Welcome to bus travel! :-) I work for [Busbud][1], a bus travel site. **This trip requires you to take three buses each way** 1. A long trip on Greyhound from Toronto to Chicago, crossing the border at Windsor/Detroit. 2. A short hop from Chicago up to Milwaukee on Greyhound. 3. A medium distance trip across Wisconsin operated by Greyhound's partner company Jefferson Lines. **Booking your trip** We've done some [research on when to book at Busbud][2]. Your ticket is rather complicated (two countries, three buses, two bus companies) but you should still get a major discount for booking around a month in advance. A possible hack to saving money is looking at booking all three tickets separately, each: Toronto-Chicago, Chicago-Milwaukee and Milwaukee-Winona. However these are tight connections and you can't expect any assistance if you miss your connection on separate tickets, they may not be honoured for the next bus if you miss the connection. If you want more flexibility, booking last minute is always an option, but it will probably be a lot more expensive. Booking online is also usually much cheaper than booking at the station. **Stops** As mentioned in [blackbird57's answer](https://travel.stackexchange.com/a/73964/2643) you can find info on the stop [locations on Greyhound.com][3]. You can also use their [live bus tracker](http://bustracker.greyhound.com/) while traveling to get updates of exactly where the bus is. **Luggage** At Busbud, we've [summarized Greyhound and Jefferson's luggage policies][4]. Normally at stops the station staff or driver will help you transfer bags, but not always. At the border in Windsor/Detroit you may have to take your bag from underneath the bus and carry it through customs and immigration. Chicago is a particularly chaotic station in my experience, you should ask the driver and see to it that the bag gets moved. If in doubt of what you need to do, just ask the driver! **Stops and connections** Note that this itinerary has pretty short connection times. Greyhound and Jefferson will do their best to make sure you make your connections but if something happens, like a big delay at the border, and your inbound bus arrives late the connecting bus can't always wait. Normally in this case they'll just transfer your ticket over and put you on the following bus. On the way to Minnesota the big challenge is that there's only one bus a day from Milwaukee to Winona. If you do miss that connection, there is an Amtrak train later in the day that leaves from the same station in Milwaukee (Intermodal Station) to Winona. It's hard to stay what accommodations Greyhound will make in case you get stuck in Milwaukee, if any, other than telling you can take the bus the next day, in that case you may want to know about the Amtrak option before you get stuck in Milwaukee overnight. **If in doubt about anything** Just be assertive and friendly and ask the driver! PS: if you end up having a bit of extra time in Milwaukee you can run over to the [great coffee shop across the street][5] and also note in general the food options in the station itself are a bit more extensive in Milwaukee than in Chicago. [1]: https://www.busbud.com/ [2]: https://www.busbud.com/blog/busbud-launches-the-dollar-bus-club/ [3]: http://locations.greyhound.com/ [4]: https://www.busbud.com/blog/much-luggage-can-take-bus-us/ [5]: https://www.google.com/maps/dir/Stone+Creek+Coffee+Roasters,+422+North+5th+Street,+Milwaukee,+WI+53203/43.0345359,-87.9175046/@43.0347607,-87.9180206,18.93z/data=!4m9!4m8!1m5!1m1!1s0x8805199ec7f57ecf:0x25a3e257535ad9f4!2m2!1d-87.9171589!2d43.0352307!1m0!3e2