There are 5 ways to get from Chicago to Windsor by train, bus, car, plane, or bus (Flixbus, Greyhound)
Select an option below to see step-by-step directions and to compare ticket prices and travel times in Rome2Rio's travel planner.
Train, bus
best- Take the train from Chicago Union Station to Milwaukeetrain Hiawatha Service / ...
- Take the bus from Milwaukee, WI - Amtrak to Madison, WI-Lake St.bus Daily Route / ...
4h 10m$80–129Drive 152.2 mi
cheapest- Drive from Chicago to Windsorcar 152.2 mi
2h 31m$28–41Fly
- Fly from Chicago O'Hare International Airport (ORD) to Dane County Regional Airport-Truax Field (MSN)plane ORD - MSN
3h 3m$82–425Bus
- Take the bus from W Jackson Blvd, after S Clinton St to 250 N. Lake St - Madison UW Campusbus Van Galder
5h 4m$49–81Bus #2
- Take the bus from Chicago Bus Station to Madisonbus FlixBus 2548 / ...
5h 4m$50–79
Chicago O'Hare International Airport (ORD) to Dane County Regional Airport-Truax Field (MSN) flights
Questions & Answers
The cheapest way to get from Chicago to Windsor is to drive which costs $27 - $40 and takes 2h 31m.
The fastest way to get from Chicago to Windsor is to drive which takes 2h 31m and costs $27 - $40.
No, there is no direct bus from Chicago to Windsor. However, there are services departing from W Jackson Blvd, after S Clinton St and arriving at Hanson at Metro Garage via East Campus. The journey, including transfers, takes approximately 5h 4m.
The distance between Chicago and Windsor is 177 miles. The road distance is 153.1 miles.
The best way to get from Chicago to Windsor without a car is to train and bus which takes 4h 10m and costs $75 - $130.
It takes approximately 4h 10m to get from Chicago to Windsor, including transfers.
Chicago to Windsor bus services, operated by Rockland Coaches, depart from W Jackson Blvd, after S Clinton St station.
The best way to get from Chicago to Windsor is to fly which takes 3h 3m and costs $80 - $430. Alternatively, you can bus, which costs $45 - $85 and takes 5h 4m.
Chicago to Windsor bus services, operated by Rockland Coaches, arrive at 250 N. Lake St - Madison UW Campus station.
Yes, the driving distance between Chicago to Windsor is 153 miles. It takes approximately 2h 31m to drive from Chicago to Windsor.
What companies run services between Chicago, IL, USA and Windsor, WI, USA?
American Airlines and United Airlines fly from Chicago O'Hare International Airport (ORD) to Dane County Regional Airport-Truax Field (MSN) hourly. Alternatively, Rockland Coaches operates a bus from W Jackson Blvd, after S Clinton St to 250 N. Lake St - Madison UW Campus hourly. Tickets cost $25–55 and the journey takes 3h 50m.
- Website
- united.com
Flights from Chicago O'Hare International Airport to Dane County Regional Airport-Truax Field
- Ave. Duration
- 1h 9m
- When
- Every day
- Estimated price
- $50–380
- Website
- aa.com
Flights from Chicago O'Hare International Airport to Dane County Regional Airport-Truax Field
- Ave. Duration
- 1h 9m
- When
- Every day
- Estimated price
- $50–380
Rome2Rio's guide to Amtrak
Contact DetailsContact Details
- Phone
- +1 800-872-7245
- Website
- amtrak.com
Train from Chicago Union Station to Milwaukee
- Ave. Duration
- 1h 29m
- Frequency
- Every 4 hours
- Estimated price
- $27–55
- Website
- https://www.amtrak.com/home.html
#mediaviewer/File:Super_Dome_car.jpg "Hiawatha dome car")
- Phone
- +1 414-266-4409
- [email protected]
- Website
- badgerbus.com
Bus from Milwaukee, WI - Amtrak to Madison, WI-Lake St.
- Ave. Duration
- 1h 35m
- Frequency
- Every 3 hours
- Estimated price
- $23–30
- Website
- https://badgerbus.com
- Phone
- +1-858-800-8898
- Website
- jeffersonlines.com
Bus from Milwaukee, WI - Amtrak to Madison, WI-Lake St.
- Ave. Duration
- 1h 15m
- Frequency
- 3 times a day
- Estimated price
- $29–40
- Book at
- https://www.jeffersonlines.com
- Adult
- $29–40
- Website
- flixbus.com
Bus from Milwaukee, WI - Amtrak to Madison, WI-Lake St.
- Ave. Duration
- 1h 45m
- Frequency
- Twice daily
- Schedules at
- flixbus.com
Bus from Chicago Bus Station to Madison
- Ave. Duration
- 3h 50m
- Frequency
- 3 times a day
- Schedules at
- flixbus.com
Rome2Rio's guide to Greyhound USA
Contact DetailsContact Details
- Phone
- +1 214-849-8100
- [email protected]
- Website
- greyhound.com
Bus from Milwaukee, WI - Amtrak to Madison, WI-Lake St.
- Ave. Duration
- 1h 30m
- Frequency
- Once daily
- Estimated price
- $12–24
- Website
- https://www.greyhound.com/
Bus from Chicago Bus Station to Madison
- Ave. Duration
- 3h 40m
- Frequency
- Once daily
- Estimated price
- $27–55
- Website
- https://www.greyhound.com/
- Phone
- +1 (855) 626-8585
- Website
- https://www.flixbus.com
Bus from Milwaukee, WI - Amtrak to Madison, WI-Lake St.
- Ave. Duration
- 1h 40m
- Frequency
- Once daily
- Estimated price
- $12–21
- Schedules at
- flixbus.com
Bus from Chicago Bus Station to Madison
- Ave. Duration
- 3h 45m
- Frequency
- Twice daily
- Estimated price
- $28–50
- Schedules at
- flixbus.com
- Website
- example.com
Bus from Milwaukee, WI - Amtrak to Madison, WI-Lake St.
- Ave. Duration
- 1h 45m
- Frequency
- Once daily
- Schedules at
- example.com
- Phone
- +1 (866) 912 - 6224
- [email protected]
- Website
- coachusa.com
Bus from W Jackson Blvd, after S Clinton St to 250 N. Lake St - Madison UW Campus
- Ave. Duration
- 3h 50m
- Frequency
- Hourly
- Estimated price
- $25–55
- Schedules at
- coachusa.com
- Adult
- $25–55
Want to know more about travelling around United States
Rome2Rio's Travel Guide series provide vital information for the global traveller. Filled with useful and timely travel information, the guides answer all the hard questions - such as 'How do I buy a ticket?', 'Should I book online before I travel? ', 'How much should I expect to pay?', 'Do the trains and buses have Wifi?' - to help you get the most out of your next trip.
Related travel guides
Travelling to the US: What do I need to know?
Read the travel guide
Why you should take the train in the US
Read the travel guide
Need to know: Greyhound
Read the travel guide
More Questions & Answers
There are 131+ hotels available in Windsor.