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Chesapeake

$55+ 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 7/25. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — RIC
jul. 23 — jul. 301
mié. 7/23
mié. 7/30
1 adult, Economy
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Cheapflights Tip: The best prices from Boston Logan Intl to Chesapeake are usually found in September 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 julio 18, 2025.

Round-trip from

$59
(Mytrip)

One-way from

$56
(Flightnetwork)

Popular in

December

Cheapest in

September

Average price

$175
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 ($85 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 July 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 julio 18, 2025.

This Mytrip deal was found by Cheapflights users on 7/17. 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.
vie. 8/112:46 pmBOS - ORF
Nonstop1h 39mAllegiant Air
lun. 8/1110:20 amORF - BOS
Nonstop1h 36mAllegiant Air
Deal found 7/17$59
This Booking.com deal was found by Cheapflights users on 7/16. 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.
lun. 8/1112:46 pmBOS - ORF
Nonstop1h 39mMultiple Airlines
vie. 8/151:39 pmORF - BOS
1 stop8h 55mMultiple Airlines
Deal found 7/16$129
This JetBlue deal was found by Cheapflights users on 7/16. 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.
vie. 8/223:18 pmBOS - ORF
Nonstop1h 44mJetBlue
mar. 8/265:57 pmORF - BOS
Nonstop1h 40mJetBlue
Deal found 7/16$147
This American Airlines deal was found by Cheapflights users on 7/17. 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.
jue. 10/27:33 amBOS - ORF
1 stop4h 43mAmerican Airlines
dom. 10/56:00 amORF - BOS
1 stop6h 16mAmerican Airlines
Deal found 7/17$177
This Delta deal was found by Cheapflights users on 7/15. 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.
mié. 8/279:20 amBOS - ORF
Nonstop1h 52mDelta
dom. 8/3111:53 amORF - BOS
Nonstop1h 52mDelta
Deal found 7/15$182
This FlightHub deal was found by Cheapflights users on 7/17. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 8/812:26 pmBOS - ORF
1 stop4h 55mSpirit Airlines
lun. 8/115:20 pmORF - BOS
1 stop6h 28mSpirit Airlines
Deal found 7/17$194

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 julio 18, 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

vie. 8/1

12:46 pm-2:25 pm

Nonstop1h 39m

Norfolk

lun. 8/11

10:20 am-11:56 am

Nonstop1h 36m

$59

BostonNorfolk

BOS - ORF

BOSORF

Boston Logan Intl

lun. 8/11

12:46 pm-2:25 pm

Nonstop1h 39m

Norfolk

vie. 8/15

1:39 pm-10:34 pm

1 stop8h 55m

$129

BostonNorfolk

BOS - ORF

BOSORF

Boston Logan Intl

vie. 8/22

3:18 pm-5:02 pm

Nonstop1h 44m

Norfolk

mar. 8/26

5:57 pm-7:37 pm

Nonstop1h 40m

$147

BostonNorfolk

BOS - ORF

BOSORF

Boston Logan Intl

jue. 10/2

11:00 am-2:51 pm

1 stop3h 51m

Norfolk

dom. 10/5

6:00 am-12:16 pm

1 stop6h 16m

$177

BostonNorfolk

BOS - ORF

BOSORF

Boston Logan Intl

mié. 8/27

9:20 am-11:12 am

Nonstop1h 52m

Norfolk

dom. 8/31

11:53 am-1:45 pm

Nonstop1h 52m

$182

BostonNorfolk

BOS - ORF

BOSORF

Boston Logan Intl

vie. 8/8

12:26 pm-5:21 pm

1 stop4h 55m

Norfolk

lun. 8/11

5:20 pm-11:48 pm

1 stop6h 28m

$194

BostonNorfolk

BOS - ORF

BOSORF

Boston Logan Intl

sáb. 9/13

5:50 am-3:10 pm

2 stops9h 20m

Norfolk

sáb. 9/20

6:20 am-10:05 am

1 stop3h 45m

$207

BostonNorfolk

BOS - ORF

BOSORF

Boston Logan Intl

vie. 7/25

12:51 pm-2:30 pm

Nonstop1h 39m

$55

BostonNorfolk

BOS - ORF

BOSORF

Boston Logan Intl

mié. 8/13

3:18 pm-5:02 pm

Nonstop1h 44m

$74

BostonNorfolk

BOS - ORF

BOSORF

Boston Logan Intl

mié. 8/13

10:34 am-4:25 pm

1 stop5h 51m

$79

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/17

Showing 1-10 of 15 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 July 11, 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 julio 18, 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 July 13, 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.

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 julio 18, 2025.
See what other customers who have flown with Southwest, Delta, and United Airlines 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.
Southwest
8.0
Very good
4,238 reviews

Overall

8.0

Food

7.0

Boarding

8.1

Comfort

8.0

Entertainment

7.6

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Southwest
8.0
Very good
4,238 reviews
Southwest
8.0
Very good
4,238 reviews

Overall

8.0

Food

7.0

Boarding

8.1

Comfort

8.0

Entertainment

7.6

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Delta
8.0
Very good
7,958 reviews
Southwest
8.0
Very good
4,238 reviews

Overall

8.0

Food

7.0

Boarding

8.1

Comfort

8.0

Entertainment

7.6

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
United Airlines
7.4
Good
8,864 reviews
Southwest
8.0
Very good
4,238 reviews

Overall

8.0

Food

7.0

Boarding

8.1

Comfort

8.0

Entertainment

7.6

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
JetBlue
7.3
Good
2,910 reviews
Southwest
8.0
Very good
4,238 reviews

Overall

8.0

Food

7.0

Boarding

8.1

Comfort

8.0

Entertainment

7.6

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,238 reviews

Overall

8.0

Food

7.0

Boarding

8.1

Comfort

8.0

Entertainment

7.6

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

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 2 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 ($56), JetBlue ($74), and Delta ($84).

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

    The top 3 most reliable airlines when flying from Boston to Chesapeake are Korean Air (83%), Delta (81%) and Republic Airways (81%).

  • 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 $250. The most popular route, (Boston Logan Intl - Norfolk), can usually be booked for $52.

  • 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

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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 julio 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
Allegiant AirCheapest$49Average$84FlexibilityNo cancel feeOn-time88%
Spirit AirlinesCheapest$59Average$165FlexibilityNo cancel feeOn-time65%
Breeze AirwaysCheapest$91Average$143FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$101Average$228FlexibilityNo cancel feeOn-time62%
DeltaCheapest$104Average$317FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$177Average$309FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$203Average$396FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$213Average$356FlexibilityNo cancel feeOn-time69%

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