There are 9 ways to get from Shepherdstown to Chicago by train, plane, train (Amtrak), bus (Greyhound), car, or subway
Select an option below to see step-by-step directions and to compare ticket prices and travel times in Rome2Rio's travel planner.
Train to Ronald Reagan Washington National Airport, fly to Chicago Midway International Airport
best- Take the train from DUFFIELDS W VA MARC eb to ROCKVILLE MARC ebtrain
- Fly from Ronald Reagan Washington National Airport (DCA) to Chicago Midway International Airport (MDW)plane DCA - MDW
5h 49m$123–691Train, train to Baltimore-Washington International Airport, fly to Chicago O'Hare International Airport
cheapest- Take the train from DUFFIELDS W VA MARC eb to Washington Union Stationtrain
- Take the train from Washington Union Station to BWI Thurgood Marshalltrain
- Fly from Baltimore-Washington International Airport (BWI) to Chicago O'Hare International Airport (ORD)plane BWI - ORD
6h 58m$86–956Train (Amtrak)
- Take the train from Martinsburg Amtrak Station to Chicago Union Stationtrain Floridian
16h 22m$405–629Bus (Greyhound)
- Take the bus from Frederick Bus Station to Chicago Bus Stationbus Greyhound US0164
17h 20m$160–227Drive 634.5 mi
- Drive from Shepherdstown to Chicagocar 634.5 mi
10h 50m$116–168Train to Ronald Reagan Washington National Airport, fly to Chicago O'Hare International Airport
- Take the train from DUFFIELDS W VA MARC eb to ROCKVILLE MARC ebtrain
- Fly from Ronald Reagan Washington National Airport (DCA) to Chicago O'Hare International Airport (ORD)plane DCA - ORD
6h 12m$143–641Train, train to Baltimore-Washington International Airport, fly to Chicago Midway International Airport
- Take the train from DUFFIELDS W VA MARC eb to Washington Union Stationtrain
- Take the train from Washington Union Station to BWI Thurgood Marshalltrain
- Fly from Baltimore-Washington International Airport (BWI) to Chicago Midway International Airport (MDW)plane BWI - MDW
6h 34m$161–886Train, subway to Washington Dulles International Airport, fly to Chicago O'Hare International Airport
- Take the train from DUFFIELDS W VA MARC eb to ROCKVILLE MARC ebtrain
- Take the subway from Metro Center, Blue/Orange/Silver Line Center Platform to Washington Dulles International Airport, Silver Line Center Platformsubway
- Fly from Washington Dulles International Airport (IAD) to Chicago O'Hare International Airport (ORD)plane IAD - ORD
6h 47m$203–360Train, subway to Washington Dulles International Airport, fly to South Bend
- Take the train from DUFFIELDS W VA MARC eb to ROCKVILLE MARC ebtrain
- Take the subway from Metro Center, Blue/Orange/Silver Line Center Platform to Washington Dulles International Airport, Silver Line Center Platformsubway
- Fly from Washington Dulles International Airport (IAD) to South Bend (SBN)plane IAD - SBN
- Take the train from South Bend Airport to Van Buren St.train
8h 21m$95–432
Ronald Reagan Washington National Airport (DCA) to Chicago Midway International Airport (MDW) flights
Comparing Your Travel Options
The cheapest way to get from Shepherdstown to Chicago is to drive which costs $110 - $170 and takes 10h 50m.
The fastest way to get from Shepherdstown to Chicago is to train and fly which takes 5h 49m and costs $120 - $700.
No, there is no direct bus from Shepherdstown to Chicago station. However, there are services departing from Route 478 at Route 180 and arriving at Chicago Bus Station via Frederick Bus Station. The journey, including transfers, takes approximately 17h 20m.
No, there is no direct train from Shepherdstown station to Chicago station. However, there are services departing from Martinsburg Amtrak Station and arriving at Chicago Union Station via . The journey, including transfers, takes approximately 16h 22m.
