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Chesapeake

$79+ 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 10/9. Fares are subject to change and may not be available on all flights or dates of travel.
PIT — RIC
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
1 adult, Economy
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Cheapflights Tip: The best prices from Pittsburgh to Chesapeake are usually found in September or May, booked 58 days in advance, depart on a Tuesday or Monday and return on a Monday

Cheap flight deals from Pittsburgh to Chesapeake

Keep the following information in mind while searching for Pittsburgh to Chesapeake flight deals. Data was last updated September 11, 2025.

Round-trip from

$154
(Southwest)

One-way from

$79
(Breeze Airways)

Popular in

January

Cheapest in

September

Average price

$249
From Pittsburgh to Chesapeake
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One-way flight from Pittsburgh to Chesapeake
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Highest demand for flights based on searches. 26% potential increase in price ($118 potential increase over avg. RT price).
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Cheapest flight prices on average. 7% potential price decrease ($24 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find 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 September 11, 2025.

This Southwest deal was found by Cheapflights users on 9/10. 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.
Wed 10/81:10 pmPIT - ORF
1 stop4h 35mSouthwest
Wed 10/155:35 amORF - PIT
1 stop6h 50mSouthwest
Deal found 9/10$154
This Breeze Airways deal was found by Cheapflights users on 9/10. 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.
Fri 9/264:48 pmPIT - ORF
Nonstop1h 18mBreeze Airways
Mon 9/292:46 pmORF - PIT
Nonstop1h 22mBreeze Airways
Deal found 9/10$158
This Southwest deal was found by Cheapflights users on 9/8. 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.
Wed 10/294:00 pmPIT - ORF
1 stop5h 05mSouthwest
Wed 11/56:05 amORF - PIT
2 stops8h 50mSouthwest
Deal found 9/8$159
This Southwest deal was found by Cheapflights users on 9/8. 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.
Wed 11/51:20 pmPIT - ORF
2 stops8h 40mSouthwest
Wed 11/126:05 amORF - PIT
2 stops8h 50mSouthwest
Deal found 9/8$164
This Southwest deal was found by Cheapflights users on 9/10. 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.
Wed 10/159:45 amPIT - ORF
1 stop6h 40mSouthwest
Wed 10/225:35 amORF - PIT
2 stops6h 50mSouthwest
Deal found 9/10$169
This Breeze Airways deal was found by Cheapflights users on 9/11. 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 10/301:31 pmPIT - ORF
Nonstop1h 18mBreeze Airways
Sun 11/23:29 pmORF - PIT
Nonstop1h 22mBreeze Airways
Deal found 9/11$173
This American Airlines deal was found by Cheapflights users on 9/9. 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.
Sat 10/117:09 pmPIT - ORF
1 stop4h 45mAmerican Airlines
Sat 10/185:00 amORF - PIT
1 stop4h 36mAmerican Airlines
Deal found 9/9$177
This Breeze Airways deal was found by Cheapflights users on 9/9. 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 10/91:31 pmPIT - ORF
Nonstop1h 18mBreeze Airways
Sun 10/123:29 pmORF - PIT
Nonstop1h 22mBreeze Airways
Deal found 9/9$178
This Delta deal was found by Cheapflights users on 9/11. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/16:20 amPIT - ORF
1 stop6h 09mDelta
Wed 10/15:10 pmORF - PIT
1 stop5h 43mDelta
Deal found 9/11$181
This American Airlines deal was found by Cheapflights users on 9/9. 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 10/73:01 pmPIT - ORF
1 stop5h 49mAmerican Airlines
Tue 10/149:31 amORF - PIT
1 stop5h 14mAmerican Airlines
Deal found 9/9$189

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 September 11, 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 11/5

