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

$107

tomorrow

$106

Thursday

Friday

$95

Saturday

Sunday

$104

Monday

Cheapest bus trips today
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	$107	A Bus from Greyhound US goes from Greyhound Bus Station, Winston-Salem, NC (USA) at 3/24/2026 6:55:00 AM to 95th Red Line Station, Chicago (USA) arriving at 3/25/2026 9:50:00 AM. 50 Economy ticket for $107 per person are available. Travel duration is 27h 55m
Greyhound US	25h 40m	10:25 AM	Winston-Salem, NC	Greyhound Bus Station	11:05 AM	Chicago	95th Red Line Station	Economy	$107	A Bus from Greyhound US goes from Greyhound Bus Station, Winston-Salem, NC (USA) at 3/24/2026 10:25:00 AM to 95th Red Line Station, Chicago (USA) arriving at 3/25/2026 11:05:00 AM. 50 Economy ticket for $107 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	$107	A Bus from Greyhound US goes from Greyhound Bus Station, Winston-Salem, NC (USA) at 3/24/2026 4:35:00 PM to 95th Red Line Station, Chicago (USA) arriving at 3/25/2026 5:05:00 PM. 50 Economy ticket for $107 per person are available. Travel duration is 25h 30m
Greyhound US	30h 40m	5:55 PM	Winston-Salem, NC	Greyhound Bus Station	11:35 PM	Chicago	95th Red Line Station	Economy	$107	A Bus from Greyhound US goes from Greyhound Bus Station, Winston-Salem, NC (USA) at 3/24/2026 5:55:00 PM to 95th Red Line Station, Chicago (USA) arriving at 3/25/2026 11:35:00 PM. 50 Economy ticket for $107 per person are available. Travel duration is 30h 40m
Greyhound US	39h 5m	5:55 PM	Winston-Salem, NC	Greyhound Bus Station	8:00 AM	Chicago	Canal & Van Buren	Economy	$112	A Bus from Greyhound US goes from Greyhound Bus Station, Winston-Salem, NC (USA) at 3/24/2026 5:55:00 PM to Canal & Van Buren, Chicago (USA) arriving at 3/26/2026 8:00:00 AM. 50 Economy ticket for $112 per person are available. Travel duration is 39h 5m

Cheapest bus trips tomorrow
BertCompanyCountOneCompanyName	Duration	Departure time	From	Departure	Arrival time	To	Destination	Seat classes	Price
Greyhound US	26h 5m	6:55 AM	Winston-Salem, NC	Greyhound Bus Station	8:00 AM	Chicago	Union Station	Economy	$106	A Bus from Greyhound US goes from Greyhound Bus Station, Winston-Salem, NC (USA) at 3/25/2026 6:55:00 AM to Union Station, Chicago (USA) arriving at 3/26/2026 8:00:00 AM. 50 Economy ticket for $106 per person are available. Travel duration is 26h 5m
Greyhound US	26h 30m	6:55 AM	Winston-Salem, NC	Greyhound Bus Station	8:25 AM	Chicago	Downtown Bus Station	Economy	$106	A Bus from Greyhound US goes from Greyhound Bus Station, Winston-Salem, NC (USA) at 3/25/2026 6:55:00 AM to Downtown Bus Station, Chicago (USA) arriving at 3/26/2026 8:25:00 AM. 50 Economy ticket for $106 per person are available. Travel duration is 26h 30m
Greyhound US	26h 5m	10:25 AM	Winston-Salem, NC	Greyhound Bus Station	11:30 AM	Chicago	Downtown Bus Station	Economy	$106	A Bus from Greyhound US goes from Greyhound Bus Station, Winston-Salem, NC (USA) at 3/25/2026 10:25:00 AM to Downtown Bus Station, Chicago (USA) arriving at 3/26/2026 11:30:00 AM. 50 Economy ticket for $106 per person are available. Travel duration is 26h 5m
Greyhound US	27h 15m	5:55 PM	Winston-Salem, NC	Greyhound Bus Station	8:10 PM	Chicago	Downtown Bus Station	Economy	$106	A Bus from Greyhound US goes from Greyhound Bus Station, Winston-Salem, NC (USA) at 3/25/2026 5:55:00 PM to Downtown Bus Station, Chicago (USA) arriving at 3/26/2026 8:10:00 PM. 50 Economy ticket for $106 per person are available. Travel duration is 27h 15m
Greyhound US	39h 5m	5:55 PM	Winston-Salem, NC	Greyhound Bus Station	8:00 AM	Chicago	Union Station	Economy	$107	A Bus from Greyhound US goes from Greyhound Bus Station, Winston-Salem, NC (USA) at 3/25/2026 5:55:00 PM to Union Station, Chicago (USA) arriving at 3/27/2026 8:00:00 AM. 50 Economy ticket for $107 per person are available. Travel duration is 39h 5m

