You can't be in Calgary and not do Banff; and if you're visiting Banff, you have to spend at least a night or two in Calgary. On our first visit, we did a day trip to Banff, but the second time around we stayed overnight. This is the way to do it. It's just too beautiful to see in one day.
2024 Update: It turns out you can do Calgary without visiting Banff--you just have to be going onward to the Yukon. In that case, a couple nights in Calgary on a long connection is just fine.
Newfoundland and Labrador - This trip was a long time coming! And when we finally did have it planned in 2020, well, you know. So finally in 2022 we got to visit St. John's and the easternmost point of North America! It was worth the wait. It's a small city whose beauty lies not only in the intense, rugged nature that surrounds it, but in the architecture and design of the place as well. Back in the 1970's, people started using bright, bold colors for the exteriors of buildings to inject life into the town. These "Jellybean Row Houses" are everywhere now, and they give the city such a distinct, memorable sense of place. It wouldn't be St. John's without them! We also really appreciated the walkability off the town. Walking trails connect all parts of town, and you can choose more strenuous, adrenaline-inducing trails (like we accidentally did on our hike up Signal Hill) or easy beginner's routes. Then there's the food--everything we ate was incredible! Stick to moose, cod, and mussels, and you can't go wrong. Honestly, even the water tasted great. It was so clean and pure!
Nova Scotia - After our first trip to Halifax in 2011, I commented that there was so much more to Halifax than we imagined! We expected a sleepy little fishing town; while we got that, we also got amazing food, unusual attractions, and a Harbourwalk that's over a mile long. In the 11 years since we'd been, Halifax has been growing! It is no longer a sleepy little fishing town--in any way. The boardwalk is bustling and has more restaurants, cafes, and shops than we could possibly have visited. But it's not just the harbour front that's been developing--there are new restaurants and hotels all over the city. Someone in St. John's told us that Halifax is St. John's in the future. That made a lot more sense having seen how it's changed.
With the recent reduction in flights, there aren't a lot of options for getting to St. John's, and even Halifax no longer has direct flights from Chicago. Once you're there, downtown St. John's is a quick 15-minute ride from the airport--not so much for Halifax. Luckily, both cities are totally walkable once you're in town.
If you don't have the time or money to visit New Zealand, I might recommend Victoria as a substitute. Parts of this city had such a New Zealand feel to them that I am certain I will get them confused in the future when I think back on this trip. It also had a bit of Scotland and Savannah, while other parts were classic Canada. The food outdid anything we had in Vancouver, and there were more attractions within walking distance (but don't worry--we still love Vancouver!).
Our 2017 visit to Vancouver was a lucky circumstance of being able to arrange bookends there on our way to Beijing--and it sure was nice to breathe clean cool air before and after that! Vancouver is a great city, and we were especially lucky on this trip: The sun was shining, and we've never seen the city so alive with people.
It's a solid four hours from Chicago to Vancouver, so make sure you have a comfortable seat. Although I am very against it in principle, for a flight of this length, I recommend paying for a good seat.
It's a shame Victoria requires a connecting flight (even if it is only 14 minutes from YVR to YYJ), because in 2017 we had close calls in both directions. That said, if this city were to ever show up on sale in the future, I would book it without question. Alternatively, you can fly to Seattle and take a ferry (direct or from Port Angeles) which lands you conveniently in the heart of town.
You can tell from the number of times we've been to Toronto that we love it--but who knew Ottawa was so cool? It's architecturally pleasing, there's a lot to do, the food is great, and you can walk to Quebec if you want a totally different atmosphere.
United and American have flights that go direct from Chicago to Toronto and Ottawa. But if you want better entertainment systems, go with Air Canada. Toronto has a high-speed airport train (UP Express) that goes from the airport to Union Station in 25 minutes. It's a great option for avoiding traffic and metered taxis on the way back to the airport.
I love Québec City! It's like a little Europe in North America. We've been twice now (March 2007 and August 2011) and would easily go back a third time. Montréal is nice--good restaurants and museums--but twice is probably enough for me.
