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 | ||||
Greyhound + FlixBus | Bus | Chicago 95Th & Dan Ryan | 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 | ||||
FlixBus + Greyhound | Bus | Chicago 95Th & Dan Ryan | Winston Salem Greyhound Bus Station | No tags |
Get from Chicago to Winston-Salem
The journey takes about 1 day, 15 minutes and with fares starting at just TRY 3,648, 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)
Compare bus companies
Greyhound Lines offers the most comprehensive intercity bus services in the United States. They operate a modern, environmentally friendly fleet that serves more than 2400 destinations and carries nearly 16 million passengers annually. When traveling with them, you can expect free WiFi, onboard entertainment, bathrooms, power outlets and decent legroom. One of the great perks of Greyhound is that they connect big cities and smaller towns in the US, where you usually can't get to by train or plane. If you're looking for safe and affordable transportation, Greyhound is a great choice.
Greyhound Chicago Winston-Salem recent customer reviews
I will never ride this busline again
Edwardo B.
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 TRY 3,648. The average price for this route is around TRY 4,923. 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 1d , covering a distance of 558 miles (900 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?
Several major bus companies operate on this route with 7 buses available per day.
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 5:25am. 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 22.483824999999996 kg of CO₂, making it a highly eco-friendly travel option and recommended mode of travel by Busbud.
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 May 11, 2026 with a price of TRY 3,732To 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 TRY 3,732 to TRY 8,301 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 TRY 3,732 which is on 2026-05-11.
