Take the Grey Hound.
You could take a train from Toronto to Sarnia. From there, you'd have to figure out how to cross the bridge to Port Huron, MI, and catch the train from there to Chicago. I'm not even sure about the running times for this.
You can go by plane train or bus.
For just a weekend plane is the way to go.
Porter Airline out of Midway is best option.
The Toronto Island Airport Terminal is walking distance to hotels.
Train or bus takes too long for just a weekend visit.
[ Youtube.com Link ] Low fare about $170 round trip.
Flight about 2 hours.
You will need a Passport to fly.
No. There IS NO direct passenger rail service between Toronto and the USA. To get from Toronto to Chicago, you'll have to ride a bus to Dearborn, MI and then transfer to an Amtrak train to Chicago.
Go to the train station and ask them
Hi so train sounds like the best method along with a taxi.
You could get there by train but it would take a day or so, like 24 hours. There is no direct service. Even the bus takes 12 hours one way, which is a long time to travel to spend a weekend.
Flying would be best, the flight is a little less than 2 hours, and it actually doesn't have to cost all that much more than taking a bus. Try Porter Airlines