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Chesapeake

$52+ 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 5/30. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — RIC
Apr 29 — May 61
Tue 4/29
Tue 5/6
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 62 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 April 24, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$84
(Gotogate)

One-way from

$52
(Booking.com)

Popular in

December

Cheapest in

September

Average price

$254
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. 26% potential increase in price ($86 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% 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 April 24, 2025.

This Gotogate deal was found by Cheapflights users on 4/23. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/612:53 pmBOS - ORF
Nonstop1h 36mAllegiant Air
Fri 6/1310:28 amORF - BOS
Nonstop1h 35mAllegiant Air
Deal found 4/23$84
This Booking.com deal was found by Cheapflights users on 4/23. 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.
Fri 5/3012:50 pmBOS - ORF
Nonstop1h 39mMultiple Airlines
Mon 6/212:13 pmORF - BOS
1 stop11h 34mMultiple Airlines
Deal found 4/23$150
This Cheapflightsfares deal was found by Cheapflights users on 4/21. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/284:50 pmBOS - ORF
Nonstop1h 40mSpirit Airlines
Mon 5/57:25 pmORF - BOS
Nonstop1h 39mSpirit Airlines
Deal found 4/21$157
This JetBlue deal was found by Cheapflights users on 4/22. 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.
Thu 5/293:30 pmBOS - ORF
Nonstop1h 35mJetBlue
Fri 6/66:00 pmORF - BOS
Nonstop1h 29mJetBlue
Deal found 4/22$187
This CheapOair deal was found by Cheapflights users on 4/22. 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.
Wed 5/78:00 amBOS - ORF
1 stop26h 31mFrontier
Sun 5/1111:21 amORF - BOS
1 stop13h 44mFrontier
Deal found 4/22$201
This Delta deal was found by Cheapflights users on 4/23. 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.
Wed 6/259:30 amBOS - ORF
Nonstop1h 53mDelta
Sat 7/57:00 amORF - BOS
1 stop3h 59mDelta
Deal found 4/23$222
This American Airlines deal was found by Cheapflights users on 4/23. 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.
Thu 5/299:10 amBOS - ORF
1 stop5h 34mAmerican Airlines
Mon 6/25:32 pmORF - BOS
1 stop3h 48mAmerican Airlines
Deal found 4/23$231
This United Airlines deal was found by Cheapflights users on 4/23. 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.
Fri 5/97:14 pmBOS - ORF
1 stop4h 32mUnited Airlines
Sun 5/116:10 amORF - BOS
1 stop6h 48mUnited Airlines
Deal found 4/23$242
This Southwest deal was found by Cheapflights users on 4/23. 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 5/107:30 amBOS - ORF
2 stops9h 10mSouthwest
Sun 5/118:55 pmORF - BOS
1 stop3h 20mSouthwest
Deal found 4/23$328

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 April 24, 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 6/6

