HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Chesapeake

$123+ Cheap flights from Pittsburgh (PIT) to Chesapeake, VA

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 2/3. Fares are subject to change and may not be available on all flights or dates of travel.
PIT — RIC
Feb 11 — Feb 181
Wed 2/11
Wed 2/18
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Pittsburgh to Chesapeake with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.
Cheapflights Tip: The best prices from Pittsburgh to Chesapeake are usually found in September or November, booked 58 days in advance, depart on a Tuesday or Monday and return on a Friday

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 January 12, 2026.

Most accurate provider

Mytrip
3 stars

Most trusted provider

Mytrip
3 stars

Round-trip from

$123
(Kiwi.com)

Popular in

January

Cheapest in

September

Average price

$534
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
Highest demand for flights based on searches. 25% potential increase in price ($101 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 7% potential price decrease ($21 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals

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 January 12, 2026.

This Kiwi.com deal was found by Cheapflights users on 1/12. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/36:15 pm
PIT
-
ORF
1 stop24h 23m
Spirit Airlines
Tue 2/107:33 pm
ORF
-
PIT
1 stop14h 07m
Spirit Airlines
Deal found 1/12$123
This Kiwi.com deal was found by Cheapflights users on 1/11. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/46:00 am
PIT
-
ORF
1 stop12h 26m
Spirit Airlines
Mon 3/97:31 pm
ORF
-
PIT
1 stop28h 28m
Spirit Airlines
Deal found 1/11$145
This Kiwi.com deal was found by Cheapflights users on 1/11. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/119:21 am
PIT
-
ORF
Nonstop1h 19m
Breeze Airways
Mon 9/1411:25 am
ORF
-
PIT
Nonstop1h 23m
Breeze Airways
Deal found 1/11$157
This Kiwi.com deal was found by Cheapflights users on 1/11. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/256:00 am
PIT
-
ORF
1 stop13h 31m
Spirit Airlines
Tue 4/148:29 pm
ORF
-
PIT
1 stop27h 13m
Spirit Airlines
Deal found 1/11$166
This Kiwi.com deal was found by Cheapflights users on 1/11. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/710:45 am
PIT
-
ORF
1 stop8h 46m
Multiple Airlines
Wed 4/227:00 am
ORF
-
PIT
1 stop7h 04m
Multiple Airlines
Deal found 1/11$184
This Kiwi.com deal was found by Cheapflights users on 1/10. 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.
Wed 1/286:00 am
PIT
-
ORF
2 stops12h 25m
Spirit Airlines
Thu 1/297:33 pm
ORF
-
PIT
1 stop14h 07m
Spirit Airlines
Deal found 1/10$188
This Kiwi.com deal was found by Cheapflights users on 1/12. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 1/266:00 am
PIT
-
ORF
1 stop12h 38m
Multiple Airlines
Tue 1/278:05 am
ORF
-
PIT
2 stops15h 39m
Multiple Airlines
Deal found 1/12$189
This Mytrip deal was found by Cheapflights users on 1/11. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 1/266:00 am
PIT
-
ORF
1 stop12h 38m
Spirit Airlines
Fri 1/307:33 pm
ORF
-
PIT
1 stop14h 07m
Spirit Airlines
Deal found 1/11$190
This Kiwi.com deal was found by Cheapflights users on 1/11. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/26:00 am
PIT
-
ORF
1 stop13h 29m
Spirit Airlines
Sat 5/96:05 am
ORF
-
PIT
1 stop10h 15m
Spirit Airlines
Deal found 1/11$193

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 January 12, 2026.
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

