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$41+ Cheap flights from Chesapeake, VA to Massachusetts

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 6/1. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — BOS
Apr 29 — May 61
Tue 4/29
Tue 5/6
1 adult, Economy
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Cheap flight deals from Chesapeake to Massachusetts

Keep the following information in mind while searching for Chesapeake to Massachusetts flight deals. Data was last updated April 24, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$91
(Kiwi.com)

One-way from

$41
(Priceline)

Popular in

December

Cheapest in

August

Average price

$251
Provider with most accurate pricing for Norfolk-Boston Logan Intl flight deals.
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Provider most trusted by Cheapflights users for Norfolk-Boston Logan Intl flights.
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From Chesapeake to Massachusetts
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One-way flight from Chesapeake to Massachusetts
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Highest demand for flights based on searches. 32% potential increase in price ($114 potential increase over avg. RT price).
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Cheapest flight prices on average. 6% potential price decrease ($15 potential savings vs. average RT price).
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Average for round-trip flights in April 2025
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Find flight deals from Chesapeake to Massachusetts

Cheapest flights from Chesapeake to Massachusetts
Explore the most affordable flight options available from Chesapeake to Massachusetts. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 24, 2025.

This Kiwi.com deal was found by Cheapflights users on 4/23. 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 8/289:49 amORF - BDL
Nonstop1h 25mBreeze Airways
Mon 9/17:00 amBDL - ORF
Nonstop1h 32mBreeze Airways
Deal found 4/23$91
This Kiwi.com deal was found by Cheapflights users on 4/23. 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.
Mon 6/2310:28 amORF - BOS
Nonstop1h 35mAllegiant Air
Mon 6/3012:53 pmBOS - ORF
Nonstop1h 36mAllegiant Air
Deal found 4/23$117
This Booking.com deal was found by Cheapflights users on 4/23. 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.
Fri 6/131:51 pmORF - BOS
1 stop9h 56mMultiple Airlines
Mon 6/1612:53 pmBOS - ORF
Nonstop1h 36mMultiple Airlines
Deal found 4/23$148
This Priceline deal was found by Cheapflights users on 4/23. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/1111:21 amORF - BDL
1 stop7h 53mMultiple Airlines
Wed 5/147:05 amBDL - ORF
Nonstop1h 32mMultiple Airlines
Deal found 4/23$156
This JetBlue deal was found by Cheapflights users on 4/23. 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.
Sat 5/106:00 pmORF - BOS
Nonstop1h 29mJetBlue
Sun 5/113:30 pmBOS - ORF
Nonstop1h 35mJetBlue
Deal found 4/23$187
This Mytrip deal was found by Cheapflights users on 4/22. 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.
Thu 5/1512:13 pmORF - BOS
1 stop11h 34mSpirit Airlines
Tue 5/205:42 pmBOS - ORF
1 stop16h 47mSpirit Airlines
Deal found 4/22$189
This CheapOair deal was found by Cheapflights users on 4/22. 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.
Thu 5/1511:21 amORF - BOS
1 stop13h 44mFrontier
Sat 5/178:00 amBOS - ORF
1 stop26h 31mFrontier
Deal found 4/22$191
This Delta deal was found by Cheapflights users on 4/22. 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.
Mon 6/94:33 pmORF - BDL
1 stop7h 09mDelta
Wed 6/118:10 amBDL - ORF
1 stop7h 18mDelta
Deal found 4/22$199
This American Airlines deal was found by Cheapflights users on 4/23. 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 5/105:00 amORF - BOS
1 stop4h 28mAmerican Airlines
Mon 5/126:00 amBOS - ORF
1 stop4h 11mAmerican Airlines
Deal found 4/23$207
This American Airlines deal was found by Cheapflights users on 4/24. 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.
Mon 5/128:24 pmORF - BDL
1 stop4h 28mAmerican Airlines
Thu 5/157:46 pmBDL - ORF
1 stop3h 29mAmerican Airlines
Deal found 4/24$209
This Delta deal was found by Cheapflights users on 4/23. 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 5/1011:50 amORF - BOS
Nonstop1h 54mDelta
Mon 5/125:00 pmBOS - ORF
1 stop5h 07mDelta
Deal found 4/23$222
This Southwest deal was found by Cheapflights users on 4/23. 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.
Sun 5/118:55 pmORF - BDL
1 stop3h 10mSouthwest
Wed 5/146:20 amBDL - ORF
1 stop4h 05mSouthwest
Deal found 4/23$235

Cheapflights Fare Finder

Customize your flight search to find flights from Chesapeake to Massachusetts 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 April 24, 2025.
Use the filters below to find and compare flights from Chesapeake to Massachusetts that are best for you.