Cheapest bus trips Friday
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	$95	A Bus from Greyhound US goes from Greyhound Bus Station, Winston-Salem, NC (USA) at 3/27/2026 10:25:00 AM to 95th Red Line Station, Chicago (USA) arriving at 3/28/2026 11:05:00 AM. 50 Economy ticket for $95 per person are available. Travel duration is 25h 40m
Greyhound US	27h 55m	6:55 AM	Winston-Salem, NC	Greyhound Bus Station	9:50 AM	Chicago	95th Red Line Station	Economy	$97	A Bus from Greyhound US goes from Greyhound Bus Station, Winston-Salem, NC (USA) at 3/27/2026 6:55:00 AM to 95th Red Line Station, Chicago (USA) arriving at 3/28/2026 9:50:00 AM. 50 Economy ticket for $97 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	$97	A Bus from Greyhound US goes from Greyhound Bus Station, Winston-Salem, NC (USA) at 3/27/2026 4:35:00 PM to 95th Red Line Station, Chicago (USA) arriving at 3/28/2026 5:05:00 PM. 50 Economy ticket for $97 per person are available. Travel duration is 25h 30m
Greyhound US	30h 40m	5:55 PM	Winston-Salem, NC	Greyhound Bus Station	11:35 PM	Chicago	95th Red Line Station	Economy	$97	A Bus from Greyhound US goes from Greyhound Bus Station, Winston-Salem, NC (USA) at 3/27/2026 5:55:00 PM to 95th Red Line Station, Chicago (USA) arriving at 3/28/2026 11:35:00 PM. 50 Economy ticket for $97 per person are available. Travel duration is 30h 40m
Greyhound US	28h 45m	10:25 AM	Winston-Salem, NC	Greyhound Bus Station	2:10 PM	Chicago	Canal & Van Buren	Economy	$104	A Bus from Greyhound US goes from Greyhound Bus Station, Winston-Salem, NC (USA) at 3/27/2026 10:25:00 AM to Canal & Van Buren, Chicago (USA) arriving at 3/28/2026 2:10:00 PM. 50 Economy ticket for $104 per person are available. Travel duration is 28h 45m

Cheapest bus trips Sunday
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	$104	A Bus from Greyhound US goes from Greyhound Bus Station, Winston-Salem, NC (USA) at 3/29/2026 10:25:00 AM to 95th Red Line Station, Chicago (USA) arriving at 3/30/2026 11:05:00 AM. 50 Economy ticket for $104 per person are available. Travel duration is 25h 40m
Greyhound US	27h 55m	6:55 AM	Winston-Salem, NC	Greyhound Bus Station	9:50 AM	Chicago	95th Red Line Station	Economy	$105	A Bus from Greyhound US goes from Greyhound Bus Station, Winston-Salem, NC (USA) at 3/29/2026 6:55:00 AM to 95th Red Line Station, Chicago (USA) arriving at 3/30/2026 9:50:00 AM. 50 Economy ticket for $105 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	$105	A Bus from Greyhound US goes from Greyhound Bus Station, Winston-Salem, NC (USA) at 3/29/2026 4:35:00 PM to 95th Red Line Station, Chicago (USA) arriving at 3/30/2026 5:05:00 PM. 50 Economy ticket for $105 per person are available. Travel duration is 25h 30m
Greyhound US	30h 40m	5:55 PM	Winston-Salem, NC	Greyhound Bus Station	11:35 PM	Chicago	95th Red Line Station	Economy	$105	A Bus from Greyhound US goes from Greyhound Bus Station, Winston-Salem, NC (USA) at 3/29/2026 5:55:00 PM to 95th Red Line Station, Chicago (USA) arriving at 3/30/2026 11:35:00 PM. 50 Economy ticket for $105 per person are available. Travel duration is 30h 40m

Best Price Offer: The price for the cheapest bus from Winston-Salem, NC to Chicago is $93 on 4/2/2026. 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.

Friday is the busiest day, with more than 16 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 25 buses from Winston-Salem, NC to Chicago, while Afternoon sees the fewest connections between Winston-Salem, NC and Chicago, with 19 offers.

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

Compare all providers like Greyhound US that travel 11 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 $93!

Cheapest Bus	$93
Fastest Bus	22h 40m
Earliest Bus	6:55 AM
Latest Bus	5:55 PM
Daily Bus Routes	11 Ø
Distance	562.8 miles
Bus Companies	Greyhound US

Cheapest bus connections from Winston-Salem, NC to Chicago

Every day, 11 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 03/24/2026 and for the following days.

Sunday

Monday

Tuesday

Wednesday

Thursday

Friday

Saturday

Sunday 03/22

Monday 03/23

Tuesday 03/24

$107

Wednesday 03/25

$106

Thursday 03/26

Friday 03/27

$99

Saturday 03/28

Sunday 03/29

$104

Monday 03/30

Tuesday 03/31

$110

Wednesday 04/01

$111

Thursday 04/02

$93

Friday 04/03

Saturday 04/04

$118

Sunday 04/05

$97

Monday 04/06

$108

Tuesday 04/07

$113

Wednesday 04/08

$96

Thursday 04/09

$104

Friday 04/10

$115

Saturday 04/11

$102

Sunday 04/12

$105

Monday 04/13

$100

Tuesday 04/14

$121

Wednesday 04/15

$105

Thursday 04/16

$96

Friday 04/17

$101

Saturday 04/18

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 $95, Friday is the cheapest day for a bus from Winston-Salem, NC to Chicago. Tuesday instead is the most expensive day with prices starting from $107.

Morning is the cheapest day time for bus tickets from Winston-Salem, NC to Chicago, with $95. Afternoon is the most expensive time of the day with prices starting from $97.

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 $93 and takes 24h 40m 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 $93 and $114. 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 11 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 $113. 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 11 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 11 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!