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Chesapeake

$58+ 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 1/24. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — RIC
Jan 14 — Jan 211
Wed 1/14
Wed 1/21
1 adult, Economy
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Cheapflights Tip: The best prices from Boston Logan Intl to Chesapeake are usually found in June or July, booked 51 days in advance, depart on a Monday or Friday and return on a Friday

Cheap 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 December 15, 2025.

This Kiwi.com deal was found by Cheapflights users on 12/13. 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.
Tue 12/168:11 pmBOS - ORF
1 stop22h 50mMultiple Airlines
Mon 1/127:33 pmORF - BOS
2 stops29h 40mMultiple Airlines
Deal found 12/13$264
This United Airlines deal was found by Cheapflights users on 12/12. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/256:45 amBOS - ORF
1 stop4h 14mUnited Airlines
Mon 1/56:21 pmORF - BOS
1 stop4h 38mUnited Airlines
Deal found 12/12$319
This American Airlines deal was found by Cheapflights users on 12/14. 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.
Fri 12/1910:55 amBOS - ORF
1 stop6h 00mAmerican Airlines
Sun 12/216:55 amORF - BOS
1 stop6h 21mAmerican Airlines
Deal found 12/14$332
This Mytrip deal was found by Cheapflights users on 12/13. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/148:11 pmBOS - ORF
1 stop11h 32mSpirit Airlines
Sun 12/217:40 pmORF - BOS
1 stop14h 21mSpirit Airlines
Deal found 12/13$339
This Frontier deal was found by Cheapflights users on 12/14. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/196:00 amBOS - ORF
1 stop7h 39mFrontier
Fri 12/262:34 pmORF - BOS
1 stop10h 40mFrontier
Deal found 12/14$342
This Kiwi.com deal was found by Cheapflights users on 12/13. 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.
Sun 12/1412:57 pmBOS - ORF
1 stop22h 23mMultiple Airlines
Tue 12/168:11 pmORF - BOS
1 stop27h 45mMultiple Airlines
Deal found 12/13$343
This United Airlines deal was found by Cheapflights users on 12/13. 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.
Thu 12/257:44 pmBOS - ORF
1 stop3h 57mUnited Airlines
Fri 1/27:55 pmORF - BOS
1 stop3h 59mUnited Airlines
Deal found 12/13$349
This Expedia deal was found by Cheapflights users on 12/14. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/1812:29 pmBOS - ORF
1 stop6h 16mMultiple Airlines
Sat 12/205:47 pmORF - BOS
1 stop7h 27mMultiple Airlines
Deal found 12/14$353
This Mytrip deal was found by Cheapflights users on 12/13. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/165:45 amBOS - ORF
1 stop13h 31mSpirit Airlines
Mon 1/127:33 pmORF - BOS
3 stops22h 11mSpirit Airlines
Deal found 12/13$393

Find flight deals from Boston to Chesapeake

Keep the following information in mind while searching for Boston to Chesapeake flight deals. Data was last updated December 15, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$199
(Kiwi.com)

One-way from

$58
(Mytrip)

Popular in

November

Cheapest in

June

Average price

$357
Provider with most accurate pricing for Boston Logan Intl-Norfolk flight deals.
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Provider most trusted by Cheapflights users for Boston Logan Intl-Norfolk flights.
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From Boston Logan Intl to Chesapeake
Search Deals
One-way flight from Boston Logan Intl to Chesapeake
Search Deals
Highest demand for flights based on searches. 20% potential increase in price ($64 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($12 potential savings vs. average RT price).
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Average for round-trip flights in December 2025
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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 December 15, 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

