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Chesapeake

$84+ 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 5/20. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — RIC
avr. 7 — avr. 141
lun. 4/7
lun. 4/14
1 adult, Economy
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Cheapflights Tip: The best prices from Boston Logan Intl to Chesapeake are usually found in September or May, booked 51 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 avril 2, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$117
(Mytrip)

One-way from

$84
(Southwest)

Popular in

December

Cheapest in

September

Average price

$241
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
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One-way flight from Boston Logan Intl to Chesapeake
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Highest demand for flights based on searches. 25% potential increase in price ($84 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 April 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 avril 2, 2025.

This Mytrip deal was found by Cheapflights users on 4/1. 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.
ven. 5/2312:50 pmBOS - ORF
Nonstop1h 39mAllegiant Air
lun. 5/2610:26 amORF - BOS
Nonstop1h 34mAllegiant Air
Deal found 4/1$117
This Kiwi.com deal was found by Cheapflights users on 4/1. 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.
sam. 5/34:50 pmBOS - ORF
Nonstop1h 40mSpirit Airlines
dim. 5/47:25 pmORF - BOS
Nonstop1h 39mSpirit Airlines
Deal found 4/1$119
This Booking.com deal was found by Cheapflights users on 4/1. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sam. 5/38:00 amBOS - ORF
1 stop26h 31mMultiple Airlines
lun. 5/57:25 pmORF - BOS
Nonstop1h 39mMultiple Airlines
Deal found 4/1$134
This CheapOair deal was found by Cheapflights users on 4/2. 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.
mer. 5/78:00 amBOS - ORF
1 stop26h 31mFrontier
dim. 5/1111:21 amORF - BOS
1 stop13h 44mFrontier
Deal found 4/2$160
This JetBlue deal was found by Cheapflights users on 4/1. 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.
mar. 5/63:32 pmBOS - ORF
Nonstop1h 35mJetBlue
sam. 5/106:00 pmORF - BOS
Nonstop1h 29mJetBlue
Deal found 4/1$187
This Southwest deal was found by Cheapflights users on 4/1. 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.
jeu. 5/15:30 amBOS - ORF
1 stop4h 50mSouthwest
lun. 5/57:30 pmORF - BOS
1 stop3h 45mSouthwest
Deal found 4/1$222
This Delta deal was found by Cheapflights users on 4/1. 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.
mer. 9/34:00 pmBOS - ORF
1 stop7h 11mDelta
mar. 9/912:50 pmORF - BOS
Nonstop1h 51mDelta
Deal found 4/1$237
This American Airlines deal was found by Cheapflights users on 4/1. 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.
ven. 4/256:20 pmBOS - ORF
1 stop3h 10mAmerican Airlines
ven. 5/25:49 amORF - BOS
1 stop3h 53mAmerican Airlines
Deal found 4/1$259
This United Airlines deal was found by Cheapflights users on 4/1. 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.
sam. 5/33:05 pmBOS - ORF
1 stop6h 49mUnited Airlines
lun. 5/56:27 amORF - BOS
1 stop4h 12mUnited Airlines
Deal found 4/1$267

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 avril 2, 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

