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Chesapeake

$57+ 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 8/11. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — RIC
Aug 3 — Aug 101
Sun 8/3
Sun 8/10
1 adult, Economy
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Cheapflights Tip: The best prices from Boston Logan Intl to Chesapeake are usually found in July 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 July 29, 2025.

Round-trip from

$92
(Mytrip)

One-way from

$57
(Flightnetwork)

Popular in

December

Cheapest in

July

Average price

$173
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. 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 July 29, 2025.

This Mytrip deal was found by Cheapflights users on 7/29. 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.
Fri 8/812:46 pmBOS - ORF
Nonstop1h 39mAllegiant Air
Mon 8/1110:20 amORF - BOS
Nonstop1h 36mAllegiant Air
Deal found 7/29$92
This Booking.com deal was found by Cheapflights users on 7/28. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/1112:46 pmBOS - ORF
Nonstop1h 39mMultiple Airlines
Fri 8/151:39 pmORF - BOS
1 stop8h 55mMultiple Airlines
Deal found 7/28$138
This JetBlue deal was found by Cheapflights users on 7/27. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/193:18 pmBOS - ORF
Nonstop1h 44mJetBlue
Wed 8/275:57 pmORF - BOS
Nonstop1h 40mJetBlue
Deal found 7/27$147
This Southwest deal was found by Cheapflights users on 7/28. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/128:30 amBOS - ORF
1 stop8h 15mSouthwest
Sat 11/154:10 pmORF - BOS
1 stop5h 45mSouthwest
Deal found 7/28$167
This American Airlines deal was found by Cheapflights users on 7/28. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/65:43 pmBOS - ORF
1 stop5h 21mAmerican Airlines
Mon 9/84:04 pmORF - BOS
1 stop4h 21mAmerican Airlines
Deal found 7/28$177
This CheapOair deal was found by Cheapflights users on 7/28. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/156:30 amBOS - ORF
1 stop6h 14mSpirit Airlines
Mon 8/181:39 pmORF - BOS
1 stop8h 55mSpirit Airlines
Deal found 7/28$181
This Delta deal was found by Cheapflights users on 7/29. 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.
Sat 8/308:15 amBOS - ORF
Nonstop1h 54mDelta
Sun 8/3111:53 amORF - BOS
Nonstop1h 52mDelta
Deal found 7/29$182
This United Airlines deal was found by Cheapflights users on 7/28. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/126:00 amBOS - ORF
1 stop4h 49mUnited Airlines
Sun 11/166:25 pmORF - BOS
1 stop4h 22mUnited Airlines
Deal found 7/28$188
This Frontier deal was found by Cheapflights users on 7/27. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/249:20 amBOS - ORF
1 stop11h 47mFrontier
Sun 8/319:52 pmORF - BOS
1 stop12h 31mFrontier
Deal found 7/27$198

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 July 29, 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 8/8

12:46 pm-2:25 pm

Nonstop1h 39m

Norfolk

Mon 8/11

10:20 am-11:56 am

Nonstop1h 36m

$92

BostonNorfolk

BOS - ORF

BOSORF

Boston Logan Intl

Mon 8/11

12:46 pm-2:25 pm

Nonstop1h 39m

Norfolk

Fri 8/15

1:39 pm-10:34 pm

1 stop8h 55m

$138

BostonNorfolk

BOS - ORF

BOSORF

Boston Logan Intl

Tue 8/19

3:18 pm-5:02 pm

Nonstop1h 44m

Norfolk

Wed 8/27

5:57 pm-7:37 pm

Nonstop1h 40m

$147

BostonNorfolk

BOS - ORF

BOSORF

Boston Logan Intl

Mon 8/25

12:30 pm-5:21 pm

1 stop4h 51m

Norfolk

Tue 8/26

6:11 pm-9:53 pm

1 stop3h 42m

$167

BostonNorfolk

BOS - ORF

BOSORF

Boston Logan Intl

Sat 8/23

5:35 am-1:30 pm

1 stop7h 55m

Norfolk

Tue 8/26

10:40 am-7:10 pm

2 stops8h 30m

$172

BostonNorfolk

BOS - ORF

BOSORF

Boston Logan Intl

Fri 8/15

6:30 am-12:44 pm

1 stop6h 14m

Norfolk

Mon 8/18

1:39 pm-10:34 pm

1 stop8h 55m

$181

BostonNorfolk

BOS - ORF

BOSORF

Boston Logan Intl

Sat 8/30

8:15 am-10:09 am

Nonstop1h 54m

Norfolk

Sun 8/31

11:53 am-1:45 pm

Nonstop1h 52m

$182

BostonNorfolk

BOS - ORF

BOSORF

Boston Logan Intl

Sun 8/24

9:20 am-9:07 pm

1 stop11h 47m

Norfolk

Sun 8/31

9:52 pm-10:23 am

1 stop12h 31m

$198

BostonNorfolk

BOS - ORF

BOSORF

Boston Logan Intl

Mon 8/11

12:46 pm-2:25 pm

Nonstop1h 39m

$57

BostonNorfolk

BOS - ORF

BOSORF

Boston Logan Intl

Wed 9/17

9:29 am-11:18 am

Nonstop1h 49m

$84

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/28

Showing 1-10 of 16 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 July 25, 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 July 29, 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 27, 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.

How much does it cost to fly round-trip from Boston to Chesapeake?

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 July 29, 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

Boarding

8.1

Comfort

8.0

Food

7.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Southwest
8.0
Very good
4,238 reviews
Southwest
8.0
Very good
4,238 reviews

Overall

8.0

Boarding

8.1

Comfort

8.0

Food

7.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Delta
8.0
Very good
7,977 reviews
Southwest
8.0
Very good
4,238 reviews

Overall

8.0

Boarding

8.1

Comfort

8.0

Food

7.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
United Airlines
7.4
Good
8,899 reviews
Southwest
8.0
Very good
4,238 reviews

Overall

8.0

Boarding

8.1

Comfort

8.0

Food

7.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
JetBlue
7.3
Good
2,913 reviews
Southwest
8.0
Very good
4,238 reviews

Overall

8.0

Boarding

8.1

Comfort

8.0

Food

7.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,238 reviews

Overall

8.0

Boarding

8.1

Comfort

8.0

Food

7.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.

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 3 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 ($57), Delta ($84), 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 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 $73. On average you can expect to pay $249. The most popular route, (Boston Logan Intl - Norfolk), can usually be booked for $112.

  • 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.

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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 July 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
Allegiant AirCheapest$49Average$82FlexibilityNo cancel feeOn-time88%
Spirit AirlinesCheapest$59Average$168FlexibilityNo cancel feeOn-time65%
Breeze AirwaysCheapest$91Average$143FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$103Average$228FlexibilityNo cancel feeOn-time62%
DeltaCheapest$104Average$316FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$176Average$312FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$196Average$389FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$213Average$356FlexibilityNo cancel feeOn-time69%

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