Next bus departures
| Operated by | Vehicle type | Departure time | Departure location | Trip duration | Arrival time | Arrival location | Recommended | Price and booking link |
|---|---|---|---|---|---|---|---|---|
 | Bus | Chicago 95Th & Dan Ryan | Winston Salem Greyhound Bus Station | Cheapest | ||||
| Bus | Downtown Greyhound Station | Winston Salem Greyhound Bus Station | Fastest | ||||
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: Yesterday at 5:27 PM CST.
Get from Chicago to Winston-Salem
The journey takes about 23 hours 50 minutes and with fares starting at just $109, 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 traveling from Chicago to Winston-Salem by bus
Please note that schedules, routes, or operator details shown here may be updated or vary at the time of your trip.
How much is the bus ticket from Chicago to Winston-Salem?
The cheapest bus tickets from Chicago to Winston-Salem start from $109. The average price for this route is around $155. Busbud recommends that you book your tickets in advance for a better chance to get the lowest possible price.
How long is the bus ride from Chicago to Winston-Salem?
The average bus trip duration from Chicago to Winston-Salem is 23h 50m, covering a distance of 562 miles (906 km). The quickest bus can get you there in 18h 30m and is operated by Greyhound.
Which bus companies service the Chicago to Winston-Salem route?
What is the earliest and latest departure time for the bus from Chicago to Winston-Salem?
The earliest bus departs from Chicago to Winston-Salem at 12:30am. And the latest bus departs at 11:50pm.
What are the CO₂ emissions for the bus trip from Chicago to Winston-Salem?
A bus trip from Chicago to Winston-Salem generates an estimated 23 kg of CO₂, making it a highly eco-friendly travel option and recommended mode of travel by Busbud.
What is the best bus company from Chicago to Winston-Salem?
According to Busbud customers, the highest-rated bus company on this route is Greyhound, with an average rating of 3.5 out of 5 stars based on 87387 reviews.
Which bus company has the best Wi-Fi from Chicago to Winston-Salem?
Based on reviews on Busbud, the bus company FlixBus has the best Wi-Fi rating with a score of 2.7.
Which bus company has the most timely service from Chicago to Winston-Salem?
According to Busbud traveller reviews, the most timely bus company on this route is FlixBus, with a punctuality rating of 3.9 out of 5 stars.
Which bus company has the cleanest buses from Chicago to Winston-Salem?
According to Busbud traveller reviews, the bus company with the cleanest buses on this route is FlixBus, with a cleanliness rating of 4.1 out of 5 stars.
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 Dec 2, 2025 with a price of $103To 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 $103 to $366 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 $103 which is on 2025-12-02.
