Bus Winston-Salem, NC to Chicago: Compare prices and save money

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

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

today

tomorrow

$149

Wednesday

$162

Thursday

Friday

$169

Saturday

Sunday

$163

Cheapest bus trips tomorrow
BertCompanyCountOneCompanyName	Duration	Departure time	From	Departure	Arrival time	To	Destination	Seat classes	Price
Greyhound US	25h 30m	4:35 PM	Winston-Salem, NC	Greyhound Bus Station	5:05 PM	Chicago	95th Red Line Station	Economy	$149	A Bus from Greyhound US goes from Greyhound Bus Station, Winston-Salem, NC (USA) at 12/23/2025 4:35:00 PM to 95th Red Line Station, Chicago (USA) arriving at 12/24/2025 5:05:00 PM. 50 Economy ticket for $149 per person are available. Travel duration is 25h 30m
Greyhound US	29h 45m	6:15 PM	Winston-Salem, NC	Greyhound Bus Station	11:00 PM	Chicago	95th Red Line Station	Economy	$149	A Bus from Greyhound US goes from Greyhound Bus Station, Winston-Salem, NC (USA) at 12/23/2025 6:15:00 PM to 95th Red Line Station, Chicago (USA) arriving at 12/24/2025 11:00:00 PM. 50 Economy ticket for $149 per person are available. Travel duration is 29h 45m
Greyhound US	38h 45m	6:15 PM	Winston-Salem, NC	Greyhound Bus Station	8:00 AM	Chicago	Union Station	Economy	$155	A Bus from Greyhound US goes from Greyhound Bus Station, Winston-Salem, NC (USA) at 12/23/2025 6:15:00 PM to Union Station, Chicago (USA) arriving at 12/25/2025 8:00:00 AM. 50 Economy ticket for $155 per person are available. Travel duration is 38h 45m
Greyhound US	23h 40m	4:35 PM	Winston-Salem, NC	Greyhound Bus Station	3:15 PM	Chicago	Downtown Bus Station	Economy	$156	A Bus from Greyhound US goes from Greyhound Bus Station, Winston-Salem, NC (USA) at 12/23/2025 4:35:00 PM to Downtown Bus Station, Chicago (USA) arriving at 12/24/2025 3:15:00 PM. 50 Economy ticket for $156 per person are available. Travel duration is 23h 40m
Greyhound US	26h 55m	6:15 PM	Winston-Salem, NC	Greyhound Bus Station	8:10 PM	Chicago	Downtown Bus Station	Economy	$156	A Bus from Greyhound US goes from Greyhound Bus Station, Winston-Salem, NC (USA) at 12/23/2025 6:15:00 PM to Downtown Bus Station, Chicago (USA) arriving at 12/24/2025 8:10:00 PM. 50 Economy ticket for $156 per person are available. Travel duration is 26h 55m

Cheapest bus trips Wednesday
BertCompanyCountOneCompanyName	Duration	Departure time	From	Departure	Arrival time	To	Destination	Seat classes	Price
Greyhound US	25h 40m	10:25 AM	Winston-Salem, NC	Greyhound Bus Station	11:05 AM	Chicago	95th Red Line Station	Economy	$162	A Bus from Greyhound US goes from Greyhound Bus Station, Winston-Salem, NC (USA) at 12/24/2025 10:25:00 AM to 95th Red Line Station, Chicago (USA) arriving at 12/25/2025 11:05:00 AM. 50 Economy ticket for $162 per person are available. Travel duration is 25h 40m
Greyhound US	25h 30m	4:35 PM	Winston-Salem, NC	Greyhound Bus Station	5:05 PM	Chicago	95th Red Line Station	Economy	$162	A Bus from Greyhound US goes from Greyhound Bus Station, Winston-Salem, NC (USA) at 12/24/2025 4:35:00 PM to 95th Red Line Station, Chicago (USA) arriving at 12/25/2025 5:05:00 PM. 50 Economy ticket for $162 per person are available. Travel duration is 25h 30m
Greyhound US	29h 45m	6:15 PM	Winston-Salem, NC	Greyhound Bus Station	11:00 PM	Chicago	95th Red Line Station	Economy	$163	A Bus from Greyhound US goes from Greyhound Bus Station, Winston-Salem, NC (USA) at 12/24/2025 6:15:00 PM to 95th Red Line Station, Chicago (USA) arriving at 12/25/2025 11:00:00 PM. 50 Economy ticket for $163 per person are available. Travel duration is 29h 45m
Greyhound US	27h 55m	6:55 AM	Winston-Salem, NC	Greyhound Bus Station	9:50 AM	Chicago	95th Red Line Station	Economy	$170	A Bus from Greyhound US goes from Greyhound Bus Station, Winston-Salem, NC (USA) at 12/24/2025 6:55:00 AM to 95th Red Line Station, Chicago (USA) arriving at 12/25/2025 9:50:00 AM. 50 Economy ticket for $170 per person are available. Travel duration is 27h 55m

