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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 11/6. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — PIT
Nov 28 — Dec 51
Fri 11/28
Fri 12/5
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 October 29, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$165
(Kiwi.com)

One-way from

$89
(Breeze Airways)

Popular in

February

Cheapest in

September

Average price

$316
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. 10% potential increase in price ($34 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($10 potential savings vs. average RT price).
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Average for round-trip flights in October 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 October 29, 2025.

This Kiwi.com deal was found by Cheapflights users on 10/29. 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 11/133:29 pmORF - PIT
Nonstop1h 22mBreeze Airways
Thu 11/201:31 pmPIT - ORF
Nonstop1h 18mBreeze Airways
Deal found 10/29$164
This Kiwi.com deal was found by Cheapflights users on 10/28. 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 12/43:29 pmORF - PIT
Nonstop1h 22mBreeze Airways
Sun 12/71:31 pmPIT - ORF
Nonstop1h 18mBreeze Airways
Deal found 10/28$165
This Delta deal was found by Cheapflights users on 10/27. 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.
Mon 12/154:58 pmORF - PIT
1 stop6h 14mDelta
Tue 12/166:26 amPIT - ORF
1 stop5h 52mDelta
Deal found 10/27$177
This Kiwi.com deal was found by Cheapflights users on 10/29. 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 11/133:29 pmORF - PIT
Nonstop1h 22mMultiple Airlines
Mon 11/1712:14 pmPIT - ORF
1 stop6h 44mMultiple Airlines
Deal found 10/29$180
This Kiwi.com deal was found by Cheapflights users on 10/29. 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 11/133:29 pmORF - PIT
Nonstop1h 22mMultiple Airlines
Thu 11/208:01 amPIT - ORF
1 stop12h 30mMultiple Airlines
Deal found 10/29$183
This Mytrip deal was found by Cheapflights users on 10/29. 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.
Thu 11/137:53 pmORF - PIT
1 stop15h 16mSpirit Airlines
Mon 11/1710:15 amPIT - ORF
1 stop8h 43mSpirit Airlines
Deal found 10/29$188
This Kiwi.com deal was found by Cheapflights users on 10/28. 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 12/43:29 pmORF - PIT
Nonstop1h 22mMultiple Airlines
Sat 12/65:05 pmPIT - ORF
1 stop26h 11mMultiple Airlines
Deal found 10/28$190
This Kiwi.com deal was found by Cheapflights users on 10/28. 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 12/810:05 pmORF - PIT
1 stop10h 41mBreeze Airways
Thu 12/111:31 pmPIT - ORF
Nonstop1h 18mBreeze Airways
Deal found 10/28$192
This Mytrip deal was found by Cheapflights users on 10/28. 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.
Thu 12/48:11 pmORF - PIT
1 stop13h 47mSpirit Airlines
Sun 12/710:53 amPIT - ORF
1 stop8h 23mSpirit Airlines
Deal found 10/28$195

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 October 29, 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 11/13

3:29 pm-4:51 pm

Nonstop1h 22m

Pittsburgh

Thu 11/20

1:31 pm-2:49 pm

Nonstop1h 18m

$164

NorfolkPittsburgh

ORF - PIT

ORFPIT

Norfolk

Thu 12/4

1:20 pm-6:23 pm

1 stop5h 03m

Pittsburgh

Sat 12/6

5:43 pm-12:16 am

1 stop6h 33m

$177

NorfolkPittsburgh

ORF - PIT

ORFPIT

Norfolk

Mon 12/8

5:40 am-9:46 am

1 stop4h 06m

Pittsburgh

Thu 12/11

7:05 am-11:33 am

1 stop4h 28m

$177

NorfolkPittsburgh

ORF - PIT

ORFPIT

Norfolk

Mon 12/15

4:58 pm-11:12 pm

1 stop6h 14m

Pittsburgh

Tue 12/16

6:26 am-12:18 pm

1 stop5h 52m

$177

NorfolkPittsburgh

ORF - PIT

ORFPIT

Norfolk

Thu 11/13

3:29 pm-4:51 pm

Nonstop1h 22m

Pittsburgh

Thu 11/20

8:01 am-8:31 pm

1 stop12h 30m

$183

NorfolkPittsburgh

ORF - PIT

ORFPIT

Norfolk

Thu 11/13

7:53 pm-11:09 am

1 stop15h 16m

Pittsburgh

Mon 11/17

10:15 am-6:58 pm

1 stop8h 43m

$188

NorfolkPittsburgh

ORF - PIT

ORFPIT

Norfolk

Thu 12/4

3:29 pm-4:51 pm

Nonstop1h 22m

Pittsburgh

Sat 12/6

5:05 pm-7:16 pm

1 stop26h 11m

$190

NorfolkPittsburgh

ORF - PIT

ORFPIT

Norfolk

Thu 11/13

2:00 pm-6:21 am

2 stops16h 21m

Pittsburgh

Mon 11/17

12:14 pm-6:58 pm

1 stop6h 44m

$191

NorfolkPittsburgh

ORF - PIT

ORFPIT

Norfolk

Thu 12/4

8:11 pm-9:58 am

1 stop13h 47m

Pittsburgh

Sun 12/7

10:53 am-7:16 pm

1 stop8h 23m

$195

NorfolkPittsburgh

ORF - PIT

ORFPIT

Norfolk

Thu 11/6

3:29 pm-4:51 pm

Nonstop1h 22m

$89

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/28

Showing 1-10 of 18 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 October 24, 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 October 29, 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 October 26, 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 October 29, 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
221 reviews

Crew

8.7

Entertainment

6.6

Food

6.7

Overall

8.1

Boarding

8.3

Comfort

8.2

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
221 reviews
Breeze Airways
8.1
Very good
221 reviews

Crew

8.7

Entertainment

6.6

Food

6.7

Overall

8.1

Boarding

8.3

Comfort

8.2

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
4,242 reviews
Breeze Airways
8.1
Very good
221 reviews

Crew

8.7

Entertainment

6.6

Food

6.7

Overall

8.1

Boarding

8.3

Comfort

8.2

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
7,993 reviews
Breeze Airways
8.1
Very good
221 reviews

Crew

8.7

Entertainment

6.6

Food

6.7

Overall

8.1

Boarding

8.3

Comfort

8.2

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
8,998 reviews
Breeze Airways
8.1
Very good
221 reviews

Crew

8.7

Entertainment

6.6

Food

6.7

Overall

8.1

Boarding

8.3

Comfort

8.2

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
11,030 reviews
Breeze Airways
8.1
Very good
221 reviews

Crew

8.7

Entertainment

6.6

Food

6.7

Overall

8.1

Boarding

8.3

Comfort

8.2

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, American Airlines, and Delta can get you from Chesapeake to Pittsburgh in just under 1h 22m. Your travel time can differ by up to 3h 41m. 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?

    $89 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 Spirit Airlines and Southwest, with prices starting from $93 and $140, 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 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 October 29, 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$364FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$206Average$358FlexibilityNo cancel feeOn-time71%

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