Bus Chicago to Winston-Salem, NC - Compare all Companies

Compare all timetables for the bus from Chicago to Winston-Salem, NC

Here is a selection of the cheapest bus trips from the schedule from Chicago to Winston-Salem, NC from various bus operators like Greyhound US for the next days.

today

tomorrow

$168

Monday

Tuesday

$179

Wednesday

Thursday

Friday

$170

Cheapest bus trips tomorrow
BertCompanyCountOneCompanyName	Duration	Departure time	From	Departure	Arrival time	To	Destination	Seat classes	Price
Greyhound US	30h 35m	11:10 PM	Chicago	Union Station	6:45 AM	Winston-Salem, NC	Greyhound Bus Station	Economy	$168	A Bus from Greyhound US goes from Union Station, Chicago (USA) at 12/21/2025 11:10:00 PM to Greyhound Bus Station, Winston-Salem, NC (USA) arriving at 12/23/2025 6:45:00 AM. 50 Economy ticket for $168 per person are available. Travel duration is 30h 35m
Greyhound US	18h 30m	2:45 PM	Chicago	Downtown Bus Station	10:15 AM	Winston-Salem, NC	Greyhound Bus Station	Economy	$170	A Bus from Greyhound US goes from Downtown Bus Station, Chicago (USA) at 12/21/2025 2:45:00 PM to Greyhound Bus Station, Winston-Salem, NC (USA) arriving at 12/22/2025 10:15:00 AM. 50 Economy ticket for $170 per person are available. Travel duration is 18h 30m
Greyhound US	23h 15m	10:00 AM	Chicago	Union Station	10:15 AM	Winston-Salem, NC	Greyhound Bus Station	Economy	$187	A Bus from Greyhound US goes from Union Station, Chicago (USA) at 12/21/2025 10:00:00 AM to Greyhound Bus Station, Winston-Salem, NC (USA) arriving at 12/22/2025 10:15:00 AM. 50 Economy ticket for $187 per person are available. Travel duration is 23h 15m
Greyhound US	23h 50m	6:10 AM	Chicago	Downtown Bus Station	7:00 AM	Winston-Salem, NC	Greyhound Bus Station	Economy	$206	A Bus from Greyhound US goes from Downtown Bus Station, Chicago (USA) at 12/21/2025 6:10:00 AM to Greyhound Bus Station, Winston-Salem, NC (USA) arriving at 12/22/2025 7:00:00 AM. 50 Economy ticket for $206 per person are available. Travel duration is 23h 50m

Did you know that if you travel from Chicago to Winston-Salem, NC via Charlotte, you can save more than $26? You can find the corresponding connections below.
- Busbud
  
  23h 50m
  
  0
  
  6:10 AM
  
  Chicago
  Downtown Bus Station
  
  5:00 AM
  
  Charlotte
  W Trade St
  
  0
  
  Economy
  
  $119
  
  A Bus from Busbud goes from Downtown Bus Station, Chicago (USA) at 12/23/2025 6:10:00 AM to W Trade St, Charlotte (USA) arriving at 12/24/2025 5:00:00 AM. 50 Economy ticket for $119 per person are available. Travel duration is 21h 50m
- FlixBus
  
  1h 40m
  
  0
  
  5:20 AM
  
  Charlotte
  W Trade St
  
  7:00 AM
  
  Winston-Salem, NC
  Greyhound Bus Station
  
  0
  
  Economy
  
  $23
  
  A Bus from FlixBus goes from W Trade St, Charlotte (USA) at 12/24/2025 5:20:00 AM to Greyhound Bus Station, Winston-Salem, NC (USA) arriving at 12/24/2025 7:00:00 AM. 50 Economy ticket for $23 per person are available. Travel duration is 1h 40m
Travel time is 4h 20m longer, but you will save $26

