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Chesapeake

$94+ Cheap flights from Pittsburgh (PIT) 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 1/1. Fares are subject to change and may not be available on all flights or dates of travel.
PIT — RIC
Jan 27 — Feb 31
Tue 1/27
Tue 2/3
1 adult, Economy
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Cheapflights Tip: The best prices from Pittsburgh to Chesapeake are usually found in September or November, booked 58 days in advance, depart on a Tuesday or Monday and return on a Saturday

Cheap flight deals from Pittsburgh to Chesapeake

Cheapest flights from Pittsburgh to Chesapeake
Explore the most affordable flight options available from Pittsburgh to Chesapeake. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 28, 2025.

This Kiwi.com deal was found by Cheapflights users on 12/26. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/3012:29 pmPIT - ORF
1 stop28h 37mMultiple Airlines
Thu 1/13:29 pmORF - PIT
Nonstop1h 22mMultiple Airlines
Deal found 12/26$384
This Breeze Airways deal was found by Cheapflights users on 12/26. 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 Breeze Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/281:31 pmPIT - ORF
Nonstop1h 18mBreeze Airways
Thu 1/13:29 pmORF - PIT
Nonstop1h 22mBreeze Airways
Deal found 12/26$433
This Kiwi.com deal was found by Cheapflights users on 12/27. 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 12/297:55 pmPIT - ORF
1 stop13h 52mMultiple Airlines
Mon 1/53:01 pmORF - PIT
1 stop18h 57mMultiple Airlines
Deal found 12/27$440
This Kiwi.com deal was found by Cheapflights users on 12/25. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/297:55 pmPIT - ORF
1 stop13h 52mBreeze Airways
Wed 12/3110:05 pmORF - PIT
1 stop10h 41mBreeze Airways
Deal found 12/25$485
This United Airlines deal was found by Cheapflights users on 12/25. 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.
Wed 12/317:55 pmPIT - ORF
1 stop14h 00mUnited Airlines
Sat 1/310:46 amORF - PIT
1 stop3h 16mUnited Airlines
Deal found 12/25$574
This Kiwi.com deal was found by Cheapflights users on 12/26. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/309:28 pmPIT - ORF
1 stop11h 08mBreeze Airways
Thu 1/19:45 pmORF - PIT
2 stops21h 30mBreeze Airways
Deal found 12/26$598
This Kiwi.com deal was found by Cheapflights users on 12/26. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/297:55 pmPIT - ORF
1 stop13h 52mMultiple Airlines
Tue 12/303:11 pmORF - PIT
1 stop7h 48mMultiple Airlines
Deal found 12/26$602
This Southwest deal was found by Cheapflights users on 12/27. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/295:50 amPIT - ORF
2 stops8h 55mSouthwest
Mon 1/54:15 pmORF - PIT
2 stops7h 55mSouthwest
Deal found 12/27$639

Find flight deals from Pittsburgh to Chesapeake

Keep the following information in mind while searching for Pittsburgh to Chesapeake flight deals. Data was last updated December 28, 2025.

Most accurate provider

Mytrip
3 stars

Most trusted provider

Mytrip
3 stars

Round-trip from

$116
(Kiwi.com)

One-way from

$94
(Kiwi.com)

Popular in

January

Cheapest in

September

Average price

$320
Provider with most accurate pricing for Pittsburgh-Norfolk flight deals.
Search Deals
Provider most trusted by Cheapflights users for Pittsburgh-Norfolk flights.
Search Deals
From Pittsburgh to Chesapeake
Search Deals
One-way flight from Pittsburgh to Chesapeake
Search Deals
Highest demand for flights based on searches. 27% potential increase in price ($115 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 8% potential price decrease ($25 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Pittsburgh 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 December 28, 2025.
Use the filters below to find and compare flights from Pittsburgh to Chesapeake that are best for you.

