Find coaches from Windsor, ON, CA to Chicago

Find affordable coach tickets from Windsor, ON, CA to Chicago with flexible options. Book your journey now

Join 75M+ travellers booking 2M+ routes across 85+ countries.
Enjoy our 24/7 customer service to assist you at every stage.
Cancel anytime and receive a 100% refund, no reason needed.
Today31 Aug
Tomorrow1 Sept
from US$69
Tue2 Sept
Wed3 Sept
from US$48
Thu4 Sept
Fri5 Sept
Sat6 Sept
Sun7 Sept

Cheap buses leaving tomorrow

One passenger / one way

  • This trip is recommended because it is the: Cheapest
    Departure time: 1 September at
    Departure city: Windsor
    Departure location: Windsor (International Transit Centre)
    Arrival time: 1 September at
    Destination city: Chicago
    Destination location: Chicago 95Th & Dan Ryan
    Operated by: FlixBusFlixBus
    Vehicle: BusDuration:
  • This trip is recommended because it is the: Fastest
    Departure time: 1 September at
    Departure city: Windsor
    Departure location: Windsor (International Transit Centre)
    Arrival time: 1 September at
    Destination city: Chicago
    Destination location: Downtown Greyhound Station
    Operated by: FlixBusFlixBus
    Vehicle: BusDuration:
  • Departure time: 1 September at
    Departure city: Windsor
    Departure location: Windsor (International Transit Centre)
    Arrival time: 1 September at
    Destination city: Chicago
    Destination location: Downtown Greyhound Station
    Operated by: FlixBusFlixBus
    Vehicle: BusDuration:
  • Departure time: 1 September at
    Departure city: Windsor
    Departure location: Windsor (International Transit Centre)
    Arrival time: 1 September at
    Destination city: Chicago
    Destination location: Downtown Greyhound Station
    Operated by: FlixBus + Greyhound Lines, Inc.
    FlixBus + Greyhound Lines, Inc.
    Vehicle: BusDuration:
  • Departure time: 1 September at
    Departure city: Windsor
    Departure location: Windsor (International Transit Centre)
    Arrival time: 2 September at
    Destination city: Chicago
    Destination location: Downtown Greyhound Station
    Operated by: FlixBus + Greyhound Lines, Inc.
    FlixBus + Greyhound Lines, Inc.
    Vehicle: BusDuration:

Accepted payments

  • Visa
  • MasterCard
  • American Express
  • China Union Pay
  • Diners Club Canada
  • Discover Click to Pay
  • JCB payment
  • Klarna (Pay over time)
  • Google Pay

Bus Windsor, ON, CA to Chicago: Trip Overview

Average ticket priceUS$69
Average bus trip duration10h
Number of daily buses8
Earliest bus departure05:00
Distance239 miles
Latest bus departure20:35

Windsor to Chicago Bus

Busbud helps you find a bus from Windsor to Chicago. Get the best fare and schedule, book a round trip ticket or find buses with WiFi and electrical outlets.

We make sure you can find a bus service from Windsor to Chicago from the most reliable bus companies operating this trip.

Discover how much the bus trip from Windsor to Chicago will cost you. Use our filters and sorting features to find the cheapest bus tickets or luxury buses.

Frequently asked questions on the trip Windsor, ON, CA - Chicago

  1. What's the distance between Windsor and Chicago by coach?

    The distance between Windsor and Chicago by coach is approximately 240 miles (387 km).

  2. How can I get from Windsor to Chicago without driving?

    You can travel to Chicago from Windsor by coach, which provides a smooth ride and an affordable and convenient trip. You can also consider rideshare services depending on your preferences.

Find cheapest prices for buses

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

Best price found
29/08
US$101
30/08
US$59
Today
US$58
01/09
US$61
02/09
No data
03/09
No data
04/09
No data
05/09
US$56
busbud logoThe cheapest trip from Windsor, ON, CA to Chicago was searched and found on 5 Sept 2025 with a price of US$56

To save money and be sure you have the best seat, it's a good idea to buy your bus tickets from Windsor, ON, CA to Chicago as early as possible.

You can expect to pay from US$56 to US$113 for a bus ticket from Windsor, ON, CA to Chicago based on the last 2 days. You can expect to find the cheapest price for the trip at US$56, which is on 2025-09-05.

About Bus Travel

Bus Travel Tips

Make friends with the driver. They usually know a lot about your destination and may even recommend which side of the bus to sit on to get the best views on the road between Windsor and Chicago!

Start sightseeing the minute your bus leaves the station. If you're on the night bus from Windsor to Chicago, get comfy and count the stars.

Buses have the smallest carbon footprint of all motorized transport modes. A bus going from Windsor to Chicago will emit half the CO2 emitted by a train, and radically less than a car or an airplane.

Make a music playlist for your bus ride from Windsor to Chicago, and enjoy the scenery to tunes from your own personal soundtrack.

Did you know?

The bus driver with the longest career in the world drove more than 2,000,000 miles and is a happy World Record holder.

Did you know there are on average 4,400 intercity bus departures every day in the US only? This number has been growing for 9 years in a row, yay!

One of the longest bus route in the world goes all the way from Ontario to Alberta in Canada (with the same bus). This trip is 3,435 km or 2,135 miles long and the price is a bit under $100.

Will you be returning to Windsor, ON, CA by bus?

Bus from Chicago to Windsor, ON, CA

Why choose Busbud?

The Best Way To Book Bus and Train Tickets

Busbud makes bus travel easy. We help travellers find a bus, plot routes, and book intercity bus tickets all over the world. With Busbud, wherever you go, you have a worldwide bus station within reach and available in your own language and currency. With Busbud, you can buy tickets with confidence. We ensure that you make the most out of your bus trip by partnering up with reliable bus companies from all around the world such as Greyhound, Eurolines, ALSA, OUIBUS (BlaBlaBus), National Express and many others.

People from around the world trust Busbud

‌

Popular Buses Connecting Windsor

Buses Leaving from Windsor

Buses Going to Windsor

Popular Buses Connecting Chicago

Buses Leaving from Chicago

Buses Going to Chicago