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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 2/3. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — BOS
ene. 26 — feb. 21
dom. 1/26
dom. 2/2
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 enero 21, 2025.

Round-trip from

$75
(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 enero 21, 2025.

This Mytrip deal was found by Cheapflights users on 1/21. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 1/319:14 pmORF - BDL
Nonstop1h 26mBreeze Airways
dom. 2/27:05 amBDL - ORF
Nonstop1h 34mBreeze Airways
Deal found 1/21$75
This Cheapflightsfares deal was found by Cheapflights users on 1/20. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 5/163:20 pmORF - BOS
Nonstop1h 40mSpirit Airlines
dom. 5/1812:50 pmBOS - ORF
Nonstop1h 40mSpirit Airlines
Deal found 1/20$96
This Cheapflightsfares deal was found by Cheapflights users on 1/20. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 2/136:20 pmORF - BOS
1 stop6h 24mFrontier
jue. 2/206:00 amBOS - ORF
1 stop7h 15mFrontier
Deal found 1/20$136
This FlightHub deal was found by Cheapflights users on 1/20. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 2/75:25 amORF - BOS
1 stop9h 05mMultiple Airlines
lun. 2/106:00 amBOS - ORF
1 stop8h 56mMultiple Airlines
Deal found 1/20$137
This Cheapflightsfares deal was found by Cheapflights users on 1/20. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 6/2310:28 amORF - BOS
Nonstop1h 35mAllegiant Air
lun. 6/3012:53 pmBOS - ORF
Nonstop1h 36mAllegiant Air
Deal found 1/20$141
This JetBlue deal was found by Cheapflights users on 1/20. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 8/96:50 pmORF - BOS
Nonstop1h 41mJetBlue
mié. 8/134:05 pmBOS - ORF
Nonstop1h 49mJetBlue
Deal found 1/20$157
This Delta deal was found by Cheapflights users on 1/20. 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.
lun. 2/36:47 amORF - BDL
1 stop6h 31mDelta
sáb. 2/82:23 pmBDL - ORF
1 stop4h 59mDelta
Deal found 1/20$199
This American Airlines deal was found by Cheapflights users on 1/21. 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.
jue. 2/64:30 pmORF - BOS
1 stop5h 56mAmerican Airlines
dom. 2/97:36 pmBOS - ORF
1 stop3h 49mAmerican Airlines
Deal found 1/21$217
This Delta deal was found by Cheapflights users on 1/20. 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.
mar. 2/45:30 amORF - ALB
1 stop6h 20mDelta
sáb. 2/82:12 pmALB - ORF
1 stop7h 09mDelta
Deal found 1/20$247
This United Airlines deal was found by Cheapflights users on 1/21. 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.
vie. 2/216:00 amORF - BOS
1 stop3h 50mUnited Airlines
vie. 2/286:31 pmBOS - ORF
1 stop4h 55mUnited Airlines
Deal found 1/21$267
This Southwest deal was found by Cheapflights users on 1/21. 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.
jue. 3/68:20 pmORF - ALB
1 stop3h 45mSouthwest
dom. 3/95:40 amALB - ORF
1 stop4h 50mSouthwest
Deal found 1/21$277
This Mytrip deal was found by Cheapflights users on 1/20. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 2/35:25 amORF - BDL
2 stops17h 05mMultiple Airlines
sáb. 2/89:30 amBDL - ORF
2 stops26h 09mMultiple Airlines
Deal found 1/20$282

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 enero 21, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

