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Chesapeake

$82+ 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 5/27. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — RIC
Jun 6 — Jun 131
Sat 6/6
Sat 6/13
1 adult, Economy
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Cheapflights Tip: The best prices from Boston Logan Intl to Chesapeake are usually found in June or July, booked 63 days in advance, depart on a Monday or Friday 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 May 7, 2026.

This Cheapflightsfares deal was found by Cheapflights users on 5/2. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/288:15 am
BOS
-
ORF
Nonstop1h 45m
JetBlue
Mon 6/110:50 am
ORF
-
BOS
Nonstop1h 41m
JetBlue
Deal found 5/2$192
This Super.com deal was found by Cheapflights users on 5/3. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/288:15 am
BOS
-
ORF
Nonstop1h 45m
JetBlue
Tue 6/210:50 am
ORF
-
BOS
Nonstop1h 39m
JetBlue
Deal found 5/3$195
This Southwest deal was found by Cheapflights users on 5/6. 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 5/234:50 pm
BOS
-
ORF
1 stop6h 15m
Southwest
Thu 5/282:30 pm
ORF
-
BOS
1 stop5h 35m
Southwest
Deal found 5/6$197
This Delta deal was found by Cheapflights users on 5/2. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/238:45 am
BOS
-
ORF
Nonstop1h 47m
Delta
Sun 5/2411:20 am
ORF
-
BOS
Nonstop1h 48m
Delta
Deal found 5/2$198
This Kiwi.com deal was found by Cheapflights users on 5/2. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/166:00 am
BOS
-
ORF
1 stop29h 26m
Frontier
Tue 6/2312:21 pm
ORF
-
BOS
1 stop13h 06m
Frontier
Deal found 5/2$199
This Kiwi.com deal was found by Cheapflights users on 5/4. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/38:44 am
BOS
-
ORF
2 stops26h 27m
Frontier
Wed 6/1012:21 pm
ORF
-
BOS
1 stop19h 31m
Frontier
Deal found 5/4$201
This Southwest deal was found by Cheapflights users on 5/6. 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 6/311:40 am
BOS
-
ORF
2 stops9h 10m
Southwest
Mon 6/156:10 pm
ORF
-
BOS
1 stop3h 30m
Southwest
Deal found 5/6$202
This Kiwi.com deal was found by Cheapflights users on 5/2. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/276:00 am
BOS
-
ORF
1 stop29h 11m
Frontier
Sun 5/3112:06 pm
ORF
-
BOS
1 stop19h 43m
Frontier
Deal found 5/2$204
This Kiwi.com deal was found by Cheapflights users on 5/2. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/298:44 am
BOS
-
ORF
2 stops26h 31m
Frontier
Tue 6/212:06 pm
ORF
-
BOS
1 stop13h 18m
Frontier
Deal found 5/2$205
This Southwest deal was found by Cheapflights users on 5/3. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/68:40 am
BOS
-
ORF
2 stops14h 25m
Southwest
Sun 6/75:50 am
ORF
-
BOS
1 stop4h 00m
Southwest
Deal found 5/3$208
This Kiwi.com deal was found by Cheapflights users on 5/4. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/139:14 am
BOS
-
ORF
1 stop26h 07m
Frontier
Wed 8/1912:21 pm
ORF
-
BOS
1 stop13h 06m
Frontier
Deal found 5/4$210

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 May 7, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$195
(Super.com)

One-way from

$82
(Kiwi.com)

Popular in

November

Cheapest in

June

Average price

$217
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. 13% potential increase in price ($40 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($10 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 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 May 7, 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

