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- This trip is recommended because it is the: CheapestDeparture time: June 6 atDeparture city: ChicagoDeparture location: 537-517 W. Jackson BlvdArrival time: June 8 atDestination city: Winston-SalemDestination location: Winston Salem Greyhound Bus StationOperated by: Greyhound Lines, Inc.
Vehicle: BusDuration: - This trip is recommended because it is the: FastestDeparture time: June 6 atDeparture city: ChicagoDeparture location: Downtown Greyhound StationArrival time: June 7 atDestination city: Winston-SalemDestination location: Winston Salem Greyhound Bus StationOperated by: Greyhound Lines, Inc.Vehicle: BusDuration:
- Departure time: June 6 atDeparture city: ChicagoDeparture location: Downtown Greyhound StationArrival time: June 7 atDestination city: Winston-SalemDestination location: Winston Salem Greyhound Bus StationOperated by: Greyhound Lines, Inc.Vehicle: BusDuration:
- Departure time: June 6 atDeparture city: ChicagoDeparture location: Chicago 95Th & Dan RyanArrival time: June 7 atDestination city: Winston-SalemDestination location: Winston Salem Greyhound Bus StationOperated by: Greyhound Lines, Inc.Vehicle: BusDuration:
Last refresh of the prices: Last Wednesday at 7:18 PM CDT.
Prices and availability are subject to change.
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Bus Chicago to Winston-Salem: Trip Overview
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Chicago to Winston-Salem Bus
Busbud helps you find a bus from Chicago to Winston-Salem. Get the best fare and schedule, book a round trip ticket or find buses with WiFi and electrical outlets.
We make sure you can find a bus service from Chicago to Winston-Salem from the most reliable bus companies operating this trip.
Discover how much the bus trip from Chicago to Winston-Salem will cost you. Use our filters and sorting features to find the cheapest bus tickets or luxury buses.
Where are the popular stops in Chicago and Winston-Salem?
Frequently asked questions on the trip Chicago - Winston-Salem
How long does it take to get to Winston-Salem from Chicago by bus?
The bus ride from Chicago to Winston-Salem takes 23h 10m, on average. For the shortest travel time, select the fastest bus available, which will take you to Winston-Salem in about 18h 25m.
What is the distance between Chicago and Winston-Salem?
Chicago and Winston-Salem are 906 km (562 miles) apart.
What are the departure and arrival locations for buses traveling from Chicago to Winston-Salem?
Buses departing from Downtown Greyhound Station in Chicago will take you to Winston Salem Greyhound Bus Station in Winston-Salem.
What is the cheapest way to get from Chicago to Winston-Salem?
The least expensive option to go from Chicago to Winston-Salem would be going by bus. With a starting ticket price of US$140, this bus becomes your top pick for this journey.
How much is the bus from Chicago to Winston-Salem?
The bus from Chicago to Winston-Salem will cost you US$180, on average.
Is it possible to travel by overnight bus from Chicago to Winston-Salem?
Yes! If you're heading from Chicago to Winston-Salem, you'll find buses departing until 11:50pm and arriving the next day.
Find cheapest prices for buses
Price is for a one-way ticket for one passenger and based on past searches.
The cheapest trip from Chicago to Winston-Salem was searched and found on Jun 6, 2025 with a price of US$129To save money and be sure you have the best seat, it's a good idea to buy your bus tickets from Chicago to Winston-Salem, as early as possible.
About Bus Travel
Bus Travel Tips
Make friends with the driver. They usually know a lot about your destination and may even recommend which side of the bus to sit on to get the best views on the road between Chicago and Winston-Salem!
Start sightseeing the minute your bus leaves the station. If you're on the night bus from Chicago to Winston-Salem, get comfy and count the stars.
Buses have one of the smallest carbon footprints of motorized transport modes. A bus going from Chicago to Winston-Salem will emit less CO2 than a car or an airplane.
Make a music playlist for your bus ride from Chicago to Winston-Salem, and enjoy the scenery to tunes from your own personal soundtrack.
Did you know?
It takes 27 hours to go by bus from Lima to Cusco, one of the craziest bus trips on the world. This route is used daily by locals and backpackers.
The bus driver with the longest career in the world drove more than 2,000,000 miles and is a happy World Record holder.
One of the longest bus route in the world goes all the way from Ontario to Alberta in Canada (with the same bus). This trip is 3,435 km or 2,135 miles long and the price is a bit under $100.
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