5:45 am-9:25 am

1 stop3h 40m

Norfolk

Wed 11/12

6:05 am-11:50 am

1 stop5h 45m

$154

PittsburghNorfolk

PIT - ORF

PITORF

Pittsburgh

Wed 10/8

1:10 pm-5:45 pm

1 stop4h 35m

Norfolk

Wed 10/15

5:35 am-12:25 pm

1 stop6h 50m

$154

PittsburghNorfolk

PIT - ORF

PITORF

Pittsburgh

Wed 10/29

5:50 am-11:05 am

1 stop5h 15m

Norfolk

Wed 11/5

6:15 pm-9:55 pm

1 stop3h 40m

$154

PittsburghNorfolk

PIT - ORF

PITORF

Pittsburgh

Thu 10/2

1:31 pm-2:49 pm

Nonstop1h 18m

Norfolk

Sun 10/5

3:29 pm-4:51 pm

Nonstop1h 22m

$173

PittsburghNorfolk

PIT - ORF

PITORF

Pittsburgh

Thu 10/30

1:31 pm-2:49 pm

Nonstop1h 18m

Norfolk

Sun 11/2

3:29 pm-4:51 pm

Nonstop1h 22m

$173

PittsburghNorfolk

PIT - ORF

PITORF

Pittsburgh

Thu 10/9

1:31 pm-2:49 pm

Nonstop1h 18m

Norfolk

Sun 10/12

3:29 pm-4:51 pm

Nonstop1h 22m

$178

PittsburghNorfolk

PIT - ORF

PITORF

Pittsburgh

Wed 11/5

1:00 pm-5:54 pm

1 stop4h 54m

Norfolk

Wed 11/12

10:00 am-2:11 pm

1 stop4h 11m

$181

PittsburghNorfolk

PIT - ORF

PITORF

Pittsburgh

Thu 11/27

1:31 pm-2:49 pm

Nonstop1h 18m

$79

PittsburghNorfolk

PIT - ORF

PITORF

Pittsburgh

Thu 10/9

1:31 pm-2:49 pm

Nonstop1h 18m

$79

PittsburghNorfolk

PIT - ORF

PITORF

Pittsburgh

Wed 10/8

10:24 am-4:22 pm

1 stop5h 58m

$91

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/8

Showing 1-10 of 18 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 August 29, 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, January is the cheapest month in which you can book a flight from Pittsburgh to Chesapeake (average of $281). Flying from Pittsburgh to Chesapeake in March is currently the most expensive (average of $351). 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.

What is the cheapest time of day to fly from PIT to C6E?

Find hourly flight availability from Pittsburgh to Chesapeake. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 11, 2025.

When flying from Pittsburgh to Chesapeake, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

What is the cheapest day to fly from Pittsburgh to Chesapeake?

Use this chart to determine the cheapest time to fly round-trip from Pittsburgh to Chesapeake. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Pittsburgh to Chesapeake flight should consider departing on Wednesday evenings when fares are most often at their lowest. Monday evenings flights should be avoided if possible as fares are typically the most expensive at this time.

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 September 11, 2025.
Get a feel of what it's like to fly with Southwest, Breeze Airways, 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.
Southwest
8.0
Very good
4,248 reviews

Food

7.0

Boarding

8.1

Overall

8.0

Entertainment

7.5

Crew

8.6

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,248 reviews
Southwest
8.0
Very good
4,248 reviews

Food

7.0

Boarding

8.1

Overall

8.0

Entertainment

7.5

Crew

8.6

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Breeze Airways
8.0
Very good
205 reviews
Southwest
8.0
Very good
4,248 reviews

Food

7.0

Boarding

8.1

Overall

8.0

Entertainment

7.5

Crew

8.6

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Delta
8.0
Very good
7,960 reviews
Southwest
8.0
Very good
4,248 reviews

Food

7.0

Boarding

8.1

Overall

8.0

Entertainment

7.5

Crew

8.6

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
United Airlines
7.4
Good
8,937 reviews
Southwest
8.0
Very good
4,248 reviews

Food

7.0

Boarding

8.1

Overall

8.0

Entertainment

7.5

Crew

8.6

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,248 reviews

Food

7.0

Boarding

8.1

Overall

8.0

Entertainment

7.5

Crew

8.6

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

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 3h 40m. There are 330 mi between Pittsburgh and Chesapeake.

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

    For one-way options, check prices for Breeze Airways. According to our data, you can fly for as low as $79. Users have also found prices from $91 and $91 on Delta and American Airlines, 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, January is the cheapest month in which you can book a flight from Pittsburgh to Chesapeake (average of $281). Flying from Pittsburgh to Chesapeake in March is currently the most expensive (average of $351). 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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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 September 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
Breeze AirwaysCheapest$102Average$184FlexibilityNo cancel feeOn-timeN/A
DeltaCheapest$128Average$297FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$176Average$351FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$198Average$406FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$227Average$387FlexibilityNo cancel feeOn-time69%

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