There are 7 ways to get from Chesapeake to Massachusetts by plane, train (Amtrak), bus (Flixbus), car, train, or bus (Greyhound)
Select an option below to see step-by-step directions and to compare ticket prices and travel times in Rome2Rio's travel planner.
Fly to Boston Logan Airport
best- Fly from Norfolk International Airport (ORF) to Boston Logan Airport (BOS)plane ORF - BOS
2h 35m$96–446Bus via New York
cheapest- Take the bus from Norfolk to New York, Chinatown-152 East Broadwaybus Hampton
- Take the bus from NYC Downtown to Bostonbus FlixBus 2611
13h 54m$62–152Train (Amtrak)
- Take the train from Norfolk to Bostontrain Northeast Regional
13h 12m$370–600Drive 557.9 mi
- Drive from Chesapeake to Bostoncar 557.9 mi
11h 4m$96–138Fly to Theodore Francis Green State Airport, train
- Fly from Norfolk International Airport (ORF) to Theodore Francis Green State Airport (PVD)plane ORF - PVD
- Take the train from TF Green Airport to South Stationtrain
4h 22m$177–449Fly to Bradley International Airport, train
- Fly from Norfolk International Airport (ORF) to Bradley International Airport (BDL)plane ORF - BDL
- Take the train from Hartford Amtrak Station to Springfieldtrain
4h 12m$213–657Bus (Greyhound)
- Take the bus from Norfolk to Port Authority Bus Terminalbus Greyhound US0355
- Take the bus from Port Authority Bus Terminal to Bostonbus Greyhound US0230 / ...
15h 47m$107–172
Chesapeake to Massachusetts by train (Amtrak)
Comparing Your Travel Options
The cheapest way to get from Chesapeake to Massachusetts is to bus via New York which costs $60 - $160 and takes 13h 54m.
The fastest way to get from Chesapeake to Massachusetts is to fly which takes 2h 35m and costs $95 - $450.
No, there is no direct bus from Chesapeake to Massachusetts. However, there are services departing from Dntc and arriving at Boston via Norfolk and NYC Downtown. The journey, including transfers, takes approximately 13h 54m.
Yes, there is a direct train departing from Norfolk and arriving at Boston. Services depart five times a week, and operate Monday to Friday. The journey takes approximately 13h 12m.
The distance between Chesapeake and Massachusetts is 482 miles. The road distance is 561.1 miles.
The best way to get from Chesapeake to Massachusetts without a car is to train which takes 13h 12m and costs $370 - $600.
It takes approximately 2h 35m to get from Chesapeake to Massachusetts, including transfers.
Chesapeake to Massachusetts bus services, operated by Hi Bus, depart from Norfolk station.
Chesapeake to Massachusetts train services, operated by Amtrak, depart from Norfolk station.
The best way to get from Chesapeake to Massachusetts is to fly which takes 2h 35m and costs $95 - $450. Alternatively, you can train, which costs $370 - $600 and takes 13h 12m, you could also bus via New York, which costs $60 - $160 and takes 13h 54m.
What companies run services between Chesapeake, City of Chesapeake, VA, USA and Massachusetts, USA?
JetBlue Airways, Delta, and three other airlines fly from Norfolk International Airport (ORF) to Boston Logan Airport (BOS) every 4 hours. Alternatively, Amtrak operates a train from Norfolk to Boston 5 times a week. Tickets cost $370–600 and the journey takes 13h 12m.
