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$79+ 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 11/6. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — PIT
Oct 14 — Oct 211
Tue 10/14
Tue 10/21
1 adult, Economy
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Cheapflights Tip: The best prices from Chesapeake to Pittsburgh are usually found in July or August, booked 42 days in advance, depart on a Monday or Wednesday 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 September 14, 2025.

Round-trip from

$159
(Southwest)

One-way from

$79
(Breeze Airways)

Popular in

February

Cheapest in

July

Average price

$360
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. 7% potential increase in price ($26 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($9 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 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 September 14, 2025.

This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/208:35 pmORF - PIT
1 stop3h 00mSouthwest
Wed 10/221:10 pmPIT - ORF
1 stop2h 45mSouthwest
Deal found 9/12$159
This Breeze Airways 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 Breeze Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/163:29 pmORF - PIT
Nonstop1h 22mBreeze Airways
Sun 10/191:31 pmPIT - ORF
Nonstop1h 18mBreeze Airways
Deal found 9/13$163
This Breeze Airways 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 Breeze Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/53:29 pmORF - PIT
Nonstop1h 22mBreeze Airways
Thu 10/91:31 pmPIT - ORF
Nonstop1h 18mBreeze Airways
Deal found 9/12$173
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.
Sat 10/46:00 amORF - PIT
1 stop3h 44mDelta
Wed 10/810:13 amPIT - ORF
1 stop3h 48mDelta
Deal found 9/13$177
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/1111:20 amORF - PIT
1 stop4h 40mSouthwest
Tue 10/141:10 pmPIT - ORF
1 stop2h 45mSouthwest
Deal found 9/12$179
This United Airlines deal was found by Cheapflights users on 9/11. 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.
Mon 10/137:59 pmORF - PIT
1 stop3h 16mUnited Airlines
Thu 10/166:15 amPIT - ORF
1 stop3h 22mUnited Airlines
Deal found 9/11$181
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/43:15 pmORF - PIT
1 stop4h 40mSouthwest
Wed 10/83:00 pmPIT - ORF
2 stops6h 50mSouthwest
Deal found 9/13$182
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 10/247:16 pmORF - PIT
1 stop4h 24mUnited Airlines
Sat 10/256:15 amPIT - ORF
1 stop3h 22mUnited Airlines
Deal found 9/12$192
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/306:08 amORF - PIT
1 stop3h 41mDelta
Fri 10/37:05 amPIT - ORF
1 stop4h 27mDelta
Deal found 9/12$195
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/56:00 amORF - PIT
1 stop3h 54mDelta
Thu 10/97:21 amPIT - ORF
1 stop4h 08mDelta
Deal found 9/12$198

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 September 14, 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

Thu 10/16

3:29 pm-4:51 pm

Nonstop1h 22m

Pittsburgh

Sun 10/19

1:31 pm-2:49 pm

Nonstop1h 18m

$163

NorfolkPittsburgh

ORF - PIT

ORFPIT

Norfolk

Sun 10/5

3:29 pm-4:51 pm

Nonstop1h 22m

Pittsburgh

Thu 10/9

1:31 pm-2:49 pm

Nonstop1h 18m

$173

NorfolkPittsburgh

ORF - PIT

ORFPIT

Norfolk

Sat 10/4

6:00 am-9:44 am

1 stop3h 44m

Pittsburgh

Wed 10/8

10:13 am-2:01 pm

1 stop3h 48m

$177

NorfolkPittsburgh

ORF - PIT

ORFPIT

Norfolk

Sat 10/11

11:20 am-4:00 pm

1 stop4h 40m

Pittsburgh

Tue 10/14

1:10 pm-3:55 pm

1 stop2h 45m

$179

NorfolkPittsburgh

ORF - PIT

ORFPIT

Norfolk

Sat 11/1

4:10 pm-9:05 pm

1 stop4h 55m

Pittsburgh

Mon 11/3

2:11 pm-9:38 pm

1 stop7h 27m

$179

NorfolkPittsburgh

ORF - PIT

ORFPIT

Norfolk

Sat 10/25

12:35 pm-3:39 pm

1 stop3h 04m

Pittsburgh

Mon 10/27

6:17 am-12:18 pm

1 stop6h 01m

$179

NorfolkPittsburgh

ORF - PIT

ORFPIT

Norfolk

Mon 10/13

7:59 pm-11:15 pm

1 stop3h 16m

Pittsburgh

Thu 10/16

6:15 am-9:37 am

1 stop3h 22m

$181

NorfolkPittsburgh

ORF - PIT

ORFPIT

Norfolk

Sat 10/4

3:15 pm-7:55 pm

1 stop4h 40m

Pittsburgh

Wed 10/8

3:00 pm-9:50 pm

2 stops6h 50m

$182

NorfolkPittsburgh

ORF - PIT

ORFPIT

Norfolk

Fri 10/24

7:16 pm-11:40 pm

1 stop4h 24m

Pittsburgh

Sat 10/25

6:15 am-9:37 am

1 stop3h 22m

$192

NorfolkPittsburgh

ORF - PIT

ORFPIT

Norfolk

Tue 9/30

6:08 am-9:49 am

1 stop3h 41m

Pittsburgh

Fri 10/3

7:05 am-11:32 am

1 stop4h 27m

$195

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/12

Showing 1-10 of 21 results
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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 September 12, 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 September 14, 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 September 7, 2025.

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

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 September 14, 2025.
Peruse reviews from past customers who have flown with Southwest, Breeze Airways, and Delta from Chesapeake to Pittsburgh to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,247 reviews

Overall

8.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Comfort

8.0

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
4,247 reviews
Southwest
8.0
Very good
4,247 reviews

Overall

8.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Comfort

8.0

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
4,247 reviews

Overall

8.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Comfort

8.0

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
7,959 reviews
Southwest
8.0
Very good
4,247 reviews

Overall

8.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Comfort

8.0

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
8,934 reviews
Southwest
8.0
Very good
4,247 reviews

Overall

8.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Comfort

8.0

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
4,247 reviews

Overall

8.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Comfort

8.0

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 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 5 different airlines.

  • How long is the flight from Chesapeake to Pittsburgh?

    Breeze Airways, Delta, and Southwest can get you from Chesapeake to Pittsburgh in just under 1h 22m. Your travel time can differ by up to 3h 18m. Chesapeake and Pittsburgh are separated by a distance of 330 mi. Both multi-stop and nonstop flights can be found to your destination and back.

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

    $79 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 Delta and Spirit Airlines, with prices starting from $89 and $109, 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 Pittsburgh?

Book flights to Pittsburgh if you plan to visit one of these locations
Mars
Steubenville
Monroeville
Washington
Wexford
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 5 airlines flying from Chesapeake to Pittsburgh

Discover the top 5 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 September 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
Breeze AirwaysCheapest$66Average$206FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$156Average$336FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$168Average$380FlexibilityNo cancel feeOn-time69%
DeltaCheapest$176Average$332FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$218Average$403FlexibilityNo cancel feeOn-time71%

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