There are 9 ways to get from Chicago to Walpole by plane, train, train (Amtrak), bus (Flixbus), car, or bus
Select an option below to see step-by-step directions and to compare ticket prices and travel times in Rome2Rio's travel planner.
Fly Chicago O'Hare International Airport to Boston Logan Airport, train
best- Fly from Chicago O'Hare International Airport (ORD) to Boston Logan Airport (BOS)plane ORD - BOS
- Take the train from Back Bay to Walpoletrain
6h 13m$194–523Fly Chicago O'Hare International Airport to Theodore Francis Green State Airport, train
cheapest- Fly from Chicago O'Hare International Airport (ORD) to Theodore Francis Green State Airport (PVD)plane ORD - PVD
- Take the train from TF Green Airport to Readvilletrain
7h 44m$76–367Train (Amtrak)
- Take the train from Chicago Union Station to Bostontrain Lake Shore Limited
23h 41m$280–608Bus
- Take the bus from Chicago Bus Station to New York Midtownbus FlixBus N2641 / ...
- Take the bus from New York, NY - W 42nd Street and 9th Avenue to Boston, MA - Dalton and Belvidere Streetbus New York
24h 17m$181–365Drive 975.5 mi
- Drive from Chicago to Walpolecar 975.5 mi
16h 49m$178–258Fly Chicago Midway International Airport to Boston Logan Airport
- Fly from Chicago Midway International Airport (MDW) to Boston Logan Airport (BOS)plane MDW - BOS
5h 55m$124–623Fly Chicago Midway International Airport to Theodore Francis Green State Airport, train
- Fly from Chicago Midway International Airport (MDW) to Theodore Francis Green State Airport (PVD)plane MDW - PVD
- Take the train from TF Green Airport to Readvilletrain
7h 17m$102–497Fly Chicago Midway International Airport to Manchester Airport, bus
- Fly from Chicago Midway International Airport (MDW) to Manchester Airport (MHT)plane MDW - MHT
- Take the bus from Boston Manchester Airport to Bostonbus
7h 45m$144–730Fly Chicago Midway International Airport to Bradley International Airport, bus
- Fly from Chicago Midway International Airport (MDW) to Bradley International Airport (BDL)plane MDW - BDL
- Take the bus from Hartford Union Station to Bostonbus
8h 44m$130–653
Chicago to Walpole by train (Amtrak)
Questions & Answers
The cheapest way to get from Chicago to Walpole is to fly and train which costs $75 - $370 and takes 7h 44m.
The fastest way to get from Chicago to Walpole is to fly which takes 5h 55m and costs $120 - $650.
No, there is no direct bus from Chicago station to Walpole. However, there are services departing from Chicago Bus Station and arriving at Main St @ Glenwood Ave via New York, NY - W 42nd Street and 9th Avenue, Huntington Ave @ Belvidere St and Forest Hills. The journey, including transfers, takes approximately 24h 17m.
No, there is no direct train from Chicago station to Walpole. However, there are services departing from Chicago Union Station and arriving at Walpole via South Station. The journey, including transfers, takes approximately 23h 41m.
The distance between Chicago and Walpole is 916 miles. The road distance is 981.2 miles.
The best way to get from Chicago to Walpole without a car is to train which takes 23h 41m and costs $280 - $650.
It takes approximately 6h 13m to get from Chicago to Walpole, including transfers.
Chicago to Walpole bus services, operated by Flixbus USA, depart from Chicago Bus Station.
Chicago to Walpole train services, operated by Amtrak, depart from Chicago Union Station.
The best way to get from Chicago to Walpole is to train which takes 23h 41m and costs $280 - $650. Alternatively, you can bus, which costs $180 - $370 and takes 24h 17m, you could also fly, which costs $120 - $650 and takes 5h 55m.
What companies run services between Chicago, IL, USA and Walpole, MA, USA?
Amtrak operates a train from Chicago Union Station to Boston once daily. Tickets cost $270–600 and the journey takes 22h 2m. Alternatively, you can take a bus from Chicago Bus Station to Main St @ Glenwood Ave via New York Midtown, New York, NY - W 42nd Street and 9th Avenue, Boston, MA - Dalton and Belvidere Street, Huntington Ave @ Belvidere St, and Forest Hills in around 24h 17m.