Sat 5/30

5:25 am-9:40 am

1 stop4h 15m

Norfolk

Mon 6/1

5:25 pm-11:55 pm

1 stop6h 30m

$197

BostonNorfolk

BOS - ORF

BOSORF

Boston Logan Intl

Thu 6/4

5:25 pm-11:35 pm

1 stop6h 10m

Norfolk

Tue 6/9

12:25 pm-3:40 pm

1 stop3h 15m

$197

BostonNorfolk

BOS - ORF

BOSORF

Boston Logan Intl

Thu 5/28

1:20 pm-9:35 pm

2 stops8h 15m

Norfolk

Mon 6/1

5:25 pm-11:55 pm

1 stop6h 30m

$202

BostonNorfolk

BOS - ORF

BOSORF

Boston Logan Intl

Wed 7/1

5:00 pm-10:35 pm

1 stop5h 35m

Norfolk

Sun 7/5

5:50 am-9:50 am

1 stop4h 00m

$237
Quickest round-trip

BostonNorfolk

BOS - ORF

BOSORF

Boston Logan Intl

Thu 6/11

3:21 pm-5:04 pm

Nonstop1h 43m

Norfolk

Mon 6/15

5:59 pm-7:42 pm

Nonstop1h 43m

$257

BostonNorfolk

BOS - ORF

BOSORF

Boston Logan Intl

Fri 5/22

6:40 pm-12:51 am

1 stop6h 11m

Norfolk

Sun 5/24

10:17 am-4:40 pm

1 stop6h 23m

$267

BostonNorfolk

BOS - ORF

BOSORF

Boston Logan Intl

Sat 5/23

8:15 am-10:00 am

Nonstop1h 45m

Norfolk

Wed 5/27

10:50 am-12:31 pm

Nonstop1h 41m

$282

BostonNorfolk

BOS - ORF

BOSORF

Boston Logan Intl

Thu 9/10

9:00 am-10:55 am

Nonstop1h 55m

Norfolk

Sun 9/13

5:00 pm-6:56 pm

Nonstop1h 56m

$318

BostonNorfolk

BOS - ORF

BOSORF

Boston Logan Intl

Sun 6/28

5:45 am-9:39 am

1 stop3h 54m

Norfolk

Sat 7/4

5:00 pm-1:14 am

1 stop8h 14m

$323

BostonNorfolk

BOS - ORF

BOSORF

Boston Logan Intl

Thu 6/25

6:00 am-9:40 am

1 stop3h 40m

Norfolk

Mon 6/29

11:55 am-1:51 pm

Nonstop1h 56m

$327

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/4

Showing 1-10 of 24 resultsSorted by cheapest first
1
2
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 May 7, 2026.

It’s typically best to fly out from Boston to Chesapeake in the evening. Doing so could potentially save you 40% on the flight price compared to flying at noon, which is usually more expensive.

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 May 2, 2026.

Travelers seeking maximum savings on their Boston to Chesapeake flight should consider departing on Tuesday evenings 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.

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 May 7, 2026.

The most flights from BOS to C6E are scheduled on a Thursday (18 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (4 on average).

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 May 7, 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
4,302 reviews

Food

7.0

Crew

8.6

Overall

7.9

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Southwest
7.9
Good
4,302 reviews
Southwest
7.9
Good
4,302 reviews

Food

7.0

Crew

8.6

Overall

7.9

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Delta
7.9
Good
8,458 reviews
Southwest
7.9
Good
4,302 reviews

Food

7.0

Crew

8.6

Overall

7.9

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Allegiant Air
7.3
Good
708 reviews
Southwest
7.9
Good
4,302 reviews

Food

7.0

Crew

8.6

Overall

7.9

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
American Airlines
7.1
Good
11,669 reviews
Southwest
7.9
Good
4,302 reviews

Food

7.0

Crew

8.6

Overall

7.9

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
JetBlue
7.1
Good
2,980 reviews
Southwest
7.9
Good
4,302 reviews

Food

7.0

Crew

8.6

Overall

7.9

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

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 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, 2 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 43m. Boston and Chesapeake are separated by a distance of 468 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • 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 ($48), Spirit Airlines ($81), and Delta ($83).

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

    The top 3 most reliable airlines when flying from Boston to Chesapeake are WestJet (100%), EL AL (99%) and Kenya Airways (86%).

  • 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 $387. The most popular route, (Boston Logan Intl - Norfolk), can usually be booked for $172.

  • 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 May 7, 2026.
AirlineCheapestAverageFlexibilityOn-time
Allegiant AirCheapest$49Average$74FlexibilityNo cancel feeOn-time88%
DeltaCheapest$84Average$282FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$96Average$250FlexibilityNo cancel feeOn-time62%
Breeze AirwaysCheapest$106Average$165FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$156Average$303FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$166Average$276FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$176Average$360FlexibilityNo cancel feeOn-time71%

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