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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 8/25. Fares are subject to change and may not be available on all flights or dates of travel.
PIT — RIC
Aug 2 — Aug 91
Sat 8/2
Sat 8/9
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 Tuesday

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 28, 2025.

Round-trip from

$158
(Breeze Airways)

One-way from

$79
(Breeze Airways)

Popular in

January

Cheapest in

May

Average price

$307
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 ($119 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 28, 2025.

This Breeze Airways deal was found by Cheapflights users on 7/28. 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 9/54:48 pmPIT - ORF
Nonstop1h 18mBreeze Airways
Mon 9/82:46 pmORF - PIT
Nonstop1h 22mBreeze Airways
Deal found 7/28$158
This Mytrip deal was found by Cheapflights users on 7/27. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/307:08 amPIT - ORF
1 stop9h 17mSpirit Airlines
Sat 9/65:38 pmORF - PIT
1 stop15h 52mSpirit Airlines
Deal found 7/27$170
This Delta deal was found by Cheapflights users on 7/28. 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 9/178:05 amPIT - ORF
1 stop5h 57mDelta
Wed 10/16:00 amORF - PIT
1 stop3h 54mDelta
Deal found 7/28$197
This Southwest deal was found by Cheapflights users on 7/28. 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.
Sat 8/236:45 amPIT - ORF
1 stop6h 15mSouthwest
Sun 8/318:30 amORF - PIT
1 stop4h 35mSouthwest
Deal found 7/28$217
This Mytrip deal was found by Cheapflights users on 7/26. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/151:00 pmPIT - ORF
Nonstop1h 18mMultiple Airlines
Mon 8/185:20 pmORF - PIT
1 stop15h 55mMultiple Airlines
Deal found 7/26$233
This American Airlines deal was found by Cheapflights users on 7/28. 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.
Fri 8/294:20 pmPIT - ORF
1 stop4h 50mAmerican Airlines
Sun 8/318:36 amORF - PIT
1 stop4h 39mAmerican Airlines
Deal found 7/28$248
This Mytrip deal was found by Cheapflights users on 7/26. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/77:00 amPIT - ORF
1 stop13h 36mAllegiant Air
Sun 8/105:54 pmORF - PIT
1 stop5h 40mAllegiant Air
Deal found 7/26$260

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 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

Fri 9/5

4:48 pm-6:06 pm

Nonstop1h 18m

Norfolk

Mon 9/8

2:46 pm-4:08 pm

Nonstop1h 22m

$158

PittsburghNorfolk

PIT - ORF

PITORF

Pittsburgh

Sat 8/30

7:08 am-4:25 pm

1 stop9h 17m

Norfolk

Sat 9/6

5:38 pm-9:30 am

1 stop15h 52m

$170

PittsburghNorfolk

PIT - ORF

PITORF

Pittsburgh

Wed 9/17

8:05 am-2:02 pm

1 stop5h 57m

Norfolk

Wed 10/1

6:00 am-9:54 am

1 stop3h 54m

$197

PittsburghNorfolk

PIT - ORF

PITORF

Pittsburgh

Sat 8/23

6:45 am-1:00 pm

1 stop6h 15m

Norfolk

Sun 8/31

8:30 am-1:05 pm

1 stop4h 35m

$217

PittsburghNorfolk

PIT - ORF

PITORF

Pittsburgh

Fri 8/15

1:00 pm-2:18 pm

Nonstop1h 18m

Norfolk

Mon 8/18

5:20 pm-9:15 am

1 stop15h 55m

$233

PittsburghNorfolk

PIT - ORF

PITORF

Pittsburgh

Fri 8/29

4:20 pm-9:10 pm

1 stop4h 50m

Norfolk

Sun 8/31

8:36 am-1:15 pm

1 stop4h 39m

$248

PittsburghNorfolk

PIT - ORF

PITORF

Pittsburgh

Thu 8/7

7:00 am-8:36 pm

1 stop13h 36m

Norfolk

Sun 8/10

5:54 pm-11:34 pm

1 stop5h 40m

$260

PittsburghNorfolk

PIT - ORF

PITORF

Pittsburgh

Mon 8/25

1:00 pm-2:18 pm

Nonstop1h 18m

$79

PittsburghNorfolk

PIT - ORF

PITORF

Pittsburgh

Wed 8/20

7:08 am-4:25 pm

1 stop9h 17m

$85

PittsburghNorfolk

PIT - ORF

PITORF

Pittsburgh

Wed 8/20

1:00 pm-4:23 pm

1 stop3h 23m

$99

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/27

Showing 1-10 of 15 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 25, 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 28, 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 28, 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
4,237 reviews

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Overall

8.0

Food

7.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Southwest
8.0
Very good
4,237 reviews
Southwest
8.0
Very good
4,237 reviews

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Overall

8.0

Food

7.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Delta
8.0
Very good
7,971 reviews
Southwest
8.0
Very good
4,237 reviews

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Overall

8.0

Food

7.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Breeze Airways
8.0
Very good
190 reviews
Southwest
8.0
Very good
4,237 reviews

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Overall

8.0

Food

7.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
United Airlines
7.4
Good
8,893 reviews
Southwest
8.0
Very good
4,237 reviews

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Overall

8.0

Food

7.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,237 reviews

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Overall

8.0

Food

7.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.

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 $79. Users have also found prices from $85 and $124 on Spirit Airlines and Allegiant Air, 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 28, 2025.
AirlineCheapestAverageFlexibilityOn-time
Breeze AirwaysCheapest$99Average$175FlexibilityNo cancel feeOn-timeN/A
DeltaCheapest$144Average$296FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$176Average$352FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$186Average$387FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$200Average$344FlexibilityNo cancel feeOn-time71%

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