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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 2/28. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — RIC
Feb 28 — Mar 71
Sat 2/28
Sat 3/7
1 adult, Economy
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Cheapflights Tip: The best prices from Boston Logan Intl to Chesapeake are usually found in June or May, booked 67 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 January 29, 2026.

This Kiwi.com deal was found by Cheapflights users on 1/28. 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.
Fri 2/205:27 am
BOS
-
ORF
1 stop12h 59m
Multiple Airlines
Thu 2/2611:46 am
ORF
-
BOS
2 stops11h 58m
Multiple Airlines
Deal found 1/28$210
This Kiwi.com deal was found by Cheapflights users on 1/28. 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.
Fri 2/205:27 am
BOS
-
ORF
1 stop12h 59m
Multiple Airlines
Fri 2/2711:32 am
ORF
-
BOS
1 stop13h 41m
Multiple Airlines
Deal found 1/28$211
This American Airlines deal was found by Cheapflights users on 1/27. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/2012:26 pm
BOS
-
ORF
1 stop5h 57m
American Airlines
Tue 2/246:15 am
ORF
-
BOS
1 stop4h 05m
American Airlines
Deal found 1/27$212
This Kiwi.com deal was found by Cheapflights users on 1/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/265:27 am
BOS
-
ORF
1 stop12h 59m
Spirit Airlines
Tue 3/37:31 pm
ORF
-
BOS
2 stops16h 17m
Spirit Airlines
Deal found 1/27$214
This CheapOair deal was found by Cheapflights users on 1/27. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/205:40 am
BOS
-
ORF
1 stop14h 06m
Spirit Airlines
Wed 3/258:41 pm
ORF
-
BOS
1 stop18h 47m
Spirit Airlines
Deal found 1/27$217
This Kiwi.com deal was found by Cheapflights users on 1/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/185:50 pm
BOS
-
ORF
2 stops17h 01m
Multiple Airlines
Sun 3/111:32 am
ORF
-
BOS
1 stop13h 40m
Multiple Airlines
Deal found 1/27$218
This Kiwi.com deal was found by Cheapflights users on 1/28. 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.
Fri 2/205:27 am
BOS
-
ORF
1 stop12h 59m
Multiple Airlines
Wed 2/257:00 am
ORF
-
BOS
2 stops16h 44m
Multiple Airlines
Deal found 1/28$219
This Kiwi.com deal was found by Cheapflights users on 1/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/2712:43 pm
BOS
-
ORF
1 stop9h 07m
Multiple Airlines
Mon 3/211:39 am
ORF
-
BOS
1 stop13h 34m
Multiple Airlines
Deal found 1/27$220
This Kiwi.com deal was found by Cheapflights users on 1/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/2112:35 pm
BOS
-
ORF
2 stops9h 15m
Multiple Airlines
Fri 2/2711:32 am
ORF
-
BOS
1 stop13h 41m
Multiple Airlines
Deal found 1/27$221
This Kiwi.com deal was found by Cheapflights users on 1/28. 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.
Sat 2/75:53 pm
BOS
-
ORF
2 stops16h 50m
Multiple Airlines
Mon 2/911:43 am
ORF
-
BOS
1 stop13h 30m
Multiple Airlines
Deal found 1/28$222
This Kiwi.com deal was found by Cheapflights users on 1/26. 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 2/202:23 pm
BOS
-
ORF
1 stop7h 27m
Multiple Airlines
Tue 2/241:02 pm
ORF
-
BOS
2 stops12h 11m
Multiple Airlines
Deal found 1/26$223

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 January 29, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$210
(Kiwi.com)

One-way from

$58
(Expedia)

Popular in

November

Cheapest in

June

Average price

$291
Provider with most accurate pricing for Boston Logan Intl-Norfolk flight deals.
Search Deals
Provider most trusted by Cheapflights users for Boston Logan Intl-Norfolk flights.
Search Deals
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. 17% potential increase in price ($55 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($12 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals

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 January 29, 2026.
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

