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$72+ 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 5/8. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — PIT
Apr 9 — Apr 161
Thu 4/9
Thu 4/16
1 adult, Economy
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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 March 10, 2026.

This Kiwi.com deal was found by Cheapflights users on 3/9. 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 5/1511:25 am
ORF
-
PIT
Nonstop1h 23m
Breeze Airways
Mon 5/189:21 am
PIT
-
ORF
Nonstop1h 19m
Breeze Airways
Deal found 3/9$167
This Kiwi.com deal was found by Cheapflights users on 3/9. 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 5/811:25 am
ORF
-
PIT
Nonstop1h 23m
Breeze Airways
Sun 5/1012:21 pm
PIT
-
ORF
1 stop4h 26m
Breeze Airways
Deal found 3/9$211
This Kiwi.com deal was found by Cheapflights users on 3/7. 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 5/158:57 pm
ORF
-
PIT
1 stop20h 23m
Multiple Airlines
Mon 5/189:21 am
PIT
-
ORF
Nonstop1h 19m
Multiple Airlines
Deal found 3/7$227
This Booking.com deal was found by Cheapflights users on 3/8. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/2211:25 am
ORF
-
PIT
Nonstop1h 23m
Breeze Airways
Sun 5/2412:21 pm
PIT
-
ORF
1 stop4h 26m
Breeze Airways
Deal found 3/8$228
This Breeze Airways deal was found by Cheapflights users on 3/9. 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 5/1511:25 am
ORF
-
PIT
Nonstop1h 23m
Breeze Airways
Sun 5/1712:21 pm
PIT
-
ORF
1 stop4h 26m
Breeze Airways
Deal found 3/9$236
This Kiwi.com deal was found by Cheapflights users on 3/7. 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 5/1511:25 am
ORF
-
PIT
Nonstop1h 23m
Multiple Airlines
Sun 5/176:35 am
PIT
-
ORF
1 stop13h 27m
Multiple Airlines
Deal found 3/7$260
This Kiwi.com deal was found by Cheapflights users on 3/6. 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 3/1911:50 am
ORF
-
PIT
2 stops21h 48m
Multiple Airlines
Tue 3/246:00 am
PIT
-
ORF
1 stop13h 46m
Multiple Airlines
Deal found 3/6$262
This United Airlines deal was found by Cheapflights users on 3/5. 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.
Tue 5/58:00 am
ORF
-
PIT
1 stop7h 21m
United Airlines
Sat 5/95:15 pm
PIT
-
ORF
1 stop6h 17m
United Airlines
Deal found 3/5$265
This Kiwi.com deal was found by Cheapflights users on 3/5. 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 4/2011:27 am
ORF
-
PIT
2 stops36h 32m
Multiple Airlines
Sun 4/266:15 pm
PIT
-
ORF
1 stop25h 47m
Multiple Airlines
Deal found 3/5$270

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 March 10, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$167
(Kiwi.com)

One-way from

$72
(Booking.com)

Popular in

March

Cheapest in

September

Average price

$356
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. 9% potential increase in price ($29 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($7 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 2026
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 March 10, 2026.
Use the filters below to find and compare flights from Chesapeake to Pittsburgh that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

