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$36+ 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 1/4. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — BOS
Dec 27 — Jan 31
Fri 12/27
Fri 1/3
1 adult, Economy
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Cheap flight deals from Chesapeake to Massachusetts

Discover tips and strategies to find the most affordable flight options for your journey from Chesapeake (C6E) to Massachusetts (USMA). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated December 22, 2024.

Round-trip from

$54
(Mytrip)

One-way from

$36
(Mytrip)
From Chesapeake to Massachusetts
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One-way flight from Chesapeake to Massachusetts
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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 December 22, 2024.

This Breeze Airways deal was found by Cheapflights users on 12/22. 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 Breeze Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/268:23 pmORF - BDL
Nonstop1h 26mBreeze Airways
Mon 12/307:15 amBDL - ORF
Nonstop1h 33mBreeze Airways
Deal found 12/22$138
This Frontier deal was found by Cheapflights users on 12/22. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/316:59 pmORF - BOS
1 stop5h 36mFrontier
Sun 1/55:45 amBOS - ORF
1 stop8h 41mFrontier
Deal found 12/22$296
This Delta deal was found by Cheapflights users on 12/22. 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 12/307:10 amORF - BDL
1 stop4h 48mDelta
Wed 1/226:05 amBDL - ORF
1 stop6h 08mDelta
Deal found 12/22$336
This American Airlines deal was found by Cheapflights users on 12/21. 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 12/319:52 amORF - ALB
1 stop4h 13mAmerican Airlines
Sun 1/55:42 amALB - ORF
1 stop3h 40mAmerican Airlines
Deal found 12/21$342
This FlightHub deal was found by Cheapflights users on 12/22. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/299:45 amORF - BOS
1 stop7h 37mSpirit Airlines
Wed 1/18:30 pmBOS - ORF
1 stop12h 20mSpirit Airlines
Deal found 12/22$353
This Mytrip deal was found by Cheapflights users on 12/22. 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.
Sun 12/299:45 amORF - BOS
1 stop7h 37mMultiple Airlines
Sun 1/53:23 pmBOS - ORF
2 stops17h 09mMultiple Airlines
Deal found 12/22$427
This Southwest deal was found by Cheapflights users on 12/21. 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 12/288:25 pmORF - BOS
1 stop3h 40mSouthwest
Sat 1/410:25 amBOS - ORF
1 stop5h 25mSouthwest
Deal found 12/21$471
This Southwest deal was found by Cheapflights users on 12/22. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/278:40 pmORF - BDL
1 stop3h 15mSouthwest
Tue 12/314:10 pmBDL - ORF
1 stop5h 40mSouthwest
Deal found 12/22$497
This Delta deal was found by Cheapflights users on 12/20. 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 12/254:41 pmORF - ALB
1 stop4h 58mDelta
Wed 1/15:45 amALB - ORF
1 stop6h 27mDelta
Deal found 12/20$517
This United Airlines deal was found by Cheapflights users on 12/21. 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.
Mon 12/238:00 pmORF - BOS
1 stop3h 59mUnited Airlines
Sat 1/47:37 pmBOS - ORF
1 stop3h 53mUnited Airlines
Deal found 12/21$551
This American Airlines deal was found by Cheapflights users on 12/22. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/265:52 amORF - BDL
1 stop12h 27mAmerican Airlines
Mon 12/305:58 amBDL - ORF
1 stop10h 10mAmerican Airlines
Deal found 12/22$567
This United deal was found by Cheapflights users on 12/21. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/306:00 amORF - BDL
1 stop17h 59mUnited Airlines
Wed 1/226:00 amBDL - ORF
2 stops17h 26mUnited Airlines
Deal found 12/21$607

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 December 22, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

