There are 5 ways to get from Chester to Chicago by plane, bus (Flixbus, Greyhound), train (Amtrak), or car
Select an option below to see step-by-step directions and to compare ticket prices and travel times in Rome2Rio's travel planner.
Fly to Chicago Midway International Airport
best- Fly from Richmond International Airport (RIC) to Chicago Midway International Airport (MDW)plane RIC - MDW
3h 8m$132–528Fly to Chicago O'Hare International Airport
cheapest- Fly from Richmond International Airport (RIC) to Chicago O'Hare International Airport (ORD)plane RIC - ORD
3h 34m$107–388Bus
- Take the bus from Richmond to Washington Union Stationbus FlixBus N2471 / ...
- Take the bus from Washington Union Station to Chicago Bus Stationbus Greyhound US0164
20h 26m$187–276Train (Amtrak)
- Take the train from Petersburg Amtrak Station to Chicago Union Stationtrain Floridian
21h 57m$520–835Drive 768.1 mi
- Drive from Chester to Chicagocar 768.1 mi
13h 55m$132–190
Richmond International Airport (RIC) to Chicago Midway International Airport (MDW) flights
Comparing Your Travel Options
The cheapest way to get from Chester to Chicago is to drive which costs $130 - $190 and takes 13h 55m.
The fastest way to get from Chester to Chicago is to fly which takes 3h 8m and costs $130 - $550.
No, there is no direct bus from Chester to Chicago station. However, there are services departing from Richmond and arriving at Chicago Bus Station via Washington Union Station. The journey, including transfers, takes approximately 20h 26m.
No, there is no direct train from Chester station to Chicago station. However, there are services departing from Petersburg Amtrak Station and arriving at Chicago Union Station via . The journey, including transfers, takes approximately 21h 57m.
The distance between Chester and Chicago is 657 miles. The road distance is 772.6 miles.
The best way to get from Chester to Chicago without a car is to bus which takes 20h 26m and costs $180 - $280.
It takes approximately 3h 8m to get from Chester to Chicago, including transfers.
Chester to Chicago bus services, operated by Flixbus USA, depart from Richmond station.
Chester to Chicago train services, operated by Amtrak, depart from Petersburg Amtrak Station.
The best way to get from Chester to Chicago is to fly which takes 3h 8m and costs $130 - $550. Alternatively, you can bus, which costs $180 - $280 and takes 20h 26m, you could also train, which costs $500 - $850 and takes 21h 57m.
What companies run services between Chester, VA, USA and Chicago, IL, USA?
Southwest Airlines and Delta fly from Richmond International Airport (RIC) to Chicago Midway International Airport (MDW) 5 times a day. Alternatively, you can take a vehicle from Chester to Chicago Bus Station via Richmond and Washington Union Station in around 20h 26m.
- Website
- united.com
Flights from Richmond International Airport to Chicago O'Hare International Airport
- Ave. Duration
- 2h 33m
- When
- Every day
- Estimated price
- $60–330
Flights from Richmond International Airport to Chicago O'Hare International Airport via Washington Dulles
- Ave. Duration
- 4h 36m
- When
- Every day
- Estimated price
- $60–340
- Website
- southwest.com
Flights from Richmond International Airport to Chicago Midway International Airport
- Ave. Duration
- 2h 5m
- When
- Monday, Tuesday, Wednesday, Thursday, Friday, and Sunday
- Estimated price
- $85–470
Flights from Richmond International Airport to Chicago Midway International Airport via Baltimore
- Ave. Duration
- 3h 57m
- When
- Saturday
- Estimated price
- $90–490
Flights from Richmond International Airport to Chicago Midway International Airport via Nashville
- Ave. Duration
- 4h 48m
- When
- Monday, Thursday, Tuesday, Wednesday, Friday, and Sunday
- Estimated price
- $100–550
- Website
- aa.com
Flights from Richmond International Airport to Chicago O'Hare International Airport
- Ave. Duration
- 2h 32m
- When
- Every day
- Estimated price
- $60–330
Flights from Richmond International Airport to Chicago O'Hare International Airport via Charlotte
- Ave. Duration
- 4h 49m
- When
- Every day
- Estimated price
- $70–370
- Website
- delta.com
Flights from Richmond International Airport to Chicago Midway International Airport via Detroit
- Ave. Duration
- 4h 46m
- When
- Every day
- Estimated price
- $85–480
Flights from Richmond International Airport to Chicago Midway International Airport via Atlanta
- Ave. Duration
- 4h 54m
- When
- Monday, Tuesday, Wednesday, Thursday, Friday, and Sunday
- Estimated price
- $110–600
Flights from Richmond International Airport to Chicago O'Hare International Airport via Detroit
- Ave. Duration
- 4h 24m
- When
- Every day
- Estimated price
- $60–340
Rome2Rio's guide to Amtrak
Contact Details
- Phone
- +1 800-872-7245
- Website
- Amtrak
Train from Petersburg Amtrak Station to Chicago Union Station
- Ave. Duration
- 21h 41m
- Frequency
- Once daily
- Estimated price
- $490–800
- Website
- Amtrak
- Phone
- +1 (855) 626-8585
- Website
- Flixbus USA
Bus from Richmond to Washington Union Station
- Ave. Duration
- 1h 55m
- Frequency
- Every 4 hours
- Estimated price
- $17–26
- Schedules at
- Flixbus USA
Rome2Rio's guide to Greyhound USA
Contact Details
- Phone
- +1 214-849-8100
- [email protected]
- Website
- Greyhound
Bus from Richmond to Washington Union Station
- Ave. Duration
- 1h 50m
- Frequency
- Every 4 hours
- Estimated price
- $19–29
- Website
- Greyhound
Bus from Washington Union Station to Chicago Bus Station
- Ave. Duration
- 17h 10m
- Frequency
- Twice daily
- Estimated price
- $130–200
- Website
- Greyhound
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Booking & Getting There
Chester to Chicago bus services, operated by Flixbus USA, arrive at Washington Union Station.
Chicago is 1h behind Chester. It is currently 8:58 PM in Chester and 7:58 PM in Chicago.
Chester to Chicago train services, operated by Amtrak, arrive at Chicago Union Station.
Yes, the driving distance between Chester to Chicago is 773 miles. It takes approximately 13h 55m to drive from Chester to Chicago.
Book your Chester to Chicago train tickets online with Omio.
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