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$89+ 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 1/4. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — PIT
Jan 25 — Feb 11
Sun 1/25
Sun 2/1
1 adult, Economy
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Cheapflights Tip: The best prices from Chesapeake to Pittsburgh are usually found in November or September, booked 42 days in advance, depart on a Saturday or Monday and return on a Tuesday

Cheap 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 December 26, 2025.

This Kiwi.com deal was found by Cheapflights users on 12/24. 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.
Sun 12/283:29 pmORF - PIT
Nonstop1h 22mBreeze Airways
Thu 1/11:31 pmPIT - ORF
Nonstop1h 18mBreeze Airways
Deal found 12/24$207
This Kiwi.com deal was found by Cheapflights users on 12/25. 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.
Sun 12/283:29 pmORF - PIT
Nonstop1h 22mMultiple Airlines
Fri 1/212:51 pmPIT - ORF
1 stop23h 19mMultiple Airlines
Deal found 12/25$361
This Kiwi.com deal was found by Cheapflights users on 12/24. 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.
Sun 12/283:29 pmORF - PIT
Nonstop1h 22mMultiple Airlines
Tue 12/3012:29 pmPIT - ORF
1 stop28h 37mMultiple Airlines
Deal found 12/24$371
This United Airlines deal was found by Cheapflights users on 12/24. 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 12/2810:46 amORF - PIT
1 stop3h 17mUnited Airlines
Thu 1/11:59 pmPIT - ORF
2 stops9h 42mUnited Airlines
Deal found 12/24$482
This Kiwi.com deal was found by Cheapflights users on 12/24. 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.
Mon 12/2910:05 pmORF - PIT
1 stop10h 41mBreeze Airways
Sat 1/38:21 amPIT - ORF
1 stop23h 42mBreeze Airways
Deal found 12/24$505
This Kiwi.com deal was found by Cheapflights users on 12/24. 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.
Sat 12/2710:05 pmORF - PIT
1 stop10h 41mBreeze Airways
Sat 1/38:21 amPIT - ORF
1 stop23h 42mBreeze Airways
Deal found 12/24$550
This Kiwi.com deal was found by Cheapflights users on 12/26. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/2710:05 pmORF - PIT
1 stop10h 41mMultiple Airlines
Fri 1/212:51 pmPIT - ORF
1 stop25h 15mMultiple Airlines
Deal found 12/26$552

Find flight deals from Chesapeake to Pittsburgh

Keep the following information in mind while searching for Chesapeake to Pittsburgh flight deals. Data was last updated December 26, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$137
(Kiwi.com)

One-way from

$89
(Breeze Airways)

Popular in

February

Cheapest in

November

Average price

$366
Provider with most accurate pricing for Norfolk-Pittsburgh flight deals.
Search Deals
Provider most trusted by Cheapflights users for Norfolk-Pittsburgh flights.
Search Deals
From Chesapeake to Pittsburgh
Search Deals
One-way flight from Chesapeake to Pittsburgh
Search Deals
Highest demand for flights based on searches. 14% potential increase in price ($48 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($12 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals

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 December 26, 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 2/5