The distance between Shepherdstown and Chicago is 685 miles. The road distance is 638.2 miles.
The best way to get from Shepherdstown to Chicago without a car is to train which takes 16h 22m and costs $400 - $650.
It takes approximately 5h 49m to get from Shepherdstown to Chicago, including transfers.
Shepherdstown to Chicago bus services, operated by Greyhound USA, depart from Frederick Bus Station.
Shepherdstown to Chicago train services, operated by Amtrak, depart from Martinsburg Amtrak Station.
The best way to get from Shepherdstown to Chicago is to train which takes 16h 22m and costs $400 - $650. Alternatively, you can bus, which costs $160 - $230 and takes 17h 20m.
What companies run services between Shepherdstown, WV, USA and Chicago, IL, USA?
Amtrak operates a train from Martinsburg Amtrak Station to Chicago Union Station once daily. Tickets cost $380–600 and the journey takes 16h 8m. Alternatively, Greyhound USA operates a bus from Frederick Bus Station to Chicago Bus Station once daily. Tickets cost $120–180 and the journey takes 15h 20m.
- Website
- southwest.com
Flights from Ronald Reagan Washington National Airport to Chicago Midway International Airport
- Ave. Duration
- 2h 3m
- When
- Every day
- Estimated price
- $100–650
Flights from Baltimore-Washington International Airport to Chicago Midway International Airport
- Ave. Duration
- 2h 2m
- When
- Every day
- Estimated price
- $85–490
Flights from Baltimore-Washington International Airport to Chicago Midway International Airport via Pittsburgh
- Ave. Duration
- 3h 27m
- When
- Monday to Wednesday
- Estimated price
- $85–490
Flights from Baltimore-Washington International Airport to Chicago Midway International Airport via Columbus
- Ave. Duration
- 3h 40m
- When
- Tuesday and Wednesday
- Estimated price
- $85–490
Flights from Baltimore-Washington International Airport to Chicago Midway International Airport via Cleveland
- Ave. Duration
- 3h 35m
- When
- Saturday
- Estimated price
- $85–490
Flights from Baltimore-Washington International Airport to Chicago Midway International Airport via Detroit
- Ave. Duration
- 3h 50m
- When
- Tuesday and Wednesday
- Estimated price
- $85–500
- Website
- aa.com
Flights from Ronald Reagan Washington National Airport to Chicago O'Hare International Airport
- Ave. Duration
- 2h 26m
- When
- Every day
- Estimated price
- $80–460
Flights from Baltimore-Washington International Airport to Chicago O'Hare International Airport
- Ave. Duration
- 2h 31m
- When
- Every day
- Estimated price
- $65–370
Flights from Washington Dulles International Airport to South Bend via Charlotte
- Ave. Duration
- 4h 34m
- When
- Every day
- Estimated price
- $85–450
- Website
- united.com
Flights from Ronald Reagan Washington National Airport to Chicago O'Hare International Airport
- Ave. Duration
- 2h 24m
- When
- Every day
- Estimated price
- $80–460
Flights from Washington Dulles International Airport to Chicago O'Hare International Airport
- Ave. Duration
- 2h 21m
- When
- Every day
- Estimated price
- $50–300
Flights from Washington Dulles International Airport to Chicago O'Hare International Airport via Johnstown
- Ave. Duration
- 3h 45m
- When
- Monday, Wednesday, Thursday, Friday, and Sunday
- Estimated price
- $50–310
Flights from Washington Dulles International Airport to Chicago O'Hare International Airport via Charlottesville
- Ave. Duration
- 3h 51m
- When
- Monday, Tuesday, Wednesday, Thursday, Friday, and Sunday