ven. 5/23

12:50 pm-2:29 pm

Nonstop1h 39m

Norfolk

lun. 5/26

10:26 am-12:00 pm

Nonstop1h 34m

$117

BostonNorfolk

BOS - ORF

BOSORF

Boston Logan Intl

sam. 5/3

4:50 pm-6:30 pm

Nonstop1h 40m

Norfolk

dim. 5/4

7:25 pm-9:04 pm

Nonstop1h 39m

$119

BostonNorfolk

BOS - ORF

BOSORF

Boston Logan Intl

sam. 5/3

8:00 am-10:31 am

1 stop26h 31m

Norfolk

lun. 5/5

7:25 pm-9:04 pm

Nonstop1h 39m

$134

BostonNorfolk

BOS - ORF

BOSORF

Boston Logan Intl

mer. 5/7

8:00 am-10:31 am

1 stop26h 31m

Norfolk

dim. 5/11

11:21 am-1:05 am

1 stop13h 44m

$160

BostonNorfolk

BOS - ORF

BOSORF

Boston Logan Intl

mar. 5/6

3:32 pm-5:07 pm

Nonstop1h 35m

Norfolk

sam. 5/10

6:00 pm-7:29 pm

Nonstop1h 29m

$187

BostonNorfolk

BOS - ORF

BOSORF

Boston Logan Intl

jeu. 5/1

5:30 am-10:20 am

1 stop4h 50m

Norfolk

lun. 5/5

7:30 pm-11:15 pm

1 stop3h 45m

$222

BostonNorfolk

BOS - ORF

BOSORF

Boston Logan Intl

mer. 9/3

4:00 pm-11:11 pm

1 stop7h 11m

Norfolk

mar. 9/9

12:50 pm-2:41 pm

Nonstop1h 51m

$237

BostonNorfolk

BOS - ORF

BOSORF

Boston Logan Intl

ven. 4/25

6:20 pm-9:30 pm

1 stop3h 10m

Norfolk

ven. 5/2

5:49 am-9:42 am

1 stop3h 53m

$259

BostonNorfolk

BOS - ORF

BOSORF

Boston Logan Intl

sam. 5/3

3:05 pm-9:54 pm

1 stop6h 49m

Norfolk

lun. 5/5

6:27 am-10:39 am

1 stop4h 12m

$267

BostonNorfolk

BOS - ORF

BOSORF

Boston Logan Intl

mar. 5/20

6:05 am-10:25 am

1 stop4h 20m

$84

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/1

Showing 1-10 of 18 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 March 28, 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, 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 June is currently the most expensive (average of $372). 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 avril 2, 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 March 30, 2025.

Travelers seeking maximum savings on their Boston to Chesapeake flight should consider departing on Saturday at noon 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 avril 2, 2025.

The most flights from BOS to C6E are scheduled on a Tuesday (22 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (8 on average).

Rainfall in Chesapeake by month

Plan your trip to Chesapeake by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chesapeake ranges from 2.9 - 5.8 inches per month. July is typically the wettest month, when rainfall can reach 5.8 in. November is typically the driest time to visit Chesapeake when rainfall is around 2.9 in.

Temperature in Chesapeake by month

Plan your trip to Chesapeake by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chesapeake, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 78.8 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 42.8 F).

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 avril 2, 2025.
Read reviews from past customers who have flown Southwest, Delta and United Airlines from Boston to Chesapeake. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,272 reviews

Comfort

8.0

Crew

8.6

Overall

8.0

Boarding

8.2

Entertainment

7.6

Food

7.1

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Southwest
8.0
Very good
4,272 reviews
Southwest
8.0
Very good
4,272 reviews

Comfort

8.0

Crew

8.6

Overall

8.0

Boarding

8.2

Entertainment

7.6

Food

7.1

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Delta
8.0
Very good
7,898 reviews
Southwest
8.0
Very good
4,272 reviews

Comfort

8.0

Crew

8.6

Overall

8.0

Boarding

8.2

Entertainment

7.6

Food

7.1

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
United Airlines
7.4
Good
8,615 reviews
Southwest
8.0
Very good
4,272 reviews

Comfort

8.0

Crew

8.6

Overall

8.0

Boarding

8.2

Entertainment

7.6

Food

7.1

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
JetBlue
7.3
Good
2,922 reviews
Southwest
8.0
Very good
4,272 reviews

Comfort

8.0

Crew

8.6

Overall

8.0

Boarding

8.2

Entertainment

7.6

Food

7.1

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Allegiant Air
7.3
Good
731 reviews
Southwest
8.0
Very good
4,272 reviews

Comfort

8.0

Crew

8.6

Overall

8.0

Boarding

8.2

Entertainment

7.6

Food

7.1

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

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.

  • 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 Southwest ($84), Frontier ($86), and Spirit Airlines ($87).

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

    The top 3 most reliable airlines when flying from Boston to Chesapeake are ITA Airways (100%), Virgin Atlantic (86%) and Delta (85%).

  • What are the cheapest flights from Boston to Chesapeake?

    The cheapest flight price from Boston to Chesapeake is $88. On average you can expect to pay $363. The most popular route, (Boston Logan Intl - Norfolk), can usually be booked for $87.

  • 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 June is currently the most expensive (average of $372). 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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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 avril 2, 2025.
AirlineCheapestAverageFlexibilityOn-time
Allegiant AirCheapest$59Average$100FlexibilityNo cancel feeOn-time88%
Breeze AirwaysCheapest$62Average$126FlexibilityNo cancel feeOn-timeN/A
Spirit AirlinesCheapest$70Average$178FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$103Average$227FlexibilityNo cancel feeOn-time62%
DeltaCheapest$104Average$326FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$176Average$325FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$181Average$331FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$198Average$397FlexibilityNo cancel feeOn-time63%

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