 | Flytrippers cofounder |
Just a few days after returning from my month-long trip to Europe, I was already off on another trip. This one is a bleisure trip (blending business and leisure), like many of my journeys. Between 4 events in 4 different cities, I managed to squeeze in 2 concerts in 2 other cities.
The initial stretch had 5 flights in 4 days (and an event/concert on all 4 of those evenings). That’s certainly quite intense, but it had been a while since I’ve had anything like that (and I frankly love it anyway).
This trip stems from my usual 2 fall speaking engagements, and as always, you can follow along live in my Instagram stories. Flytrippers aims to help you travel for less through our 3 types of content, namely flight deals, travel rewards, and tips/inspiration/news.
Here’s the overview of my North American trip.
Reason for my North American trip
I’m sharing why I’m doing this trip, to get straight to the point right at the beginning (as in all our posts).
Here are the 5 main reasons:
- Get together with our community at the Flytrippers meetup
- Speak at the Chicago Points Travel Festival again
- Attend a PR event in Toronto
- See 2 concerts in 2 other cities in between
- Facilitate an entrepreneurship event at LSU again
Get together with our community at the Flytrippers meetup
For the first time in many years, we organized Flytrippers meet-ups to spend a fun evening talking about travel with some of you in our amazing community.
The first one in Québec City was a few days before my actual departure (that one was just a same-day trip from my home in Trois-Rivières). The second was in Montréal, where I also took the opportunity to spend 3 nights with my girlfriend at the very nice Fairmont The Queen Elizabeth for Thanksgiving weekend.
Thanks to all who joined us at the meet-ups; it was great! We only had a few of the 50 tickets left for each event, which is great given that we announced them with less than 2 weeks notice.
If you want another opportunity to meet me and Flytrippers’ other co-founder Kevin, our full-day Flytrippers conference for travel rewards is April 24th in Montreal if you speak French, or we’ll also be at the Points Travel Festival in Toronto on April 17th.
Speak at the Chicago Points Travel Festival again
Since we’re on the topic of the Points Travel Festival, that’s the main driver for the USA portion of this trip. I was once again a speaker at the flagship Chicago event last weekend (it’s from Friday evening to Sunday).
Unfortunately, it had been sold out for months; if you want to attend one of the USA’s biggest travel rewards events on October 15-17 2027, be quick to buy tickets in the coming weeks when they’re released (I’ll let you know in our free newsletter).
This year, I spoke about hotel elite status and airline-hotel partnerships. There have been a lot of very interesting developments recently in terms of hotel rewards for Canadian travelers (Accor, Hyatt); don’t miss posts about this very soon.
This year, I flew in for the event only and did not visit Chicago at all. I’ve been many times, and this was how I was able to fit in an extra concert and a short hop back home to make my girlfriend happy.
Attend a PR event in Toronto
Between the meetup and the Chicago conference, I was invited to a PR event in Toronto.
Unfortunately, I can’t tell you anything at all about this yet, but I promise I will as soon as the embargo is lifted.
I can and will say that I’m very excited to share this news.
Make sure to sign up for our free newsletter specifically for travel rewards to never miss anything in that wonderful world.
See 2 concerts in 2 other cities in between
I’ve always wanted to see a concert at Red Rocks Amphitheater, an absolutely unique outdoor venue in Colorado. It was always certain I’d go; it was a matter of when.
So when one of my favorite bands announced a one-night-only full play of their iconic album for its 20-year anniversary at Red Rocks… I figured this was the absolute perfect time to go. Taking Back Sunday’s 2006 album Louder Now was part of the soundtrack of my youth, so it was an amazing evening.
It was perfect timing, 2 days before the Chicago conference and the day after the Toronto event. Then, instead of flying from Denver to Chicago, I first stopped in St. Louis, Missouri (as one does, right).
One of my new favorite bands (Beauty School Dropout) is on tour, and this was the only easy way for me to see them this fall. Flights from Denver to St. Louis were slightly cheaper than those to Chicago, flights from St. Louis to Chicago were just $70, and hotels were a bit cheaper in St. Louis… so it was basically free.
