Bus Tickets from Windsor, ON, CA to Chicago

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TodayAug 31
TomorrowSep 1
from US$69
TueSep 2
WedSep 3
from US$48
ThuSep 4
FriSep 5
SatSep 6
SunSep 7

Cheap buses leaving tomorrow

One passenger / one way

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

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Bus Windsor, ON, CA to Chicago: Trip Overview

Average Ticket PriceUS$69
Average Bus Trip Duration10h
Number of daily buses8
Earliest bus departure5:00am
Distance384 km
Latest bus departure8:35pm

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. How far is Windsor from Chicago?

    The distance covered from Windsor to Chicago is 387 km (240 miles).

  2. What are the departure and arrival locations for buses traveling from Windsor to Chicago?

    Buses traveling this route start their trip at 181 Goyeau St, in Windsor, and end it at Downtown Greyhound Station, in Chicago.

Find cheapest prices for buses

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

Best price found
08-29
US$101
08-30
US$59
Today
US$58
09-01
US$61
09-02
No data
09-03
No data
09-04
No data
09-05
US$56
busbud logoThe cheapest trip from Windsor, ON, CA to Chicago was searched and found on Sep 5, 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 one of the smallest carbon footprints of motorized transport modes. A bus going from Windsor to Chicago will emit less CO2 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

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