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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 5/30. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — BOS
Feb 25 — Mar 41
Tue 2/25
Tue 3/4
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 February 20, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$92
(Gotogate)

One-way from

$41
(Priceline)

Popular in

December

Cheapest in

July

Average price

$306
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
Search Deals
Highest demand for flights based on searches. 31% potential increase in price ($109 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 February 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 February 20, 2025.

This Gotogate deal was found by Cheapflights users on 2/20. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/289:14 pmORF - BDL
Nonstop1h 26mBreeze Airways
Mon 3/37:00 amBDL - ORF
Nonstop1h 34mBreeze Airways
Deal found 2/20$76
This Cheapflightsfares deal was found by Cheapflights users on 2/18. 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.
Sun 4/136:44 pmORF - BOS
Nonstop1h 40mSpirit Airlines
Tue 4/154:09 pmBOS - ORF
Nonstop1h 40mSpirit Airlines
Deal found 2/18$106
This Priceline deal was found by Cheapflights users on 2/18. 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.
Thu 4/106:44 pmORF - BOS
Nonstop1h 40mMultiple Airlines
Sun 4/135:05 amBOS - ORF
1 stop5h 52mMultiple Airlines
Deal found 2/18$124
This Frontier deal was found by Cheapflights users on 2/20. 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 4/65:41 pmORF - BOS
1 stop7h 06mFrontier
Sun 4/135:30 amBOS - ORF
1 stop5h 33mFrontier
Deal found 2/20$150
This JetBlue Airways deal was found by Cheapflights users on 2/19. 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 Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/236:00 pmORF - BOS
Nonstop1h 29mJetBlue
Tue 5/273:30 pmBOS - ORF
Nonstop1h 35mJetBlue
Deal found 2/19$172
This Delta deal was found by Cheapflights users on 2/19. 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.
Fri 3/217:02 pmORF - BDL
1 stop5h 09mDelta
Sat 3/225:24 pmBDL - ORF
1 stop6h 39mDelta
Deal found 2/19$177
This Mytrip deal was found by Cheapflights users on 2/19. 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.
Wed 3/197:41 pmORF - BDL
2 stops26h 39mMultiple Airlines
Wed 3/2610:45 amBDL - ORF
2 stops25h 02mMultiple Airlines
Deal found 2/19$178
This CheapOair deal was found by Cheapflights users on 2/18. 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 3/611:25 amORF - BDL
1 stop23h 16mSpirit Airlines
Mon 3/1011:36 amBDL - ORF
1 stop22h 54mSpirit Airlines
Deal found 2/18$199
This Southwest deal was found by Cheapflights users on 2/19. 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.
Fri 3/218:20 pmORF - BOS
1 stop3h 45mSouthwest
Mon 3/249:00 amBOS - ORF
1 stop5h 05mSouthwest
Deal found 2/19$217
This United Airlines deal was found by Cheapflights users on 2/19. 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 6/46:00 amORF - BOS
1 stop6h 18mUnited Airlines
Sun 6/87:09 pmBOS - ORF
1 stop4h 35mUnited Airlines
Deal found 2/19$247
This Delta deal was found by Cheapflights users on 2/20. 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.
Wed 3/195:30 amORF - ALB
1 stop5h 59mDelta
Wed 3/196:58 pmALB - ORF
1 stop5h 05mDelta
Deal found 2/20$247
This Delta deal was found by Cheapflights users on 2/20. 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.
Thu 5/87:00 amORF - BOS
1 stop4h 22mDelta
Sun 5/119:00 amBOS - ORF
Nonstop1h 56mDelta
Deal found 2/20$252

Find flights from Chesapeake to Massachusetts within your budget

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 February 20, 2025.

