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

$89

Tuesday

Wednesday

$92

Thursday

Friday

$85

Saturday

$89

Cheapest bus trips tomorrow
BertCompanyCountOneCompanyName	Duration	Departure time	From	Departure	Arrival time	To	Destination	Seat classes	Price
Greyhound US	27h 55m	6:55 AM	Winston-Salem, NC	Greyhound Bus Station	9:50 AM	Chicago	95th Red Line Station	Economy	$89	A Bus from Greyhound US goes from Greyhound Bus Station, Winston-Salem, NC (USA) at 7/27/2026 6:55:00 AM to 95th Red Line Station, Chicago (USA) arriving at 7/28/2026 9:50:00 AM. 50 Economy ticket for $89 per person are available. Travel duration is 27h 55m
Greyhound US	26h 50m	4:35 PM	Winston-Salem, NC	Greyhound Bus Station	6:25 PM	Chicago	95th Red Line Station	Economy	$89	A Bus from Greyhound US goes from Greyhound Bus Station, Winston-Salem, NC (USA) at 7/27/2026 4:35:00 PM to 95th Red Line Station, Chicago (USA) arriving at 7/28/2026 6:25:00 PM. 50 Economy ticket for $89 per person are available. Travel duration is 26h 50m
Greyhound US	30h 40m	5:55 PM	Winston-Salem, NC	Greyhound Bus Station	11:35 PM	Chicago	95th Red Line Station	Economy	$89	A Bus from Greyhound US goes from Greyhound Bus Station, Winston-Salem, NC (USA) at 7/27/2026 5:55:00 PM to 95th Red Line Station, Chicago (USA) arriving at 7/28/2026 11:35:00 PM. 50 Economy ticket for $89 per person are available. Travel duration is 30h 40m
Greyhound US	25h 45m	10:20 AM	Winston-Salem, NC	Greyhound Bus Station	11:05 AM	Chicago	95th Red Line Station	Economy	$99	A Bus from Greyhound US goes from Greyhound Bus Station, Winston-Salem, NC (USA) at 7/27/2026 10:20:00 AM to 95th Red Line Station, Chicago (USA) arriving at 7/28/2026 11:05:00 AM. 50 Economy ticket for $99 per person are available. Travel duration is 25h 45m
Greyhound US	26h 5m	6:55 AM	Winston-Salem, NC	Greyhound Bus Station	8:00 AM	Chicago	Canal & Van Buren	Economy	$102	A Bus from Greyhound US goes from Greyhound Bus Station, Winston-Salem, NC (USA) at 7/27/2026 6:55:00 AM to Canal & Van Buren, Chicago (USA) arriving at 7/28/2026 8:00:00 AM. 50 Economy ticket for $102 per person are available. Travel duration is 26h 5m

Cheapest bus trips Wednesday
BertCompanyCountOneCompanyName	Duration	Departure time	From	Departure	Arrival time	To	Destination	Seat classes	Price
Greyhound US	28h 5m	4:35 PM	Winston-Salem, NC	Greyhound Bus Station	7:40 PM	Chicago	95th Red Line Station	Economy	$92	A Bus from Greyhound US goes from Greyhound Bus Station, Winston-Salem, NC (USA) at 7/29/2026 4:35:00 PM to 95th Red Line Station, Chicago (USA) arriving at 7/30/2026 7:40:00 PM. 50 Economy ticket for $92 per person are available. Travel duration is 28h 5m
Greyhound US	30h 40m	5:55 PM	Winston-Salem, NC	Greyhound Bus Station	11:35 PM	Chicago	95th Red Line Station	Economy	$92	A Bus from Greyhound US goes from Greyhound Bus Station, Winston-Salem, NC (USA) at 7/29/2026 5:55:00 PM to 95th Red Line Station, Chicago (USA) arriving at 7/30/2026 11:35:00 PM. 50 Economy ticket for $92 per person are available. Travel duration is 30h 40m
Greyhound US	25h 45m	10:20 AM	Winston-Salem, NC	Greyhound Bus Station	11:05 AM	Chicago	95th Red Line Station	Economy	$93	A Bus from Greyhound US goes from Greyhound Bus Station, Winston-Salem, NC (USA) at 7/29/2026 10:20:00 AM to 95th Red Line Station, Chicago (USA) arriving at 7/30/2026 11:05:00 AM. 50 Economy ticket for $93 per person are available. Travel duration is 25h 45m
Greyhound US	23h 40m	4:35 PM	Winston-Salem, NC	Greyhound Bus Station	3:15 PM	Chicago	Downtown Bus Station	Economy	$97	A Bus from Greyhound US goes from Greyhound Bus Station, Winston-Salem, NC (USA) at 7/29/2026 4:35:00 PM to Downtown Bus Station, Chicago (USA) arriving at 7/30/2026 3:15:00 PM. 50 Economy ticket for $97 per person are available. Travel duration is 23h 40m
Greyhound US	27h 15m	5:55 PM	Winston-Salem, NC	Greyhound Bus Station	8:10 PM	Chicago	Downtown Bus Station	Economy	$98	A Bus from Greyhound US goes from Greyhound Bus Station, Winston-Salem, NC (USA) at 7/29/2026 5:55:00 PM to Downtown Bus Station, Chicago (USA) arriving at 7/30/2026 8:10:00 PM. 50 Economy ticket for $98 per person are available. Travel duration is 27h 15m