Facilitate an entrepreneurship event at LSU again
Finally, I’m once again facilitating an entrepreneurship event at LSU (Louisiana State University) in Baton Rouge. It’s the 9th time, so it’s definitely a fall tradition for me by now.
(As mentioned, I actually went back home for 3 nights before this particular event to make my girlfriend happy, but I figured it was simpler to just combine this all in this trip overview post since it’s almost at the same time!)
This one will also be more like a business trip, as I won’t really be visiting much.
I do have 1 night in New Orleans before and after (I almost always choose that airport as it’s cheaper) and this time I even built in 1 night in New York City on the return as I enjoyed my last few (short) trips in that iconic city.
Itinerary of my North American trip
I’m sharing the general itinerary of my trip, to give you the outline of the destinations I’ll visit (and you can follow me in my Instagram stories).
Here’s my itinerary on a map.
This trip will last a total of 15 days.
Here are the destinations I’ll visit during my trip:
- Montreal, Québec 🇨🇦
- 3 nights
- Toronto, Ontario 🇨🇦
- 1 night
- Denver, Colorado 🇺🇸
- 1 night
- St. Louis, Missouri 🇺🇸
- 1 night
- Chicago, Illinois 🇺🇸
- 3 nights
- New Orleans, Louisiana 🇺🇸
- 2 nights (split)
- Baton Rouge, Louisiana 🇺🇸
- 2 nights
- New York, New York 🇺🇸
- 1 night
Montreal, Québec 🇨🇦
Our Flytrippers meetup was downtown, a few blocks from the iconic Fairmont The Queen Elizabeth hotel.
I’ll share a full review of the hotel soon, but I can tell you it was really great.
I had already been there, but it was a long time ago in another life when I worked in consulting. Most importantly, it was before the property’s major renovations.
My girlfriend and I took it easy; we walked around downtown a bit and enjoyed the hotel’s pool, hot tub, and sauna.
Toronto, Ontario 🇨🇦
I started the outside-Québec portion of the trip by testing the new Air Canada shuttle between downtown Montréal and the airport, and it was great. I’ll share a post about that too soon.
Before my Air Canada flight (on a narrowbody with the very nice completely revamped cabins), I also tested the newly renovated Domestic Maple Leaf Lounge, and it was very nice. Certainly a nice improvement, even if it’s just prettier and not bigger.
I went and grabbed some items at the Air Canada Café Lounge next door too. When I arrived in Toronto, I happened to be chatting with a friend from Montréal whom I don’t see often… who told me she had also just arrived at her hotel in downtown Toronto. What a nice coincidence! So we went for a drink at Café Landwer.
I spent an exceptional evening at a PR event and stayed at a nice hotel. I’ll share some very interesting news soon, as soon as the embargo is lifted.
Denver, Colorado 🇺🇸
I visited 2 lounges in Toronto and then took a flight to Denver on United. It was very comfortable thanks to the free Economy Plus seats, a nice perk of Marriott Titanium elite status (which offers a status match to United Silver).
This is the USA, so Red Rocks Amphitheater is literally inaccessible by public transit. And I’m savvy enough not to take an Uber to a concert with a 10,000-person capacity.
So I had to rent a car for the first time in a surprisingly long time. It cost 80 USD for the day, which was pretty expensive. Obviously, I declined the insurance scam and paid with my Amex Platinum Card, which covers that for free (like all good cards).
The advantage of having a car is being able to pick a cheaper hotel farther away. I stayed at the Spark by Hilton Denver East I 70, to try this new affordable Hilton brand. It was fine.
St. Louis, Missouri 🇺🇸
I enjoyed the American Airlines Admirals Club lounge in Denver and took a Denver–Chicago–St. Louis flight because connecting flights are almost always cheaper. It cost only 100 USD.
I’ve already been to St. Louis but that was about 25 years ago, so I at least went back to see the Gateway Arch again even though I was in town for less than 24 hours (it’s the world’s tallest arch and the Western Hemisphere’s tallest monument).
My concert was right near downtown, which is connected to the airport by the metro system (even a second-tier city like St. Louis has that; imagine how embarrassing the situation is in Montréal). So I chose a downtown hotel and walked to the Old Rock House venue (established in 1818).