12:53 pm-2:29 pm

Nonstop1h 36m

Norfolk

Fri 6/13

10:28 am-12:03 pm

Nonstop1h 35m

$84

BostonNorfolk

BOS - ORF

BOSORF

Boston Logan Intl

Fri 5/30

12:50 pm-2:29 pm

Nonstop1h 39m

Norfolk

Mon 6/2

12:13 pm-11:47 pm

1 stop11h 34m

$150

BostonNorfolk

BOS - ORF

BOSORF

Boston Logan Intl

Thu 5/29

3:30 pm-5:05 pm

Nonstop1h 35m

Norfolk

Fri 6/6

6:00 pm-7:29 pm

Nonstop1h 29m

$187

BostonNorfolk

BOS - ORF

BOSORF

Boston Logan Intl

Wed 5/7

8:00 am-10:31 am

1 stop26h 31m

Norfolk

Sun 5/11

11:21 am-1:05 am

1 stop13h 44m

$201

BostonNorfolk

BOS - ORF

BOSORF

Boston Logan Intl

Mon 5/5

4:50 pm-6:30 pm

Nonstop1h 40m

Norfolk

Sun 5/11

12:13 pm-11:47 pm

1 stop11h 34m

$206

BostonNorfolk

BOS - ORF

BOSORF

Boston Logan Intl

Wed 6/25

9:30 am-11:23 am

Nonstop1h 53m

Norfolk

Sat 7/5

7:00 am-10:59 am

1 stop3h 59m

$222

BostonNorfolk

BOS - ORF

BOSORF

Boston Logan Intl

Thu 5/29

9:10 am-2:44 pm

1 stop5h 34m

Norfolk

Mon 6/2

5:32 pm-9:20 pm

1 stop3h 48m

$231

BostonNorfolk

BOS - ORF

BOSORF

Boston Logan Intl

Sat 9/6

9:10 am-4:00 pm

1 stop6h 50m

Norfolk

Mon 9/8

7:30 pm-11:20 pm

1 stop3h 50m

$237

BostonNorfolk

BOS - ORF

BOSORF

Boston Logan Intl

Fri 5/9

7:14 pm-11:46 pm

1 stop4h 32m

Norfolk

Sun 5/11

6:10 am-12:58 pm

1 stop6h 48m

$242

BostonNorfolk

BOS - ORF

BOSORF

Boston Logan Intl

Fri 5/30

12:50 pm-2:29 pm

Nonstop1h 39m

$52

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/23

Showing 1-10 of 18 results
1
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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 April 18, 2025.

To ensure you get the cheapest price possible for a flight from Boston to Chesapeake, you should look to book at least 62 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 April 24, 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 April 24, 2025.

The most flights from BOS to C6E are scheduled on a Wednesday (28 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (6 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 April 24, 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
4,287 reviews

Food

7.1

Crew

8.6

Comfort

8.0

Boarding

8.2

Entertainment

7.6

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Southwest
8.0
Very good
4,287 reviews
Southwest
8.0
Very good
4,287 reviews

Food

7.1

Crew

8.6

Comfort

8.0

Boarding

8.2

Entertainment

7.6

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Delta
8.0
Very good
7,920 reviews
Southwest
8.0
Very good
4,287 reviews

Food

7.1

Crew

8.6

Comfort

8.0

Boarding

8.2

Entertainment

7.6

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
United Airlines
7.4
Good
8,685 reviews
Southwest
8.0
Very good
4,287 reviews

Food

7.1

Crew

8.6

Comfort

8.0

Boarding

8.2

Entertainment

7.6

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
JetBlue
7.3
Good
2,924 reviews
Southwest
8.0
Very good
4,287 reviews

Food

7.1

Crew

8.6

Comfort

8.0

Boarding

8.2

Entertainment

7.6

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Allegiant Air
7.3
Good
734 reviews
Southwest
8.0
Very good
4,287 reviews

Food

7.1

Crew

8.6

Comfort

8.0

Boarding

8.2

Entertainment

7.6

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!

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 Allegiant Air ($52), Spirit Airlines ($95), and Frontier ($101).

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

    The top 3 most reliable airlines when flying from Boston to Chesapeake are LATAM Airlines (100%), Scandinavian Airlines (100%) and WestJet (100%).

  • 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 $296. The most popular route, (Boston Logan Intl - Norfolk), can usually be booked for $84.

  • 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 April 24, 2025.
AirlineCheapestAverageFlexibilityOn-time
Breeze AirwaysCheapest$52Average$126FlexibilityNo cancel feeOn-timeN/A
Allegiant AirCheapest$54Average$94FlexibilityNo cancel feeOn-time88%
Spirit AirlinesCheapest$67Average$169FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$103Average$224FlexibilityNo cancel feeOn-time62%
DeltaCheapest$105Average$321FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$176Average$314FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$181Average$323FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$203Average$393FlexibilityNo cancel feeOn-time63%

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