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 O'Hare 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 O'Hare International Airport (ORD)plane DCA - ORD
5h 52m$153–891Train, 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 49m$81–926Train (Amtrak)
- Take the train from Martinsburg Amtrak Station to Chicago Union Stationtrain Floridian
16h 22m$195–439Bus (Greyhound)
- Take the bus from Frederick Bus Station to Chicago Bus Stationbus Greyhound US0164
17h 25m$140–217Drive 634.5 mi
- Drive from Shepherdstown to Chicagocar 634.5 mi
10h 50m$116–168Train to Ronald Reagan Washington National Airport, fly to Chicago Midway 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 Midway International Airport (MDW)plane DCA - MDW
5h 44m$123–641Train, 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$141–886Train, 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 45m$203–940Train, 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 11m$125–602
Ronald Reagan Washington National Airport (DCA) to Chicago O'Hare International Airport (ORD) 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 44m and costs $120 - $650.
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 25m.
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 703 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 $190 - $440.
It takes approximately 5h 52m 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 $190 - $440. Alternatively, you can bus, which costs $140 - $220 and takes 17h 25m.
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 $170–410 and the journey takes 16h 8m. Alternatively, Greyhound USA operates a bus from Frederick Bus Station to Chicago Bus Station once daily. Tickets cost $100–170 and the journey takes 15h 25m.
- Website
- united.com
Flights from Ronald Reagan Washington National Airport to Chicago O'Hare International Airport
- Ave. Duration
- 2h 9m
- When
- Every day
- Estimated price
- $80–460
Flights from Washington Dulles International Airport to Chicago O'Hare International Airport
- Ave. Duration
- 2h 17m
- When
- Every day
- Estimated price
- $50–290
Flights from Washington Dulles International Airport to Chicago O'Hare International Airport via Johnstown
- Ave. Duration
- 3h 30m
- When
- Every day
- Estimated price
- $50–300
Flights from Washington Dulles International Airport to Chicago O'Hare International Airport via Clarksburg
- Ave. Duration
- 3h 36m
- When
- Every day
- Estimated price
- $50–300
Flights from Washington Dulles International Airport to Chicago O'Hare International Airport via Columbus
- Ave. Duration
- 4h 22m
- When
- Every day
- Estimated price
- $50–300
Flights from Washington Dulles International Airport to Chicago O'Hare International Airport via Pittsburgh
- Ave. Duration
- 4h 30m
- When
- Every day
- Estimated price
- $50–300
Flights from Baltimore-Washington International Airport to Chicago O'Hare International Airport
- Ave. Duration
- 2h 14m
- When
- Every day
- Estimated price
- $60–340
Flights from Washington Dulles International Airport to South Bend
- Ave. Duration
- 1h 46m
- When
- Every day
- Estimated price
- $90–550
Flights from Washington Dulles International Airport to South Bend via Chicago O'Hare International Airport
- Ave. Duration
- 4h 17m
- When
- Every day
- Estimated price
- $100–600
- 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 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 25m
- Frequency
- Once daily
- Estimated price
- $100–170
- Website
- Greyhound
Want to know more about travelling around United States
Rome2Rio's Travel Guide series provide vital information for the global traveller. Filled with useful and timely travel information, the guides answer all the hard questions - such as 'How do I buy a ticket?', 'Should I book online before I travel? ', 'How much should I expect to pay?', 'Do the trains and buses have Wifi?' - to help you get the most out of your next trip.
Related travel guides
Travelling to the US: What do I need to know?
Read the travel guide
Why you should take the train in the US
Read the travel guide
Need to know: Greyhound
Read the travel guide
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 12:16 AM in Shepherdstown and 11:16 PM 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 1301+ hotels available in Chicago.