Fri 2/20

12:04 pm-5:04 pm

1 stop5h 00m

Norfolk

Tue 2/24

8:08 am-12:06 pm

1 stop3h 58m

$207

BostonNorfolk

BOS - ORF

BOSORF

Boston Logan Intl

Tue 1/27

2:40 pm-8:30 pm

1 stop5h 50m

Norfolk

Fri 1/30

12:40 pm-4:10 pm

1 stop3h 30m

$207

BostonNorfolk

BOS - ORF

BOSORF

Boston Logan Intl

Fri 1/23

12:16 pm-4:43 pm

1 stop4h 27m

Norfolk

Tue 1/27

7:26 pm-11:51 pm

1 stop4h 25m

$207

BostonNorfolk

BOS - ORF

BOSORF

Boston Logan Intl

Fri 1/30

12:16 pm-4:43 pm

1 stop4h 27m

Norfolk

Sun 2/1

1:35 pm-7:02 pm

1 stop5h 27m

$207

BostonNorfolk

BOS - ORF

BOSORF

Boston Logan Intl

Thu 2/26

5:27 am-6:26 pm

1 stop12h 59m

Norfolk

Sat 2/28

6:45 am-2:38 pm

1 stop7h 53m

$228

BostonNorfolk

BOS - ORF

BOSORF

Boston Logan Intl

Sun 1/4

5:35 am-9:30 am

1 stop3h 55m

Norfolk

Fri 1/9

12:40 pm-4:10 pm

1 stop3h 30m

$242

BostonNorfolk

BOS - ORF

BOSORF

Boston Logan Intl

Fri 1/30

3:43 pm-9:50 pm

1 stop6h 07m

Norfolk

Sun 2/1

6:45 am-2:38 pm

1 stop7h 53m

$246

BostonNorfolk

BOS - ORF

BOSORF

Boston Logan Intl

Tue 1/6

6:00 pm-10:06 pm

1 stop4h 06m

Norfolk

Wed 1/14

6:05 am-10:19 am

1 stop4h 14m

$259

BostonNorfolk

BOS - ORF

BOSORF

Boston Logan Intl

Thu 3/12

5:45 am-9:44 am

1 stop3h 59m

Norfolk

Sun 3/15

6:00 am-11:06 am

1 stop5h 06m

$275

BostonNorfolk

BOS - ORF

BOSORF

Boston Logan Intl

Fri 1/16

6:17 pm-11:27 pm

1 stop5h 10m

Norfolk

Mon 1/19

6:30 am-1:13 pm

1 stop6h 43m

$279

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/13

Showing 1-10 of 20 results
1
2

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 December 12, 2025.

To ensure you get the cheapest price possible for a flight from Boston to Chesapeake, you should look to book at least 51 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, July is the cheapest month in which you can book a flight from Boston to Chesapeake (average of $52). Flying from Boston to Chesapeake in April is currently the most expensive (average of $88). 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 December 15, 2025.

It’s typically best to fly out from Boston to Chesapeake in the evening. Doing so could potentially save you 43% on the flight price compared to flying at noon, which is usually more expensive.

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 December 13, 2025.

Travelers seeking maximum savings on their Boston to Chesapeake flight should consider departing on Tuesday evenings when fares are most often at their lowest. Saturday 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 December 15, 2025.

The most flights from BOS to C6E are scheduled on a Sunday (28 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (5 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 December 15, 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
7.9
Good
8,007 reviews

Boarding

8.1

Overall

7.9

Crew

8.5

Food

7.3

Entertainment

7.9

Comfort

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Delta
7.9
Good
8,007 reviews
Delta
7.9
Good
8,007 reviews

Boarding

8.1

Overall

7.9

Crew

8.5

Food

7.3

Entertainment

7.9

Comfort

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
American Airlines
7.2
Good
11,052 reviews
Delta
7.9
Good
8,007 reviews

Boarding

8.1

Overall

7.9

Crew

8.5

Food

7.3

Entertainment

7.9

Comfort

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
JetBlue
7.2
Good
2,895 reviews
Delta
7.9
Good
8,007 reviews

Boarding

8.1

Overall

7.9

Crew

8.5

Food

7.3

Entertainment

7.9

Comfort

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Allegiant Air
7.2
Good
700 reviews
Delta
7.9
Good
8,007 reviews

Boarding

8.1

Overall

7.9

Crew

8.5

Food

7.3

Entertainment

7.9

Comfort

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Spirit Airlines
6.3
Okay
8,186 reviews
Delta
7.9
Good
8,007 reviews

Boarding

8.1

Overall

7.9

Crew

8.5

Food

7.3

Entertainment

7.9

Comfort

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.

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 1 outbound flight to Chesapeake per day from 8 airlines. Boston Logan Intl is conveniently located just 2.6 mi from Boston’s city center.

  • How popular is this Boston to Chesapeake flight route?

    Within the past month, 1 users have taken a look at flights from Boston Logan Intl to Chesapeake.

  • How long is the flight from Boston to Chesapeake?

    Departing from Boston to Chesapeake will take you 5h. Boston and Chesapeake are separated by a distance of 468 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • 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 Spirit Airlines ($40), Allegiant Air ($48), and Breeze Airways ($70).

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

    The top 3 most reliable airlines when flying from Boston to Chesapeake are United Airlines (100%), Aeromexico (100%) and Delta (81%).

  • 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 $221. The most popular route, (Boston Logan Intl - Norfolk), can usually be booked for $115.

  • 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, July is the cheapest month in which you can book a flight from Boston to Chesapeake (average of $52). Flying from Boston to Chesapeake in April is currently the most expensive (average of $88). 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.

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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 December 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
Allegiant AirCheapest$49Average$82FlexibilityNo cancel feeOn-time88%
Spirit AirlinesCheapest$59Average$190FlexibilityNo cancel feeOn-time65%
Breeze AirwaysCheapest$91Average$159FlexibilityNo cancel feeOn-timeN/A
DeltaCheapest$103Average$309FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$105Average$229FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$156Average$273FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$166Average$318FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$166Average$332FlexibilityNo cancel feeOn-time71%

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