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Chesapeake

$79+ Cheap flights from Boston (BOS) to Chesapeake, VA

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 11/4. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — RIC
Oct 14 — Oct 211
Tue 10/14
Tue 10/21
1 adult, Economy
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Cheapflights Tip: The best prices from Boston Logan Intl to Chesapeake are usually found in July or June, booked 69 days in advance, depart on a Monday or Friday and return on a Friday

Cheap flight deals from Boston to Chesapeake

Keep the following information in mind while searching for Boston to Chesapeake flight deals. Data was last updated September 14, 2025.

Round-trip from

$109
(Southwest)

One-way from

$79
(United Airlines)

Popular in

December

Cheapest in

July

Average price

$224
From Boston Logan Intl to Chesapeake
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One-way flight from Boston Logan Intl to Chesapeake
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Highest demand for flights based on searches. 24% potential increase in price ($80 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($10 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find flight deals from Boston to Chesapeake

Cheapest flights from Boston to Chesapeake
Explore the most affordable flight options available from Boston to Chesapeake. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 14, 2025.

This Southwest deal was found by Cheapflights users on 9/12. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/225:30 amBOS - ORF
1 stop5h 35mSouthwest
Wed 10/292:55 pmORF - BOS
1 stop6h 15mSouthwest
Deal found 9/12$109
This Southwest deal was found by Cheapflights users on 9/12. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/35:45 amBOS - ORF
1 stop5h 55mSouthwest
Sun 12/711:35 amORF - BOS
1 stop5h 40mSouthwest
Deal found 9/12$132
This JetBlue deal was found by Cheapflights users on 9/12. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/278:00 amBOS - ORF
Nonstop1h 56mJetBlue
Tue 9/3010:41 amORF - BOS
Nonstop1h 41mJetBlue
Deal found 9/12$137
This Southwest deal was found by Cheapflights users on 9/12. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/35:35 amBOS - ORF
1 stop5h 50mSouthwest
Mon 10/68:35 pmORF - BOS
1 stop3h 20mSouthwest
Deal found 9/12$138
This JetBlue deal was found by Cheapflights users on 9/12. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/278:00 amBOS - ORF
Nonstop1h 56mJetBlue
Wed 10/110:23 amORF - BOS
Nonstop1h 41mJetBlue
Deal found 9/12$142
This Southwest deal was found by Cheapflights users on 9/12. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/45:05 amBOS - ORF
1 stop4h 15mSouthwest
Sat 10/183:15 pmORF - BOS
1 stop5h 35mSouthwest
Deal found 9/12$147
This Delta deal was found by Cheapflights users on 9/13. 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.
Sat 9/278:35 amBOS - ORF
Nonstop1h 51mDelta
Sat 9/275:30 pmORF - BOS
Nonstop1h 56mDelta
Deal found 9/13$157
This American Airlines deal was found by Cheapflights users on 9/13. 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.
Sat 9/276:29 amBOS - ORF
1 stop5h 45mAmerican Airlines
Sat 9/275:16 pmORF - BOS
1 stop5h 34mAmerican Airlines
Deal found 9/13$159
This United Airlines deal was found by Cheapflights users on 9/13. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/16:00 amBOS - ORF
1 stop4h 49mUnited Airlines
Wed 10/85:40 pmORF - BOS
1 stop5h 16mUnited Airlines
Deal found 9/13$162
This American Airlines deal was found by Cheapflights users on 9/12. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/46:29 amBOS - ORF
1 stop5h 45mAmerican Airlines
Sat 10/116:07 amORF - BOS
1 stop4h 09mAmerican Airlines
Deal found 9/12$167

Cheapflights Fare Finder

 
Customize your flight search to find flights from Boston 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 September 14, 2025.
Use the filters below to find and compare flights from Boston to Chesapeake that are best for you.

