Next bus departures
| 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 | Chicago 95Th & Dan Ryan | Cheapest | ||||
| Bus | Winston Salem Greyhound Bus Station | Downtown Greyhound Station | Fastest | ||||
Greyhound Lines, Inc. + FlixBus | Bus | Winston Salem Greyhound Bus Station | 537-517 W. Jackson Blvd | No tags |
Last refresh of the prices: Yesterday at 5:56 PM EST.
Get from Winston-Salem to Chicago
The journey takes about 1 day, 2 hours 55 minutes, and with fares starting at just $181, 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 87430 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 $197
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 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 Winston-Salem to Chicago?
The cheapest bus tickets from Winston-Salem to Chicago start from $181. The average price for this route is around $301. 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 Winston-Salem to Chicago?
The average bus travel time from Winston-Salem to Chicago is 1d 2h, covering a distance of 893 km. The quickest bus can get 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 are the earliest and latest departure times for the bus from Winston-Salem to Chicago?
The earliest bus departs from Winston-Salem to Chicago at 6:55am. And the latest bus departs at 6:15pm.
What are the CO₂ emissions for the bus trip from Winston-Salem to Chicago?
A bus trip from Winston-Salem to Chicago generates an estimated 22 kg of CO₂, making it a highly eco-friendly travel option and a mode of travel recommended 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 Winston-Salem to Chicago was searched and found on Dec 18, 2025 with a price of $207To 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 $207 to $397 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 $207 which is on 2025-12-18.
