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$81+ Cheap flights from Chesapeake, VA to Pittsburgh (PIT)

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 5/16. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — PIT
Apr 29 — May 61
Tue 4/29
Tue 5/6
1 adult, Economy
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Cheapflights Tip: The best prices from Chesapeake to Pittsburgh are usually found in September or May, booked 42 days in advance, depart on a Monday or Thursday and return on a Tuesday

Cheap flight deals from Chesapeake to Pittsburgh

Keep the following information in mind while searching for Chesapeake to Pittsburgh flight deals. Data was last updated April 24, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$253
(Southwest)

One-way from

$81
(Priceline)

Popular in

February

Cheapest in

September

Average price

$335
Provider with most accurate pricing for Norfolk-Pittsburgh flight deals.
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Provider most trusted by Cheapflights users for Norfolk-Pittsburgh flights.
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From Chesapeake to Pittsburgh
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One-way flight from Chesapeake to Pittsburgh
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Highest demand for flights based on searches. 9% potential increase in price ($31 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($10 potential savings vs. average RT price).
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Average for round-trip flights in April 2025
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Find flight deals from Chesapeake to Pittsburgh

Cheapest flights from Chesapeake to Pittsburgh
Explore the most affordable flight options available from Chesapeake to Pittsburgh. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 24, 2025.

This Southwest deal was found by Cheapflights users on 4/23. 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.
Mon 6/25:05 pmORF - PIT
1 stop6h 15mSouthwest
Sat 6/76:15 pmPIT - ORF
1 stop4h 20mSouthwest
Deal found 4/23$253
This American Airlines deal was found by Cheapflights users on 4/23. 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.
Mon 5/191:24 pmORF - PIT
1 stop3h 33mAmerican Airlines
Thu 5/227:40 pmPIT - ORF
1 stop4h 15mAmerican Airlines
Deal found 4/23$255
This Delta deal was found by Cheapflights users on 4/23. 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.
Fri 7/256:50 pmORF - PIT
1 stop4h 16mDelta
Mon 7/281:00 pmPIT - ORF
1 stop5h 10mDelta
Deal found 4/23$266
This FlightHub deal was found by Cheapflights users on 4/23. 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.
Mon 5/191:01 pmORF - PIT
Nonstop1h 23mMultiple Airlines
Thu 5/227:00 amPIT - ORF
1 stop7h 16mMultiple Airlines
Deal found 4/23$326
This Kiwi.com deal was found by Cheapflights users on 4/23. 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 7/2510:59 amORF - PIT
Nonstop1h 21mBreeze Airways
Mon 7/281:00 pmPIT - ORF
Nonstop1h 18mBreeze Airways
Deal found 4/23$343
This United Airlines deal was found by Cheapflights users on 4/23. 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.
Sun 11/96:00 amORF - PIT
1 stop3h 36mUnited Airlines
Tue 11/117:00 amPIT - ORF
1 stop7h 16mUnited Airlines
Deal found 4/23$362

Cheapflights Fare Finder

Customize your flight search to find flights from Chesapeake to Pittsburgh 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 April 24, 2025.
Use the filters below to find and compare flights from Chesapeake to Pittsburgh that are best for you.