Fly from

Boston

Fly to

Chesapeake

Route

Depart

Return

Price

BostonNorfolk

BOS - ORF

BOSORF

Boston Logan Intl

Tue 9/30

8:00 am-9:56 am

Nonstop1h 56m

Norfolk

Tue 10/7

10:25 am-12:06 pm

Nonstop1h 41m

$142

BostonNorfolk

BOS - ORF

BOSORF

Boston Logan Intl

Sat 9/27

8:00 am-9:56 am

Nonstop1h 56m

Norfolk

Wed 10/1

10:23 am-12:04 pm

Nonstop1h 41m

$142

BostonNorfolk

BOS - ORF

BOSORF

Boston Logan Intl

Wed 12/3

9:10 am-11:12 am

Nonstop2h 02m

Norfolk

Sun 12/7

11:52 am-1:35 pm

Nonstop1h 43m

$147

BostonNorfolk

BOS - ORF

BOSORF

Boston Logan Intl

Thu 10/23

9:07 am-11:03 am

Nonstop1h 56m

Norfolk

Sat 10/25

5:15 pm-7:06 pm

Nonstop1h 51m

$147

BostonNorfolk

BOS - ORF

BOSORF

Boston Logan Intl

Sat 9/27

8:35 am-10:26 am

Nonstop1h 51m

Norfolk

Sat 9/27

5:30 pm-7:26 pm

Nonstop1h 56m

$157

BostonNorfolk

BOS - ORF

BOSORF

Boston Logan Intl

Sat 10/4

9:38 am-4:31 pm

1 stop6h 53m

Norfolk

Sat 10/18

8:30 am-12:24 pm

1 stop3h 54m

$167

BostonNorfolk

BOS - ORF

BOSORF

Boston Logan Intl

Sat 9/27

5:30 am-9:38 am

1 stop4h 08m

Norfolk

Sun 9/28

6:00 am-11:08 am

1 stop5h 08m

$174

BostonNorfolk

BOS - ORF

BOSORF

Boston Logan Intl

Fri 9/26

9:29 am-11:18 am

Nonstop1h 49m

Norfolk

Sat 9/27

5:30 pm-7:26 pm

Nonstop1h 56m

$187

BostonNorfolk

BOS - ORF

BOSORF

Boston Logan Intl

Mon 11/17

5:30 am-9:46 am

1 stop4h 16m

Norfolk

Fri 11/21

6:00 am-10:43 am

1 stop4h 43m

$192

BostonNorfolk

BOS - ORF

BOSORF

Boston Logan Intl

Mon 9/22

6:30 pm-10:41 pm

1 stop4h 11m

Norfolk

Sat 9/27

5:30 pm-7:26 pm

Nonstop1h 56m

$197

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/13

Showing 1-10 of 23 results
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Best time to book a flight from Boston to Chesapeake

Have a flexible travel schedule? Discover the best time to fly to Chesapeake from Boston 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 Boston to Chesapeake

How far ahead should I book a flight from Boston to Chesapeake?

Use this chart to determine the optimal time to book a round-trip flight from Boston to Chesapeake. Price data was last updated on September 12, 2025.

To ensure you get the cheapest price possible for a flight from Boston to Chesapeake, you should look to book at least 69 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

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

Currently, January is the cheapest month in which you can book a flight from Boston to Chesapeake (average of $281). Flying from Boston to Chesapeake in March is currently the most expensive (average of $351). 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 BOS to C6E?

Find hourly flight availability from Boston to Chesapeake. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 14, 2025.

When flying from Boston to Chesapeake, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

What is the cheapest day to fly from Boston to Chesapeake?

Use this chart to determine the cheapest time to fly round-trip from Boston to Chesapeake. Price data was last updated on September 7, 2025.

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

Weekly flight availability from Boston to Chesapeake

Explore weekly flight availability from Boston to Chesapeake. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated September 14, 2025.

The most flights from BOS to C6E are scheduled on a Sunday (33 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (7 on average).

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 September 14, 2025.
See what other customers who have flown with Delta, American Airlines, and JetBlue from Boston to Chesapeake have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,956 reviews

Comfort

7.9

Overall

8.0

Crew

8.5

Food

7.3

Boarding

8.2

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Delta
8.0
Very good
7,956 reviews
Delta
8.0
Very good
7,956 reviews

Comfort

7.9

Overall

8.0

Crew

8.5

Food

7.3

Boarding

8.2

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,956 reviews

Comfort

7.9

Overall

8.0

Crew

8.5

Food

7.3

Boarding

8.2

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
JetBlue
7.2
Good
2,912 reviews
Delta
8.0
Very good
7,956 reviews

Comfort

7.9

Overall

8.0

Crew

8.5

Food

7.3

Boarding

8.2

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Allegiant Air
7.2
Good
699 reviews
Delta
8.0
Very good
7,956 reviews

Comfort

7.9

Overall

8.0

Crew

8.5

Food

7.3

Boarding

8.2

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Spirit Airlines
6.3
Okay
8,016 reviews
Delta
8.0
Very good
7,956 reviews

Comfort

7.9

Overall

8.0

Crew

8.5

Food

7.3

Boarding

8.2

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

Related info for your journey

Find useful and relevant information for your journey from Boston 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 Boston to Chesapeake?

    Most people fly from Boston Logan Intl (BOS) if they book a flight from Boston to Chesapeake. On average, Logan Intl has 3 outbound flights to Chesapeake per day from 8 airlines. Boston Logan Intl is conveniently located just 2.6 mi from Boston’s city center.

  • How long is the flight from Boston to Chesapeake?

    Departing from Boston to Chesapeake will take you 1h 56m. Boston and Chesapeake are separated by a distance of 468 mi. Generally, flights for this route are nonstop.

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

    The cheapest airlines for a one-way flight from Boston to Chesapeake are United Airlines ($79), Delta ($79), and Southwest ($81).

  • What are the most reliable airlines from Boston to Chesapeake?

    The top 3 most reliable airlines when flying from Boston to Chesapeake are Aeromexico (100%), Delta (85%) and Republic Airways (85%).

  • What are the cheapest flights from Boston to Chesapeake?

    The cheapest flight price from Boston to Chesapeake is $78. On average you can expect to pay $285. The most popular route, (Boston Logan Intl - Norfolk), can usually be booked for $114.

  • Can I find deals for flights from Boston to Chesapeake that include hotel bookings?

    Yes. In addition to deals on Boston to Chesapeake flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Boston to Chesapeake?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Boston to Chesapeake.

  • Can I find deals for business class flights from Boston to Chesapeake?

    Yes. Cheapflights offers flight deals from Boston 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 Boston to Chesapeake?

    Currently, January is the cheapest month in which you can book a flight from Boston to Chesapeake (average of $281). Flying from Boston to Chesapeake in March is currently the most expensive (average of $351). 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

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Alternative routes for Boston to Chesapeake

See prices for flight routes from nearby airports that may be better suited for you.
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Top 8 airlines flying from Boston to Chesapeake

Discover the top 8 airlines that operate flights from Boston 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 September 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
Allegiant AirCheapest$49Average$82FlexibilityNo cancel feeOn-time88%
Spirit AirlinesCheapest$59Average$189FlexibilityNo cancel feeOn-time65%
Breeze AirwaysCheapest$91Average$135FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$104Average$226FlexibilityNo cancel feeOn-time62%
DeltaCheapest$106Average$313FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$156Average$326FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$175Average$325FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$196Average$387FlexibilityNo cancel feeOn-time63%

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