Previously seen journeys
| 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 £90, 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 87397 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 Wi-Fi. Greyhound ticket prices on this trip start at £90
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 by bus from Winston-Salem to Chicago
How far is Chicago from Winston-Salem by coach?
The journey from Winston-Salem to Chicago by coach covers an approximate distance of 562 miles (906 km).
What is the best way to go from Winston-Salem to Chicago without flying?
You can choose the coach to travel this route. The coach ensures a pleasant travel experience, granting you the opportunity to appreciate the scenery as you make your way to your final stop. 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 Winston-Salem to Chicago was searched and found on 28 Nov 2025 with a price of £137To 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 £137 to £224 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 £137, which is on 2025-11-28.
