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$83+ 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 12/9. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — PIT
Dec 13 — Dec 201
Sat 12/13
Sat 12/20
1 adult, Economy
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Cheapflights Tip: The best prices from Chesapeake to Pittsburgh are usually found in September or July, 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 November 13, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$158
(Breeze Airways)

One-way from

$83
(Kiwi.com)

Popular in

November

Cheapest in

September

Average price

$481
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. 17% potential increase in price ($66 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($15 potential savings vs. average RT price).
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Average for round-trip flights in November 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 November 13, 2025.

This Breeze Airways deal was found by Cheapflights users on 11/12. 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.
Thu 12/43:29 pmORF - PIT
Nonstop1h 22mBreeze Airways
Sun 12/71:31 pmPIT - ORF
Nonstop1h 18mBreeze Airways
Deal found 11/12$158
This Breeze Airways deal was found by Cheapflights users on 11/12. 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 12/143:29 pmORF - PIT
Nonstop1h 22mBreeze Airways
Sun 12/211:31 pmPIT - ORF
Nonstop1h 18mBreeze Airways
Deal found 11/12$168
This American Airlines deal was found by Cheapflights users on 11/13. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/169:06 amORF - PIT
1 stop5h 33mAmerican Airlines
Tue 12/166:35 pmPIT - ORF
1 stop3h 35mAmerican Airlines
Deal found 11/13$171
This Delta deal was found by Cheapflights users on 11/11. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/96:59 pmORF - PIT
1 stop4h 09mDelta
Wed 12/107:05 amPIT - ORF
1 stop4h 28mDelta
Deal found 11/11$177
This Kiwi.com deal was found by Cheapflights users on 11/13. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/310:05 pmORF - PIT
1 stop10h 41mBreeze Airways
Thu 12/41:31 pmPIT - ORF
Nonstop1h 18mBreeze Airways
Deal found 11/13$194
This Priceline deal was found by Cheapflights users on 11/11. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/163:29 pmORF - PIT
Nonstop1h 22mBreeze Airways
Thu 11/201:31 pmPIT - ORF
Nonstop1h 18mBreeze Airways
Deal found 11/11$198
This Kiwi.com deal was found by Cheapflights users on 11/12. 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.
Thu 12/48:11 pmORF - PIT
1 stop13h 47mMultiple Airlines
Sun 12/79:28 pmPIT - ORF
1 stop11h 08mMultiple Airlines
Deal found 11/12$213
This Kiwi.com deal was found by Cheapflights users on 11/11. 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 12/28:02 pmORF - PIT
2 stops17h 17mMultiple Airlines
Thu 12/41:31 pmPIT - ORF
Nonstop1h 18mMultiple Airlines
Deal found 11/11$215
This Delta deal was found by Cheapflights users on 11/13. 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.
Wed 12/37:00 amORF - PIT
1 stop4h 46mDelta
Thu 12/46:26 amPIT - ORF
1 stop5h 52mDelta
Deal found 11/13$228
This Kiwi.com deal was found by Cheapflights users on 11/13. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/253:29 pmORF - PIT
Nonstop1h 22mMultiple Airlines
Mon 12/295:54 pmPIT - ORF
1 stop20h 22mMultiple Airlines
Deal found 11/13$231

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 November 13, 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 12/4