- Website
- southwest.com
Flights from Norfolk International Airport to Boston Logan Airport via Baltimore
- Ave. Duration
- 3h 44m
- When
- Every day
- Estimated price
- $70–420
Flights from Norfolk International Airport to Theodore Francis Green State Airport via Baltimore
- Ave. Duration
- 3h 26m
- When
- Tuesday, Wednesday, Monday, Thursday, Friday, and Sunday
- Estimated price
- $45–280
Flights from Norfolk International Airport to Bradley International Airport via Baltimore
- Ave. Duration
- 3h 10m
- When
- Monday, Thursday, Friday, and Sunday
- Estimated price
- $90–550
- Website
- united.com
Flights from Norfolk International Airport to Boston Logan Airport via Washington Dulles
- Ave. Duration
- 4h 2m
- When
- Every day
- Estimated price
- $75–430
Flights from Norfolk International Airport to Theodore Francis Green State Airport via Washington Dulles
- Ave. Duration
- 3h 41m
- When
- Monday, Wednesday, Thursday, Friday, Sunday, and Saturday
- Estimated price
- $45–290
Flights from Norfolk International Airport to Bradley International Airport via Washington Dulles
- Ave. Duration
- 3h 36m
- When
- Monday, Tuesday, Wednesday, Thursday, Friday, and Sunday
- Estimated price
- $95–600
- Website
- aa.com
Flights from Norfolk International Airport to Boston Logan Airport via Reagan Washington
- Ave. Duration
- 3h 38m
- When
- Every day
- Estimated price
- $70–420
Flights from Norfolk International Airport to Boston Logan Airport via Philadelphia
- Ave. Duration
- 3h 59m
- When
- Every day
- Estimated price
- $70–410
Flights from Norfolk International Airport to Theodore Francis Green State Airport via Philadelphia
- Ave. Duration
- 3h 32m
- When
- Every day
- Estimated price
- $45–280
Flights from Norfolk International Airport to Bradley International Airport via Reagan Washington
- Ave. Duration
- 3h 46m
- When
- Wednesday
- Estimated price
- $90–600
- Website
- delta.com
Flights from Norfolk International Airport to Boston Logan Airport
- Ave. Duration
- 1h 53m
- When
- Every day
- Estimated price
- $65–410
Flights from Norfolk International Airport to Boston Logan Airport via New York La Guardia
- Ave. Duration
- 3h 55m
- When
- Sunday
- Estimated price
- $65–410
- Website
- flybreeze.com
Flights from Norfolk International Airport to Theodore Francis Green State Airport
- Ave. Duration
- 1h 27m
- When
- Monday, Friday, Thursday, Sunday, Wednesday, and Saturday
- Estimated price
- $140–400
Flights from Norfolk International Airport to Bradley International Airport
- Ave. Duration
- 1h 27m
- When
- Tuesday, Thursday, Sunday, Monday, and Friday
- Estimated price
- $170–600
- Website
- jetblue.com
Flights from Norfolk International Airport to Boston Logan Airport
- Ave. Duration
- 2h 14m
- When
- Every day
- Estimated price
- $65–410
Rome2Rio's guide to Amtrak
Contact Details
- Phone
- +1 800-872-7245
- Website
- Amtrak
Train from Norfolk to Boston
- Ave. Duration
- 13h 12m
- Frequency
- 5 times a week
- Estimated price
- $370–600
- Website
- Amtrak
Train from Hartford Amtrak Station to Springfield
- Ave. Duration
- 37 min
- Frequency
- Every 3 hours
- Estimated price
- $13–22
- Website
- Amtrak
Train from TF Green Airport to South Station
- Ave. Duration
- 1h 29m
- Frequency
- Every 4 hours
- Estimated price
- $9–16
- Website
- Massachusetts Bay Transportation Authority
- Website
- MBTA: World Cup 2026
- Adult
- $9–16
- Phone
- +1 212 625 8882
- [email protected]
- Website
- hibusny.com
Bus from Norfolk to New York, Chinatown-152 East Broadway
- Ave. Duration
- 6h 20m
- Frequency
- Once daily
- Estimated price
- $30–100
- Schedules at
- hibusny.com
- Adult
- $30–100
- Phone
- +1 (855) 626-8585
- Website
- Flixbus USA
Bus from NYC Downtown to Boston
- Ave. Duration
- 5h
- Frequency
- Every 2 hours
- Estimated price
- $30–50
- Schedules at
- Flixbus USA
- Phone
- +1 214-849-8100
- [email protected]
- Website
- Greyhound
Bus from Norfolk to Port Authority Bus Terminal
- Ave. Duration
- 8h 35m
- Frequency
- Twice daily
- Estimated price
- $70–110
- Website
- Greyhound
Bus from Port Authority Bus Terminal to Boston
- Ave. Duration
- 5h 4m
- Frequency
- Hourly
- Estimated price
- $35–60
- Website
- Greyhound
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Booking & Getting There
Chesapeake to Massachusetts bus services, operated by Hi Bus, arrive at New York, Chinatown-152 East Broadway station.
Chesapeake to Massachusetts train services, operated by Amtrak, arrive at Boston station.
Yes, the driving distance between Chesapeake to Massachusetts is 561 miles. It takes approximately 11h 4m to drive from Chesapeake to Massachusetts.
Book your Chesapeake to Massachusetts train tickets online with Omio.
There are 1802+ hotels available in Massachusetts.