Cheapest bus trips Tuesday
BertCompanyCountOneCompanyName	Duration	Departure time	From	Departure	Arrival time	To	Destination	Seat classes	Price
Greyhound US	18h 30m	2:45 PM	Chicago	Downtown Bus Station	10:15 AM	Winston-Salem, NC	Greyhound Bus Station	Economy	$179	A Bus from Greyhound US goes from Downtown Bus Station, Chicago (USA) at 12/23/2025 2:45:00 PM to Greyhound Bus Station, Winston-Salem, NC (USA) arriving at 12/24/2025 10:15:00 AM. 50 Economy ticket for $179 per person are available. Travel duration is 18h 30m
Greyhound US	30h 35m	11:10 PM	Chicago	Union Station	6:45 AM	Winston-Salem, NC	Greyhound Bus Station	Economy	$192	A Bus from Greyhound US goes from Union Station, Chicago (USA) at 12/23/2025 11:10:00 PM to Greyhound Bus Station, Winston-Salem, NC (USA) arriving at 12/25/2025 6:45:00 AM. 50 Economy ticket for $192 per person are available. Travel duration is 30h 35m
Greyhound US	23h 15m	10:00 AM	Chicago	Union Station	10:15 AM	Winston-Salem, NC	Greyhound Bus Station	Economy	$202	A Bus from Greyhound US goes from Union Station, Chicago (USA) at 12/23/2025 10:00:00 AM to Greyhound Bus Station, Winston-Salem, NC (USA) arriving at 12/24/2025 10:15:00 AM. 50 Economy ticket for $202 per person are available. Travel duration is 23h 15m
Greyhound US	23h 50m	6:10 AM	Chicago	Downtown Bus Station	7:00 AM	Winston-Salem, NC	Greyhound Bus Station	Economy	$225	A Bus from Greyhound US goes from Downtown Bus Station, Chicago (USA) at 12/23/2025 6:10:00 AM to Greyhound Bus Station, Winston-Salem, NC (USA) arriving at 12/24/2025 7:00:00 AM. 50 Economy ticket for $225 per person are available. Travel duration is 23h 50m

Did you know that if you travel from Chicago to Winston-Salem, NC via Charlotte, you can save more than $37? You can find the corresponding connections below.
- Busbud
  
  23h 50m
  
  0
  
  6:10 AM
  
  Chicago
  Downtown Bus Station
  
  5:00 AM
  
  Charlotte
  W Trade St
  
  0
  
  Economy
  
  $119
  
  A Bus from Busbud goes from Downtown Bus Station, Chicago (USA) at 12/23/2025 6:10:00 AM to W Trade St, Charlotte (USA) arriving at 12/24/2025 5:00:00 AM. 50 Economy ticket for $119 per person are available. Travel duration is 21h 50m
- FlixBus
  
  1h 40m
  
  0
  
  5:20 AM
  
  Charlotte
  W Trade St
  
  7:00 AM
  
  Winston-Salem, NC
  Greyhound Bus Station
  
  0
  
  Economy
  
  $23
  
  A Bus from FlixBus goes from W Trade St, Charlotte (USA) at 12/24/2025 5:20:00 AM to Greyhound Bus Station, Winston-Salem, NC (USA) arriving at 12/24/2025 7:00:00 AM. 50 Economy ticket for $23 per person are available. Travel duration is 1h 40m
Travel time is 4h 20m longer, but you will save $37

Cheapest bus trips Friday
BertCompanyCountOneCompanyName	Duration	Departure time	From	Departure	Arrival time	To	Destination	Seat classes	Price
Greyhound US	18h 30m	2:45 PM	Chicago	Downtown Bus Station	10:15 AM	Winston-Salem, NC	Greyhound Bus Station	Economy	$170	A Bus from Greyhound US goes from Downtown Bus Station, Chicago (USA) at 12/26/2025 2:45:00 PM to Greyhound Bus Station, Winston-Salem, NC (USA) arriving at 12/27/2025 10:15:00 AM. 50 Economy ticket for $170 per person are available. Travel duration is 18h 30m
Greyhound US	30h 35m	11:10 PM	Chicago	Union Station	6:45 AM	Winston-Salem, NC	Greyhound Bus Station	Economy	$192	A Bus from Greyhound US goes from Union Station, Chicago (USA) at 12/26/2025 11:10:00 PM to Greyhound Bus Station, Winston-Salem, NC (USA) arriving at 12/28/2025 6:45:00 AM. 50 Economy ticket for $192 per person are available. Travel duration is 30h 35m
Greyhound US	23h 15m	10:00 AM	Chicago	Union Station	10:15 AM	Winston-Salem, NC	Greyhound Bus Station	Economy	$194	A Bus from Greyhound US goes from Union Station, Chicago (USA) at 12/26/2025 10:00:00 AM to Greyhound Bus Station, Winston-Salem, NC (USA) arriving at 12/27/2025 10:15:00 AM. 50 Economy ticket for $194 per person are available. Travel duration is 23h 15m
Greyhound US	23h 50m	6:10 AM	Chicago	Downtown Bus Station	7:00 AM	Winston-Salem, NC	Greyhound Bus Station	Economy	$207	A Bus from Greyhound US goes from Downtown Bus Station, Chicago (USA) at 12/26/2025 6:10:00 AM to Greyhound Bus Station, Winston-Salem, NC (USA) arriving at 12/27/2025 7:00:00 AM. 50 Economy ticket for $207 per person are available. Travel duration is 23h 50m

Did you know that if you travel from Chicago to Winston-Salem, NC via Charlotte, you can save more than $28? You can find the corresponding connections below.
- Busbud
  
