Our Canadian Road Trip

Travel blogger road trip to Canada from Chicago. Bridge into Canada from USA near Windsor.

Dave and I have done our fair share of road trips from Chicago, but our Canadian road trip was the first time we crossed international lines!

Back in the summer, Dave and I were watching a Cubs game at the Toronto Bluejays on TV and I mentioned how I’d surprisingly never been to Canada. He had been to Toronto once or twice for work but hadn’t visited for fun or branched out from Toronto. Since we’ve gotten in the habit of taking a road trip over Christmas for the last four years, we started plotting our Canada road trip route!

Canadian Road Trip from USA

Dave is off the week between Christmas and New Year’s, so we try to take advantage of that time to travel. We started dating in 2020, so for the first few years, we had to rely on driving and social distancing. Now that flying is an option, we’ve looked into international destinations, but finding a dog sitter for Marley over the holidays is tricky.

I’ve always wanted to go to the European Christmas markets, but after doing some research earlier this year, I realized that all of the markets close by Christmas Eve. December is the worst time to travel for both Dave and my job, so we scratched that idea pretty quickly.

We had both heard that Quebec City, Canada feels like a charming European city and since it’s drivable from Chicago, we started plotting our road trip route to Canada from the US.

Chicago travel blogger shares Canadian road trip route through Toronto, Montreal, Quebec City, Vermont, and New York

Our Canadian Road Trip Route

It’s an eight-hour drive to Toronto from Chicago and you lose an hour along the way. We spent two nights in Toronto before driving the six hours to Montreal. We spent three nights in Montreal before taking the three-hour drive to Quebec City and got to spend two days there while ringing in the New Year!

The only issue with our plan was that we’d be 16 hours from home on New Year’s Day. Since New Year’s Day fell on a Monday this year, Dave had to be back online for work on Tuesday. Dave’s company is fully remote and I’m able to work from anywhere, so we hatched a plan to find an Airbnb in Vermont to work from during the week.

We found the cutest house on a little lake outside of Burlington, Vermont, so we worked from ‘home’ there last week. It was the coziest! We had a fire going every day and a snow-covered lake to look at out the windows. There was plenty of space to spread out, too, as there was a big dining table, a kitchen counter, as well as a desk upstairs in the main bedroom.

We drove into Burlington each night for dinner and had some of the most incredible meals, which neither of us was expecting. After dinner, we would come home to relieve Marley, drink some local cider, and work on a big puzzle by the fire. I’ve mainly had my phone on DND for the past two weeks and have been checked out of social media, which has been such a relaxing change of pace!

On Friday morning, we checked out of our Airbnb early and made the 7-hour drive to Buffalo, NY. Dave was planning to take his internal calls from the house that day, but checkout was at 10:30 am, and with the warnings of a Noreaster on the way, we decided to get on the road EARLY instead of staying local to work at a coffee shop. It wasn’t the most flawless plan, as we were driving through the wilderness and cell service was nearly non-existent for the first few hours of the drive, but it was absolutely beautiful!

Our night in Buffalo wasn’t too thrilling, but we got to bed early and got on the road even earlier on Saturday morning for our 8.5-hour drive back to Chicago. We’ve spent a lot of time in our vehicle these last two weeks, but it truly was such a wonderful trip.

I’ll be sharing a Travel Guide with our light itinerary from each destination in the weeks to come, but please let me know if you have any specific questions about the drive that I can answer!

Canadian Road Trip FAQs

1. How was it driving on the highway in Canada?

We’ve surprisingly had very little snow during our trip, which has been a bit of a bummer as I was hoping for scenic snowscapes. But it’s been very helpful for driving safety! We’ve had a lot of rain, though. There were a few hours on the drive from Toronto to Montreal where visibility was low and the driving conditions were pretty dismal, but other than that, it hasn’t been bad at all!

They drive on the same side of the road in Canada as we do in the United States! In Ontario, every sign has English on it, and I believe most of them in Quebec did, as well.

2. Will you be doing any more Canada road trips or Canada travel?

We’d love to! We both loved Quebec and would go back to Montreal or Quebec City in a heartbeat! Since we just did Eastern Canada, I’d love to explore Western Canada next. Banff National Park and Lake Louise look absolutely breathtaking and I’d love to check out Vancouver in British Columbia, too. I know there are many other beautiful parks to check out as well… Jasper National Park, Forillon National Park, Cape Breton Highlands National Park on Cape Breton Island, Vancouver Island, Icefields Parkway, etc.

Once we were already as far east as Quebec City, we kept saying how cool it would be to keep going towards Nova Scotia, Prince Edward Island, or even take Marley up to visit her homeland in Labrador. Maybe summertime would be best for those jaunts, though!

3. Did you see Niagara Falls when you were in Buffalo?

Sadly, no. We could have made time on Friday afternoon, but Dave went as a kid and I was quite tired from the snowy drive on Friday. On Saturday, we were on the road by 7 am to get back to Chicago at a decent hour on Saturday night.

My word of advice would be to load the first half of your trip with the sites you want see when energy levels are at their highest! After two weeks, I was ready to get home and get unpacked before the week started.

4. Did you see any National Historic Sites?

We saw a fair amount of historic buildings and areas within Toronto, Montreal, and Quebec City, but we didn’t stop off at any sites or national parks along the drives. We did get to drive through some pretty wilderness areas, though!

5. Was it easy to cross the border with a dog?

It was unbelievably easy! We had all of her paperwork from her veterinarian, as well as individually packaged food from The Farmer’s Dog, but it was never checked.