There are 8 ways to get from Chester to Chicago by plane, train (Amtrak), bus (Greyhound), car, 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 Philadelphia International Airport to Chicago Midway International Airport
best- Fly from Philadelphia International Airport (PHL) to Chicago Midway International Airport (MDW)plane PHL - MDW
4h 5m$145–379Bus via Baltimore (Greyhound)
cheapest- Take the bus from Wilmington Bus Station to Baltimore Downtown Bus Stationbus Greyhound US0305 / ...
- Take the bus from Baltimore Downtown Bus Station to Chicago Bus Stationbus Greyhound US0164
22h 14m$124–212Train via Washington (Amtrak)
- Take the train from Wilmington to Washington Union Stationtrain Northeast Regional / ...
- Take the train from Rockville Amtrak to Chicago Union Stationtrain Floridian
21h 16m$210–1,097Drive 749.3 mi
- Drive from Chester to Chicagocar 749.3 mi
12h 27m$137–198Fly Philadelphia International Airport to Chicago O'Hare International Airport
- Fly from Philadelphia International Airport (PHL) to Chicago O'Hare International Airport (ORD)plane PHL - ORD
4h 36m$125–229Train to Baltimore-Washington International Airport, fly to Chicago Midway International Airport
- Take the train from Wilmington to BWI Thurgood Marshalltrain
- Fly from Baltimore-Washington International Airport (BWI) to Chicago Midway International Airport (MDW)plane BWI - MDW
5h 39m$143–909Bus (Flixbus)
- Take the bus from Philadelphia Bus Station to Chicago Bus Stationbus FlixBus N2642
22h 46m$135–218Train (Amtrak)
- Take the train from Wilmington to Chicago Union Stationtrain Cardinal
27h 59m$253–604
Chester to Chicago by train and subway (Amtrak)
Comparing Your Travel Options
The cheapest way to get from Chester to Chicago is to bus via Baltimore which costs $120 - $220 and takes 22h 14m.
The fastest way to get from Chester to Chicago is to fly which takes 4h 5m and costs $140 - $380.
No, there is no direct bus from Chester station to Chicago station. However, there are services departing from Wilmington Bus Station and arriving at Chicago Bus Station via Baltimore Downtown Bus Station. The journey, including transfers, takes approximately 22h 14m.
No, there is no direct train from Chester to Chicago station. However, there are services departing from Chester Transit Center and arriving at Chicago Union Station via Wilmington, Union Station, Red Line Center Platform and Rockville Amtrak. The journey, including transfers, takes approximately 21h 16m.
The distance between Chester and Chicago is 688 miles. The road distance is 753.6 miles.
The best way to get from Chester to Chicago without a car is to train via Washington which takes 21h 16m and costs $210 - $1,100.
It takes approximately 4h 5m to get from Chester to Chicago, including transfers.
Chester to Chicago bus services, operated by Greyhound USA, depart from Wilmington Bus Station.
Chester to Chicago train services, operated by Amtrak, depart from Wilmington station.
The best way to get from Chester to Chicago is to fly which takes 4h 5m and costs $140 - $380. Alternatively, you can train via Washington, which costs $210 - $1,100 and takes 21h 16m, you could also bus via Baltimore, which costs $120 - $220 and takes 22h 14m.
What companies run services between Chester, PA, USA and Chicago, IL, USA?
Southwest Airlines flies from Philadelphia International Airport (PHL) to Chicago Midway International Airport (MDW) 4 times a day. Alternatively, you can take a train from Chester Transit Center to Chicago Union Station via Wilmington, Washington Union Station, Union Station, Red Line Center Platform, Rockville, Red Line Center Platform, and Rockville Amtrak in around 21h 16m.
- Website
- southwest.com
Flights from Philadelphia International Airport to Chicago Midway International Airport
- Ave. Duration
- 2h 8m
- When
- Every day
- Estimated price
- $85–480
Flights from Baltimore-Washington International Airport to Chicago Midway International Airport
- Ave. Duration
- 2h 1m
- When
- Every day
- Estimated price
- $75–430
Flights from Baltimore-Washington International Airport to Chicago Midway International Airport via Pittsburgh
- Ave. Duration
- 3h 20m
- When
- Tuesday and Wednesday
- Estimated price
- $75–430
Flights from Baltimore-Washington International Airport to Chicago Midway International Airport via Columbus
- Ave. Duration
- 3h 45m
- When
- Monday, Thursday, Friday, and Sunday
- Estimated price
- $75–430
Flights from Baltimore-Washington International Airport to Chicago Midway International Airport via Detroit
- Ave. Duration
- 3h 55m
- When
- Tuesday, Wednesday, and Sunday
- Estimated price
- $75–430
Rome2Rio's guide to Amtrak
Contact DetailsContact Details
- Phone
- +1 800-872-7245
- Website
- Amtrak
Train from Wilmington to Washington Union Station
- Ave. Duration
- 1h 35m
- Frequency
- Hourly
- Estimated price
- $26–65
- Website
- Amtrak
Train from Rockville Amtrak to Chicago Union Station
- Ave. Duration
- 17h 24m
- Frequency
- Once daily
- Estimated price
- $180–440
- Website
- Amtrak
Train from Wilmington to BWI Thurgood Marshall
- Ave. Duration
- 1h 2m
- Frequency
- Hourly
- Estimated price
- $19–50
- Website
- Amtrak
Train from Wilmington to Chicago Union Station
- Ave. Duration
- 26h 40m
- 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 Wilmington Bus Station to Baltimore Downtown Bus Station
- Ave. Duration
- 1h 15m
- Frequency
- 4 times a day
- Estimated price
- $11–18
- Website
- Greyhound
Bus from Baltimore Downtown Bus Station to Chicago Bus Station
- Ave. Duration
- 18h 40m
- Frequency
- Twice daily
- Estimated price
- $110–190
- Website
- Greyhound
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Booking & Getting There
Chester to Chicago bus services, operated by Greyhound USA, arrive at Baltimore Downtown Bus Station.
Chicago is 1h behind Chester. It is currently 8:11 PM in Chester and 7:11 PM in Chicago.
Chester to Chicago train services, operated by Amtrak, arrive at Washington Union Station.
Yes, the driving distance between Chester to Chicago is 754 miles. It takes approximately 12h 27m to drive from Chester to Chicago.
There are 1301+ hotels available in Chicago.