- Estimated price
- $55–310
Flights from Washington Dulles International Airport to Chicago O'Hare International Airport via Clarksburg
- Ave. Duration
- 3h 54m
- When
- Every day
- Estimated price
- $50–300
Flights from Washington Dulles International Airport to Chicago O'Hare International Airport via Pittsburgh
- Ave. Duration
- 4h 10m
- When
- Monday, Tuesday, Wednesday, Thursday, Friday, and Sunday
- Estimated price
- $50–300
Flights from Washington Dulles International Airport to Chicago O'Hare International Airport via Columbus
- Ave. Duration
- 4h 12m
- When
- Every day
- Estimated price
- $50–300
Flights from Washington Dulles International Airport to Chicago O'Hare International Airport via Cleveland
- Ave. Duration
- 4h 13m
- When
- Saturday
- Estimated price
- $50–310
Flights from Baltimore-Washington International Airport to Chicago O'Hare International Airport
- Ave. Duration
- 2h 20m
- When
- Every day
- Estimated price
- $65–370
Flights from Washington Dulles International Airport to South Bend
- Ave. Duration
- 1h 57m
- When
- Every day
- Estimated price
- $60–380
Flights from Washington Dulles International Airport to South Bend via Chicago O'Hare International Airport
- Ave. Duration
- 4h 31m
- When
- Every day
- Estimated price
- $70–410
- Website
- delta.com
Flights from Baltimore-Washington International Airport to Chicago Midway International Airport via Detroit
- Ave. Duration
- 3h 57m
- When
- Monday, Tuesday, Wednesday, Thursday, Friday, and Sunday
- Estimated price
- $85–500
Flights from Baltimore-Washington International Airport to Chicago O'Hare International Airport via Detroit
- Ave. Duration
- 4h 39m
- When
- Every day
- Estimated price
- $65–380
Flights from Washington Dulles International Airport to South Bend via Detroit
- Ave. Duration
- 3h 41m
- When
- Every day
- Estimated price
- $65–380
- Website
- flyfrontier.com
Flights from Baltimore-Washington International Airport to Chicago O'Hare International Airport
- Ave. Duration
- 2h 30m
- When
- Monday, Thursday, Friday, and Sunday
- Estimated price
- $100–360
- Website
- flybreeze.com
Flights from Washington Dulles International Airport to South Bend
- Ave. Duration
- 1h 56m
- When
- Monday and Friday
- Estimated price
- $140–900
- Phone
- 1-866-743-3682
- Website
- Maryland Transit
Train from DUFFIELDS W VA MARC eb to ROCKVILLE MARC eb
- Ave. Duration
- 1h 8m
- Frequency
- Twice daily
- Estimated price
- $2–11
- Website
- Maryland Transit
- Standard Fare
- $2–11
Train from DUFFIELDS W VA MARC eb to ROCKVILLE MARC eb
- Ave. Duration
- 1h 8m
- Frequency
- Twice daily
- Estimated price
- $2–11
- Website
- Maryland Transit
- Standard Fare
- $2–11
Train from DUFFIELDS W VA MARC eb to Washington Union Station
- Ave. Duration
- 1h 51m
- Frequency
- Twice daily
- Estimated price
- $2–13
- Website
- Maryland Transit
- Standard Fare
- $2–13
Train from Washington Union Station to BWI Thurgood Marshall
- Ave. Duration
- 35 min
- Frequency
- Hourly
- Estimated price
- $2–9
- Website
- Maryland Transit
- Standard Fare
- $2–9
Train from DUFFIELDS W VA MARC eb to ROCKVILLE MARC eb
- Ave. Duration
- 1h 8m
- Frequency
- Twice daily
- Estimated price
- $2–11
- Website
- Maryland Transit
- Standard Fare
- $2–11
Train from DUFFIELDS W VA MARC eb to Washington Union Station
- Ave. Duration
- 1h 51m
- Frequency
- Twice daily
- Estimated price
- $2–13
- Website
- Maryland Transit
- Standard Fare
- $2–13