NorfolkPittsburgh

ORF - PIT

ORFPIT

Norfolk

Tue 5/5

8:00 am-3:21 pm

1 stop7h 21m

Pittsburgh

Sat 5/9

5:15 pm-11:32 pm

1 stop6h 17m

$265

NorfolkPittsburgh

ORF - PIT

ORFPIT

Norfolk

Tue 5/5

4:25 pm-10:10 pm

1 stop5h 45m

Pittsburgh

Fri 5/8

5:00 pm-10:55 pm

1 stop5h 55m

$272

NorfolkPittsburgh

ORF - PIT

ORFPIT

Norfolk

Wed 4/29

7:55 pm-11:20 pm

1 stop3h 25m

Pittsburgh

Mon 5/4

7:52 pm-11:50 pm

1 stop3h 58m

$273

NorfolkPittsburgh

ORF - PIT

ORFPIT

Norfolk

Tue 5/5

12:45 pm-10:10 pm

2 stops9h 25m

Pittsburgh

Sat 5/9

8:25 am-6:10 pm

2 stops9h 45m

$275

NorfolkPittsburgh

ORF - PIT

ORFPIT

Norfolk

Thu 4/23

6:00 am-10:19 am

1 stop4h 19m

Pittsburgh

Mon 4/27

7:13 am-11:41 am

1 stop4h 28m

$291

NorfolkPittsburgh

ORF - PIT

ORFPIT

Norfolk

Tue 4/28

12:45 pm-5:55 pm

1 stop5h 10m

Pittsburgh

Fri 5/1

5:00 pm-10:55 pm

1 stop5h 55m

$299

NorfolkPittsburgh

ORF - PIT

ORFPIT

Norfolk

Sat 5/23

5:39 pm-11:23 pm

1 stop5h 44m

Pittsburgh

Sun 5/24

8:36 am-3:14 pm

1 stop6h 38m

$304

NorfolkPittsburgh

ORF - PIT

ORFPIT

Norfolk

Fri 5/15

2:30 pm-8:00 pm

1 stop5h 30m

Pittsburgh

Sun 5/17

6:10 am-9:20 am

1 stop3h 10m

$308

NorfolkPittsburgh

ORF - PIT

ORFPIT

Norfolk

Sat 5/23

6:00 am-1:09 pm

1 stop7h 09m

Pittsburgh

Mon 5/25

7:24 pm-12:41 am

1 stop5h 17m

$309
Quickest round-trip

NorfolkPittsburgh

ORF - PIT

ORFPIT

Norfolk

Wed 7/22

10:45 am-2:03 pm

1 stop3h 18m

Pittsburgh

Wed 7/29

7:59 pm-11:44 pm

1 stop3h 45m

$322

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/5

Showing 1-10 of 22 resultsSorted by cheapest first
1
2
3

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

What is the cheapest month to book a flight from Chesapeake to Pittsburgh?

Currently, June is the cheapest month in which you can book a flight from Chesapeake to Pittsburgh (average of $79). Flying from Chesapeake to Pittsburgh in January is currently the most expensive (average of $304). 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.

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 March 10, 2026.
Peruse reviews from past customers who have flown with Breeze Airways,Southwest, andDelta 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
8.1
Very good
271 reviews

Boarding

8.3

Food

6.6

Comfort

8.2

Entertainment

6.6

Crew

8.7

Overall

8.1

Reviews

1 / 17
2.0
Mediocre

Justine,Jan 2026

RDU - MCO

1/10, I have never experienced the amount of delays, my flight was supposed to board at 8:34pm, we didn’t board until 3:35am from RDU. The staff got rude and very disrespectful when you asked what was going on it was like we didn’t board until something wrong or were pestering them for answers. I was 1 question 1 time, they were not communicating with us at all. So when our plane was now 6+ hrs delayed and nothing was being said to us .. yeah I think we have a right to ask a question. Everything took so long and was such a process; I have never experienced this before and I’m a frequent flyer, breeze makes spirit airlines look like a 100/10 airline.
Breeze Airways
8.1
Very good
271 reviews
Breeze Airways
8.1
Very good
271 reviews

Boarding

8.3

Food

6.6

Comfort

8.2

Entertainment

6.6

Crew

8.7

Overall

8.1

Reviews

1 / 17
2.0
Mediocre

Justine,Jan 2026

RDU - MCO

1/10, I have never experienced the amount of delays, my flight was supposed to board at 8:34pm, we didn’t board until 3:35am from RDU. The staff got rude and very disrespectful when you asked what was going on it was like we didn’t board until something wrong or were pestering them for answers. I was 1 question 1 time, they were not communicating with us at all. So when our plane was now 6+ hrs delayed and nothing was being said to us .. yeah I think we have a right to ask a question. Everything took so long and was such a process; I have never experienced this before and I’m a frequent flyer, breeze makes spirit airlines look like a 100/10 airline.
Southwest
8.0
Very good
4,317 reviews
Breeze Airways
8.1
Very good
271 reviews

