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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 7/30. Fares are subject to change and may not be available on all flights or dates of travel.
PIT — RIC
Jul 23 — Jul 301
Wed 7/23
Wed 7/30
1 adult, Economy
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Cheapflights Tip: The best prices from Pittsburgh to Chesapeake are usually found in May or September, booked 49 days in advance, depart on a Wednesday or Tuesday 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 July 18, 2025.

Round-trip from

$163
(Breeze Airways)

One-way from

$94
(Breeze Airways)

Popular in

January

Cheapest in

May

Average price

$308
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 ($117 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 July 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 July 18, 2025.

This Breeze Airways deal was found by Cheapflights users on 7/17. 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 9/124:48 pmPIT - ORF
Nonstop1h 18mBreeze Airways
Fri 9/192:46 pmORF - PIT
Nonstop1h 22mBreeze Airways
Deal found 7/17$163
This Delta deal was found by Cheapflights users on 7/15. 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.
Sat 8/302:00 pmPIT - ORF
1 stop4h 03mDelta
Sat 9/66:00 amORF - PIT
1 stop3h 45mDelta
Deal found 7/15$197
This Southwest deal was found by Cheapflights users on 7/15. 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.
Tue 8/512:05 pmPIT - ORF
1 stop2h 55mSouthwest
Tue 8/122:20 pmORF - PIT
2 stops7h 00mSouthwest
Deal found 7/15$202
This United Airlines deal was found by Cheapflights users on 7/17. 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 8/98:05 pmPIT - ORF
1 stop3h 42mUnited Airlines
Tue 8/125:05 pmORF - PIT
1 stop6h 53mUnited Airlines
Deal found 7/17$204
This American Airlines deal was found by Cheapflights users on 7/15. 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 7/291:08 pmPIT - ORF
1 stop5h 43mAmerican Airlines
Tue 8/55:14 pmORF - PIT
1 stop4h 43mAmerican Airlines
Deal found 7/15$217
This Mytrip deal was found by Cheapflights users on 7/16. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/66:20 amPIT - ORF
1 stop10h 05mSpirit Airlines
Sat 8/912:11 pmORF - PIT
1 stop11h 04mSpirit Airlines
Deal found 7/16$220
This Mytrip deal was found by Cheapflights users on 7/17. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/91:21 pmPIT - ORF
2 stops18h 54mMultiple Airlines
Tue 8/125:50 amORF - PIT
1 stop13h 26mMultiple Airlines
Deal found 7/17$252

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 July 18, 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

Fri 9/12

4:48 pm-6:06 pm

Nonstop1h 18m

Norfolk

Fri 9/19

2:46 pm-4:08 pm

Nonstop1h 22m

$163

PittsburghNorfolk

PIT - ORF

PITORF

Pittsburgh

Sat 8/30

2:00 pm-6:03 pm

1 stop4h 03m

Norfolk

Sat 9/6

6:00 am-9:45 am

1 stop3h 45m

$197

PittsburghNorfolk

PIT - ORF

PITORF

Pittsburgh

Tue 8/5

12:05 pm-3:00 pm

1 stop2h 55m

Norfolk

Tue 8/12

2:20 pm-9:20 pm

2 stops7h 00m

$202

PittsburghNorfolk

PIT - ORF

PITORF

Pittsburgh

Sat 8/9

8:05 pm-11:47 pm

1 stop3h 42m

Norfolk

Tue 8/12

5:05 pm-11:58 pm

1 stop6h 53m

$204

PittsburghNorfolk

PIT - ORF

PITORF

Pittsburgh

Tue 7/29

1:08 pm-6:51 pm

1 stop5h 43m

Norfolk

Tue 8/5

5:14 pm-9:57 pm

1 stop4h 43m

$217

PittsburghNorfolk

PIT - ORF

PITORF

Pittsburgh

Wed 8/6

6:20 am-4:25 pm

1 stop10h 05m

Norfolk

Sat 8/9

12:11 pm-11:15 pm

1 stop11h 04m

$220

PittsburghNorfolk

PIT - ORF

PITORF

Pittsburgh

Sat 8/9

1:21 pm-8:15 am

2 stops18h 54m

Norfolk

Tue 8/12

5:50 am-7:16 pm

1 stop13h 26m

$252

PittsburghNorfolk

PIT - ORF

PITORF

Pittsburgh

Wed 7/30

8:12 pm-9:30 pm

Nonstop1h 18m

$79

PittsburghNorfolk

PIT - ORF

PITORF

Pittsburgh

Tue 8/5

7:02 am-11:40 am

1 stop4h 38m

$99

PittsburghNorfolk

PIT - ORF

PITORF

Pittsburgh

Tue 8/5

6:10 am-3:00 pm

2 stops8h 50m

$104

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/15

Showing 1-10 of 14 results
1
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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 July 11, 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 49 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 July 18, 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 Thursday at noon 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 July 18, 2025.
Get a feel of what it's like to fly with Southwest, Delta, and Breeze Airways 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
4,239 reviews

Food

7.0

Crew

8.6

Entertainment

7.6

Comfort

8.0

Overall

8.0

Boarding

8.1

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Southwest
8.0
Very good
4,239 reviews
Southwest
8.0
Very good
4,239 reviews

Food

7.0

Crew

8.6

Entertainment

7.6

Comfort

8.0

Overall

8.0

Boarding

8.1

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Delta
8.0
Very good
7,959 reviews
Southwest
8.0
Very good
4,239 reviews

Food

7.0

Crew

8.6

Entertainment

7.6

Comfort

8.0

Overall

8.0

Boarding

8.1

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Breeze Airways
8.0
Very good
187 reviews
Southwest
8.0
Very good
4,239 reviews

Food

7.0

Crew

8.6

Entertainment

7.6

Comfort

8.0

Overall

8.0

Boarding

8.1

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
United Airlines
7.4
Good
8,864 reviews
Southwest
8.0
Very good
4,239 reviews

Food

7.0

Crew

8.6

Entertainment

7.6

Comfort

8.0

Overall

8.0

Boarding

8.1

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
JetBlue
7.3
Good
2,909 reviews
Southwest
8.0
Very good
4,239 reviews

Food

7.0

Crew

8.6

Entertainment

7.6

Comfort

8.0

Overall

8.0

Boarding

8.1

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

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.

  • 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 $94. Users have also found prices from $104 and $116 on Southwest and Spirit 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 July 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
Breeze AirwaysCheapest$99Average$175FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$186Average$386FlexibilityNo cancel feeOn-time69%
DeltaCheapest$191Average$296FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$216Average$354FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$224Average$338FlexibilityNo cancel feeOn-time71%

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