  23h 50m
  
  0
  
  6:10 AM
  
  Chicago
  Downtown Bus Station
  
  5:00 AM
  
  Charlotte
  W Trade St
  
  0
  
  Economy
  
  $119
  
  A Bus from Busbud goes from Downtown Bus Station, Chicago (USA) at 12/23/2025 6:10:00 AM to W Trade St, Charlotte (USA) arriving at 12/24/2025 5:00:00 AM. 50 Economy ticket for $119 per person are available. Travel duration is 21h 50m
- FlixBus
  
  1h 40m
  
  0
  
  5:20 AM
  
  Charlotte
  W Trade St
  
  7:00 AM
  
  Winston-Salem, NC
  Greyhound Bus Station
  
  0
  
  Economy
  
  $23
  
  A Bus from FlixBus goes from W Trade St, Charlotte (USA) at 12/24/2025 5:20:00 AM to Greyhound Bus Station, Winston-Salem, NC (USA) arriving at 12/24/2025 7:00:00 AM. 50 Economy ticket for $23 per person are available. Travel duration is 1h 40m
Travel time is 4h 20m longer, but you will save $28

Best Price Offer: The price for the cheapest bus from Chicago to Winston-Salem, NC is $152 on 12/19/2025. Flexible travelers save on ticket prices.

Frequency of bus connections between Chicago and Winston-Salem, NC

See here how frequent the connections between Chicago and Winston-Salem, NC are, during different times and days of the week.

Sunday is the busiest day, with more than 4 daily buses from Chicago to Winston-Salem, NC. Sunday has instead the fewest connections, with only 4 daily coaches between Chicago and Winston-Salem, NC.

The busiest time of the day is the Morning, with 6 buses from Chicago to Winston-Salem, NC, while Afternoon sees the fewest connections between Chicago and Winston-Salem, NC, with 3 offers.

Facts about the bus from Chicago to Winston-Salem, NC

Compare all providers like Greyhound US that travel 4 times every day by bus from Chicago to Winston-Salem, NC in one click! Book your bus ticket from Chicago to Winston-Salem, NC starting from $152!

Cheapest Bus	$152
Fastest Bus	19h 30m
Earliest Bus	6:10 AM
Latest Bus	11:10 PM
Daily Bus Routes	4 Ø
Distance	562.8 miles
Bus Companies	Greyhound US

Cheapest bus connections from Chicago to Winston-Salem, NC

Every day, 4 buses from 1 bus companies leave Chicago for Winston-Salem, NC: in the table below, you will find the cheapest prices for a bus ticket for this route, starting from 12/20/2025 and for the following days.

Sunday

Monday

Tuesday

Wednesday

Thursday

Friday

Saturday

Sunday 12/14

Monday 12/15

Tuesday 12/16

Wednesday 12/17

Thursday 12/18

Friday 12/19

Saturday 12/20

Sunday 12/21

$168

Monday 12/22

Tuesday 12/23

$179

Wednesday 12/24

Thursday 12/25

Friday 12/26

$170

Saturday 12/27

Sunday 12/28

$160

Monday 12/29

Tuesday 12/30

Wednesday 12/31

Thursday 01/01

Friday 01/02

Saturday 01/03

Sunday 01/04

Monday 01/05

Tuesday 01/06

Wednesday 01/07

Thursday 01/08

Friday 01/09

Saturday 01/10

The cheapest time to travel from Chicago to Winston-Salem, NC

See here on which day and which time of the day you can find the cheapest bus ticket from Chicago to Winston-Salem, NC, for the next 30 days.

With a price starting from $160, Sunday is the cheapest day for a bus from Chicago to Winston-Salem, NC. Tuesday instead is the most expensive day with prices starting from $179.

Evening is the cheapest day time for bus tickets from Chicago to Winston-Salem, NC, with $168. Morning is the most expensive time of the day with prices starting from $187.

How to save money travelling from Chicago to Winston-Salem, NC

Travel can be expensive, but it doesn't need to be! Do you want to avoid paying a terrible price for your trip? Then follow these quick steps to save money:

Book the ticket from Chicago to Winston-Salem, NC in advance! The earlier you book, the cheaper usually the price is. Also, you will be sure to have a place on the bus from Chicago to Winston-Salem, NC, compared instead if you buy it at the last moment, or directly at the station.

If you can, avoid travelling at peak times. Instead of weekend, try travelling during the week. Travelling in the evening or at night it’s also cheaper, and later buses from Chicago to Winston-Salem, NC are also emptier.

All bus stations and stops in Chicago and Winston-Salem, NC

In the map below, you can see where to find all bus stations in Chicago and Winston-Salem, NC.

