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Chesapeake

$114+ 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 8/31. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — RIC
Aug 4 — Aug 111
Tue 8/4
Tue 8/11
1 adult, Economy
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Cheapflights Tip: The best prices from Boston Logan Intl to Chesapeake are usually found in August or October, booked 37 days in advance, depart on a Wednesday or Monday 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 July 5, 2026.

This American Airlines deal was found by Cheapflights users on 6/30. 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 8/146:00 am
BOS
-
ORF
1 stop5h 03m
American Airlines
Tue 8/186:00 am
ORF
-
BOS
1 stop6h 16m
American Airlines
Deal found 6/30$207
This American Airlines deal was found by Cheapflights users on 7/4. 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.
Tue 8/185:53 pm
BOS
-
ORF
1 stop4h 41m
American Airlines
Tue 8/256:00 am
ORF
-
BOS
1 stop5h 29m
American Airlines
Deal found 7/4$208
This Cheapflightsfares deal was found by Cheapflights users on 6/30. 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.
Tue 9/154:15 pm
BOS
-
ORF
Nonstop1h 55m
JetBlue
Sat 9/197:27 pm
ORF
-
BOS
Nonstop2h 19m
JetBlue
Deal found 6/30$209
This Cheapflightsfares deal was found by Cheapflights users on 6/30. 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.
Thu 7/303:27 pm
BOS
-
ORF
Nonstop1h 43m
JetBlue
Mon 8/36:00 pm
ORF
-
BOS
Nonstop1h 43m
JetBlue
Deal found 6/30$219
This Cheapflightsfares deal was found by Cheapflights users on 6/30. 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.
Thu 9/104:15 pm
BOS
-
ORF
Nonstop1h 55m
JetBlue
Sun 9/137:27 pm
ORF
-
BOS
Nonstop2h 19m
JetBlue
Deal found 6/30$224
This United Airlines deal was found by Cheapflights users on 7/3. 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.
Sat 8/226:00 pm
BOS
-
ORF
1 stop5h 02m
United Airlines
Sat 8/297:59 pm
ORF
-
BOS
1 stop4h 00m
United Airlines
Deal found 7/3$226
This JetBlue deal was found by Cheapflights users on 7/2. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/12:05 pm
BOS
-
ORF
Nonstop1h 43m
JetBlue
Wed 9/24:40 pm
ORF
-
BOS
Nonstop2h 19m
JetBlue
Deal found 7/2$227
This United Airlines deal was found by Cheapflights users on 7/1. 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.
Fri 9/116:00 pm
BOS
-
ORF
1 stop4h 54m
United Airlines
Sun 9/136:02 am
ORF
-
BOS
1 stop3h 46m
United Airlines
Deal found 7/1$228
This Cheapflightsfares deal was found by Cheapflights users on 6/30. 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 7/203:27 pm
BOS
-
ORF
Nonstop1h 43m
JetBlue
Tue 7/216:00 pm
ORF
-
BOS
Nonstop1h 43m
JetBlue
Deal found 6/30$229
This Frontier deal was found by Cheapflights users on 7/1. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/110:04 am
BOS
-
ORF
1 stop10h 35m
Frontier
Wed 8/59:34 pm
ORF
-
BOS
1 stop11h 35m
Frontier
Deal found 7/1$230
This Cheapflightsfares deal was found by Cheapflights users on 7/1. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/124:15 pm
BOS
-
ORF
Nonstop1h 55m
JetBlue
Mon 9/147:27 pm
ORF
-
BOS
Nonstop2h 19m
JetBlue
Deal found 7/1$234

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 July 5, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$207
(American Airlines)

One-way from

$114
(JetBlue)

Popular in

November

Cheapest in

August

Average price

$285
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. 6% potential increase in price ($18 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($9 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 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 July 5, 2026.
Use the filters below to find and compare flights from Boston to Chesapeake that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

