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Chesapeake

$72+ 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 9/28. Fares are subject to change and may not be available on all flights or dates of travel.
PIT — RIC
Oct 15 — Oct 221
Wed 10/15
Wed 10/22
1 adult, Economy
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Cheapflights Tip: The best prices from Pittsburgh to Chesapeake are usually found in August or September, 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 15, 2025.

Round-trip from

$172
(Kiwi.com)

One-way from

$72
(Cheapflightsfares)

Popular in

January

Cheapest in

August

Average price

$240
From Pittsburgh to Chesapeake
Search Deals
One-way flight from Pittsburgh to Chesapeake
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Highest demand for flights based on searches. 26% potential increase in price ($116 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 15, 2025.

This Breeze Airways deal was found by Cheapflights users on 9/15. 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 Breeze Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/224:48 pmPIT - ORF
Nonstop1h 18mBreeze Airways
Mon 9/292:46 pmORF - PIT
Nonstop1h 22mBreeze Airways
Deal found 9/15$168
This Kiwi.com deal was found by Cheapflights users on 9/14. 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.
Fri 9/264:48 pmPIT - ORF
Nonstop1h 18mBreeze Airways
Mon 9/292:46 pmORF - PIT
Nonstop1h 22mBreeze Airways
Deal found 9/14$172
This Breeze Airways deal was found by Cheapflights users on 9/15. 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 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 9/15$173
This Delta deal was found by Cheapflights users on 9/15. 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.
Thu 10/307:21 amPIT - ORF
1 stop4h 09mDelta
Mon 11/36:40 pmORF - PIT
1 stop4h 11mDelta
Deal found 9/15$177
This Priceline deal was found by Cheapflights users on 9/14. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/510:24 amPIT - ORF
1 stop6h 33mMultiple Airlines
Sun 10/123:29 pmORF - PIT
Nonstop1h 22mMultiple Airlines
Deal found 9/14$182
This Breeze Airways deal was found by Cheapflights users on 9/15. 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 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 9/15$183
This Southwest deal was found by Cheapflights users on 9/14. 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 10/79:45 amPIT - ORF
2 stops8h 00mSouthwest
Wed 10/152:55 pmORF - PIT
2 stops8h 10mSouthwest
Deal found 9/14$187
This Delta deal was found by Cheapflights users on 9/13. 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 10/18:05 amPIT - ORF
1 stop5h 57mDelta
Wed 10/16:22 pmORF - PIT
1 stop4h 38mDelta
Deal found 9/13$189
This Kiwi.com deal was found by Cheapflights users on 9/14. 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 10/91:31 pmPIT - ORF
Nonstop1h 18mMultiple Airlines
Thu 10/165:24 amORF - PIT
1 stop12h 22mMultiple Airlines
Deal found 9/14$208
This United Airlines deal was found by Cheapflights users on 9/12. 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 10/106:15 amPIT - ORF
1 stop3h 22mUnited Airlines
Sun 10/126:00 amORF - PIT
1 stop4h 46mUnited Airlines
Deal found 9/12$210
This Kiwi.com deal was found by Cheapflights users on 9/14. 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 9/309:28 pmPIT - ORF
1 stop11h 08mMultiple Airlines
Mon 10/65:38 pmORF - PIT
1 stop5h 57mMultiple Airlines
Deal found 9/14$212

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 15, 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

Thu 10/2

1:31 pm-2:49 pm

Nonstop1h 18m

Norfolk

Sun 10/5

3:29 pm-4:51 pm

Nonstop1h 22m

$172

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

Tue 10/7

5:50 am-11:05 am

1 stop5h 15m

Norfolk

Wed 10/15

2:55 pm-6:00 pm

1 stop3h 05m

$177

PittsburghNorfolk

PIT - ORF

PITORF

Pittsburgh

Wed 11/5

1:00 pm-6:00 pm

1 stop5h 00m

Norfolk

Wed 11/12

5:40 am-9:46 am

1 stop4h 06m

$177

PittsburghNorfolk

PIT - ORF

PITORF

Pittsburgh

Thu 10/30

7:21 am-11:30 am

1 stop4h 09m

Norfolk

Mon 11/3

6:40 pm-10:51 pm

1 stop4h 11m

$177

PittsburghNorfolk

PIT - ORF

PITORF

Pittsburgh

Mon 10/6

6:00 am-11:25 am

1 stop5h 25m

Norfolk

Mon 10/13

8:35 pm-11:35 pm

1 stop3h 00m

$177

PittsburghNorfolk

PIT - ORF

PITORF

Pittsburgh

Tue 11/4

5:10 pm-11:05 pm

1 stop5h 55m

Norfolk

Tue 11/11

6:03 am-9:51 am

1 stop3h 48m

$177

PittsburghNorfolk

PIT - ORF

PITORF

Pittsburgh

Sat 10/11

6:00 am-9:20 am

1 stop3h 20m

Norfolk

Sat 10/18

6:20 am-12:00 pm

1 stop5h 40m

$177

PittsburghNorfolk

PIT - ORF

PITORF

Pittsburgh

Sun 9/28

10:24 am-4:57 pm

1 stop6h 33m

$72

PittsburghNorfolk

PIT - ORF

PITORF

Pittsburgh

Thu 10/9

1:31 pm-2:49 pm

Nonstop1h 18m

$84

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/15

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 September 12, 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 15, 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 15, 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
4,242 reviews

Crew

8.6

Comfort

8.0

Overall

8.0

Entertainment

7.5

Boarding

8.1

Food

7.0

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
4,242 reviews
Southwest
8.0
Very good
4,242 reviews

Crew

8.6

Comfort

8.0

Overall

8.0

Entertainment

7.5

Boarding

8.1

Food

7.0

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
4,242 reviews

Crew

8.6

Comfort

8.0

Overall

8.0

Entertainment

7.5

Boarding

8.1

Food

7.0

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
7,954 reviews
Southwest
8.0
Very good
4,242 reviews

Crew

8.6

Comfort

8.0

Overall

8.0

Entertainment

7.5

Boarding

8.1

Food

7.0

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
8,929 reviews
Southwest
8.0
Very good
4,242 reviews

Crew

8.6

Comfort

8.0

Overall

8.0

Entertainment

7.5

Boarding

8.1

Food

7.0

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
4,242 reviews

Crew

8.6

Comfort

8.0

Overall

8.0

Entertainment

7.5

Boarding

8.1

Food

7.0

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 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 Frontier. According to our data, you can fly for as low as $72. Users have also found prices from $84 and $89 on Breeze Airways and Southwest, 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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Alternative routes for Pittsburgh to Chesapeake

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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 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
Breeze AirwaysCheapest$102Average$185FlexibilityNo cancel feeOn-timeN/A
DeltaCheapest$128Average$291FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$176Average$346FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$198Average$405FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$227Average$380FlexibilityNo cancel feeOn-time69%

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