Did you know that if you travel from Winston-Salem, NC to Chicago via Salisbury, NC, you can save more than $27? You can find the corresponding connections below.
- FlixBus
  
  29h 45m
  
  0
  
  6:15 PM
  
  Winston-Salem, NC
  Greyhound Bus Station
  
  6:55 PM
  
  Salisbury, NC
  Greyhound bus station
  
  0
  
  Economy
  
  $13
  
  A Bus from FlixBus goes from Greyhound Bus Station, Winston-Salem, NC (USA) at 12/23/2025 6:15:00 PM to Greyhound bus station, Salisbury, NC (USA) arriving at 12/23/2025 6:55:00 PM. 50 Economy ticket for $13 per person are available. Travel duration is 0h 40m
- FlixBus
  
  28h 55m
  
  0
  
  7:05 PM
  
  Salisbury, NC
  Greyhound bus station
  
  11:00 PM
  
  Chicago
  95th Red Line Station
  
  0
  
  Economy
  
  $122
  
  A Bus from FlixBus goes from Greyhound bus station, Salisbury, NC (USA) at 12/23/2025 7:05:00 PM to 95th Red Line Station, Chicago (USA) arriving at 12/24/2025 11:00:00 PM. 50 Economy ticket for $122 per person are available. Travel duration is 28h 55m
Travel time is 5h 15m longer, but you will save $27

Cheapest bus trips Friday
BertCompanyCountOneCompanyName	Duration	Departure time	From	Departure	Arrival time	To	Destination	Seat classes	Price
Greyhound US	27h 15m	5:55 PM	Winston-Salem, NC	Greyhound Bus Station	8:10 PM	Chicago	Downtown Bus Station	Economy	$169	A Bus from Greyhound US goes from Greyhound Bus Station, Winston-Salem, NC (USA) at 12/26/2025 5:55:00 PM to Downtown Bus Station, Chicago (USA) arriving at 12/27/2025 8:10:00 PM. 50 Economy ticket for $169 per person are available. Travel duration is 27h 15m
Greyhound US	23h 40m	4:35 PM	Winston-Salem, NC	Greyhound Bus Station	3:15 PM	Chicago	Downtown Bus Station	Economy	$174	A Bus from Greyhound US goes from Greyhound Bus Station, Winston-Salem, NC (USA) at 12/26/2025 4:35:00 PM to Downtown Bus Station, Chicago (USA) arriving at 12/27/2025 3:15:00 PM. 50 Economy ticket for $174 per person are available. Travel duration is 23h 40m
Greyhound US	27h 50m	7:10 AM	Winston-Salem, NC	Greyhound Bus Station	10:00 AM	Chicago	Downtown Bus Station	Economy	$176	A Bus from Greyhound US goes from Greyhound Bus Station, Winston-Salem, NC (USA) at 12/26/2025 7:10:00 AM to Downtown Bus Station, Chicago (USA) arriving at 12/27/2025 10:00:00 AM. 50 Economy ticket for $176 per person are available. Travel duration is 27h 50m
Greyhound US	30h 5m	5:55 PM	Winston-Salem, NC	Greyhound Bus Station	11:00 PM	Chicago	95th Red Line Station	Economy	$180	A Bus from Greyhound US goes from Greyhound Bus Station, Winston-Salem, NC (USA) at 12/26/2025 5:55:00 PM to 95th Red Line Station, Chicago (USA) arriving at 12/27/2025 11:00:00 PM. 50 Economy ticket for $180 per person are available. Travel duration is 30h 5m
Greyhound US	25h 30m	4:35 PM	Winston-Salem, NC	Greyhound Bus Station	5:05 PM	Chicago	95th Red Line Station	Economy	$186	A Bus from Greyhound US goes from Greyhound Bus Station, Winston-Salem, NC (USA) at 12/26/2025 4:35:00 PM to 95th Red Line Station, Chicago (USA) arriving at 12/27/2025 5:05:00 PM. 50 Economy ticket for $186 per person are available. Travel duration is 25h 30m