95th Red Line Station

W. 95th St 14

Downtown Bus Station

West Harrison Street 630-670

Union Station

S Canal St 225

Cumberland CTA

N Cumberland Ave 5800

Canal & Van Buren

S Canal St 310-320

Greyhound Bus Station

W 5th St 100

Hong Kong King Buffet

Silas Creek Pkwy 1237

Forsyth Hospital

Silas Creek Pkwy 3333

E Sprague St

E Sprague St 841

Hicks St.

Service and Comfort on the bus from Chicago to Winston-Salem, NC

Want to know which seat classes are available on the buses from Chicago to Winston-Salem, NC? Or which bus companies serve the route Chicago to Winston-Salem, NC? Below you will find answers to your questions.

FAQs about the Chicago to Winston-Salem, NC bus

How much does a Chicago Winston-Salem, NC bus trip cost?

This depends on, among other things, the day and time of travel. The cheapest trip is available from $152 and takes 31h 35m to reach Winston-Salem, NC. Compare offers to save money!

How much could I save by comparing buses from Chicago to Winston-Salem, NC?

This route is offered by 1 companies with a range of ticket prices between $152 and $225. Thus, we recommend booking your ticket as early as possible to make sure you get the cheapest bus ticket to Winston-Salem, NC.

On average, how many connections are available from Chicago to Winston-Salem, NC each day?

Every day, the Chicago to Winston-Salem, NC bus route is served by approximately 4 connections. With our search, you can compare bus times to find the perfect trip.

How long does a bus journey from Chicago to Winston-Salem, NC take?

The fastest bus from Chicago to Winston-Salem, NC is offered by Greyhound US and takes 19h 30m. Bus tickets for this connection cost $170. In this context, bear in mind that the journey can take longer due to traffic.

What time is the first bus from Chicago to Winston-Salem, NC?

The earliest bus arriving in Winston-Salem, NC from Chicago starts at 6:10 AM. However, information regarding departure times may differ on weekends and holidays. Simply use our search to find exact times for your planned travel date.

What time is the last bus from Chicago to Winston-Salem, NC?

The latest bus trip departing from Chicago for Winston-Salem, NC starts at 11:10 PM. Please note that departure times may differ on weekends and holidays. So just use our search to find the exact times for your planned travel date.

Which bus companies operate the Chicago Winston-Salem, NC route?

When traveling by bus from Chicago to Winston-Salem, NC, passengers can travel with Greyhound US. With our search, you can compare all available bus tickets to book the one that works for you.

Is there a direct bus between Chicago and Winston-Salem, NC?

You can check all the direct connections between Chicago and Winston-Salem, NC by using our search and looking at the Changes section in our filters. These are some of the companies which offer a direct bus: Greyhound US.

What can I take with me on the Chicago to Winston-Salem, NC bus route?

Depending on which provider you travel with, what you're allowed to bring with you can vary. Generally, you can take a suitcase and hand luggage with you on the Chicago Winston-Salem, NC bus route free of charge. Simply use our search to find a bus that is best suited to your needs for your planned travel date.

What equipment is available for the Chicago Winston-Salem, NC bus route?

The equipment on board differs depending on the provider. However, many long-distance buses have WiFi so you can tell your friends your exact location during the journey. To make traveling even more pleasant, air conditioning systems provide ventilation. It is best to use our search to get precise information about the equipment of the bus from Chicago to Winston-Salem, NC on your planned travel date.

How does CheckMyBus find the best bus deals from Chicago to Winston-Salem, NC?

CheckMyBus collaborates directly with companies around the world to provide you with the best options when searching for a trip. We retrieve their first-hand data to show you real-time prices, schedules, and seat availability for 4 daily trips between Chicago and Winston-Salem, NC. With the most up-to-date information from verified sources, you can fairly compare all available options and choose the trip that suits you best.

How does CheckMyBus technology work for trips from Chicago to Winston-Salem, NC?

Prices and availability for 4 trips between Chicago and Winston-Salem, NC change constantly. To provide you with the most up-to-date information, we connect directly with bus operators, Online Travel Agencies (OTAs), and Global Distribution Systems (GDS) via real-time interfaces (APIs). The data collected from these sources undergoes strict quality checks, is processed within our infrastructure, and is then presented to you on our search results pages. Visit our About Us page to learn more.

Available seat classes which are offered on the bus route Chicago to Winston-Salem, NC

Economy

The cheapest option available for your ticket, it usually comes with reclinable seats and AC.

More bus routes to Chicago and to Winston-Salem, NC

Here’s an overview of the most popular bus routes to Chicago and to Winston-Salem, NC. Simply click on the connection of your choice, and you will find all the details about your bus route!