7:33 pm-9:40 am

1 stop14h 07m

Pittsburgh

Sun 2/8

5:50 pm-6:38 pm

1 stop24h 48m

$137

NorfolkPittsburgh

ORF - PIT

ORFPIT

Norfolk

Wed 1/28

8:00 am-11:44 pm

2 stops15h 44m

Pittsburgh

Sat 1/31

5:50 pm-6:38 pm

1 stop24h 48m

$180

NorfolkPittsburgh

ORF - PIT

ORFPIT

Norfolk

Sat 1/10

6:45 am-11:44 pm

2 stops16h 59m

Pittsburgh

Wed 1/14

5:50 pm-6:38 pm

1 stop24h 48m

$190

NorfolkPittsburgh

ORF - PIT

ORFPIT

Norfolk

Fri 1/23

7:33 pm-9:40 am

1 stop14h 07m

Pittsburgh

Sun 1/25

5:50 pm-10:48 am

2 stops16h 58m

$207

NorfolkPittsburgh

ORF - PIT

ORFPIT

Norfolk

Sun 1/4

3:29 pm-4:51 pm

Nonstop1h 22m

Pittsburgh

Thu 1/8

5:50 pm-5:06 pm

2 stops23h 16m

$235

NorfolkPittsburgh

ORF - PIT

ORFPIT

Norfolk

Thu 2/5

1:01 pm-5:11 pm

1 stop4h 10m

Pittsburgh

Sun 2/8

6:19 am-12:10 pm

1 stop5h 51m

$259

NorfolkPittsburgh

ORF - PIT

ORFPIT

Norfolk

Fri 1/9

6:45 am-11:44 pm

3 stops16h 59m

Pittsburgh

Sun 1/11

6:00 am-6:38 pm

1 stop12h 38m

$264

NorfolkPittsburgh

ORF - PIT

ORFPIT

Norfolk

Fri 1/16

6:00 am-11:24 am

1 stop5h 24m

Pittsburgh

Sun 1/18

10:23 am-2:59 pm

1 stop4h 36m

$272

NorfolkPittsburgh

ORF - PIT

ORFPIT

Norfolk

Tue 1/20

6:30 am-12:10 pm

1 stop5h 40m

Pittsburgh

Tue 1/27

6:25 am-5:50 pm

2 stops11h 25m

$273

NorfolkPittsburgh

ORF - PIT

ORFPIT

Norfolk

Tue 1/13

8:05 am-9:40 am

2 stops25h 35m

Pittsburgh

Fri 1/16

1:00 pm-9:50 pm

1 stop8h 50m

$275

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/25

Showing 1-10 of 18 results
1
2

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 December 19, 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, May is the cheapest month in which you can book a flight from Chesapeake to Pittsburgh (average of $75). Flying from Chesapeake to Pittsburgh in January is currently the most expensive (average of $233). 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 December 26, 2025.

A simple way to save on the total cost of your ticket is to fly from Chesapeake to Pittsburgh at noon. If you’re flexible enough to do this you can expect to save up to 20% on your trip compared to booking a flight in the evening.

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 December 20, 2025.

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

How much does it cost to fly round-trip from Chesapeake to Pittsburgh?

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 December 26, 2025.
Peruse reviews from past customers who have flown with Breeze Airways, Southwest, 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.
Breeze Airways
8.2
Very good
249 reviews

Entertainment

6.7

Boarding

8.4

Crew

8.8

Overall

8.2

Comfort

8.2

Food

6.7

Reviews

1 / 16
10.0
Excellent

Anonymous,Dec 2025

RSW - ISP

There was no food offered so I had to just put okay. Other than that all was great.
Breeze Airways
8.2
Very good
249 reviews
Breeze Airways
8.2
Very good
249 reviews

Entertainment

6.7

Boarding

8.4

Crew

8.8

Overall

8.2

Comfort

8.2

Food

6.7

Reviews

1 / 16
10.0
Excellent

Anonymous,Dec 2025

RSW - ISP

There was no food offered so I had to just put okay. Other than that all was great.
Southwest
8.0
Very good
4,258 reviews
Breeze Airways
8.2
Very good
249 reviews

Entertainment

6.7

Boarding

8.4

Crew

8.8

Overall

8.2

Comfort

8.2

Food

6.7

Reviews

1 / 16
10.0
Excellent

Anonymous,Dec 2025

RSW - ISP

There was no food offered so I had to just put okay. Other than that all was great.
Delta
7.9
Good
8,014 reviews
Breeze Airways
8.2
Very good
249 reviews

Entertainment

6.7

Boarding

8.4

Crew

8.8

Overall

8.2

Comfort

8.2

Food

6.7

Reviews

1 / 16
10.0
Excellent

Anonymous,Dec 2025

RSW - ISP

There was no food offered so I had to just put okay. Other than that all was great.
United Airlines
7.4
Good
9,115 reviews
Breeze Airways
8.2
Very good
249 reviews

Entertainment

6.7

Boarding

8.4

Crew

8.8

Overall

8.2

Comfort

8.2

Food

6.7

Reviews

1 / 16
10.0
Excellent

Anonymous,Dec 2025

RSW - ISP

There was no food offered so I had to just put okay. Other than that all was great.
American Airlines
7.2
Good
11,064 reviews
Breeze Airways
8.2
Very good
249 reviews

Entertainment

6.7

Boarding

8.4

Crew

8.8

Overall

8.2

Comfort

8.2

Food

6.7

Reviews

1 / 16
10.0
Excellent

Anonymous,Dec 2025

RSW - ISP

There was no food offered so I had to just put okay. Other than that all was great.

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?

    Spirit Airlines can get you from Chesapeake to Pittsburgh in just under 14h 07m. Your travel time can differ by up to . Chesapeake and Pittsburgh are separated by a distance of 330 mi.

  • 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 American Airlines and Delta, with prices starting from $87 and $98, 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, May is the cheapest month in which you can book a flight from Chesapeake to Pittsburgh (average of $75). Flying from Chesapeake to Pittsburgh in January is currently the most expensive (average of $233). 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
Washington
Monroeville
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 December 26, 2025.
AirlineCheapestAverageFlexibilityOn-time
Breeze AirwaysCheapest$93Average$215FlexibilityNo cancel feeOn-timeN/A
DeltaCheapest$153Average$321FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$156Average$328FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$168Average$353FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$206Average$365FlexibilityNo cancel feeOn-time71%

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