There are 8 ways to get from Chicago to Greenbrier by bus (Greyhound), train, bus, car, plane, 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.
Bus via Indianapolis
best- Take the bus from Chicago Bus Station to Indianapolis Union Stationbus Greyhound US0100 / ...
- Take the bus from Indianapolis Union Station to Paoli Walmartbus Indianapolis
6h 59m$84–129Drive 275.7 mi
cheapest- Drive from Chicago to Greenbriercar 275.7 mi
5h 35m$51–73Train, bus
- Take the train from Chicago Union Station to Indianapolistrain Cardinal
- Take the bus from Indianapolis Union Station to Paoli Walmartbus Indianapolis
8h 48m$119–206Fly Chicago Midway International Airport to Louisville International Airport, drive
- Fly from Chicago Midway International Airport (MDW) to Louisville International Airport (SDF)plane MDW - SDF
- Drive from Louisville-Airport-SDF to Greenbriercar
4h 19m$88–571Bus
- Take the bus from Chicago Bus Station to Bloomingtonbus FlixBus 2515 / ...
- Take the bus from Bloomington, IN to Paoli Walmartbus Indianapolis
7h 44m$82–120Fly Chicago O'Hare International Airport to Louisville International Airport, drive
- Fly from Chicago O'Hare International Airport (ORD) to Louisville International Airport (SDF)plane ORD - SDF
- Drive from Louisville-Airport-SDF to Greenbriercar
4h 51m$78–451Fly Chicago O'Hare International Airport to Owensboro–Daviess County Regional Airport, drive
- Fly from Chicago O'Hare International Airport (ORD) to Owensboro–Daviess County Regional Airport (OWB)plane ORD - OWB
- Drive from Owensboro–Daviess County Regional Airport (OWB) to Greenbriercar
5h 7m$96–236Fly Chicago O'Hare International Airport to Evansville, bus
- Fly from Chicago O'Hare International Airport (ORD) to Evansville (EVV)plane ORD - EVV
- Take the bus from Evansville, IN to Paoli Walmartbus
6h 49m$120–398
Chicago Midway International Airport (MDW) to Louisville International Airport (SDF) flights
Questions & Answers
The cheapest way to get from Chicago to Greenbrier is to drive which costs $50 - $75 and takes 5h 35m.
The fastest way to get from Chicago to Greenbrier is to fly and drive which takes 4h 19m and costs $85 - $600.
No, there is no direct bus from Chicago station to Greenbrier. However, there are services departing from Chicago Bus Station and arriving at Paoli Walmart via Indianapolis Union Station. The journey, including transfers, takes approximately 6h 59m.
The distance between Chicago and Greenbrier is 288 miles. The road distance is 277.3 miles.
The best way to get from Chicago to Greenbrier without a car is to bus via Indianapolis which takes 6h 59m and costs $80 - $130.
It takes approximately 6h 59m to get from Chicago to Greenbrier, including transfers.
Chicago to Greenbrier bus services, operated by Greyhound USA, depart from Chicago Bus Station.
Chicago to Greenbrier bus services, operated by Greyhound USA, arrive at Indianapolis Union Station.
Greenbrier is 1h ahead of Chicago. It is currently 10:35 AM in Chicago and 11:35 AM in Greenbrier.
Yes, the driving distance between Chicago to Greenbrier is 277 miles. It takes approximately 5h 35m to drive from Chicago to Greenbrier.
What companies run services between Chicago, IL, USA and Greenbrier, Orange County, IN, USA?
You can take a bus from Chicago Bus Station to Greenbrier via Indianapolis Union Station and Paoli Walmart in around 6h 59m.
- Website
- southwest.com
Flights from Chicago Midway International Airport to Louisville International Airport
- Ave. Duration
- 1h 16m
- When
- Every day
- Estimated price
- $75–550
Flights from Chicago Midway International Airport to Louisville International Airport via Nashville
- Ave. Duration
- 3h 15m
- When
- Sunday
- Estimated price
- $110–650
- Website
- united.com
Flights from Chicago O'Hare International Airport to Louisville International Airport
- Ave. Duration
- 1h 37m
- When
- Every day
- Estimated price
- $65–430
- Website
- aa.com
Flights from Chicago O'Hare International Airport to Louisville International Airport
- Ave. Duration
- 1h 34m
- When
- Every day
- Estimated price
- $65–430
Flights from Chicago O'Hare International Airport to Evansville
- Ave. Duration
- 1h 22m
- When
- Every day
- Estimated price
- $40–290
- Website
- contouraviation.com
Flights from Chicago O'Hare International Airport to Owensboro–Daviess County Regional Airport
- Ave. Duration
- 1h 35m
- When
- Every day
- Estimated price
- $80–210
Rome2Rio's guide to Amtrak
Contact DetailsContact Details
- Phone
- +1 800-872-7245
- Website
- Amtrak
Train from Chicago Union Station to Indianapolis
- Ave. Duration
- 4h 54m
- Frequency
- 3 times a week
- Estimated price
- $60–130
- 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 Indianapolis Union Station
- Ave. Duration
- 3h 5m
- Frequency
- 5 times a day
- Estimated price
- $26–55
- Website
- Greyhound
- Phone
- +1 502-368-5644 x 135
- Website
- Miller Transportation
Bus from Indianapolis Union Station to Paoli Walmart
- Ave. Duration
- 2h 25m
- Frequency
- Once daily
- Estimated price
- $30–45
- Website
- Miller Transportation
Bus from Indianapolis Union Station to Paoli Walmart
- Ave. Duration
- 2h 25m
- Frequency
- Once daily
- Estimated price
- $30–45
- Website
- Miller Transportation
Bus from Bloomington, IN to Paoli Walmart
- Ave. Duration
- 1h 15m
- Frequency
- Once daily
- Estimated price
- $18–28
- Website
- Miller Transportation
Bus from Evansville, IN to Paoli Walmart
- Ave. Duration
- 2h
- Frequency
- Once daily
- Estimated price
- $30–45
- Website
- Miller Transportation
- Phone
- +1 (855) 626-8585
- Website
- Flixbus USA
Bus from Chicago Bus Station to Bloomington
- Ave. Duration
- 5h
- Frequency
- Twice daily
- Estimated price
- $35–60
- Schedules at
- Flixbus USA
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More Questions & Answers
There are 20+ hotels available in Greenbrier.