Wed 2/18

5:50 pm-10:51 am

2 stops17h 01m

Norfolk

Sun 3/1

11:32 am-1:12 am

1 stop13h 40m

$219

BostonNorfolk

BOS - ORF

BOSORF

Boston Logan Intl

Thu 5/7

8:50 am-10:32 am

Nonstop1h 42m

Norfolk

Mon 5/11

11:24 am-1:02 pm

Nonstop1h 38m

$222

BostonNorfolk

BOS - ORF

BOSORF

Boston Logan Intl

Thu 2/19

5:50 pm-10:37 am

2 stops16h 47m

Norfolk

Sun 3/1

11:32 am-1:12 am

1 stop13h 40m

$233

BostonNorfolk

BOS - ORF

BOSORF

Boston Logan Intl

Fri 2/20

2:23 pm-9:50 pm

1 stop7h 27m

Norfolk

Wed 2/25

7:31 pm-5:15 pm

1 stop21h 44m

$240

BostonNorfolk

BOS - ORF

BOSORF

Boston Logan Intl

Thu 7/16

5:30 pm-7:20 pm

Nonstop1h 50m

Norfolk

Tue 7/21

8:15 pm-9:56 pm

Nonstop1h 41m

$242

BostonNorfolk

BOS - ORF

BOSORF

Boston Logan Intl

Fri 2/20

6:00 am-9:50 pm

2 stops15h 50m

Norfolk

Sun 3/1

11:32 am-1:12 am

1 stop13h 40m

$242

BostonNorfolk

BOS - ORF

BOSORF

Boston Logan Intl

Fri 5/1

11:16 am-5:49 pm

1 stop6h 33m

Norfolk

Mon 5/4

11:24 am-1:02 pm

Nonstop1h 38m

$244

BostonNorfolk

BOS - ORF

BOSORF

Boston Logan Intl

Tue 2/17

6:00 am-6:26 pm

2 stops12h 26m

Norfolk

Mon 3/2

11:39 am-1:13 am

1 stop13h 34m

$248

BostonNorfolk

BOS - ORF

BOSORF

Boston Logan Intl

Thu 2/26

7:45 am-2:22 pm

1 stop6h 37m

Norfolk

Mon 3/2

8:05 pm-11:57 pm

1 stop3h 52m

$257

BostonNorfolk

BOS - ORF

BOSORF

Boston Logan Intl

Thu 2/26

6:00 am-2:22 pm

1 stop8h 22m

Norfolk

Tue 3/3

6:00 am-12:53 pm

1 stop6h 53m

$257

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/28

Showing 1-10 of 21 results
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2
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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 January 23, 2026.

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 January 29, 2026.

It’s typically best to fly out from Boston to Chesapeake in the evening. Doing so could potentially save you 39% 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 January 24, 2026.

Travelers seeking maximum savings on their Boston to Chesapeake flight should consider departing on Tuesday evenings when fares are most often at their lowest. Sunday mornings 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 January 29, 2026.

The most flights from BOS to C6E are scheduled on a Thursday (16 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (2 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 January 29, 2026.
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
8,127 reviews

Boarding

8.1

Comfort

7.9

Crew

8.5

Entertainment

7.8

Overall

7.9

Food

7.2

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
8,127 reviews
Delta
7.9
Good
8,127 reviews

Boarding

8.1

Comfort

7.9

Crew

8.5

Entertainment

7.8

Overall

7.9

Food

7.2

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
11,206 reviews
Delta
7.9
Good
8,127 reviews

Boarding

8.1

Comfort

7.9

Crew

8.5

Entertainment

7.8

Overall

7.9

Food

7.2

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
2,892 reviews
Delta
7.9
Good
8,127 reviews

Boarding

8.1

Comfort

7.9

Crew

8.5

Entertainment

7.8

Overall

7.9

Food

7.2

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
706 reviews
Delta
7.9
Good
8,127 reviews

Boarding

8.1

Comfort

7.9

Crew

8.5

Entertainment

7.8

Overall

7.9

Food

7.2

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
8,389 reviews
Delta
7.9
Good
8,127 reviews

Boarding

8.1

Comfort

7.9

Crew

8.5

Entertainment

7.8

Overall

7.9

Food

7.2

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 0 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 popular is this Boston to Chesapeake flight route?

    Within the past month, 2 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 1h 42m. 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 ($46), 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 Air France (85%).

  • What are the cheapest flights from Boston to Chesapeake?

    The cheapest flight price from Boston to Chesapeake is $73. On average you can expect to pay $233. The most popular route, (Boston Logan Intl - Norfolk), can usually be booked for $154.

  • 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 January 29, 2026.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$47Average$171FlexibilityNo cancel feeOn-time65%
Allegiant AirCheapest$48Average$78FlexibilityNo cancel feeOn-time88%
DeltaCheapest$89Average$280FlexibilityNo cancel feeOn-timeN/A
Breeze AirwaysCheapest$91Average$161FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$92Average$224FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$156Average$272FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$166Average$279FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$166Average$316FlexibilityNo cancel feeOn-time71%

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