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: Yesterday at 12:32 PM EST.
Get from Winston-Salem to Chicago
The journey takes about 1 day, 2 hours 55 minutes, and with fares starting at just R 2 026, it presents an excellent value for a comfortable ride.
Compare bus companies
Based on 87382 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 2 026
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.
Where are the popular stops in Winston-Salem and Chicago?
Frequently asked questions about travelling from Winston-Salem to Chicago by bus
How much does a bus ticket from Winston-Salem to Chicago cost?
The bus ticket price from Winston-Salem to Chicago starts at R 2 026. The best way to find cheap bus tickets from Winston-Salem to Chicago is to book your tickets as early as possible. Prices tend to rise as your travel date approaches, so book in advance to secure the best prices!
How long is the bus ride from Winston-Salem to Chicago?
The average travel time between Winston-Salem and Chicago is around 1d 2h, although the fastest bus will take about 23h 40m. This is the time it takes to travel the 906 km that separates the two cities.
How many daily bus connections are there between Winston-Salem and Chicago?
The number of buses from Winston-Salem to Chicago can differ depending on the day of the week. On average, there are 12 on this route. Some buses run direct routes, while others have layovers. Simplify your bus trip from Winston-Salem to Chicago by comparing and selecting the bus that fits your travel style and budget on Busbud.
Which bus companies travel from Winston-Salem to Chicago?
When taking the bus from Winston-Salem to Chicago, you can travel comfortably and safely with Greyhound.
What are the departure and arrival stations when taking the bus from Winston-Salem to Chicago?
Buses travelling between Winston-Salem and Chicago leave from Winston Salem Greyhound Bus Station or E Sprague St and arrive at Downtown Greyhound Station, Chicago O'Hare International Airport, Polk St & Canal St.
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 22 Nov 2025 with a price of R 2 480To 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 2 480 to R 4 907 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 2 480, which is on 2025-11-22.
