Next bus departures
| Operated by | Vehicle type | Departure time | Departure location | Trip duration | Arrival time | Arrival location | Recommended | Price and booking link |
|---|---|---|---|---|---|---|---|---|
Greyhound Lines, Inc. + FlixBus | Bus | Winston Salem Greyhound Bus Station | Chicago 95Th & Dan Ryan | Cheapest | ||||
 | Bus | Winston Salem Greyhound Bus Station | Downtown Greyhound Station | Fastest | ||||
| Bus | Winston Salem Greyhound Bus Station | Downtown Greyhound Station | No tags | ||||
Greyhound Lines, Inc. + FlixBus | Bus | Winston Salem Greyhound Bus Station | Downtown Greyhound Station | No tags | ||||
| Bus | Winston Salem Greyhound Bus Station | Downtown Greyhound Station | No tags |
Last refresh of the prices: Last Sunday at 7:02 PM EST.
Get from Winston-Salem to Chicago
The journey takes about 1 day, 2 hours 30 minutes, and with fares starting at just R 1 705, 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
- B
Chicago O'Hare International Airport
- 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 87500 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 R 1 705
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
Please note that timetables, routes, or operator details shown here may be updated or differ at the time of your trip.
How much is the bus ticket from Winston-Salem to Chicago?
The cheapest bus tickets from Winston-Salem to Chicago start at R 1 705. The average price for this route is around R 2 837. Busbud recommends booking your tickets in advance for the best chance of getting the lowest possible price.
How long is the bus journey from Winston-Salem to Chicago?
The average bus journey time from Winston-Salem to Chicago is 1d 2h, covering a distance of 893 km. The fastest bus gets you there in 23h 40m and is operated by Greyhound.
Which bus companies service the Winston-Salem to Chicago route?
Several major bus companies operate on this route with 13 buses available per day.
What is the earliest and latest departure time for the bus from Winston-Salem to Chicago?
The earliest bus departs from Winston-Salem to Chicago at 06:55. And the latest bus departs at 18:15.
What are the CO₂ emissions for the bus trip from Winston-Salem to Chicago?
A bus trip from Winston-Salem to Chicago produces an estimated 22 kg of CO₂, making it a highly eco-friendly travel option and Busbud’s recommended way to travel.
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 14 Jan 2026 with a price of R 1 585To 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 R 1 585 to R 3 874 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 R 1 945, which is on 2026-01-18.