Fly from

Chesapeake

Fly to

Massachusetts

Route

Depart

Return

Price

NorfolkHartford

ORF - BDL

ORFBDL

Norfolk

Thu 3/6

8:24 pm-9:50 pm

Nonstop1h 26m

Hartford Bradley Intl

Mon 3/10

7:00 am-8:34 am

Nonstop1h 34m

$92

NorfolkBoston

ORF - BOS

ORFBOS

Norfolk

Sun 4/13

6:44 pm-8:24 pm

Nonstop1h 40m

Boston Logan Intl

Tue 4/15

4:09 pm-5:49 pm

Nonstop1h 40m

$106

NorfolkBoston

ORF - BOS

ORFBOS

Norfolk

Thu 4/10

6:44 pm-8:24 pm

Nonstop1h 40m

Boston Logan Intl

Sun 4/13

5:05 am-10:57 am

1 stop5h 52m

$124

NorfolkBoston

ORF - BOS

ORFBOS

Norfolk

Sun 4/6

5:41 pm-12:47 am

1 stop7h 06m

Boston Logan Intl

Sun 4/13

5:30 am-11:03 am

1 stop5h 33m

$150

NorfolkBoston

ORF - BOS

ORFBOS

Norfolk

Fri 5/23

6:00 pm-7:29 pm

Nonstop1h 29m

Boston Logan Intl

Tue 5/27

3:30 pm-5:05 pm

Nonstop1h 35m

$172

NorfolkHartford

ORF - BDL

ORFBDL

Norfolk

Fri 3/21

7:02 pm-12:11 am

1 stop5h 09m

Hartford Bradley Intl

Sat 3/22

5:24 pm-12:03 am

1 stop6h 39m

$177

NorfolkHartford

ORF - BDL

ORFBDL

Norfolk

Wed 3/19

7:41 pm-10:20 pm

2 stops26h 39m

Hartford Bradley Intl

Wed 3/26

10:45 am-11:47 am

2 stops25h 02m

$178

NorfolkHartford

ORF - BDL

ORFBDL

Norfolk

Thu 3/6

11:25 am-10:41 am

1 stop23h 16m

Hartford Bradley Intl

Mon 3/10

11:36 am-10:30 am

1 stop22h 54m

$199

NorfolkBoston

ORF - BOS

ORFBOS

Norfolk

Fri 3/21

8:20 pm-12:05 am

1 stop3h 45m

Boston Logan Intl

Mon 3/24

9:00 am-2:05 pm

1 stop5h 05m

$217

NorfolkBoston

ORF - BOS

ORFBOS

Norfolk

Wed 6/4

6:00 am-12:18 pm

1 stop6h 18m

Boston Logan Intl

Sun 6/8

7:09 pm-11:44 pm

1 stop4h 35m

$247

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/19

Showing 1-10 of 35 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.

Travel insights for flights from Chesapeake to Massachusetts

Get recent, data-driven insights about flights from Chesapeake to Massachusetts including ideal travel times, pricing trends, and more.

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 February 20, 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 February 20, 2025.

The most flights from C6E to USMA are scheduled on a Monday (20 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (15 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 February 20, 2025.
Read through reviews of airlines operating flights from Chesapeake to Massachusetts, such as Southwest, Breeze Airways and Delta. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,411 reviews

Food

7.1

Boarding

8.2

Overall

8.1

Entertainment

7.6

Comfort

8.1

Crew

8.7

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Southwest
8.1
Very good
4,411 reviews
Southwest
8.1
Very good
4,411 reviews

Food

7.1

Boarding

8.2

Overall

8.1

Entertainment

7.6

Comfort

8.1

Crew

8.7

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Breeze Airways
8.1
Very good
150 reviews
Southwest
8.1
Very good
4,411 reviews

Food

7.1

Boarding

8.2

Overall

8.1

Entertainment

7.6

Comfort

8.1

Crew

8.7

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Delta
8.0
Very good
8,219 reviews
Southwest
8.1
Very good
4,411 reviews

Food

7.1

Boarding

8.2

Overall

8.1

Entertainment

7.6

Comfort

8.1

Crew

8.7

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

JetBlue
7.4
Good
3,070 reviews
Southwest
8.1
Very good
4,411 reviews

Food

7.1

Boarding

8.2

Overall

8.1

Entertainment

7.6

Comfort

8.1

Crew

8.7

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

United Airlines
7.4
Good
8,765 reviews
Southwest
8.1
Very good
4,411 reviews

Food

7.1

Boarding

8.2

Overall

8.1

Entertainment

7.6

Comfort

8.1

Crew

8.7

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

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, 9 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 $52 and $55 on Spirit Airlines and Frontier, 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 - Hartford Bradley Intl or Norfolk - Albany 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: Scandinavian Airlines (94%), Korean Air (94%), Air France (93%).

  • What are the cheapest flights from Chesapeake to Massachusetts?

    The cheapest flight price from Chesapeake to Massachusetts is $83. On average you can expect to pay $869. The most popular route, (Norfolk - Boston Logan Intl), can usually be booked for $106.

  • 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 8 airlines flying from Chesapeake to Massachusetts

Discover the top 8 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 February 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
Allegiant AirCheapest$50Average$94FlexibilityNo cancel feeOn-time88%
Spirit AirlinesCheapest$64Average$155FlexibilityNo cancel feeOn-time65%
Breeze AirwaysCheapest$84Average$119FlexibilityNo cancel feeOn-timeN/A
DeltaCheapest$93Average$361FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$103Average$351FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$133Average$418FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$206Average$360FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$271Average$407FlexibilityNo cancel feeOn-time63%
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