Fly from

Pittsburgh

Fly to

Chesapeake

Route

Depart

Return

Price

PittsburghNorfolk

PIT - ORF

PITORF

Pittsburgh

Wed 1/21

5:50 pm-6:38 pm

1 stop24h 48m

Norfolk

Mon 1/26

7:33 pm-9:40 am

1 stop14h 07m

$116

PittsburghNorfolk

PIT - ORF

PITORF

Pittsburgh

Thu 2/5

11:00 am-10:04 pm

1 stop11h 04m

Norfolk

Fri 2/6

7:33 pm-9:40 am

1 stop14h 07m

$159

PittsburghNorfolk

PIT - ORF

PITORF

Pittsburgh

Thu 1/1

1:31 pm-2:49 pm

Nonstop1h 18m

Norfolk

Sun 1/4

3:29 pm-4:51 pm

Nonstop1h 22m

$188

PittsburghNorfolk

PIT - ORF

PITORF

Pittsburgh

Sat 1/17

1:00 pm-9:50 pm

1 stop8h 50m

Norfolk

Mon 1/19

7:33 pm-9:40 am

1 stop14h 07m

$191

PittsburghNorfolk

PIT - ORF

PITORF

Pittsburgh

Fri 1/9

8:00 am-5:06 pm

2 stops9h 06m

Norfolk

Sun 1/11

7:33 pm-9:40 am

1 stop14h 07m

$227

PittsburghNorfolk

PIT - ORF

PITORF

Pittsburgh

Fri 1/9

6:00 am-6:38 pm

1 stop12h 38m

Norfolk

Sun 1/11

7:33 pm-9:40 am

1 stop14h 07m

$243

PittsburghNorfolk

PIT - ORF

PITORF

Pittsburgh

Thu 2/5

10:59 am-2:53 pm

1 stop3h 54m

Norfolk

Sun 2/8

7:01 am-11:40 am

1 stop4h 39m

$259

PittsburghNorfolk

PIT - ORF

PITORF

Pittsburgh

Wed 3/4

6:00 am-6:26 pm

1 stop12h 26m

Norfolk

Mon 3/9

6:45 am-7:54 pm

2 stops13h 09m

$279

PittsburghNorfolk

PIT - ORF

PITORF

Pittsburgh

Thu 3/5

8:00 am-10:04 pm

1 stop14h 04m

Norfolk

Mon 3/9

3:26 pm-5:38 pm

1 stop26h 12m

$281

PittsburghNorfolk

PIT - ORF

PITORF

Pittsburgh

Wed 1/21

6:25 am-5:50 pm

2 stops11h 25m

Norfolk

Mon 1/26

10:20 am-9:55 pm

2 stops11h 35m

$291

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/26

Showing 1-10 of 19 results
1
2

Best time to book a flight from Pittsburgh to Chesapeake

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

How far ahead should I book a flight from Pittsburgh to Chesapeake?

Use this chart to determine the optimal time to book a round-trip flight from Pittsburgh to Chesapeake. Price data was last updated on December 26, 2025.

The price you pay for your flight from Pittsburgh to Chesapeake may vary depending on when you book. For the best chance of a lower fare, look to book 58 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

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

Currently, September is the cheapest month in which you can book a flight from Pittsburgh to Chesapeake (average of $97). Flying from Pittsburgh to Chesapeake in April is currently the most expensive (average of $228). 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.

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 December 28, 2025.
Get a feel of what it's like to fly with Breeze Airways, Southwest, and Delta from Pittsburgh to Chesapeake by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Breeze Airways
8.2
Very good
250 reviews

Overall

8.2

Crew

8.8

Entertainment

6.7

Food

6.7

Boarding

8.4

Comfort

8.2

Reviews

1 / 16
10.0
Excellent

Anonymous,Dec 2025

RSW - ISP

There was no food offered so I had to just put okay. Other than that all was great.
Breeze Airways
8.2
Very good
250 reviews
Breeze Airways
8.2
Very good
250 reviews

Overall

8.2

Crew

8.8

Entertainment

6.7

Food

6.7

Boarding

8.4

Comfort

8.2

Reviews

1 / 16
10.0
Excellent

Anonymous,Dec 2025

RSW - ISP

There was no food offered so I had to just put okay. Other than that all was great.
Southwest
8.0
Very good
4,256 reviews
Breeze Airways
8.2
Very good
250 reviews

Overall

8.2

Crew

8.8

Entertainment

6.7

Food

6.7

Boarding

8.4

Comfort

8.2

Reviews

1 / 16
10.0
Excellent

Anonymous,Dec 2025

RSW - ISP

There was no food offered so I had to just put okay. Other than that all was great.
Delta
7.9
Good
8,017 reviews
Breeze Airways
8.2
Very good
250 reviews

Overall

8.2

Crew

8.8

Entertainment

6.7

Food

6.7

Boarding

8.4

Comfort

8.2

Reviews

1 / 16
10.0
Excellent

Anonymous,Dec 2025

RSW - ISP

There was no food offered so I had to just put okay. Other than that all was great.
United Airlines
7.4
Good
9,114 reviews
Breeze Airways
8.2
Very good
250 reviews

Overall

8.2

Crew

8.8

Entertainment

6.7

Food

6.7

Boarding

8.4

Comfort

8.2

Reviews

1 / 16
10.0
Excellent

Anonymous,Dec 2025

RSW - ISP

There was no food offered so I had to just put okay. Other than that all was great.
American Airlines
7.2
Good
11,070 reviews
Breeze Airways
8.2
Very good
250 reviews

Overall

8.2

Crew

8.8

Entertainment

6.7

Food

6.7

Boarding

8.4

Comfort

8.2

Reviews

1 / 16
10.0
Excellent

Anonymous,Dec 2025

RSW - ISP

There was no food offered so I had to just put okay. Other than that all was great.

Related info for your journey

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

    Pittsburgh (PIT), located 13.5 mi from the city center, is the airport you fly out of when you book flights from Pittsburgh to Chesapeake. 5 airlines have flights from Pittsburgh to Chesapeake on a regular basis. Booking flights from Pittsburgh to Chesapeake should not be difficult; the airport handles an average of 0 outbound flights to Chesapeake per day.

  • How long is the flight from Pittsburgh to Chesapeake?

    Departing from Pittsburgh to Chesapeake will take you 1h 18m. There are 330 mi between Pittsburgh and Chesapeake. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

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

    For one-way options, check prices for United Airlines. According to our data, you can fly for as low as $79. Users have also found prices from $81 and $88 on Breeze Airways and Delta, respectively.

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

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

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

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

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

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

    Currently, September is the cheapest month in which you can book a flight from Pittsburgh to Chesapeake (average of $97). Flying from Pittsburgh to Chesapeake in April is currently the most expensive (average of $228). 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 Pittsburgh to Chesapeake

See prices for flight routes from nearby airports that may be better suited for you.
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Top 5 airlines flying from Pittsburgh to Chesapeake

Discover the top 5 airlines that operate flights from Pittsburgh 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 December 28, 2025.
AirlineCheapestAverageFlexibilityOn-time
Breeze AirwaysCheapest$112Average$182FlexibilityNo cancel feeOn-timeN/A
DeltaCheapest$128Average$261FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$158Average$381FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$176Average$336FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$196Average$302FlexibilityNo cancel feeOn-time71%

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