There are 10 ways to get from Chicago to Chester by plane, train (Amtrak), bus (Greyhound), car, bus, train, or bus (Flixbus)
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 Midway International Airport to Philadelphia International Airport
best- Fly from Chicago Midway International Airport (MDW) to Philadelphia International Airport (PHL)plane MDW - PHL
4h 21m$144–379Fly Chicago O'Hare International Airport to Lancaster, drive
cheapest- Fly from Chicago O'Hare International Airport (ORD) to Lancaster (LNS)plane ORD - LNS
- Drive from Lancaster-Airport-LNS to Chestercar
5h 23m$68–362Train via Washington (Amtrak)
- Take the train from Chicago Union Station to Rockville Amtraktrain Floridian
- Take the train from Washington Union Station to Wilmingtontrain Carolinian / ...
20h 12m$215–1,095Bus via Baltimore (Greyhound)
- Take the bus from Chicago Bus Station to Baltimore Downtown Bus Stationbus Greyhound US0164
- Take the bus from Baltimore Downtown Bus Station to Wilmington Bus Stationbus Greyhound US0305 / ...
21h 17m$134–208Drive 749.3 mi
- Drive from Chicago to Chestercar 749.3 mi
12h 27m$137–198Fly Chicago O'Hare International Airport to Philadelphia International Airport, line 37 bus
- Fly from Chicago O'Hare International Airport (ORD) to Philadelphia International Airport (PHL)plane ORD - PHL
- Take the bus from Philadelphia Airport Terminal B to 3rd St & Madison Stbus
4h 44m$124–229Train to General Mitchell International Airport, fly to Philadelphia International Airport
- Take the train from Chicago Union Station to Milwaukeetrain
- Fly from General Mitchell International Airport (MKE) to Philadelphia International Airport (PHL)plane MKE - PHL
6h 10m$485–917Fly Chicago Midway International Airport to Baltimore-Washington International Airport, train
- Fly from Chicago Midway International Airport (MDW) to Baltimore-Washington International Airport (BWI)plane MDW - BWI
- Take the train from BWI Thurgood Marshall to Wilmingtontrain
6h 23m$144–911Bus (Flixbus)
- Take the bus from Chicago Bus Station to Philadelphia Bus Stationbus FlixBus N2642
22h 22m$142–213Train (Amtrak)
- Take the train from Chicago Union Station to Wilmingtontrain Cardinal
26h 47m$255–599
Chicago to Chester by train and subway (Amtrak)
Comparing Your Travel Options
The cheapest way to get from Chicago to Chester is to bus via Baltimore which costs $130 - $210 and takes 21h 17m.
The fastest way to get from Chicago to Chester is to fly which takes 4h 21m and costs $140 - $380.
No, there is no direct bus from Chicago station to Chester station. However, there are services departing from Chicago Bus Station and arriving at Wilmington Bus Station via Baltimore Downtown Bus Station. The journey, including transfers, takes approximately 21h 17m.
No, there is no direct train from Chicago station to Chester. However, there are services departing from Chicago Union Station and arriving at Chester Transit Center via Rockville, Red Line Center Platform, Washington Union Station and Wilmington. The journey, including transfers, takes approximately 20h 12m.
The distance between Chicago and Chester is 691 miles. The road distance is 753.7 miles.
The best way to get from Chicago to Chester without a car is to train via Washington which takes 20h 12m and costs $210 - $1,100.
It takes approximately 4h 21m to get from Chicago to Chester, including transfers.
Chicago to Chester bus services, operated by Greyhound USA, depart from Chicago Bus Station.
Chicago to Chester train services, operated by Amtrak, depart from Chicago Union Station.
The best way to get from Chicago to Chester is to fly which takes 4h 21m and costs $140 - $380. Alternatively, you can train via Washington, which costs $210 - $1,100 and takes 20h 12m, you could also bus via Baltimore, which costs $130 - $210 and takes 21h 17m.
What companies run services between Chicago, IL, USA and Chester, PA, USA?