We flew on American Airlines to Montréal and took VIA Rail from there to Québec City. This allowed us to do "end caps" in Montréal. Whenever we can, we take trains rather than drive. It's a nice break in the day where we can both read, listen to music, or take a nap.
More than once since our return from the Yukon I've been asked how I come up with these places. How did the Yukon end up on our radar? Perhaps it would be fitting to answer this by quoting the "Bard of the Yukon", Robert Service:
Wild heart, child heart, all of the world your home.
Glad heart, mad heart, what can you do but roam?
Oh, I'll beat it once more in the morning, boys,
With a pinch of tea and a crust;
For you cannot deny
When you hark to the cry
Of the Wan-der-lust.
Does that explain it?
We began in Whitehorse. The thing is that when you start your trip in Whitehorse, the capital city of 30,000 people feels small and remote and wild. We kept thinking, "This is the Yukon!" with a sense of wonder and awe. That feeling grew as we hopped on the Klondike Highway and explored other parts of the Southern Lakes region, such as the amazing little town of Carcross, by far my favorite stop. We stood in the smallest desert in the world (Carcross Desert at 1 square mile). We walked across the Yukon Suspension Bridge (technically in the northernmost part of British Columbia). We stopped to take in the beauty of the lakes and mountains along the way. And we even saw a bear, right there on the edge of the empty highway as we drove by! All of this was marvelous! Then we boarded a prop plane and flew to Dawson City. That's when we realized...this is the Yukon.
It's a scene out of the 1898 Klondike Gold Rush, with dirt roads and boardwalks, swinging saloon doors and cancan shows, and of course miners, working to get gold from the earth. But it's not 1898--this is Dawson City in 2024, and having seen the historical photos, I can tell you that, visually, not much has changed from over a century ago when Dawson was at the peak of its gold rush prosperity. Take a walk down any street in town, and I guarantee the "wild west" architectural style will make you feel like you're in an episode of Sergeant Preston. The dirt roads provide much of that effect, as dust billows up with every passing car or breeze. The boardwalks keep people from having to walk on the dirt, which is particularly useful after a heavy rain, when the roads can resemble a chocolate milkshake. Scattered throughout town are old historic buildings, some dilapidated, others restored to their former states. This adds to the feel that you have traveled back in time. You might almost expect to see Charlie Chaplin waddle into Diamond Tooth Gertie's Gambling Hall in search of Georgia. It's that kind of place.
We had bookends in Calgary on our way to and from Whitehorse on WestJet. These were the first flights in years that I can remember having empty seats next to us. It was great! After spending some days in Whitehorse, we flew on Air North to Dawson City. It was a small prop plane with no assigned seating. The seats themselves were like benches that fit two people. It was divided by an armrest, but the best part was that they did not recline. I think all aircraft should adopt this seating style in coach!
One thing worth mentioning is getting to and from the airports. In Whitehorse, it was easy, because (as I mention below) our airport provided a free shuttle. That works well on the way into town. For the return, however, you'll want a taxi ($20 CAD), because the shuttle wants to drop you off with an insane amount of time to spend at a tiny airport.
Speaking of insane amounts of time at a tiny airport, let's talk about Dawson's airport. For this journey, it is imperative that you find a hotel with a free shuttle. Our hotel picked us up but was unable to do the return trip due to their restaurant serving dinner at that time. No big deal, we thought--we'll just take a taxi. With no rideshare services available in the Yukon, the taxi company has a monopoly on this route. We found ourselves paying $60 CAD to ride in the filthiest taxi I've ever sat in. Okay, okay--there was a shuttle we could have booked, but it required us arriving two hours in advance of our flight. The Dawson City airport is the smallest airport I've ever seen. There's no security--only a small check-in counter and a small seating area for maybe 20 people. Altogether, it was about the size of our family room. As it was, we arrived just under an hour before our flight, and we still sat around bored for 30 minutes.