Cheapest bus trips Friday
BertCompanyCountOneCompanyName	Duration	Departure time	From	Departure	Arrival time	To	Destination	Seat classes	Price
Greyhound US	26h 50m	4:35 PM	Winston-Salem, NC	Greyhound Bus Station	6:25 PM	Chicago	95th Red Line Station	Economy	$85	A Bus from Greyhound US goes from Greyhound Bus Station, Winston-Salem, NC (USA) at 7/31/2026 4:35:00 PM to 95th Red Line Station, Chicago (USA) arriving at 8/1/2026 6:25:00 PM. 50 Economy ticket for $85 per person are available. Travel duration is 26h 50m
Greyhound US	30h 40m	5:55 PM	Winston-Salem, NC	Greyhound Bus Station	11:35 PM	Chicago	95th Red Line Station	Economy	$85	A Bus from Greyhound US goes from Greyhound Bus Station, Winston-Salem, NC (USA) at 7/31/2026 5:55:00 PM to 95th Red Line Station, Chicago (USA) arriving at 8/1/2026 11:35:00 PM. 50 Economy ticket for $85 per person are available. Travel duration is 30h 40m
Greyhound US	25h 45m	10:20 AM	Winston-Salem, NC	Greyhound Bus Station	11:05 AM	Chicago	95th Red Line Station	Economy	$88	A Bus from Greyhound US goes from Greyhound Bus Station, Winston-Salem, NC (USA) at 7/31/2026 10:20:00 AM to 95th Red Line Station, Chicago (USA) arriving at 8/1/2026 11:05:00 AM. 50 Economy ticket for $88 per person are available. Travel duration is 25h 45m
Greyhound US	23h 40m	4:35 PM	Winston-Salem, NC	Greyhound Bus Station	3:15 PM	Chicago	Downtown Bus Station	Economy	$97	A Bus from Greyhound US goes from Greyhound Bus Station, Winston-Salem, NC (USA) at 7/31/2026 4:35:00 PM to Downtown Bus Station, Chicago (USA) arriving at 8/1/2026 3:15:00 PM. 50 Economy ticket for $97 per person are available. Travel duration is 23h 40m
Greyhound US	27h 55m	6:55 AM	Winston-Salem, NC	Greyhound Bus Station	9:50 AM	Chicago	95th Red Line Station	Economy	$98	A Bus from Greyhound US goes from Greyhound Bus Station, Winston-Salem, NC (USA) at 7/31/2026 6:55:00 AM to 95th Red Line Station, Chicago (USA) arriving at 8/1/2026 9:50:00 AM. 50 Economy ticket for $98 per person are available. Travel duration is 27h 55m

