Overview of my North American trip in October

Andrew D'Amours Flytrippers cofounder

Just a few days after returning from my month-long trip to Europe, I was already off on another trip. This one was 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 had anything like that (and I frankly love it anyway).

This trip stemmed from my 2 usual fall speaking engagements. 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 the launch of the new Amex card 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. Flytrippers’ other co-founder, Kevin, was in Canada for the 1^st time in a long time.

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 less than 10 of the 50 tickets left for each event, which is great given that we announced them with less than 2 weeks notice. We’ll do more, and with more advance notice (I promise)!

If you want another opportunity to meet Kevin and I, our full-day Flytrippers conference for travel rewards is April 24^th in Montreal if you speak French, or we’ll also be at the Points Travel Festival in Toronto on April 17^th.

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. Like the last few years, I was once again a speaker at the flagship Chicago event (it’s from Friday evening to Sunday with 500+ participants).

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. Apart from Hilton, 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 at all, other than a few Asian restaurants (Stefan, the organizer, lived in China for a while and knows the best spots). 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 the launch of the new Amex card in Toronto

Between the meetup and the conference in Chicago, I was invited to a special Amex and Hilton event for the launch of their brand-new Hilton Honors Amex Card. It’s one of the best developments of the year for Canadian travel rewards enthusiasts. As a passionate fan, I was really excited.

The uncapped certificate you get with the welcome bonus is simply phenomenal. They wanted the exclusive evening they organized to match that too, and it was indeed very enjoyable, with a 6-course dinner inspired by 6 iconic destinations. I’m going to write a detailed post about it, for those who are interested in the behind-the-scenes side.

Including the fact that even I, the very morning of the event, still didn’t know what it was, other than that it was Amex. We’re also going to have a lot of content to help you maximize this new must-have deal. Make sure to sign up for our free newsletter specifically for travel rewards to never miss anything in that wonderful world.

Anyway, the timing of the event was also perfect, because it was the night before the concert I absolutely didn’t want to miss, and instead of sending me back to Montréal, they were even able to send me directly to Denver.

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.

Then, instead of flying from Denver to Chicago, I had an extra evening before the conference, so I first stopped in St. Louis, Missouri (as one does, right). I love concerts, so why not.

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 once again facilitated an entrepreneurship event at LSU (Louisiana State University) in Baton Rouge. It was the 9^th time, so it’s definitely a fall tradition for me by now.

(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 was also more like a pure business trip, as I didn’t really visit much. I’ve been so many times… and time is the most precious resource.

I did have 1 night in New Orleans before and after (I almost always choose that airport as it’s cheaper), a unique city. This time, I had even built in 1 night in New York City on the return for cheaper flights, but I ended up doing a free same-day change to save even more (and get home earlier).

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 (you may have seen it if you follow all my trips in real time in my Instagram stories).

Here’s my itinerary on a map.

This trip lasted a total of 15 days.

Here are the destinations I visited during my trip:

• Montreal, Québec 🇨🇦
  • 3 nights
  • 1 night (at the end)
• Toronto, Ontario 🇨🇦
  • 1 night
• Denver, Colorado 🇺🇸
  • 1 night
• St. Louis, Missouri 🇺🇸
  • 1 night
• Chicago, Illinois 🇺🇸
  • 3 nights
• New Orleans, Louisiana 🇺🇸
  • 1 night
  • 1 night (after BR)
• Baton Rouge, Louisiana 🇺🇸
  • 2 nights

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.

I also spent the last night of the trip in Montréal, because I was able to request a free same-day flight change to get home a little earlier, but buses to Trois-Rivières are very limited. I stayed at the M Montréal hostel, which is very, very, very far from being like the Fairmont, but that’s what I do when I arrive late and leave early the next day because it’s just 40 CAD.

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 (even though I’ll probably never use it again; the 747 bus is more convenient for me). 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 stopped by the Air Canada Café lounge to grab a few takeout items (gotta stock up when it’s free). But before that, I mainly tested the newly renovated Domestic Maple Leaf Lounge, and it was very beautiful. Certainly a nice improvement, even if it’s just prettier and not bigger.

In the Queen City, I was staying at the Hilton Toronto, where the event was taking place. It’s completely renovated inside and it’s really nice. When I got to my room, I happened to be chatting with a friend from Montréal 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 near the Hilton.

I then spent an exceptional evening at the Amex Hilton event, on the 31^st and top floor. The next day, just like on arrival, Amex and Hilton paid for an Uber, so after many many times in Toronto, it was the 1^st time I didn’t take the 12 CAD train that never gets stuck in traffic to get to Toronto-Pearson airport.

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, on top of the one to Aeroplan 25K).

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. 

The car cost 40 USD for the day, which is pretty expensive compared to not too long ago. Obviously, I declined the insurance scam and paid with my Amex Platinum Card, which covers that for free (like all good cards). As always, I paid for the cheapest car and as (almost) always, I got a much nicer one for free.

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 perfectly fine for 68 USD in an expensive city.

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 98 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 98 CAD. 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 the only positive. 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, rather than the crazy high cash price. 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 Trois-Rivières (where I got a smoked meat poutine; poutine is a must after every trip, even short ones), I headed out again on American Airlines, again with Alaska Atmos points. Cash prices to the US are crazy these days, as Canadian travelers have been increasing for 6 months and many airlines had cut flights.

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 and after my Baton Rouge event; I only had a few non-sleeping hours. I stayed downtown without really visiting, due to a lack of time. But I ate some Popeye’s and some Chick-fil-A (new chicken and waffles breakfast sandwich), so that’s a win overall. I stayed at the HI New Orleans Hostel once again, as I was just in and out to sleep, it’s one of the best in the US, and it costs just 34 USD.

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 didn’t go anywhere else since I’ve been so many times. I tried a new pizzeria, Rotolo’s.

I stayed 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. It’s a very peculiar one; I’ll have more on that soon!

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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.

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Featured image: My conference in Chicago and Red Rocks Amphitheater (photo credit: Andrew D’Amours/Flytrippers)