Fly from

Chesapeake

Fly to

Massachusetts

Route

Depart

Return

Price

NorfolkHartford

ORF - BDL

ORFBDL

Norfolk

Thu 8/28

9:49 am-11:14 am

Nonstop1h 25m

Hartford Bradley Intl

Mon 9/1

7:00 am-8:32 am

Nonstop1h 32m

$91

NorfolkBoston

ORF - BOS

ORFBOS

Norfolk

Fri 6/13

1:51 pm-11:47 pm

1 stop9h 56m

Boston Logan Intl

Mon 6/16

12:53 pm-2:29 pm

Nonstop1h 36m

$148

NorfolkHartford

ORF - BDL

ORFBDL

Norfolk

Sun 5/11

11:21 am-7:14 pm

1 stop7h 53m

Hartford Bradley Intl

Wed 5/14

7:05 am-8:37 am

Nonstop1h 32m

$156

NorfolkBoston

ORF - BOS

ORFBOS

Norfolk

Sat 5/10

6:00 pm-7:29 pm

Nonstop1h 29m

Boston Logan Intl

Tue 5/13

3:30 pm-5:05 pm

Nonstop1h 35m

$187

NorfolkBoston

ORF - BOS

ORFBOS

Norfolk

Thu 5/15

12:13 pm-11:47 pm

1 stop11h 34m

Boston Logan Intl

Tue 5/20

5:42 pm-10:29 am

1 stop16h 47m

$189

NorfolkBoston

ORF - BOS

ORFBOS

Norfolk

Thu 5/15

11:21 am-1:05 am

1 stop13h 44m

Boston Logan Intl

Sat 5/17

8:00 am-10:31 am

1 stop26h 31m

$191

NorfolkHartford

ORF - BDL

ORFBDL

Norfolk

Mon 6/9

4:33 pm-11:42 pm

1 stop7h 09m

Hartford Bradley Intl

Wed 6/11

8:10 am-3:28 pm

1 stop7h 18m

$199

NorfolkBoston

ORF - BOS

ORFBOS

Norfolk

Thu 5/15

8:00 pm-11:59 pm

1 stop3h 59m

Boston Logan Intl

Tue 5/20

5:30 am-9:21 am

1 stop3h 51m

$207

NorfolkHartford

ORF - BDL

ORFBDL

Norfolk

Mon 5/12

8:24 pm-12:52 am

1 stop4h 28m

Hartford Bradley Intl

Thu 5/15

7:46 pm-11:15 pm

1 stop3h 29m

$209

NorfolkBoston

ORF - BOS

ORFBOS

Norfolk

Sat 5/10

11:50 am-1:44 pm

Nonstop1h 54m

Boston Logan Intl

Wed 5/14

11:00 am-3:38 pm

1 stop4h 38m

$222

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/23

Showing 1-10 of 42 results
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Best time to book a flight from Chesapeake to Massachusetts

Have a flexible travel schedule? Discover the best time to fly to Massachusetts from Chesapeake 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 Chesapeake to Massachusetts

What is the cheapest month to book a flight from Chesapeake to Massachusetts?

Currently, January is the cheapest month in which you can book a flight from Chesapeake to Massachusetts (average of $218). Flying from Chesapeake to Massachusetts in July is currently the most expensive (average of $311). 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 C6E to MA?

Find hourly flight availability from Chesapeake to Massachusetts. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated April 24, 2025.

When flying from Chesapeake to Massachusetts, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Weekly flight availability from Chesapeake to Massachusetts

Explore weekly flight availability from Chesapeake to Massachusetts. 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 April 24, 2025.

The most flights from C6E to USMA are scheduled on a Monday (28 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (8 on average).

Rainfall in Massachusetts by month

Plan your trip to Massachusetts by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Massachusetts ranges from 3.1 - 4.0 inches per month. March is typically the wettest month, when rainfall can reach 4.0 in. July is typically the driest time to visit Massachusetts when rainfall is around 3.1 in.

Temperature in Massachusetts by month

Plan your trip to Massachusetts by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Massachusetts, 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 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 30.2 F).