Cheapest bus trips Saturday
BertCompanyCountOneCompanyName	Duration	Departure time	From	Departure	Arrival time	To	Destination	Seat classes	Price
Greyhound US	26h 50m	4:35 PM	Winston-Salem, NC	Greyhound Bus Station	6:25 PM	Chicago	95th Red Line Station	Economy	$89	A Bus from Greyhound US goes from Greyhound Bus Station, Winston-Salem, NC (USA) at 8/1/2026 4:35:00 PM to 95th Red Line Station, Chicago (USA) arriving at 8/2/2026 6:25:00 PM. 50 Economy ticket for $89 per person are available. Travel duration is 26h 50m
Greyhound US	25h 45m	10:20 AM	Winston-Salem, NC	Greyhound Bus Station	11:05 AM	Chicago	95th Red Line Station	Economy	$94	A Bus from Greyhound US goes from Greyhound Bus Station, Winston-Salem, NC (USA) at 8/1/2026 10:20:00 AM to 95th Red Line Station, Chicago (USA) arriving at 8/2/2026 11:05:00 AM. 50 Economy ticket for $94 per person are available. Travel duration is 25h 45m
Greyhound US	30h 40m	5:55 PM	Winston-Salem, NC	Greyhound Bus Station	11:35 PM	Chicago	95th Red Line Station	Economy	$96	A Bus from Greyhound US goes from Greyhound Bus Station, Winston-Salem, NC (USA) at 8/1/2026 5:55:00 PM to 95th Red Line Station, Chicago (USA) arriving at 8/2/2026 11:35:00 PM. 50 Economy ticket for $96 per person are available. Travel duration is 30h 40m
Greyhound US	27h 55m	6:55 AM	Winston-Salem, NC	Greyhound Bus Station	9:50 AM	Chicago	95th Red Line Station	Economy	$104	A Bus from Greyhound US goes from Greyhound Bus Station, Winston-Salem, NC (USA) at 8/1/2026 6:55:00 AM to 95th Red Line Station, Chicago (USA) arriving at 8/2/2026 9:50:00 AM. 50 Economy ticket for $104 per person are available. Travel duration is 27h 55m

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.

Monday is the busiest day, with more than 24 daily buses from Winston-Salem, NC to Chicago. Saturday 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 32 buses from Winston-Salem, NC to Chicago, while Afternoon sees the fewest connections between Winston-Salem, NC and Chicago, with 24 offers.

Test cheapest views

The cheapest bus for the 7/31/2026 costs just $85, from Greyhound US

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

Compare all providers like Greyhound US that travel 14 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 $85!

Cheapest Bus	$85
Fastest Bus	22h 40m
Earliest Bus	6:55 AM
Latest Bus	5:55 PM
Daily Bus Routes	14 Ø
Distance	562.8 miles
Bus Companies	Greyhound US

Cheapest bus connections from Winston-Salem, NC to Chicago

Every day, 14 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 07/26/2026 and for the following days.

Sunday

Monday

Tuesday

Wednesday

Thursday

Friday

Saturday

Sunday 07/26

Monday 07/27

$89

Tuesday 07/28

$89

Wednesday 07/29

$92

Thursday 07/30

Friday 07/31

$85

Saturday 08/01

$89

Sunday 08/02

Monday 08/03

$90

Tuesday 08/04

$93

Wednesday 08/05

Thursday 08/06

$93

Friday 08/07

$113

Saturday 08/08

$93

Sunday 08/09

$118

Monday 08/10

$107

Tuesday 08/11

$106

Wednesday 08/12

$100

Thursday 08/13

Friday 08/14

Saturday 08/15

Sunday 08/16

$89

Monday 08/17

Tuesday 08/18

Wednesday 08/19

Thursday 08/20

Friday 08/21

Saturday 08/22

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 $85, Friday is the cheapest day for a bus from Winston-Salem, NC to Chicago. Wednesday instead is the most expensive day with prices starting from $92.

Afternoon is the cheapest day time for bus tickets from Winston-Salem, NC to Chicago, with $85. Morning is the most expensive time of the day with prices starting from $88.

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

Forsyth Hospital

Silas Creek Pkwy 3333

Hong Kong King Buffet

Silas Creek Pkwy 1237

E Sprague St

E Sprague St 841

North Carolina Baptist Hospital

Queen St 2034-2020

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 $85 and takes 25h 50m 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 $85 and $123. 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 14 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 $107. 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.

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!