Fly from

Chesapeake

Fly to

Pittsburgh

Route

Depart

Return

Price

NorfolkPittsburgh

ORF - PIT

ORFPIT

Norfolk

Mon 6/2

5:05 pm-11:20 pm

1 stop6h 15m

Pittsburgh

Sat 6/7

6:15 pm-10:35 pm

1 stop4h 20m

$253

NorfolkPittsburgh

ORF - PIT

ORFPIT

Norfolk

Mon 5/19

1:24 pm-4:57 pm

1 stop3h 33m

Pittsburgh

Thu 5/22

7:40 pm-11:55 pm

1 stop4h 15m

$255

NorfolkPittsburgh

ORF - PIT

ORFPIT

Norfolk

Fri 7/25

6:50 pm-11:06 pm

1 stop4h 16m

Pittsburgh

Mon 7/28

1:00 pm-6:10 pm

1 stop5h 10m

$266

NorfolkPittsburgh

ORF - PIT

ORFPIT

Norfolk

Mon 5/19

1:01 pm-2:24 pm

Nonstop1h 23m

Pittsburgh

Thu 5/22

7:00 am-2:16 pm

1 stop7h 16m

$326

NorfolkPittsburgh

ORF - PIT

ORFPIT

Norfolk

Fri 7/25

10:59 am-12:20 pm

Nonstop1h 21m

Pittsburgh

Mon 7/28

1:00 pm-2:18 pm

Nonstop1h 18m

$343

NorfolkPittsburgh

ORF - PIT

ORFPIT

Norfolk

Thu 7/24

6:10 am-9:21 am

1 stop3h 11m

Pittsburgh

Sun 7/27

8:05 pm-11:44 pm

1 stop3h 39m

$381

NorfolkPittsburgh

ORF - PIT

ORFPIT

Norfolk

Fri 5/16

1:01 pm-2:24 pm

Nonstop1h 23m

$81

NorfolkPittsburgh

ORF - PIT

ORFPIT

Norfolk

Thu 5/29

6:00 pm-10:57 pm

1 stop4h 57m

$114

NorfolkPittsburgh

ORF - PIT

ORFPIT

Norfolk

Thu 6/5

6:06 am-9:50 am

1 stop3h 44m

$128

NorfolkPittsburgh

ORF - PIT

ORFPIT

Norfolk

Sun 10/12

6:52 pm-11:05 pm

1 stop4h 13m

$154

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/23

Showing 1-10 of 12 results
1
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Best time to book a flight from Chesapeake to Pittsburgh

Have a flexible travel schedule? Discover the best time to fly to Pittsburgh from Chesapeake 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 Chesapeake to Pittsburgh

How far ahead should I book a flight from Chesapeake to Pittsburgh?

Use this chart to determine the optimal time to book a round-trip flight from Chesapeake to Pittsburgh. Price data was last updated on April 18, 2025.

The price you pay for your flight from Chesapeake to Pittsburgh may vary depending on when you book. For the best chance of a lower fare, look to book 42 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 Chesapeake to Pittsburgh?

Currently, August is the cheapest month in which you can book a flight from Chesapeake to Pittsburgh (average of $262). Flying from Chesapeake to Pittsburgh in November is currently the most expensive (average of $333). 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 C6E to PIT?

Find hourly flight availability from Chesapeake to Pittsburgh. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated April 24, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Chesapeake to Pittsburgh as you normally would.

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

Use this chart to determine the cheapest time to fly round-trip from Chesapeake to Pittsburgh. Price data was last updated on March 30, 2025.

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

Rainfall in Pittsburgh by month

Plan your trip to Pittsburgh by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Pittsburgh ranges from 2.3 - 4.3 inches per month. June is typically the wettest month, when rainfall can reach 4.3 in. October is typically the driest time to visit Pittsburgh when rainfall is around 2.3 in.

Temperature in Pittsburgh by month

Plan your trip to Pittsburgh by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Pittsburgh, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 28.4 F).

Reviews of airlines servicing Pittsburgh

Get insights into the airlines that provide service to Pittsburgh. 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 Pittsburgh. Reviews last updated April 24, 2025.
See what other customers who have flown with Breeze Airways, Southwest and Delta from Chesapeake to Pittsburgh have to say. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Breeze Airways
8.1
Very good
159 reviews

Comfort

8.2

Food

6.7

Boarding

8.3

Crew

8.8

Overall

8.1

Entertainment

6.7

Reviews

1 / 11
10.0
Excellent

Dena,Dec 2024

LAS - BDL

It was comfortable and the crew was great! A few free snacks offered would be nice!
Breeze Airways
8.1
Very good
159 reviews
Breeze Airways
8.1
Very good
159 reviews

