Next bus departures
| Operated by | Vehicle type | Departure time | Departure location | Trip duration | Arrival time | Arrival location | Recommended | Price and booking link |
|---|---|---|---|---|---|---|---|---|
 | Bus | 537-517 W. Jackson Blvd | Winston Salem Greyhound Bus Station | Cheapest | ||||
| Bus | Downtown Greyhound Station | Winston Salem Greyhound Bus Station | Fastest | ||||
| Bus | Downtown Greyhound Station | Winston Salem Greyhound Bus Station | No tags | ||||
Greyhound Lines, Inc. + FlixBus | Bus | 537-517 W. Jackson Blvd | Winston Salem Greyhound Bus Station | No tags | ||||
FlixBus + Greyhound Lines, Inc. | Bus | Chicago 95Th & Dan Ryan | Winston Salem Greyhound Bus Station | No tags |
Last refresh of the prices: Today at 07:45 CST.
Get from Chicago to Winston-Salem
The journey takes about 23 hours 50 minutes, and with fares starting at just £85, 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 by bus from Chicago to Winston-Salem
How far is Winston-Salem from Chicago by coach?
The journey from Chicago to Winston-Salem by coach covers an approximate distance of 562 miles (906 km).
What is the best way to go from Chicago to Winston-Salem without flying?
To travel from Chicago to Winston-Salem without flying, you can take the coaches. Choosing the coach guarantees a comfortable and sustainable travel experience, allowing you to admire the views on your way to your destination. You might also find carpooling options to travel between the two cities.
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 26 Nov 2025 with a price of £104To 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 £104 to £240 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 £104, which is on 2025-11-26.