Tue 2/3

6:15 pm-5:20 pm

2 stops23h 05m

Norfolk

Tue 2/10

7:33 pm-11:44 pm

1 stop28h 11m

$142

PittsburghNorfolk

PIT - ORF

PITORF

Pittsburgh

Wed 3/4

6:00 am-6:26 pm

1 stop12h 26m

Norfolk

Mon 3/9

7:31 pm-11:59 pm

1 stop28h 28m

$145

PittsburghNorfolk

PIT - ORF

PITORF

Pittsburgh

Tue 4/7

10:45 am-7:31 pm

1 stop8h 46m

Norfolk

Wed 4/22

7:00 am-2:04 pm

1 stop7h 04m

$184

PittsburghNorfolk

PIT - ORF

PITORF

Pittsburgh

Wed 1/28

9:00 am-9:50 pm

1 stop12h 50m

Norfolk

Thu 1/29

7:33 pm-9:40 am

1 stop14h 07m

$190

PittsburghNorfolk

PIT - ORF

PITORF

Pittsburgh

Mon 1/26

5:50 pm-1:31 pm

2 stops19h 41m

Norfolk

Fri 1/30

7:33 pm-9:40 am

1 stop14h 07m

$199

PittsburghNorfolk

PIT - ORF

PITORF

Pittsburgh

Tue 3/10

6:00 am-6:26 pm

1 stop12h 26m

Norfolk

Thu 3/19

10:22 am-2:26 pm

1 stop4h 04m

$200

PittsburghNorfolk

PIT - ORF

PITORF

Pittsburgh

Fri 3/13

6:00 am-7:31 pm

1 stop13h 31m

Norfolk

Mon 3/16

8:29 pm-11:38 pm

1 stop27h 09m

$249

PittsburghNorfolk

PIT - ORF

PITORF

Pittsburgh

Tue 2/3

6:00 am-11:44 am

1 stop5h 44m

Norfolk

Tue 2/10

7:11 pm-11:38 pm

1 stop4h 27m

$257

PittsburghNorfolk

PIT - ORF

PITORF

Pittsburgh

Tue 2/3

10:05 am-2:36 pm

1 stop4h 31m

Norfolk

Tue 2/10

7:26 pm-11:29 pm

1 stop4h 03m

$257

PittsburghNorfolk

PIT - ORF

PITORF

Pittsburgh

Tue 2/3

7:17 pm-11:18 pm

1 stop4h 01m

Norfolk

Tue 2/10

11:35 am-6:00 pm

1 stop6h 25m

$257

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/11

Showing 1-10 of 18 results
1
2

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 January 9, 2026.

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 January is currently the most expensive (average of $246). 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 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 January 12, 2026.
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
258 reviews

Food

6.7

Entertainment

6.7

Overall

8.1

Comfort

8.2

Boarding

8.3

Crew

8.7

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
258 reviews
Breeze Airways
8.1
Very good
258 reviews

Food

6.7

Entertainment

6.7

Overall

8.1

Comfort

8.2

Boarding

8.3

Crew

8.7

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
4,256 reviews
Breeze Airways
8.1
Very good
258 reviews

Food

6.7

Entertainment

6.7

Overall

8.1

Comfort

8.2

Boarding

8.3

Crew

8.7

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
8,039 reviews
Breeze Airways
8.1
Very good
258 reviews

Food

6.7

Entertainment

6.7

Overall

8.1

Comfort

8.2

Boarding

8.3

Crew

8.7

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
9,150 reviews
Breeze Airways
8.1
Very good
258 reviews

Food

6.7

Entertainment

6.7

Overall

8.1

Comfort

8.2

Boarding

8.3

Crew

8.7

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
7.2
Good
11,115 reviews
Breeze Airways
8.1
Very good
258 reviews

Food

6.7

Entertainment

6.7

Overall

8.1

Comfort

8.2

Boarding

8.3

Crew

8.7

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 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 23h 05m. There are 330 mi between Pittsburgh and Chesapeake.

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

    For one-way options, check prices for United Airlines. According to our data, you can fly for as low as $79. Users have also found prices from $81 and $88 on Breeze Airways 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 January is currently the most expensive (average of $246). 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Pittsburgh to Chesapeake

See prices for flight routes from nearby airports that may be better suited for you.
John F Kennedy Intl to Raleigh flights
LaGuardia to Raleigh flights
Newark to Raleigh flights
John F Kennedy Intl to Dulles Intl flights
John F Kennedy Intl to Reagan-National flights
LaGuardia to Reagan-National flights
Newark to Greensboro flights
LaGuardia to Greensboro flights
John F Kennedy Intl to Norfolk flights
Newark to Reagan-National flights
Reagan-National to Raleigh flights
LaGuardia to Dulles Intl flights
Philadelphia to Raleigh flights
Newark to Dulles Intl flights
Newark to Norfolk flights
LaGuardia to Norfolk flights
John F Kennedy Intl to Greensboro flights
John F Kennedy Intl to Richmond flights
Dulles Intl to Raleigh flights
LaGuardia to Richmond flights
Newark to Richmond flights
Pittsburgh to Dulles Intl flights
Pittsburgh to Reagan-National flights
LaGuardia to Charlottesville flights
Dulles Intl to Greensboro flights
Reagan-National to Greensboro flights
John F Kennedy Intl to Charlottesville flights
Newark to Charlottesville flights
Philadelphia to Greensboro flights
Dulles Intl to Norfolk flights
Pittsburgh to Raleigh flights
LaGuardia to Roanoke flights
John F Kennedy Intl to Roanoke flights
Allentown to Raleigh flights
Newark to Roanoke flights
Pittsburgh to Norfolk flights
Reagan-National to Norfolk flights
Philadelphia to Norfolk flights
Dulles Intl to Roanoke flights
Philadelphia to Dulles Intl flights
Philadelphia to Reagan-National flights
Harrisburg to Raleigh flights
Philadelphia to Roanoke flights
Philadelphia to Richmond flights
Dulles Intl to Blountville flights
Scranton to Raleigh flights
Pittsburgh to Greensboro flights
Scranton to Dulles Intl flights
Reagan-National to Blountville flights
State College to Raleigh flights

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 January 12, 2026.
AirlineCheapestAverageFlexibilityOn-time
Breeze AirwaysCheapest$112Average$183FlexibilityNo cancel feeOn-timeN/A
DeltaCheapest$128Average$249FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$158Average$381FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$176Average$336FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$196Average$304FlexibilityNo cancel feeOn-time71%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.