop5h 59m

Norfolk

Wed 7/1

6:17 pm-12:36 am

1 stop6h 19m

$349

CharlestonNorfolk

CHS - ORF

CHSORF

Charleston

Fri 7/31

7:35 pm-11:35 pm

1 stop4h 00m

Norfolk

Sun 8/2

5:50 am-2:45 pm

2 stops8h 55m

$352

CharlestonNorfolk

CHS - ORF

CHSORF

Charleston

Mon 6/29

7:35 pm-11:35 pm

1 stop4h 00m

Norfolk

Thu 7/2

7:05 am-3:35 pm

2 stops8h 30m

$352

CharlestonNorfolk

CHS - ORF

CHSORF

Charleston

Sat 4/18

6:30 am-12:09 pm

1 stop5h 39m

Norfolk

Sat 4/18

5:20 pm-11:59 pm

1 stop6h 39m

$365

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/30

Showing 1-10 of 21 resultsSorted by cheapest first
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2
3

Best time to book a flight from Charleston to Chesapeake

Have a flexible travel schedule? Discover the best time to fly to Chesapeake from Charleston 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 Charleston to Chesapeake

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

Currently, May is the cheapest month in which you can book a flight from Charleston to Chesapeake (average of $42). Flying from Charleston to Chesapeake in December is currently the most expensive (average of $243). 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 Charleston 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.
Read through reviews of airlines operating flights from Charleston to Chesapeake, such as Breeze Airways,Delta, andAmerican Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.

Boarding

8.3

Overall

8.1

Comfort

8.2

Crew

8.7

Food

6.6

Entertainment

6.6

Reviews

1 / 18
4.0
Okay

Lisa,Mar 2026

ORF - JAX

*Flight was delayed twice *Once plane arrived crew closed the entryway to discuss whatever, leaving us to wait again. *Finally arriving Jax, we were delayed again for 20 minutes because another plane at the gate hadn’t pushed back Overall, score 2 out of 5. Lots of passengers upset.

Boarding

8.3

Overall

8.1

Comfort

8.2

Crew

8.7

Food

6.6

Entertainment

6.6

Reviews

1 / 18
4.0
Okay

Lisa,Mar 2026

ORF - JAX

*Flight was delayed twice *Once plane arrived crew closed the entryway to discuss whatever, leaving us to wait again. *Finally arriving Jax, we were delayed again for 20 minutes because another plane at the gate hadn’t pushed back Overall, score 2 out of 5. Lots of passengers upset.

Boarding

8.3

Overall

8.1

Comfort

8.2

Crew

8.7

Food

6.6

Entertainment

6.6

Reviews

1 / 18
4.0
Okay

Lisa,Mar 2026

ORF - JAX

*Flight was delayed twice *Once plane arrived crew closed the entryway to discuss whatever, leaving us to wait again. *Finally arriving Jax, we were delayed again for 20 minutes because another plane at the gate hadn’t pushed back Overall, score 2 out of 5. Lots of passengers upset.

Boarding

8.3

Overall

8.1

Comfort

8.2

Crew

8.7

Food

6.6

Entertainment

6.6

Reviews

1 / 18
4.0
Okay

Lisa,Mar 2026

ORF - JAX

*Flight was delayed twice *Once plane arrived crew closed the entryway to discuss whatever, leaving us to wait again. *Finally arriving Jax, we were delayed again for 20 minutes because another plane at the gate hadn’t pushed back Overall, score 2 out of 5. Lots of passengers upset.

Related info for your journey

Find useful and relevant information for your journey from Charleston 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 Charleston to Chesapeake?

    Located just 10.2 mi from the city center, Charleston is the airport most travelers will use when flying to Chesapeake from Charleston. Booking flights from Charleston (CHS) to Chesapeake should be relatively easy as there are 0 daily outbound flights to Chesapeake from 3 different airlines.

  • How popular is this Charleston to Chesapeake flight route?

  • How long is the flight from Charleston to Chesapeake?

    For as low as $232, Breeze Airways can have you in Chesapeake from Charleston in 1h 20m. Charleston and Chesapeake are separated by a distance of 351 mi. Most flights are nonstop.

  • What are the cheapest airlines to fly from Charleston to Chesapeake one-way?

    For one-way options, check prices for Breeze Airways. According to our data, you can fly for as low as $61. Users have also found prices from $86 and $98 on Southwest and Delta, respectively.

  • What are the cheapest flights from Charleston to Chesapeake?

    While on average a flight from Charleston to Chesapeake is generally $371, our data shows the cheapest flight currently is $283. When looking at the most popular route, (Charleston - Norfolk), you can expect to pay $97 for that flight.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Charleston 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 Charleston to Chesapeake?

    Currently, May is the cheapest month in which you can book a flight from Charleston to Chesapeake (average of $42). Flying from Charleston to Chesapeake in December is currently the most expensive (average of $243). 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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Alternative routes for Charleston to Chesapeake

See prices for flight routes from nearby airports that may be better suited for you.

Top 3 airlines flying from Charleston to Chesapeake

Discover the top 3 airlines that operate flights from Charleston 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
Breeze AirwaysCheapest$41Average$145FlexibilityNo cancel feeOn-timeN/A
DeltaCheapest$118Average$317FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$200Average$390FlexibilityNo cancel feeOn-time71%

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