Comfort

8.2

Food

6.7

Boarding

8.3

Crew

8.8

Overall

8.1

Entertainment

6.7

Reviews

1 / 11
10.0
Excellent

Dena,Dec 2024

LAS - BDL

It was comfortable and the crew was great! A few free snacks offered would be nice!
Southwest
8.0
Very good
4,286 reviews
Breeze Airways
8.1
Very good
159 reviews

Comfort

8.2

Food

6.7

Boarding

8.3

Crew

8.8

Overall

8.1

Entertainment

6.7

Reviews

1 / 11
10.0
Excellent

Dena,Dec 2024

LAS - BDL

It was comfortable and the crew was great! A few free snacks offered would be nice!
Delta
8.0
Very good
7,920 reviews
Breeze Airways
8.1
Very good
159 reviews

Comfort

8.2

Food

6.7

Boarding

8.3

Crew

8.8

Overall

8.1

Entertainment

6.7

Reviews

1 / 11
10.0
Excellent

Dena,Dec 2024

LAS - BDL

It was comfortable and the crew was great! A few free snacks offered would be nice!
United Airlines
7.4
Good
8,685 reviews
Breeze Airways
8.1
Very good
159 reviews

Comfort

8.2

Food

6.7

Boarding

8.3

Crew

8.8

Overall

8.1

Entertainment

6.7

Reviews

1 / 11
10.0
Excellent

Dena,Dec 2024

LAS - BDL

It was comfortable and the crew was great! A few free snacks offered would be nice!
JetBlue
7.3
Good
2,924 reviews
Breeze Airways
8.1
Very good
159 reviews

Comfort

8.2

Food

6.7

Boarding

8.3

Crew

8.8

Overall

8.1

Entertainment

6.7

Reviews

1 / 11
10.0
Excellent

Dena,Dec 2024

LAS - BDL

It was comfortable and the crew was great! A few free snacks offered would be nice!

Related info for your journey

Find useful and relevant information for your journey from Chesapeake to Pittsburgh. 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 into for flights to Pittsburgh from Chesapeake?

    Located just 13.5 mi from the city center, Pittsburgh is the airport most travelers will use when flying to Pittsburgh from Chesapeake. Booking flights from Chesapeake to Pittsburgh (PIT) should be relatively easy as there are 0 daily inbound flights from Chesapeake from 6 different airlines.

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

    $81 is the cheapest one-way deal found within the past few days, from Breeze Airways. You may also be able to find cheap deals on JetBlue and Delta, with prices starting from $114 and $128, respectively.

  • Can I find deals for flights from Chesapeake to Pittsburgh that include hotel bookings?

    Yes. In addition to deals on Chesapeake to Pittsburgh flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chesapeake to Pittsburgh?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chesapeake to Pittsburgh.

  • Can I find deals for business class flights from Chesapeake to Pittsburgh?

    Yes. Cheapflights offers flight deals from Chesapeake to Pittsburgh 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 Chesapeake to Pittsburgh?

    Currently, August is the cheapest month in which you can book a flight from Chesapeake to Pittsburgh (average of $262). Flying from Chesapeake to Pittsburgh in November is currently the most expensive (average of $333). 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

Traveling to a place near Chesapeake?

Book flights to Chesapeake if you plan to visit one of these locations
Monroeville
Washington
Steubenville
Belle Vernon

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Alternative routes for Chesapeake to Pittsburgh

See prices for flight routes from nearby airports that may be better suited for you.
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Top 6 airlines flying from Chesapeake to Pittsburgh

Discover the top 6 airlines that operate flights from Chesapeake to Pittsburgh. 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 April 24, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$107Average$196FlexibilityNo cancel feeOn-time65%
Breeze AirwaysCheapest$108Average$176FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$206Average$384FlexibilityNo cancel feeOn-time71%
DeltaCheapest$208Average$306FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$241Average$414FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$261Average$346FlexibilityNo cancel feeOn-time63%

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