What is the distance between Winston-Salem and Chicago?

Winston-Salem and Chicago are 562 miles (906 km) apart.

What are the departure and arrival stations when taking the bus from Winston-Salem to Chicago?

If you're headed to Chicago from Winston-Salem, chances are that your bus will depart from Winston Salem Greyhound Bus Station and arrive at Downtown Greyhound Station. These are the most popular departure and arrival locations on this route, but you can also find other options that could better fit your plans.

What are the best sights and things to do in Chicago?

Once in Chicago, you can start exploring the city and discover its surroundings. The top sights and things to do are Lake Michigan, Robie House, Lincoln Park Conservatory, Auditorium Building and Theatre and Chicago Shakespeare Theater on Navy Pier.

Bus Winston-Salem to Chicago from $141 | Refundable Tickets

Next bus departures

Next departures for Winston-Salem to Chicago on November 22
Operated by	Vehicle type	Departure time	Departure location	Trip duration	Arrival time	Arrival location	Recommended
Greyhound Lines, Inc. + FlixBus	Bus	4:35pm	Winston Salem Greyhound Bus Station	1d 1h	5:05pm	Chicago 95Th & Dan Ryan	Cheapest
	Bus	4:35pm	Winston Salem Greyhound Bus Station	23h 40m	3:15pm	Downtown Greyhound Station	Fastest
	Bus	6:55am	Winston Salem Greyhound Bus Station	1d 2h	8:15am	Downtown Greyhound Station	No tags
Greyhound Lines, Inc. + FlixBus	Bus	10:25am	Winston Salem Greyhound Bus Station	1d 2h	11:30am	Downtown Greyhound Station	No tags
	Bus	7:10am	Winston Salem Greyhound Bus Station	1d 3h	10:00am	Downtown Greyhound Station	No tags

Last refresh of the prices: Yesterday at 9:49 PM EST.

Get from Winston-Salem to Chicago

This route is served by bus only

The journey takes about 1 day, 2 hours 55 minutes and with fares starting at just $116, it presents an excellent value for a comfortable ride.

12bus per day

1d 2hAverage Duration

562 milesDistance

23kgCO₂ emissions

Compare bus companies

Greyhound

3.5/587,382 reviews

Staff3.6

Timeliness2.9

Cleanliness3.3

Wifi2.4

Greyhound Lines offers the most comprehensive intercity bus services in the United States. They operate a modern, environmentally friendly fleet that serves more than 2400 destinations and carries nearly 16 million passengers annually. When traveling with them, you can expect free WiFi, onboard entertainment, bathrooms, power outlets and decent legroom. One of the great perks of Greyhound is that they connect big cities and smaller towns in the US, where you usually can't get to by train or plane. If you're looking for safe and affordable transportation, Greyhound is a great choice.

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.

February 8, 2019

US bus companies: FlixBus, BlaBlaCar Bus, ALSA, Greyhound, Intercape, Trenitalia, Sindbad

Where are the popular stops in Winston-Salem and Chicago?

Stops in Winston-Salem

A - Winston Salem Greyhound Bus Station

B - E Sprague St

C - Winston-Salem Bus Stop

D - 1237 Silas Creek Pkwy

Stops in Chicago

A - Downtown Greyhound Station

B - Chicago O'Hare International Airport

C - Polk St & Canal St

D - Tornado Bus S Kedzie Ave

E - Cumberland CTA

F - Turimex California Ave

Frequently asked questions about traveling from Winston-Salem to Chicago by bus

What is the distance between Winston-Salem and Chicago?
What are the departure and arrival stations when taking the bus from Winston-Salem to Chicago?
What are the best sights and things to do in Chicago?

Find cheapest prices for buses

Price is for a one-way ticket for one passenger and based on past searches.

Best price found

11/17

$187

11/18

$187

Today

$155

11/20

No data

11/21

No data

11/22

$141

11/23

No data

11/24

No data

The cheapest trip from Winston-Salem to Chicago was searched and found on Nov 22, 2025 with a price of $141

To 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 $141 to $279 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 $141 which is on 2025-11-22.