Previously seen trips
| Operated by | Vehicle type | Departure time | Departure location | Trip duration | Arrival time | Arrival location | Recommended | Price and booking link |
|---|---|---|---|---|---|---|---|---|
 | Bus | Winston Salem Greyhound Bus Station | Downtown Greyhound Station | No tags | ||||
| Bus | Winston Salem Greyhound Bus Station | Chicago 95Th & Dan Ryan | No tags | ||||
| Bus | Winston Salem Greyhound Bus Station | 537-517 W. Jackson Blvd | No tags | ||||
FlixBus + Greyhound | Bus | Winston Salem Greyhound Bus Station | Chicago 95Th & Dan Ryan | No tags | ||||
FlixBus + Greyhound | Bus | Winston Salem Greyhound Bus Station | Downtown Greyhound Station | No tags |
Get from Winston-Salem to Chicago
The journey takes about 1 day, 2 hours 55 minutes, and with fares starting at just $167, it presents an excellent value for a comfortable ride.
Where are the popular stops in Winston-Salem and Chicago?
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)
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
Compare bus companies
Based on 87394 reviews, the company was rated 3.5 stars on Busbud. Travellers were especially satisfied with the ticket access and the temperature but often complained with the WiFi. Greyhound ticket prices on this trip start at $167
Greyhound Winston-Salem Chicago recent customer reviews
The workers were very nice but the bus was very uncomfortable I traveled 18 hours with 2 kids and no WiFi like it said there would be the drivers were friendly though
Atresha W.
Frequently asked questions about travelling from Winston-Salem to Chicago by bus
What is the distance between Winston-Salem and Chicago?
It's about 906 km (562 miles) from Winston-Salem to Chicago.
What are the departure and arrival locations for buses traveling from Winston-Salem to Chicago?
Buses departing from Winston Salem Greyhound Bus Station in Winston-Salem will take you to Downtown Greyhound Station in Chicago.
Find cheapest prices for buses
Price is for a one-way ticket for one passenger and based on past searches.
The cheapest trip from Winston-Salem to Chicago was searched and found on Nov 28, 2025 with a price of $255To save money and be sure you have the best seat, it's a good idea to buy your bus tickets from Winston-Salem to Chicago, as early as possible.
You can expect to pay from $255 to $437 for a bus ticket from Winston-Salem to Chicago based on the last 2 days. You can expect to find the cheapest price for the trip at $255 which is on 2025-11-28.