NorfolkHartford

ORF - BDL

ORFBDL

Norfolk

vie. 1/31

9:14 pm-10:40 pm

Nonstop1h 26m

Hartford Bradley Intl

dom. 2/2

7:05 am-8:39 am

Nonstop1h 34m

$75

NorfolkBoston

ORF - BOS

ORFBOS

Norfolk

vie. 5/16

3:20 pm-5:00 pm

Nonstop1h 40m

Boston Logan Intl

lun. 5/19

12:50 pm-2:30 pm

Nonstop1h 40m

$99

NorfolkBoston

ORF - BOS

ORFBOS

Norfolk

lun. 6/16

10:28 am-12:03 pm

Nonstop1h 35m

Boston Logan Intl

vie. 7/4

12:51 pm-2:30 pm

Nonstop1h 39m

$106

NorfolkBoston

ORF - BOS

ORFBOS

Norfolk

sáb. 7/12

6:50 pm-8:31 pm

Nonstop1h 41m

Boston Logan Intl

mar. 7/15

4:05 pm-5:54 pm

Nonstop1h 49m

$117

NorfolkBoston

ORF - BOS

ORFBOS

Norfolk

jue. 2/13

6:20 pm-12:44 am

1 stop6h 24m

Boston Logan Intl

jue. 2/20

6:00 am-1:15 pm

1 stop7h 15m

$136

NorfolkBoston

ORF - BOS

ORFBOS

Norfolk

jue. 2/13

6:20 pm-12:44 am

1 stop6h 24m

Boston Logan Intl

mar. 2/18

4:47 pm-3:32 pm

1 stop22h 45m

$160

NorfolkHartford

ORF - BDL

ORFBDL

Norfolk

lun. 2/3

6:47 am-1:18 pm

1 stop6h 31m

Hartford Bradley Intl

sáb. 2/8

2:23 pm-7:22 pm

1 stop4h 59m

$199

NorfolkBoston

ORF - BOS

ORFBOS

Norfolk

jue. 2/6

4:30 pm-10:26 pm

1 stop5h 56m

Boston Logan Intl

dom. 2/9

7:36 pm-11:25 pm

1 stop3h 49m

$217

NorfolkAlbany

ORF - ALB

ORFALB

Norfolk

mar. 2/4

5:30 am-11:50 am

1 stop6h 20m

Albany Intl

sáb. 2/8

2:12 pm-9:21 pm

1 stop7h 09m

$247

NorfolkBoston

ORF - BOS

ORFBOS

Norfolk

vie. 2/21

6:00 am-9:50 am

1 stop3h 50m

Boston Logan Intl

vie. 2/28

6:31 pm-11:26 pm

1 stop4h 55m

$267

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/21

Showing 1-10 of 41 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 enero 21, 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 enero 21, 2025.

The most flights from C6E to USMA are scheduled on a Tuesday (16 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 enero 21, 2025.
Read through reviews of airlines operating flights from Chesapeake to Massachusetts, such as Spirit Airlines, Frontier and American Airlines. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,662 reviews

Comfort

8.1

Food

7.2

Boarding

8.2

Overall

8.1

Entertainment

7.7

Crew

8.7

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
4,662 reviews
Southwest
8.1
Very good
4,662 reviews

Comfort

8.1

Food

7.2

Boarding

8.2

Overall

8.1

Entertainment

7.7

Crew

8.7

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
143 reviews
Southwest
8.1
Very good
4,662 reviews

Comfort

8.1

Food

7.2

Boarding

8.2

Overall

8.1

Entertainment

7.7

Crew

8.7

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
8,521 reviews
Southwest
8.1
Very good
4,662 reviews

Comfort

8.1

Food

7.2

Boarding

8.2

Overall

8.1

Entertainment

7.7

Crew

8.7

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.

JetBlue
7.4
Good
3,200 reviews
Southwest
8.1
Very good
4,662 reviews

Comfort

8.1

Food

7.2

Boarding

8.2

Overall

8.1

Entertainment

7.7

Crew

8.7

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
8,984 reviews
Southwest
8.1
Very good
4,662 reviews

Comfort

8.1

Food

7.2

Boarding

8.2

Overall

8.1

Entertainment

7.7

Crew

8.7

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 $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: ITA Airways (96%), Korean Air (95%), EL AL (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 $939. 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 enero 21, 2025.
AirlineCheapestAverageFlexibilityOn-time
Allegiant AirCheapest$50Average$93FlexibilityNo cancel feeOn-time88%
Spirit AirlinesCheapest$64Average$155FlexibilityNo cancel feeOn-time65%
Breeze AirwaysCheapest$84Average$129FlexibilityNo cancel feeOn-timeN/A
DeltaCheapest$94Average$357FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$103Average$412FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$133Average$412FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$199Average$436FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$212Average$368FlexibilityNo cancel feeOn-time69%
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