- Website
- southwest.com
Flights from Chicago Midway International Airport to Boston Logan Airport
- Ave. Duration
- 2h 16m
- When
- Every day
- Estimated price
- $110–600
Flights from Chicago Midway International Airport to Theodore Francis Green State Airport
- Ave. Duration
- 2h 10m
- When
- Every day
- Estimated price
- $90–470
Flights from Chicago Midway International Airport to Theodore Francis Green State Airport via Reagan Washington
- Ave. Duration
- 4h 15m
- When
- Sunday
- Estimated price
- $100–500
Flights from Chicago Midway International Airport to Theodore Francis Green State Airport via Baltimore
- Ave. Duration
- 4h 47m
- When
- Monday to Saturday
- Estimated price
- $95–500
Flights from Chicago Midway International Airport to Manchester Airport
- Ave. Duration
- 2h 7m
- When
- Every day
- Estimated price
- $130–700
Flights from Chicago Midway International Airport to Manchester Airport via Baltimore
- Ave. Duration
- 4h 38m
- When
- Monday to Saturday
- Estimated price
- $140–750
Flights from Chicago Midway International Airport to Bradley International Airport
- Ave. Duration
- 2h 1m
- When
- Every day
- Estimated price
- $110–600
Flights from Chicago Midway International Airport to Bradley International Airport via Baltimore
- Ave. Duration
- 4h 30m
- When
- Tuesday, Wednesday, Saturday, and Sunday
- Estimated price
- $120–650
- Website
- aa.com
Flights from Chicago O'Hare International Airport to Boston Logan Airport
- Ave. Duration
- 2h 31m
- When
- Every day
- Estimated price
- $80–410
Flights from Chicago O'Hare International Airport to Theodore Francis Green State Airport
- Ave. Duration
- 2h 26m
- When
- Every day
- Estimated price
- $65–340
Flights from Chicago O'Hare International Airport to Theodore Francis Green State Airport via Philadelphia
- Ave. Duration
- 4h 32m
- When
- Every day
- Estimated price
- $70–350
Flights from Chicago O'Hare International Airport to Theodore Francis Green State Airport via Reagan Washington
- Ave. Duration
- 4h 45m
- When
- Every day
- Estimated price
- $70–360
- Website
- united.com
Flights from Chicago O'Hare International Airport to Boston Logan Airport
- Ave. Duration
- 2h 30m
- When
- Every day
- Estimated price
- $80–410
Flights from Chicago O'Hare International Airport to Theodore Francis Green State Airport
- Ave. Duration
- 2h 28m
- When
- Every day
- Estimated price
- $65–340
Flights from Chicago O'Hare International Airport to Theodore Francis Green State Airport via Washington Dulles
- Ave. Duration
- 4h 43m
- When
- Wednesday and Tuesday
- Estimated price
- $70–360
- Website
- delta.com
Flights from Chicago O'Hare International Airport to Boston Logan Airport
- Ave. Duration
- 2h 33m
- When
- Every day
- Estimated price
- $80–410
Flights from Chicago Midway International Airport to Theodore Francis Green State Airport via Detroit
- Ave. Duration
- 3h 52m
- When
- Every day
- Estimated price
- $90–470
Flights from Chicago O'Hare International Airport to Theodore Francis Green State Airport via Detroit
- Ave. Duration
- 4h 7m
- When
- Monday, Tuesday, Wednesday, Thursday, Friday, and Sunday
- Estimated price
- $65–340
Flights from Chicago Midway International Airport to Bradley International Airport via Detroit
- Ave. Duration
- 3h 59m
- When
- Every day
- Estimated price
- $110–600
- Website
- jetblue.com
Flights from Chicago O'Hare International Airport to Boston Logan Airport
- Ave. Duration
- 2h 24m
- When
- Every day
- Estimated price
- $80–410
- Phone
- +1-617-222-3200
- Website
- mbta.com
Train from Back Bay to Walpole
- Ave. Duration
- 34 min
- Frequency
- Every 2 hours
- Estimated price
- $3–9
- Website
- https://www.mbta.com
- Adult
- $3–9
Train from TF Green Airport to Readville
- Ave. Duration
- 1h 12m
- Frequency
- Once daily
- Estimated price
- $8–14
- Website
- https://www.mbta.com
- Adult
- $8–14
Rome2Rio's guide to Amtrak
Contact Details
- Phone
- +1 800-872-7245
- Website
- amtrak.com
Train from Chicago Union Station to Boston
- Ave. Duration
- 22h 2m
- Frequency
- Once daily
- Estimated price
- $270–600
- Website
- https://www.amtrak.com/home.html
- Phone
- +1 (855) 626-8585
- Website
- https://www.flixbus.com
Bus from Chicago Bus Station to New York Midtown
- Ave. Duration
- 17h 5m
- Frequency
- 3 times a day
- Estimated price
- $110–190
- Schedules at
- flixbus.com
Bus from Hartford Union Station to Boston
- Ave. Duration
- 1h 50m
- Frequency
- 3 times a day
- Estimated price
- $13–22
- Schedules at
- flixbus.com
- Phone
- +1-844-800-6828
- pr@ourbus.com
- Website
- ourbus.com
Bus from New York, NY - W 42nd Street and 9th Avenue to Boston, MA - Dalton and Belvidere Street
- Ave. Duration
- 4h
- Frequency
- Once daily
- Estimated price
- $65–170
- Website
- https://www.ourbus.com
Rome2Rio's guide to Greyhound USA
Contact Details
- Phone
- +1 214-849-8100
- ifsr@greyhound.com
- Website
- greyhound.com
Bus from Boston Manchester Airport to Boston
- Ave. Duration
- 1h 30m
- Frequency
- Twice daily
- Estimated price
- $8–16
- Website
- https://www.greyhound.com/
Bus from Hartford Union Station to Boston
- Ave. Duration
- 1h 49m
- Frequency
- Every 2 hours
- Estimated price
- $16–35
- Website
- https://www.greyhound.com/
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More Questions & Answers
Chicago to Walpole bus services, operated by Flixbus USA, arrive at New York Midtown station.
Walpole is 1h ahead of Chicago. It is currently 2:03 PM in Chicago and 3:03 PM in Walpole.
Chicago to Walpole train services, operated by Amtrak, arrive at Boston station.
Yes, the driving distance between Chicago to Walpole is 981 miles. It takes approximately 16h 49m to drive from Chicago to Walpole.
There are 207+ hotels available in Walpole.