Reviews of airlines servicing Massachusetts

Get insights into the airlines that provide service to Massachusetts. 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 Massachusetts. Reviews last updated April 24, 2025.
Read through reviews of airlines operating flights from Chesapeake to Massachusetts, such as Breeze Airways, Southwest and Delta. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Breeze Airways
8.1
Very good
159 reviews

Crew

8.8

Comfort

8.2

Boarding

8.3

Food

6.7

Overall

8.1

Entertainment

6.7

Reviews

1 / 11
10.0
Excellent

Dena,Dec 2024

LAS - BDL

It was comfortable and the crew was great! A few free snacks offered would be nice!
Breeze Airways
8.1
Very good
159 reviews
Breeze Airways
8.1
Very good
159 reviews

Crew

8.8

Comfort

8.2

Boarding

8.3

Food

6.7

Overall

8.1

Entertainment

6.7

Reviews

1 / 11
10.0
Excellent

Dena,Dec 2024

LAS - BDL

It was comfortable and the crew was great! A few free snacks offered would be nice!
Southwest
8.0
Very good
4,286 reviews
Breeze Airways
8.1
Very good
159 reviews

Crew

8.8

Comfort

8.2

Boarding

8.3

Food

6.7

Overall

8.1

Entertainment

6.7

Reviews

1 / 11
10.0
Excellent

Dena,Dec 2024

LAS - BDL

It was comfortable and the crew was great! A few free snacks offered would be nice!
Delta
8.0
Very good
7,920 reviews
Breeze Airways
8.1
Very good
159 reviews

Crew

8.8

Comfort

8.2

Boarding

8.3

Food

6.7

Overall

8.1

Entertainment

6.7

Reviews

1 / 11
10.0
Excellent

Dena,Dec 2024

LAS - BDL

It was comfortable and the crew was great! A few free snacks offered would be nice!
United Airlines
7.4
Good
8,685 reviews
Breeze Airways
8.1
Very good
159 reviews

Crew

8.8

Comfort

8.2

Boarding

8.3

Food

6.7

Overall

8.1

Entertainment

6.7

Reviews

1 / 11
10.0
Excellent

Dena,Dec 2024

LAS - BDL

It was comfortable and the crew was great! A few free snacks offered would be nice!
JetBlue
7.3
Good
2,924 reviews
Breeze Airways
8.1
Very good
159 reviews

Crew

8.8

Comfort

8.2

Boarding

8.3

Food

6.7

Overall

8.1

Entertainment

6.7

Reviews

1 / 11
10.0
Excellent

Dena,Dec 2024

LAS - BDL

It was comfortable and the crew was great! A few free snacks offered would be nice!

Related info for your journey

Find useful and relevant information for your journey from Chesapeake to Massachusetts. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How popular is this Chesapeake to Massachusetts flight route?

    Within the past month, 7 users have taken a look at flights from Chesapeake to Massachusetts.

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

    For one-way options, check prices for Breeze Airways. According to our data, you can fly for as low as $41. Users have also found prices from $51 and $69 on Allegiant Air and Spirit Airlines, respectively.

  • What are the most popular routes from Chesapeake to Massachusetts?

    When deciding which route to take from Chesapeake to Massachusetts consider Norfolk - Boston Logan Intl, Norfolk - Albany Intl or Norfolk - Hartford Bradley Intl as they are the most popular.

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

    Looking for the most reliable airlines to get you to your destination on time? Our data shows these are most likely to get you from Chesapeake to Massachusetts on time: Aeromexico (100%), Delta (95%), Republic Airways (95%).

  • What are the cheapest flights from Chesapeake to Massachusetts?

    The cheapest flight price from Chesapeake to Massachusetts is $88. On average you can expect to pay $552. The most popular route, (Norfolk - Boston Logan Intl), can usually be booked for $83.

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

    Yes. In addition to deals on Chesapeake to Massachusetts flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chesapeake to Massachusetts?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chesapeake to Massachusetts.

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

    Yes. Cheapflights offers flight deals from Chesapeake to Massachusetts 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 Chesapeake to Massachusetts?

    Currently, January is the cheapest month in which you can book a flight from Chesapeake to Massachusetts (average of $218). Flying from Chesapeake to Massachusetts in July is currently the most expensive (average of $311). 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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Top 7 airlines flying from Chesapeake to Massachusetts

Discover the top 7 airlines that operate flights from Chesapeake to Massachusetts. 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 April 24, 2025.
AirlineCheapestAverageFlexibilityOn-time
Allegiant AirCheapest$48Average$92FlexibilityNo cancel feeOn-time88%
Spirit AirlinesCheapest$62Average$146FlexibilityNo cancel feeOn-time65%
DeltaCheapest$97Average$327FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$107Average$253FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$133Average$357FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$166Average$334FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$168Average$370FlexibilityNo cancel feeOn-time63%

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