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.

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 United Airlines ($88), JetBlue ($97), and American Airlines ($98).

Weekly flight availability from Boston to Chesapeake

The most flights from BOS to C6E are scheduled on a Monday (23 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (3 on average).

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.

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).

What are the cheapest flights from Boston to Chesapeake?

The cheapest flight price from Boston to Chesapeake is $158. On average you can expect to pay $359. The most popular route, (Boston Logan Intl - Norfolk), can usually be booked for $298.

What are the most reliable airlines from Boston to Chesapeake?

The top 3 most reliable airlines when flying from Boston to Chesapeake are Icelandair (91%), LATAM Airlines (83%) and TAP AIR PORTUGAL (81%).

What are the most popular airlines that fly from Boston to Chesapeake?

When booking a flight from Boston to Chesapeake, you may want to consider flying on JetBlue, Delta or American Airlines as they are the most popular for this route.

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 6 airlines. Boston Logan Intl is conveniently located just 2.6 mi from Boston’s city center.

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.

Find Cheap Flights from Boston to Chesapeake

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Cheapflights Tip: The best prices from Boston Logan Intl to Chesapeake are usually found in January or May, booked 83 days in advance, depart on a Thursday or Wednesday and return on a Thursday

Find flight deals from Boston to Chesapeake

Most accurate provider	FlightHub 3 stars
Most trusted provider	FlightHub 3 stars
Popular in	November
Cheapest in	January
Average price	$278

Provider with most accurate pricing for Boston Logan Intl-Norfolk flight deals.

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Highest demand for flights based on searches. 4% potential increase in price ($15 potential increase over avg. RT price).

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Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).

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Average for round-trip flights in September 2026

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Cheapflights Insights

Everything you need to know about your flight from Boston to Chesapeake

Prices

Airlines

What is the cheapest time of day to fly from BOS to C6E?

It’s typically best to fly out from Boston to Chesapeake in the afternoon. Doing so could potentially save you 16% 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?

Travelers seeking maximum savings on their Boston to Chesapeake flight should consider departing on Thursday at noon when fares are most often at their lowest. Wednesday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

Reviews of airlines servicing Chesapeake

See what other customers who have flown with Southwest,Delta, andUnited 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

4,201 reviews

Reviews

1 / 20

10.0

Excellent

Edward,Sep 2026

MCO - BWI

Changed flight which was easy. Gate Agent booked me from extra leg room seat on original flight to row 15 on new flight that did not have extra leg room - even though it was an exit row. The row in front of me with extra leg room had an empty seat.

Southwest

8.0

Very good

4,201 reviews

Southwest

8.0

Very good

4,201 reviews

Reviews

1 / 20

10.0

Excellent

Edward,Sep 2026

MCO - BWI

Delta

7.8

Good

8,611 reviews

Southwest

8.0

Very good

4,201 reviews

Reviews

1 / 20

10.0

Excellent

Edward,Sep 2026

MCO - BWI

United Airlines

7.4

Good

10,251 reviews

Southwest

8.0

Very good

4,201 reviews

Reviews

1 / 20

10.0

Excellent

Edward,Sep 2026

MCO - BWI

JetBlue

7.1

Good

3,040 reviews

Southwest

8.0

Very good

4,201 reviews

Reviews

1 / 20

10.0

Excellent

Edward,Sep 2026

MCO - BWI

American Airlines

7.0

Good

12,099 reviews

Southwest

8.0

Very good

4,201 reviews

Reviews

1 / 20

10.0

Excellent

Edward,Sep 2026

MCO - BWI

Related info for your journey

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 6 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.
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 United Airlines ($88), JetBlue ($97), and American Airlines ($98).
What are the most reliable airlines from Boston to Chesapeake?
The top 3 most reliable airlines when flying from Boston to Chesapeake are Icelandair (91%), LATAM Airlines (83%) and TAP AIR PORTUGAL (81%).
What are the cheapest flights from Boston to Chesapeake?
The cheapest flight price from Boston to Chesapeake is $158. On average you can expect to pay $359. The most popular route, (Boston Logan Intl - Norfolk), can usually be booked for $298.
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.

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Top 6 airlines flying from Boston to Chesapeake

Airline	Cheapest	Average	Flexibility	On-time
Delta	Cheapest$103	Average$324	FlexibilityNo cancel fee	On-timeN/A
Breeze Airways	Cheapest$106	Average$188	FlexibilityNo cancel fee	On-timeN/A
JetBlue	Cheapest$125	Average$298	FlexibilityNo cancel fee	On-time62%
United Airlines	Cheapest$158	Average$345	FlexibilityNo cancel fee	On-time69%
American Airlines	Cheapest$166	Average$416	FlexibilityNo cancel fee	On-time71%
Southwest	Cheapest$196	Average$346	FlexibilityNo cancel fee	On-time63%

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Cheap flights from Boston (BOS) to Chesapeake, VA

Find cheap flights from Boston to Chesapeake with Cheapflights

1. Tell us where you want to go

2. Select your favorite providers

3. Compare prices and book

Find flight deals from Boston to Chesapeake

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Popular in

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Average price

Cheapflights Insights

What is the cheapest time of day to fly from BOS to C6E?

It’s typically best to fly out from Boston to Chesapeake in the afternoon. Doing so could potentially save you 16% 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?

Travelers seeking maximum savings on their Boston to Chesapeake flight should consider departing on Thursday at noon when fares are most often at their lowest. Wednesday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

Weekly flight availability from Boston to Chesapeake

The most flights from BOS to C6E are scheduled on a Monday (23 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (3 on average).

Reviews of airlines servicing Chesapeake

See what other customers who have flown with Southwest,Delta, andUnited 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.

Related info for your journey

What airport do you fly from for flights from Boston to Chesapeake?

How popular is this Boston to Chesapeake flight route?

What are the cheapest airlines to fly from Boston to Chesapeake one-way?

What are the most reliable airlines from Boston to Chesapeake?

What are the cheapest flights from Boston to Chesapeake?

Can I find deals for flights from Boston to Chesapeake that include hotel bookings?

How can I find direct flights from Boston to Chesapeake?

Can I find deals for business class flights from Boston to Chesapeake?

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Boston to Chesapeake

See prices for flight routes from nearby airports that may be better suited for you.

Complete your trip

Complete your trip to Chesapeake by adding a car rental and/or hotel reservation to your travel itinerary.

Search flights from Boston to Chesapeake by cabin class

Find flights from Boston to Chesapeake, based on your preferred cabin class, be it economy, premium economy, business, or first class.

Boston and Chesapeake flights

Browse other Boston and Chesapeake flight options. Last updated on September 29, 2026.

Other flights from Boston

Browse through other flights departing from Boston. Flights are based on user searches made on Cheapflights and were last updated on September 29, 2026.

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Boston to Chesapeake flights

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Top 6 airlines flying from Boston to Chesapeake

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