NorfolkHartford

ORF - BDL

ORFBDL

Norfolk

Thu 1/2

8:23 pm-9:49 pm

Nonstop1h 26m

Hartford Bradley Intl

Sun 1/5

7:05 am-8:38 am

Nonstop1h 33m

$98

NorfolkBoston

ORF - BOS

ORFBOS

Norfolk

Fri 1/31

3:49 pm-12:39 am

1 stop8h 50m

Boston Logan Intl

Mon 2/3

6:00 am-2:56 pm

1 stop8h 56m

$118

NorfolkBoston

ORF - BOS

ORFBOS

Norfolk

Wed 1/22

5:25 am-3:27 pm

1 stop10h 02m

Boston Logan Intl

Tue 1/28

10:00 am-5:25 pm

1 stop7h 25m

$163

NorfolkBoston

ORF - BOS

ORFBOS

Norfolk

Thu 1/23

5:25 am-2:30 pm

1 stop9h 05m

Boston Logan Intl

Mon 1/27

2:06 pm-10:49 pm

1 stop8h 43m

$165

NorfolkHartford

ORF - BDL

ORFBDL

Norfolk

Fri 1/17

6:25 am-9:38 am

1 stop3h 13m

Hartford Bradley Intl

Mon 1/20

7:56 pm-11:34 pm

1 stop3h 38m

$195

NorfolkHartford

ORF - BDL

ORFBDL

Norfolk

Fri 1/17

5:25 am-10:59 pm

2 stops17h 34m

Hartford Bradley Intl

Mon 1/20

7:00 am-10:49 pm

1 stop15h 49m

$252

NorfolkBoston

ORF - BOS

ORFBOS

Norfolk

Tue 2/4

1:11 pm-4:49 pm

1 stop3h 38m

Boston Logan Intl

Tue 2/11

5:20 pm-9:25 pm

1 stop4h 05m

$267

NorfolkAlbany

ORF - ALB

ORFALB

Norfolk

Sat 1/25

8:04 am-12:14 pm

1 stop4h 10m

Albany Intl

Sun 1/26

5:15 pm-11:51 pm

1 stop6h 36m

$281

NorfolkHartford

ORF - BDL

ORFBDL

Norfolk

Sat 2/8

2:45 pm-9:45 pm

1 stop7h 00m

Hartford Bradley Intl

Sun 2/9

6:00 am-6:15 pm

2 stops12h 15m

$287

NorfolkBoston

ORF - BOS

ORFBOS

Norfolk

Mon 3/17

6:00 am-10:59 am

1 stop4h 59m

Boston Logan Intl

Fri 3/21

7:36 pm-11:30 pm

1 stop3h 54m

$306

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/22

Showing 1-10 of 33 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 December 22, 2024.

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 December 22, 2024.

The most flights from C6E to USMA are scheduled on a Friday (18 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (1 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 December 22, 2024.
Read through reviews of airlines operating flights from Chesapeake to Massachusetts, such as Frontier, American Airlines and Delta. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,804 reviews

Boarding

8.2

Overall

8.1

Entertainment

7.7

Crew

8.7

Comfort

8.1

Food

7.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Southwest
8.1
Very good
4,804 reviews
Southwest
8.1
Very good
4,804 reviews

Boarding

8.2

Overall

8.1

Entertainment

7.7

Crew

8.7

Comfort

8.1

Food

7.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Breeze Airways
8.1
Very good
135 reviews
Southwest
8.1
Very good
4,804 reviews

Boarding

8.2

Overall

8.1

Entertainment

7.7

Crew

8.7

Comfort

8.1

Food

7.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Delta
8.0
Very good
8,594 reviews
Southwest
8.1
Very good
4,804 reviews

Boarding

8.2

Overall

8.1

Entertainment

7.7

Crew

8.7

Comfort

8.1

Food

7.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

United Airlines
7.4
Good
9,028 reviews
Southwest
8.1
Very good
4,804 reviews

Boarding

8.2

Overall

8.1

Entertainment

7.7

Crew

8.7

Comfort

8.1

Food

7.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Allegiant Air
7.4
Good
823 reviews
Southwest
8.1
Very good
4,804 reviews

Boarding

8.2

Overall

8.1

Entertainment

7.7

Crew

8.7

Comfort

8.1

Food

7.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

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, 11 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 $36. Users have also found prices from $48 and $53 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 - 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: United Airlines (100%), Aeromexico (100%), ITA Airways (100%).

  • 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 $555. The most popular route, (Norfolk - Boston Logan Intl), can usually be booked for $96.

  • 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 December 22, 2024.
AirlineCheapestAverageFlexibilityOn-time
Allegiant AirCheapest$50Average$93FlexibilityNo cancel feeOn-time88%
Spirit AirlinesCheapest$64Average$155FlexibilityNo cancel feeOn-time65%
Breeze AirwaysCheapest$66Average$140FlexibilityNo cancel feeOn-timeN/A
DeltaCheapest$93Average$355FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$103Average$412FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$133Average$384FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$199Average$392FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$212Average$371FlexibilityNo cancel feeOn-time69%
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