Sal Getting Through the Border
Both Canadians and Americans need valid passports to cross the border between Canada and the United States. The Windsor-Detroit international border crossing is one of the most popular options, with the Windsor city bus providing direct transportation between downtown Windsor, Ontario and downtown Detroit, Michigan. Customs and immigration processing is typically quick, especially on nights when the Detroit Red Wings hockey team is playing as the bus goes directly to the hockey arena first. Another option is to take the train from Toronto to Windsor and then transfer to the international bus in Windsor.
Using Amtrak Between Windsor and Chicago
It is possible to take the train all the way from Toronto to Chicago, but it requires an overnight stay due to logistical challenges connecting the Amtrak and Via Rail systems on either side of the border. Direct rail service between Toronto and Chicago has been discussed, but there are infrastructure issues as the Detroit Amtrak station uses tracks that run north of the Detroit-Windsor rail tunnel, while the Windsor Via Rail station is located at a dead-end. Previous intercity rail routes between the cities crossed the border further north near Sarnia.
Combining Multiple Modes of Transportation
If wanting to complete the trip in one day without flying, a viable option is to take the noon Via Rail train from Toronto to Windsor, transfer to the Windsor city bus to downtown Detroit, and then take another bus to Dearborn, Michigan for an overnight stay. In the morning, one can catch the first Amtrak train from Dearborn to Chicago, allowing time to connect to other long-distance trains departing from Chicago. While involving multiple transfers, this itinerary offers an environmentally-friendly way to travel between the two cities without flying.
Flying Between Toronto and Chicago
For many travelers, flying provides the fastest route, especially on Porter Airlines which operates regional jets out of Toronto City Airport. A direct train ride on Chicago’s elevated rail system, known as “The L”, can deliver passengers right to Union Station in the heart of downtown. However, airfare prices on Porter can be quite expensive on certain travel dates. An alternative is to stay near Toronto Pearson International Airport the night before an early morning flight with a connection in Detroit, but this requires waking up before 4:00 AM to clear US customs in Toronto before a 06:00 AM departure. Connections through Detroit Airport can be tight and prone to delays.
Weighing the Pros and Cons
Each transportation option between Toronto and Chicago has its advantages and disadvantages depending on priorities like travel time, cost, convenience, and willingness to transfer between modes or endure an overnight stay. Public transportation using Amtrak and regional buses is more affordable and environmentally-friendly compared to flying, but takes much longer. Flying can save significant time, but airfare is generally the most expensive option. For those on a budget with flexibility, combining Via Rail, local buses, and Amtrak offers a multi-modal adventure without excessive out-of-pocket costs. Ultimately, assessing individual needs, preferences, and schedules will determine the best way to link Canada’s largest city to one of the dominant hubs in the American Midwest.
An Impromptu Steak Dinner in Omaha
One memorable trip involved taking the train the entire distance from Toronto to Chicago, flying was deemed too expensive that particular day. After an unexpectedly long delay in Detroit, a last-minute flight change and airport shuttle mix-up resulted in barely making the connecting flight, with no time to stop for food before traveling on to Chicago. Fortunately, the dining staff aboard the California Zephyr understood the harried situation and graciously packed takeaway meals, including steak sandwiches, for the late evening stop in Omaha, Nebraska. While not part of the original itinerary, the unexpected steak dinner in Omaha created a fun story and memory from an otherwise stressful travel experience connecting the two cities.
Conclusion
In summary, many transportation options exist to link Toronto and Chicago, each with advantages depending on priorities. Public transportation using various ground transportation can be more budget and environmentally-conscious, but takes more time and transfers compared to a direct flight. Flying is fastest but generally costlier. For those desiring a scenery-filled multi-day adventure of moderate cost, combining rail and bus services makes for an interesting multi-modal journey. Overall, considering individual circumstances like schedules, finances and tolerance for potential delays will determine the optimal connecting route between Canada’s largest city and a major U.S. Midwest metropolis. Above all, focusing on making new experiences and memories along the way can ensure even unexpected travel hiccups result in fun stories to tell.
Metro is King