Boarding

8.3

Food

6.6

Comfort

8.2

Entertainment

6.6

Crew

8.7

Overall

8.1

Reviews

1 / 17
2.0
Mediocre

Justine,Jan 2026

RDU - MCO

1/10, I have never experienced the amount of delays, my flight was supposed to board at 8:34pm, we didn’t board until 3:35am from RDU. The staff got rude and very disrespectful when you asked what was going on it was like we didn’t board until something wrong or were pestering them for answers. I was 1 question 1 time, they were not communicating with us at all. So when our plane was now 6+ hrs delayed and nothing was being said to us .. yeah I think we have a right to ask a question. Everything took so long and was such a process; I have never experienced this before and I’m a frequent flyer, breeze makes spirit airlines look like a 100/10 airline.
Delta
7.9
Good
8,276 reviews
Breeze Airways
8.1
Very good
271 reviews

Boarding

8.3

Food

6.6

Comfort

8.2

Entertainment

6.6

Crew

8.7

Overall

8.1

Reviews

1 / 17
2.0
Mediocre

Justine,Jan 2026

RDU - MCO

1/10, I have never experienced the amount of delays, my flight was supposed to board at 8:34pm, we didn’t board until 3:35am from RDU. The staff got rude and very disrespectful when you asked what was going on it was like we didn’t board until something wrong or were pestering them for answers. I was 1 question 1 time, they were not communicating with us at all. So when our plane was now 6+ hrs delayed and nothing was being said to us .. yeah I think we have a right to ask a question. Everything took so long and was such a process; I have never experienced this before and I’m a frequent flyer, breeze makes spirit airlines look like a 100/10 airline.
United Airlines
7.4
Good
9,409 reviews
Breeze Airways
8.1
Very good
271 reviews

Boarding

8.3

Food

6.6

Comfort

8.2

Entertainment

6.6

Crew

8.7

Overall

8.1

Reviews

1 / 17
2.0
Mediocre

Justine,Jan 2026

RDU - MCO

1/10, I have never experienced the amount of delays, my flight was supposed to board at 8:34pm, we didn’t board until 3:35am from RDU. The staff got rude and very disrespectful when you asked what was going on it was like we didn’t board until something wrong or were pestering them for answers. I was 1 question 1 time, they were not communicating with us at all. So when our plane was now 6+ hrs delayed and nothing was being said to us .. yeah I think we have a right to ask a question. Everything took so long and was such a process; I have never experienced this before and I’m a frequent flyer, breeze makes spirit airlines look like a 100/10 airline.
American Airlines
7.1
Good
11,414 reviews
Breeze Airways
8.1
Very good
271 reviews

Boarding

8.3

Food

6.6

Comfort

8.2

Entertainment

6.6

Crew

8.7

Overall

8.1

Reviews

1 / 17
2.0
Mediocre

Justine,Jan 2026

RDU - MCO

1/10, I have never experienced the amount of delays, my flight was supposed to board at 8:34pm, we didn’t board until 3:35am from RDU. The staff got rude and very disrespectful when you asked what was going on it was like we didn’t board until something wrong or were pestering them for answers. I was 1 question 1 time, they were not communicating with us at all. So when our plane was now 6+ hrs delayed and nothing was being said to us .. yeah I think we have a right to ask a question. Everything took so long and was such a process; I have never experienced this before and I’m a frequent flyer, breeze makes spirit airlines look like a 100/10 airline.

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?

    United Airlines and Southwest can get you from Chesapeake to Pittsburgh in just under 5h 45m. Your travel time can differ by up to 1h 36m. 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?

    $84 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, June is the cheapest month in which you can book a flight from Chesapeake to Pittsburgh (average of $79). Flying from Chesapeake to Pittsburgh in January is currently the most expensive (average of $304). 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
Chester
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 March 10, 2026.
AirlineCheapestAverageFlexibilityOn-time
Breeze AirwaysCheapest$93Average$215FlexibilityNo cancel feeOn-timeN/A
DeltaCheapest$153Average$296FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$156Average$328FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$168Average$341FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$206Average$313FlexibilityNo cancel feeOn-time71%

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