Previously seen trips
| Operated by | Vehicle type | Departure time | Departure location | Trip duration | Arrival time | Arrival location | Recommended | Price and booking link |
|---|---|---|---|---|---|---|---|---|
 | Bus | Downtown Greyhound Station | Winston Salem Greyhound Bus Station | No tags | ||||
| Bus | 537-517 W. Jackson Blvd | Winston Salem Greyhound Bus Station | No tags | ||||
| Bus | Chicago 95Th & Dan Ryan | Winston Salem Greyhound Bus Station | No tags | ||||
| Bus | Downtown Greyhound Station | Winston Salem Greyhound Bus Station | No tags | ||||
| Bus | 537-517 W. Jackson Blvd | Winston Salem Greyhound Bus Station | No tags |
Get from Chicago to Winston-Salem
The journey takes about 23 hours 50 minutes, and with fares starting at just $157, it presents an excellent value for a comfortable ride.
Where are the popular stops in Chicago and Winston-Salem?
Stops in Chicago
- A630 W Harrison St, Chicago, IL 60607, USA
- C
Polk St & Canal St
500-536 W Polk St, Chicago IL 60607, USA - D
Tornado Bus S Kedzie Ave
2807 S Kedzie Ave, Chicago, IL 60623, USA - E
Cumberland CTA
5800 N Cumberland Ave, Chicago, IL 60631, USA - F
Turimex California Ave
2139 S California Ave, Chicago, IL 60608, USA
Stops in Winston-Salem
- A
Winston Salem Greyhound Bus Station
100 W 5th St, Winston Salem, NC 27101 - B
E Sprague St
841 E Sprague St, Winston-Salem, NC 27107, USA - C
Winston-Salem Bus Stop
2500 Old Lexington Rd, Winston-Salem, NC 27107, USA - D
1237 Silas Creek Pkwy
1237 Silas Creek Pkwy., Winston-Salem, NC 27127 (Hong Kong King Buffet)
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Frequently asked questions about travelling from Chicago to Winston-Salem by bus
What is the distance between Chicago and Winston-Salem?
Chicago and Winston-Salem are 906 km (562 miles) apart.
What are the departure and arrival locations for buses traveling from Chicago to Winston-Salem?
Buses departing from Downtown Greyhound Station in Chicago will take you to Winston Salem Greyhound Bus Station in Winston-Salem.
Find cheapest prices for buses
Price is for a one-way ticket for one passenger and based on past searches.
The cheapest trip from Chicago to Winston-Salem was searched and found on Nov 26, 2025 with a price of $191To save money and be sure you have the best seat, it's a good idea to buy your bus tickets from Chicago to Winston-Salem, as early as possible.
You can expect to pay from $191 to $256 for a bus ticket from Chicago to Winston-Salem based on the last 2 days. You can expect to find the cheapest price for the trip at $191 which is on 2025-11-26.