BostonNorfolk

BOS - ORF

BOSORF

Boston Logan Intl

Wed 8/12

9:20 am-11:11 am

Nonstop1h 51m

Norfolk

Sat 8/15

6:29 pm-10:43 pm

1 stop4h 14m

$247
Quickest round-trip

BostonNorfolk

BOS - ORF

BOSORF

Boston Logan Intl

Tue 7/21

9:20 am-11:11 am

Nonstop1h 51m

Norfolk

Fri 7/31

11:55 am-1:48 pm

Nonstop1h 53m

$247

BostonNorfolk

BOS - ORF

BOSORF

Boston Logan Intl

Mon 7/27

6:05 am-11:22 am

1 stop5h 17m

Norfolk

Fri 7/31

11:55 am-1:48 pm

Nonstop1h 53m

$257

BostonNorfolk

BOS - ORF

BOSORF

Boston Logan Intl

Sun 9/6

9:20 am-11:11 am

Nonstop1h 51m

Norfolk

Wed 9/16

6:20 pm-10:26 pm

1 stop4h 06m

$262

BostonNorfolk

BOS - ORF

BOSORF

Boston Logan Intl

Fri 9/11

8:00 am-1:44 pm

1 stop5h 44m

Norfolk

Sun 9/13

11:10 am-1:02 pm

Nonstop1h 52m

$267

BostonNorfolk

BOS - ORF

BOSORF

Boston Logan Intl

Fri 8/14

9:00 am-2:01 pm

1 stop5h 01m

Norfolk

Tue 8/18

11:55 am-1:48 pm

Nonstop1h 53m

$267

BostonNorfolk

BOS - ORF

BOSORF

Boston Logan Intl

Thu 9/17

9:05 am-10:58 am

Nonstop1h 53m

Norfolk

Sun 9/20

6:00 am-10:27 am

1 stop4h 27m

$282

BostonNorfolk

BOS - ORF

BOSORF

Boston Logan Intl

Thu 9/24

9:05 am-10:58 am

Nonstop1h 53m

Norfolk

Mon 9/28

5:35 pm-11:10 pm

1 stop5h 35m

$287

BostonNorfolk

BOS - ORF

BOSORF

Boston Logan Intl

Sun 8/16

3:25 pm-5:24 pm

Nonstop1h 59m

Norfolk

Sat 8/22

5:44 pm-7:40 pm

Nonstop1h 56m

$302

BostonNorfolk

BOS - ORF

BOSORF

Boston Logan Intl

Mon 7/20

5:45 am-9:20 am

1 stop3h 35m

Norfolk

Tue 7/21

12:40 pm-11:25 pm

2 stops10h 45m

$317

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/2

Showing 1-10 of 23 resultsSorted by cheapest first
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3

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

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 5, 2026.

It’s typically best to fly out from Boston to Chesapeake in the afternoon. Doing so could potentially save you 8% on the flight price compared to flying at noon, which is usually more expensive.

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 July 5, 2026.

The most flights from BOS to C6E are scheduled on a Saturday (10 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (3 on average).

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

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 4, 2026.

Travelers seeking maximum savings on their Boston to Chesapeake flight should consider departing on Friday at noon when fares are most often at their lowest. Sunday 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 July 5, 2026.
See what other customers who have flown with Southwest,Delta, andAllegiant Air 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
7.9
Good
4,250 reviews

Entertainment

7.5

Comfort

8.0

Overall

7.9

Boarding

8.1

Crew

8.6

Food

7.0

Reviews

1 / 20
8.0
Excellent

Libby,Jun 2026

TUS - LAS

One delay in a 2 layover flight=a good trip. The crew was great.
Southwest
7.9
Good
4,250 reviews
Southwest
7.9
Good
4,250 reviews

Entertainment

7.5

Comfort

8.0

Overall

7.9

Boarding

8.1

Crew

8.6

Food

7.0

Reviews

1 / 20
8.0
Excellent

Libby,Jun 2026

TUS - LAS

One delay in a 2 layover flight=a good trip. The crew was great.
Delta
7.8
Good
8,452 reviews
Southwest
7.9
Good
4,250 reviews

Entertainment

7.5

Comfort

8.0

Overall

7.9

Boarding

8.1

Crew

8.6

Food

7.0

Reviews

1 / 20
8.0
Excellent

Libby,Jun 2026

TUS - LAS

One delay in a 2 layover flight=a good trip. The crew was great.
Allegiant Air
7.3
Good
690 reviews
Southwest
7.9
Good
4,250 reviews

Entertainment

7.5

Comfort

8.0

Overall

7.9

Boarding

8.1

Crew

8.6

Food

7.0

Reviews

1 / 20
8.0
Excellent

Libby,Jun 2026

TUS - LAS

One delay in a 2 layover flight=a good trip. The crew was great.
American Airlines
7.1
Good
11,767 reviews
Southwest
7.9
Good
4,250 reviews

Entertainment

7.5

Comfort

8.0

Overall

7.9

Boarding

8.1

Crew

8.6

Food

7.0

Reviews

1 / 20
8.0
Excellent

Libby,Jun 2026

TUS - LAS

One delay in a 2 layover flight=a good trip. The crew was great.
JetBlue
7.1
Good
3,010 reviews
Southwest
7.9
Good
4,250 reviews

Entertainment

7.5

Comfort

8.0

Overall

7.9

Boarding

8.1

Crew

8.6

Food

7.0

Reviews

1 / 20
8.0
Excellent

Libby,Jun 2026

TUS - LAS

One delay in a 2 layover flight=a good trip. The crew was great.

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 7 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, 5 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 51m. Boston and Chesapeake are separated by a distance of 468 mi. Generally, flights for this route are nonstop.

  • 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 ($49), Delta ($83), and JetBlue ($87).

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

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

  • What are the cheapest flights from Boston to Chesapeake?

    The cheapest flight price from Boston to Chesapeake is $113. On average you can expect to pay $304. The most popular route, (Boston Logan Intl - Norfolk), can usually be booked for $207.

  • 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.

See more FAQs

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Top 7 airlines flying from Boston to Chesapeake

Discover the top 7 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 5, 2026.
AirlineCheapestAverageFlexibilityOn-time
Allegiant AirCheapest$52Average$76FlexibilityNo cancel feeOn-time88%
DeltaCheapest$93Average$297FlexibilityNo cancel feeOn-timeN/A
Breeze AirwaysCheapest$106Average$188FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$118Average$265FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$156Average$321FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$166Average$306FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$176Average$395FlexibilityNo cancel feeOn-time71%

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