Train from Washington Union Station to BWI Thurgood Marshall
- Ave. Duration
- 35 min
- Frequency
- Hourly
- Estimated price
- $2–9
- Website
- Maryland Transit
- Standard Fare
- $2–9
Train from DUFFIELDS W VA MARC eb to ROCKVILLE MARC eb
- Ave. Duration
- 1h 8m
- Frequency
- Twice daily
- Estimated price
- $2–11
- Website
- Maryland Transit
- Standard Fare
- $2–11
Rome2Rio's guide to Amtrak
Contact DetailsContact Details
- Phone
- +1 800-872-7245
- Website
- Amtrak
Train from Martinsburg Amtrak Station to Chicago Union Station
- Ave. Duration
- 16h 8m
- Frequency
- Once daily
- Estimated price
- $380–600
- Website
- Amtrak
Train from Washington Union Station to BWI Thurgood Marshall
- Ave. Duration
- 35 min
- Frequency
- Every 30 minutes
- Estimated price
- $16–25
- Website
- Amtrak
Train from Washington Union Station to BWI Thurgood Marshall
- Ave. Duration
- 35 min
- Frequency
- Every 30 minutes
- Estimated price
- $16–25
- Website
- Amtrak
Rome2Rio's guide to Amtrak Acela
Contact DetailsContact Details
- Phone
- +1 800-872-7245
- Website
- Amtrak
Train from Washington Union Station to BWI Thurgood Marshall
- Ave. Duration
- 20 min
- Frequency
- Every 4 hours
- Estimated price
- $6–550
- Schedules at
- Amtrak Acela
- Website
- Amtrak
- Business Class
- $6–440
- First Class
- $100–550
Train from Washington Union Station to BWI Thurgood Marshall
- Ave. Duration
- 20 min
- Frequency
- Every 4 hours
- Estimated price
- $6–550
- Schedules at
- Amtrak Acela
- Website
- Amtrak
- Business Class
- $6–440
- First Class
- $100–550
Subway from Metro Center, Blue/Orange/Silver Line Center Platform to Washington Dulles International Airport, Silver Line Center Platform
- Ave. Duration
- 50 min
- Frequency
- Every 15 minutes
- Estimated price
- $2–3
- Website
- Washington Metropolitan Area Transit Authority
- standard fare after 9:30 p.m
- $2–3
Subway from Metro Center, Blue/Orange/Silver Line Center Platform to Washington Dulles International Airport, Silver Line Center Platform
- Ave. Duration
- 50 min
- Frequency
- Every 15 minutes
- Estimated price
- $2–3
- Website
- Washington Metropolitan Area Transit Authority
- standard fare after 9:30 p.m
- $2–3
- Phone
- +1 219-926-5744
- Website
- mysouthshoreline.com
Train from South Bend Airport to Van Buren St.
- Ave. Duration
- 2h 1m
- Frequency
- Hourly
- Estimated price
- $14–17
- Schedules at
- mysouthshoreline.com
- Adults 14-64
- $14–17
Train from South Bend Airport to Van Buren St.
- Ave. Duration
- 2h 1m
- Frequency
- Every 4 hours
- Estimated price
- $4–16
- Schedules at
- Northern Indiana Commuter Transportation District
Rome2Rio's guide to Greyhound USA
Contact DetailsContact Details
- Phone
- +1 214-849-8100
- [email protected]
- Website
- Greyhound
Bus from Frederick Bus Station to Chicago Bus Station
- Ave. Duration
- 15h 20m
- Frequency
- Once daily
- Estimated price
- $120–180
- Website
- Greyhound
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Booking & Getting There
Shepherdstown to Chicago bus services, operated by Greyhound USA, arrive at Chicago Bus Station.
Chicago is 1h behind Shepherdstown. It is currently 5:25 AM in Shepherdstown and 4:25 AM in Chicago.
Shepherdstown to Chicago train services, operated by Amtrak, arrive at Chicago Union Station.
Yes, the driving distance between Shepherdstown to Chicago is 638 miles. It takes approximately 10h 50m to drive from Shepherdstown to Chicago.
There are 1294+ hotels available in Chicago.