I stayed at the Hilton St. Louis at the Ballpark, which was only 151 CAD thanks to a pro tip. The location was ideal, and I had a view of the arch from my room. I also got to see more adults dressed as animals than I had ever seen, as there was a furry convention.
Chicago, Illinois 🇺🇸
I took a St. Louis–Chicago flight on United for $70. The Points Travel Festival conference isn’t really in Chicago, actually; it’s in Chicago’s endless suburbs. That’s why I didn’t go into the city this time.
Speakers are offered a hotel room at the Holiday Inn Chicago Oakbrook by IHG. The hotel is the conference venue, so it’s convenient. But that’s about it. IHG is not even in my top 4 programs, so I moved to the Hilton Garden Inn Chicago O’Hare Airport for the last night before my flight.
My flight to go back home for 3 days was Chicago–Québec City on American Airlines, booked for only 7,500 Alaska Airlines Atmos points (a currency no longer available with Canadian cards) and 8 USD in taxes. Having US-issued cards is worth it for way more options in terms of airline currencies.
I took advantage of an elite status match promotion last year that gave me Oneworld Sapphire status, so I had access to the more luxurious of American Airlines’ 2 airport lounge networks: Flagship Lounges. The one in Chicago is really great.
New Orleans, Louisiana 🇺🇸
After a brief return to Québec, I headed out again on American Airlines yesterday afternoon, again with Alaska Atmos points. I booked this to be able to fly out of Québec City for the first time in many years.
It’s almost always more expensive than Montréal, but not with Alaska Atmos points (fixed pricing; points of the more lucrative type). And there’s a new lounge I wanted to try. It’s an Air Canada lounge in partnership with Plaza Premium (so accessible with lounge memberships, like the one at Toronto-Bishop).
I normally already enjoy connections in Philadelphia thanks to the superb Amex Centurion Lounge, but this time I was able to try the American Airlines Flagship Lounge there too. I got fancy food and Philly cheesesteaks.
I only slept in New Orleans before heading to Baton Rouge, but after my event I’ll have yet another day in one of the most unique cities in the country.
Baton Rouge, Louisiana 🇺🇸
The bus between New Orleans and Baton Rouge costs 34 USD roundtrip, whereas the price difference for flights landing in the small city is always hundreds of dollars.
Apart from walking around the beautiful LSU campus, I won’t really visit since I’ve been so many times.
I’ll be staying at the same hotel as always, which is the closest Marriott to the LSU campus, the very average Courtyard by Marriott Baton Rouge Acadian Center/LSU Area.
It will actually almost complete my qualification for Marriott Titanium elite status, more than 2 months in advance! So the destination for my big November trip can be chosen without any need to do Marriott nights.
New York, New York 🇺🇸
Flights between Canada and the USA are terribly expensive these days, with the reduced number of flights and 6 consecutive months of increases in the number of Canadian travelers going there (compared to the very low numbers of 2025, obviously).
So I once again redeemed Alaska Atmos points for American Airlines flights, a good redemption when flights are expensive in cash (the appeal of points of the more lucrative type, in addition to luxurious business class).
LSU is fine with reimbursing me the cash value of the cheapest flight, so I prefer this. I was able to choose an itinerary which gives me a few hours in the very cool city of New York.
My girlfriend and I spent a weekend there this summer and it reminded me how unique and cool of a destination it is. I’ll stay at one of the few NYC hostels I’ve tried these past few years because hotel prices in this city are just insane and I’ll just be sleeping.
Learning how to travel for less
Join over 100,000 savvy Canadian travelers who already receive Flytrippers’ free newsletter so we can help you travel for less (and inspire you, too)!
Sign up for our free newsletter
Sign up for our newsletter
Summary
My current North American trip is mostly for business, but as always, I’m taking the opportunity to have some fun anyway. This time, it’s with concerts and a few visits to interesting cities.
What would you like to know about my current North American trip? Tell us in the comments below.
See the flight deals we spot: Cheap flights
Discover free travel with rewards: Travel rewards
Explore awesome destinations: Travel inspiration
Learn pro tricks: Travel tips
Featured image: My conference in Chicago and Red Rocks Amphitheater (photo credit: Andrew D’Amours/Flytrippers)