Did you know that if you travel from Winston-Salem, NC to Chicago via Salisbury, NC, you can save more than $34? You can find the corresponding connections below.
- FlixBus
  
  29h 45m
  
  0
  
  6:15 PM
  
  Winston-Salem, NC
  Greyhound Bus Station
  
  6:55 PM
  
  Salisbury, NC
  Greyhound bus station
  
  0
  
  Economy
  
  $13
  
  A Bus from FlixBus goes from Greyhound Bus Station, Winston-Salem, NC (USA) at 12/23/2025 6:15:00 PM to Greyhound bus station, Salisbury, NC (USA) arriving at 12/23/2025 6:55:00 PM. 50 Economy ticket for $13 per person are available. Travel duration is 0h 40m
- FlixBus
  
  28h 55m
  
  0
  
  7:05 PM
  
  Salisbury, NC
  Greyhound bus station
  
  11:00 PM
  
  Chicago
  95th Red Line Station
  
  0
  
  Economy
  
  $122
  
  A Bus from FlixBus goes from Greyhound bus station, Salisbury, NC (USA) at 12/23/2025 7:05:00 PM to 95th Red Line Station, Chicago (USA) arriving at 12/24/2025 11:00:00 PM. 50 Economy ticket for $122 per person are available. Travel duration is 28h 55m
Travel time is 7h 5m longer, but you will save $34

Cheapest bus trips Sunday
BertCompanyCountOneCompanyName	Duration	Departure time	From	Departure	Arrival time	To	Destination	Seat classes	Price
Greyhound US	30h 5m	5:55 PM	Winston-Salem, NC	Greyhound Bus Station	11:00 PM	Chicago	95th Red Line Station	Economy	$163	A Bus from Greyhound US goes from Greyhound Bus Station, Winston-Salem, NC (USA) at 12/28/2025 5:55:00 PM to 95th Red Line Station, Chicago (USA) arriving at 12/29/2025 11:00:00 PM. 50 Economy ticket for $163 per person are available. Travel duration is 30h 5m
Greyhound US	27h 55m	6:55 AM	Winston-Salem, NC	Greyhound Bus Station	9:50 AM	Chicago	95th Red Line Station	Economy	$174	A Bus from Greyhound US goes from Greyhound Bus Station, Winston-Salem, NC (USA) at 12/28/2025 6:55:00 AM to 95th Red Line Station, Chicago (USA) arriving at 12/29/2025 9:50:00 AM. 50 Economy ticket for $174 per person are available. Travel duration is 27h 55m
Greyhound US	25h 30m	4:35 PM	Winston-Salem, NC	Greyhound Bus Station	5:05 PM	Chicago	95th Red Line Station	Economy	$174	A Bus from Greyhound US goes from Greyhound Bus Station, Winston-Salem, NC (USA) at 12/28/2025 4:35:00 PM to 95th Red Line Station, Chicago (USA) arriving at 12/29/2025 5:05:00 PM. 50 Economy ticket for $174 per person are available. Travel duration is 25h 30m
Greyhound US	25h 40m	10:25 AM	Winston-Salem, NC	Greyhound Bus Station	11:05 AM	Chicago	95th Red Line Station	Economy	$192	A Bus from Greyhound US goes from Greyhound Bus Station, Winston-Salem, NC (USA) at 12/28/2025 10:25:00 AM to 95th Red Line Station, Chicago (USA) arriving at 12/29/2025 11:05:00 AM. 50 Economy ticket for $192 per person are available. Travel duration is 25h 40m

Did you know that if you travel from Winston-Salem, NC to Chicago via Salisbury, NC, you can save more than $28? You can find the corresponding connections below.
- FlixBus
  
  29h 45m
  
  0
  
  6:15 PM
  
  Winston-Salem, NC
  Greyhound Bus Station
  
  6:55 PM
  
  Salisbury, NC
  Greyhound bus station
  
  0
  
  Economy
  
  $13
  
  A Bus from FlixBus goes from Greyhound Bus Station, Winston-Salem, NC (USA) at 12/23/2025 6:15:00 PM to Greyhound bus station, Salisbury, NC (USA) arriving at 12/23/2025 6:55:00 PM. 50 Economy ticket for $13 per person are available. Travel duration is 0h 40m
- FlixBus
  
