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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 12/25. Fares are subject to change and may not be available on all flights or dates of travel.
PIT — RIC
Nov 28 — Dec 51
Fri 11/28
Fri 12/5
1 adult, Economy
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Cheapflights Tip: The best prices from Pittsburgh to Chesapeake are usually found in September or August, booked 58 days in advance, depart on a Tuesday or Monday and return on a Monday

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 October 29, 2025.

This Priceline deal was found by Cheapflights users on 10/28. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/131:31 pmPIT - ORF
Nonstop1h 18mBreeze Airways
Thu 11/203:29 pmORF - PIT
Nonstop1h 22mBreeze Airways
Deal found 10/28$162
This Breeze Airways deal was found by Cheapflights users on 10/27. 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 Breeze Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/201:31 pmPIT - ORF
Nonstop1h 18mBreeze Airways
Sun 11/233:29 pmORF - PIT
Nonstop1h 22mBreeze Airways
Deal found 10/27$173
This Kiwi.com deal was found by Cheapflights users on 10/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/131:31 pmPIT - ORF
Nonstop1h 18mMultiple Airlines
Thu 11/209:26 pmORF - PIT
1 stop12h 43mMultiple Airlines
Deal found 10/28$176
This Mytrip deal was found by Cheapflights users on 10/28. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/1110:15 amPIT - ORF
1 stop8h 43mSpirit Airlines
Wed 11/127:53 pmORF - PIT
1 stop15h 16mSpirit Airlines
Deal found 10/28$184
This Kiwi.com deal was found by Cheapflights users on 10/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/279:28 pmPIT - ORF
1 stop11h 08mBreeze Airways
Thu 12/43:29 pmORF - PIT
Nonstop1h 22mBreeze Airways
Deal found 10/28$194
This FlightHub deal was found by Cheapflights users on 10/27. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/201:31 pmPIT - ORF
Nonstop1h 18mMultiple Airlines
Sun 11/239:26 pmORF - PIT
1 stop10h 53mMultiple Airlines
Deal found 10/27$198
This Breeze Airways deal was found by Cheapflights users on 10/27. 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 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 10/27$213
This Kiwi.com deal was found by Cheapflights users on 10/27. 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.
Thu 11/201:31 pmPIT - ORF
Nonstop1h 18mMultiple Airlines
Mon 11/249:26 pmORF - PIT
1 stop10h 53mMultiple Airlines
Deal found 10/27$217

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 October 29, 2025.

Most accurate provider

Mytrip
3 stars

Most trusted provider

Mytrip
3 stars

Round-trip from

$162
(Priceline)

One-way from

$79
(Breeze Airways)

Popular in

January

Cheapest in

September

Average price

$290
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 ($123 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 8% potential price decrease ($24 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 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 October 29, 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 11/20