Southwest Airlines flies from Chicago Midway International Airport (MDW) to Philadelphia International Airport (PHL) 4 times a day. Alternatively, you can take a train from Chicago Union Station to Chester Transit Center via Rockville Amtrak, Rockville, Red Line Center Platform, Union Station, Red Line Center Platform, Washington Union Station, and Wilmington in around 20h 12m.
- Website
- southwest.com
Flights from Chicago Midway International Airport to Philadelphia International Airport
- Ave. Duration
- 1h 53m
- When
- Every day
- Estimated price
- $100–600
Flights from General Mitchell International Airport to Philadelphia International Airport via Chicago Midway International Airport
- Ave. Duration
- 3h 45m
- When
- Sunday
- Estimated price
- $120–650
Flights from General Mitchell International Airport to Philadelphia International Airport via St. Louis
- Ave. Duration
- 4h 32m
- When
- Tuesday, Wednesday, and Sunday
- Estimated price
- $160–800
Flights from General Mitchell International Airport to Philadelphia International Airport via Nashville
- Ave. Duration
- 4h 37m
- When
- Every day
- Estimated price
- $160–800
Flights from Chicago Midway International Airport to Baltimore-Washington International Airport
- Ave. Duration
- 1h 48m
- When
- Every day
- Estimated price
- $90–550
Flights from Chicago Midway International Airport to Baltimore-Washington International Airport via Indianapolis
- Ave. Duration
- 3h 46m
- When
- Sunday, Monday, Thursday, Friday, Tuesday, and Wednesday
- Estimated price
- $95–550
Flights from Chicago Midway International Airport to Baltimore-Washington International Airport via Columbus
- Ave. Duration
- 4h 20m
- When
- Tuesday and Wednesday
- Estimated price
- $90–550
Flights from Chicago Midway International Airport to Baltimore-Washington International Airport via Cleveland
- Ave. Duration
- 4h 20m
- When
- Sunday
- Estimated price
- $90–550
Rome2Rio's guide to Amtrak
Contact DetailsContact Details
- Phone
- +1 800-872-7245
- Website
- Amtrak
Train from Chicago Union Station to Rockville Amtrak
- Ave. Duration
- 16h 41m
- Frequency
- Once daily
- Estimated price
- $180–440
- Website
- Amtrak
Train from Washington Union Station to Wilmington
- Ave. Duration
- 1h 21m
- Frequency
- Hourly
- Estimated price
- $26–65
- Website
- Amtrak
Train from Chicago Union Station to Milwaukee
- Ave. Duration
- 1h 29m
- Frequency
- Every 4 hours
- Estimated price
- $20–50
- Website
- Amtrak
Train from BWI Thurgood Marshall to Wilmington
- Ave. Duration
- 1h 9m
- Frequency
- Hourly
- Estimated price
- $19–50
- Website
- Amtrak
Train from Chicago Union Station to Wilmington
- Ave. Duration
- 25h 35m
- Frequency
- 3 times a week
- Estimated price
- $250–600
- Website
- Amtrak
Rome2Rio's guide to Greyhound USA
Contact DetailsContact Details
- Phone
- +1 214-849-8100
- [email protected]
- Website
- Greyhound
Bus from Chicago Bus Station to Baltimore Downtown Bus Station
- Ave. Duration
- 17h 45m
- Frequency
- Twice daily
- Estimated price
- $120–190
- Website
- Greyhound
Bus from Baltimore Downtown Bus Station to Wilmington Bus Station
- Ave. Duration
- 1h 20m
- Frequency
- 4 times a day
- Estimated price
- $11–18
- Website
- Greyhound
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Booking & Getting There
Chicago to Chester bus services, operated by Greyhound USA, arrive at Baltimore Downtown Bus Station.
Chester is 1h ahead of Chicago. It is currently 11:23 AM in Chicago and 12:23 PM in Chester.
Chicago to Chester train services, operated by Amtrak, arrive at Rockville Amtrak station.
Yes, the driving distance between Chicago to Chester is 754 miles. It takes approximately 12h 27m to drive from Chicago to Chester.
There are 834+ hotels available in Chester.