  28h 55m
  
  0
  
  7:05 PM
  
  Salisbury, NC
  Greyhound bus station
  
  11:00 PM
  
  Chicago
  95th Red Line Station
  
  0
  
  Economy
  
  $122
  
  A Bus from FlixBus goes from Greyhound bus station, Salisbury, NC (USA) at 12/23/2025 7:05:00 PM to 95th Red Line Station, Chicago (USA) arriving at 12/24/2025 11:00:00 PM. 50 Economy ticket for $122 per person are available. Travel duration is 28h 55m
Travel time is 5h 15m longer, but you will save $28

Best Price Offer: The price for the cheapest bus from Winston-Salem, NC to Chicago is $147 on 12/21/2025. Flexible travelers save on ticket prices.

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

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

Tuesday is the busiest day, with more than 12 daily buses from Winston-Salem, NC to Chicago. Sunday has instead the fewest connections, with only 4 daily coaches between Winston-Salem, NC and Chicago.

The busiest time of the day is the Morning, with 18 buses from Winston-Salem, NC to Chicago, while Evening sees the fewest connections between Winston-Salem, NC and Chicago, with 4 offers.

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

Compare all providers like Greyhound US that travel 8 times every day by bus from Winston-Salem, NC to Chicago in one click! Book your bus ticket from Winston-Salem, NC to Chicago starting from $147!

Cheapest Bus	$147
Fastest Bus	22h 40m
Earliest Bus	6:55 AM
Latest Bus	5:55 PM
Daily Bus Routes	8 Ø
Distance	562.8 miles
Bus Companies	Greyhound US

Cheapest bus connections from Winston-Salem, NC to Chicago

Every day, 8 buses from 1 bus companies leave Winston-Salem, NC for Chicago: in the table below, you will find the cheapest prices for a bus ticket for this route, starting from 12/22/2025 and for the following days.

Sunday

Monday

Tuesday

Wednesday

Thursday

Friday

Saturday

Sunday 12/21

Monday 12/22

Tuesday 12/23

$149

Wednesday 12/24

$162

Thursday 12/25

Friday 12/26

$169

Saturday 12/27

Sunday 12/28

$163

Monday 12/29

$153

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

Sunday 01/11

Monday 01/12

Tuesday 01/13

Wednesday 01/14

Thursday 01/15

Friday 01/16

Saturday 01/17

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

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

With a price starting from $149, Tuesday is the cheapest day for a bus from Winston-Salem, NC to Chicago. Friday instead is the most expensive day with prices starting from $169.

Afternoon is the cheapest day time for bus tickets from Winston-Salem, NC to Chicago, with $149. Morning is the most expensive time of the day with prices starting from $158.

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

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 Winston-Salem, NC to Chicago 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 Winston-Salem, NC to Chicago, 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 Winston-Salem, NC to Chicago are also emptier.

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

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

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.

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

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

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

FAQs about the Winston-Salem, NC to Chicago bus

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

This depends on, among other things, the day and time of travel. The cheapest trip is available from $147 and takes 24h 30m to reach Chicago. Compare offers to save money!

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

This route is offered by 1 companies with a range of ticket prices between $147 and $230. Thus, we recommend booking your ticket as early as possible to make sure you get the cheapest bus ticket to Chicago.

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

Every day, the Winston-Salem, NC to Chicago bus route is served by approximately 8 connections. With our search, you can compare bus times to find the perfect trip.

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

The fastest bus from Winston-Salem, NC to Chicago is offered by Greyhound US and takes 22h 40m. Bus tickets for this connection cost $156. In this context, bear in mind that the journey can take longer due to traffic.

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

The earliest bus arriving in Chicago from Winston-Salem, NC starts at 6:55 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 Winston-Salem, NC to Chicago?

The latest bus trip departing from Winston-Salem, NC for Chicago starts at 5:55 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 Winston-Salem, NC Chicago route?

When traveling by bus from Winston-Salem, NC to Chicago, 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 Winston-Salem, NC and Chicago?

You can check all the direct connections between Winston-Salem, NC and Chicago 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 Winston-Salem, NC to Chicago 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 Winston-Salem, NC Chicago 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 Winston-Salem, NC Chicago 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 Winston-Salem, NC to Chicago on your planned travel date.

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

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 8 daily trips between Winston-Salem, NC and Chicago. 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 Winston-Salem, NC to Chicago?

Prices and availability for 8 trips between Winston-Salem, NC and Chicago 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 Winston-Salem, NC to Chicago

Economy

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

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

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