1:31 pm-2:49 pm

Nonstop1h 18m

Norfolk

Sun 11/23

3:29 pm-4:51 pm

Nonstop1h 22m

$173

PittsburghNorfolk

PIT - ORF

PITORF

Pittsburgh

Tue 11/11

10:15 am-6:58 pm

1 stop8h 43m

Norfolk

Wed 11/12

7:53 pm-11:09 am

1 stop15h 16m

$184

PittsburghNorfolk

PIT - ORF

PITORF

Pittsburgh

Thu 11/27

9:28 pm-8:36 am

1 stop11h 08m

Norfolk

Thu 12/4

3:29 pm-4:51 pm

Nonstop1h 22m

$194

PittsburghNorfolk

PIT - ORF

PITORF

Pittsburgh

Mon 12/1

10:42 pm-8:31 pm

2 stops21h 49m

Norfolk

Wed 12/3

8:02 pm-9:58 am

1 stop13h 56m

$208

PittsburghNorfolk

PIT - ORF

PITORF

Pittsburgh

Thu 11/27

7:05 am-11:29 am

1 stop4h 24m

Norfolk

Thu 12/4

5:40 am-9:46 am

1 stop4h 06m

$210

PittsburghNorfolk

PIT - ORF

PITORF

Pittsburgh

Thu 11/13

10:06 pm-12:24 pm

2 stops14h 18m

Norfolk

Thu 11/20

9:26 pm-10:09 am

1 stop12h 43m

$210

PittsburghNorfolk

PIT - ORF

PITORF

Pittsburgh

Sun 12/14

1:31 pm-2:49 pm

Nonstop1h 18m

Norfolk

Sun 12/28

3:29 pm-4:51 pm

Nonstop1h 22m

$228

PittsburghNorfolk

PIT - ORF

PITORF

Pittsburgh

Thu 11/20

10:42 pm-8:31 pm

2 stops21h 49m

Norfolk

Mon 11/24

9:26 pm-8:19 am

1 stop10h 53m

$246

PittsburghNorfolk

PIT - ORF

PITORF

Pittsburgh

Thu 11/13

10:06 pm-12:24 pm

2 stops14h 18m

Norfolk

Thu 11/20

7:18 pm-8:19 am

2 stops13h 01m

$246

PittsburghNorfolk

PIT - ORF

PITORF

Pittsburgh

Thu 11/27

9:28 pm-8:36 am

1 stop11h 08m

Norfolk

Thu 12/4

8:38 am-12:41 am

2 stops16h 03m

$250

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/28

Showing 1-10 of 21 results
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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 October 24, 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 $225). 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 October 29, 2025.

It’s typically best to fly out from Pittsburgh to Chesapeake in the evening. Doing so could potentially save you 40% on the flight price compared to flying at noon, which is usually more expensive.

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 Sunday at noon when fares are most often at their lowest. Sunday 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 October 29, 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
8.1
Very good
221 reviews

Entertainment

6.6

Comfort

8.2

Boarding

8.3

Overall

8.1

Crew

8.7

Food

6.7

Reviews

1 / 13
8.0
Excellent

Anonymous,Jul 2025

RIC - BDL

All went smoothly but the announcements from the crew were way to fast--approaching inaudible. Pilot announcements were perfect!
Breeze Airways
8.1
Very good
221 reviews
Breeze Airways
8.1
Very good
221 reviews

Entertainment

6.6

Comfort

8.2

Boarding

8.3

Overall

8.1

Crew

8.7

Food

6.7

Reviews

1 / 13
8.0
Excellent

Anonymous,Jul 2025

RIC - BDL

All went smoothly but the announcements from the crew were way to fast--approaching inaudible. Pilot announcements were perfect!
Southwest
8.0
Very good
4,241 reviews
Breeze Airways
8.1
Very good
221 reviews

Entertainment

6.6

Comfort

8.2

Boarding

8.3

Overall

8.1

Crew

8.7

Food

6.7

Reviews

1 / 13
8.0
Excellent

Anonymous,Jul 2025

RIC - BDL

All went smoothly but the announcements from the crew were way to fast--approaching inaudible. Pilot announcements were perfect!
Delta
7.9
Good
7,992 reviews
Breeze Airways
8.1
Very good
221 reviews

Entertainment

6.6

Comfort

8.2

Boarding

8.3

Overall

8.1

Crew

8.7

Food

6.7

Reviews

1 / 13
8.0
Excellent

Anonymous,Jul 2025

RIC - BDL

All went smoothly but the announcements from the crew were way to fast--approaching inaudible. Pilot announcements were perfect!
United Airlines
7.4
Good
8,999 reviews
Breeze Airways
8.1
Very good
221 reviews

Entertainment

6.6

Comfort

8.2

Boarding

8.3

Overall

8.1

Crew

8.7

Food

6.7

Reviews

1 / 13
8.0
Excellent

Anonymous,Jul 2025

RIC - BDL

All went smoothly but the announcements from the crew were way to fast--approaching inaudible. Pilot announcements were perfect!
American Airlines
7.2
Good
11,032 reviews
Breeze Airways
8.1
Very good
221 reviews

Entertainment

6.6

Comfort

8.2

Boarding

8.3

Overall

8.1

Crew

8.7

Food

6.7

Reviews

1 / 13
8.0
Excellent

Anonymous,Jul 2025

RIC - BDL

All went smoothly but the announcements from the crew were way to fast--approaching inaudible. Pilot announcements were perfect!

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 Breeze Airways. According to our data, you can fly for as low as $79. Users have also found prices from $87 and $89 on Spirit Airlines 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 $225). 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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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 October 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
Breeze AirwaysCheapest$102Average$181FlexibilityNo cancel feeOn-timeN/A
DeltaCheapest$128Average$290FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$176Average$339FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$196Average$338FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$227Average$369FlexibilityNo cancel feeOn-time69%

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