3:29 pm-4:51 pm

Nonstop1h 22m

Pittsburgh

Sun 12/7

1:31 pm-2:49 pm

Nonstop1h 18m

$162

NorfolkPittsburgh

ORF - PIT

ORFPIT

Norfolk

Sun 12/14

3:29 pm-4:51 pm

Nonstop1h 22m

Pittsburgh

Sun 12/21

1:31 pm-2:49 pm

Nonstop1h 18m

$168

NorfolkPittsburgh

ORF - PIT

ORFPIT

Norfolk

Tue 12/9

6:59 pm-11:08 pm

1 stop4h 09m

Pittsburgh

Wed 12/10

7:05 am-11:33 am

1 stop4h 28m

$177

NorfolkPittsburgh

ORF - PIT

ORFPIT

Norfolk

Thu 12/4

8:11 pm-9:58 am

1 stop13h 47m

Pittsburgh

Sun 12/7

9:28 pm-8:36 am

1 stop11h 08m

$213

NorfolkPittsburgh

ORF - PIT

ORFPIT

Norfolk

Tue 12/2

8:02 pm-1:19 pm

2 stops17h 17m

Pittsburgh

Thu 12/4

1:31 pm-2:49 pm

Nonstop1h 18m

$215

NorfolkPittsburgh

ORF - PIT

ORFPIT

Norfolk

Tue 12/9

10:05 am-5:35 pm

1 stop7h 30m

Pittsburgh

Wed 12/10

1:10 pm-10:00 pm

2 stops8h 50m

$252

NorfolkPittsburgh

ORF - PIT

ORFPIT

Norfolk

Tue 12/9

8:11 pm-12:41 am

1 stop28h 30m

$83

NorfolkPittsburgh

ORF - PIT

ORFPIT

Norfolk

Wed 12/31

6:20 am-9:44 am

1 stop3h 24m

$89

NorfolkPittsburgh

ORF - PIT

ORFPIT

Norfolk

Tue 12/9

7:00 am-12:41 am

2 stops41h 41m

$104

NorfolkPittsburgh

ORF - PIT

ORFPIT

Norfolk

Fri 11/21

4:06 pm-7:21 am

2 stops15h 15m

$124

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/11

Showing 1-10 of 14 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 November 7, 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 March is currently the most expensive (average of $230). 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 November 13, 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 November 2, 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.

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 November 13, 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
8.1
Very good
230 reviews

Overall

8.1

Comfort

8.2

Crew

8.7

Food

6.7

Entertainment

6.6

Boarding

8.3

Reviews

1 / 13
8.0
Excellent

Anonymous,Jul 2025

RIC - BDL

All went smoothly but the announcements from the crew were way to fast--approaching inaudible. Pilot announcements were perfect!
Breeze Airways
8.1
Very good
230 reviews
Breeze Airways
8.1
Very good
230 reviews

Overall

8.1

Comfort

8.2

Crew

8.7

Food

6.7

Entertainment

6.6

Boarding

8.3

Reviews

1 / 13
8.0
Excellent

Anonymous,Jul 2025

RIC - BDL

All went smoothly but the announcements from the crew were way to fast--approaching inaudible. Pilot announcements were perfect!
Southwest
8.0
Very good
4,236 reviews
Breeze Airways
8.1
Very good
230 reviews

Overall

8.1

Comfort

8.2

Crew

8.7

Food

6.7

Entertainment

6.6

Boarding

8.3

Reviews

1 / 13
8.0
Excellent

Anonymous,Jul 2025

RIC - BDL

All went smoothly but the announcements from the crew were way to fast--approaching inaudible. Pilot announcements were perfect!
Delta
7.9
Good
8,007 reviews
Breeze Airways
8.1
Very good
230 reviews

Overall

8.1

Comfort

8.2

Crew

8.7

Food

6.7

Entertainment

6.6

Boarding

8.3

Reviews

1 / 13
8.0
Excellent

Anonymous,Jul 2025

RIC - BDL

All went smoothly but the announcements from the crew were way to fast--approaching inaudible. Pilot announcements were perfect!
United Airlines
7.4
Good
9,015 reviews
Breeze Airways
8.1
Very good
230 reviews

Overall

8.1

Comfort

8.2

Crew

8.7

Food

6.7

Entertainment

6.6

Boarding

8.3

Reviews

1 / 13
8.0
Excellent

Anonymous,Jul 2025

RIC - BDL

All went smoothly but the announcements from the crew were way to fast--approaching inaudible. Pilot announcements were perfect!
American Airlines
7.2
Good
11,050 reviews
Breeze Airways
8.1
Very good
230 reviews

Overall

8.1

Comfort

8.2

Crew

8.7

Food

6.7

Entertainment

6.6

Boarding

8.3

Reviews

1 / 13
8.0
Excellent

Anonymous,Jul 2025

RIC - BDL

All went smoothly but the announcements from the crew were way to fast--approaching inaudible. Pilot announcements were perfect!

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 and Delta can get you from Chesapeake to Pittsburgh in just under 1h 22m. Your travel time can differ by up to 2h 47m. 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.

  • 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 March is currently the most expensive (average of $230). 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 November 13, 2025.
AirlineCheapestAverageFlexibilityOn-time
Breeze AirwaysCheapest$81Average$216FlexibilityNo cancel feeOn-timeN/A
DeltaCheapest$153Average$324FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$156Average$346FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$168Average$354FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$206Average$357FlexibilityNo cancel feeOn-time71%

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