After less than 24 hours in Québec (without even returning home) following my fall trip to Europe, I left again on Saturday for another trip. This time, it’s to our unpopular neighbor to the South… but it’s for 3 good reasons, I assure you. It’s a short 10-day stay in my current incredibly packed travel sequence.
So I’m continuing our new good habit of sharing content about our trips here (I even convinced Kevin to do it for his current trip to the Middle East… a bit more interesting than mine, obviously).
I also adapted and improved this intro post template a bit. Tell us if there’s anything else you want to know about our trips. And of course, this is in addition to my daily stories on my personal Instagram account, as with all my many trips.
Here’s the intro to my trip to the United States, specifically the reason, the context, the itinerary, and the booking. The tips and logistics, reviews, and experiences will follow soon.
Reason for my fall trip to the United States
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 3 main reasons:
- Being a speaker at a travel rewards event (Chicago Seminars)
- Attending my favorite music festival in Las Vegas (4th year in a row)
- Continuing my JetBlue flights challenge between those 2 (to get 350k pts)
First, for a few years now, I’ve been speaking at one of the biggest events in the world of travel rewards, the Chicago Seminars. At the last one, in October 2024, I committed to doing it again this year (that was before Trump was elected, by the way).
It’s so enjoyable to spend a weekend with other points enthusiasts (you should really try it if you like points). And to be a Canadian website that shines and attracts readers in the United States, we do have to go there to be better known.
Second, ever since it started (2022, 2023, 2024), I’ve been attending the pop-punk/alternative/emo music festival When We Were Young in Las Vegas. Once again, I decided last October that I would return because of the announced lineup.
The thing is, the iconic pop-punk band Panic! at the Disco is returning only for this weekend and will play their iconic debut album in its entirety. There was literally no chance I would miss that.
Finally, since these 2 events are 2 consecutive weekends, it leaves me a few days in between the 2 to continue the JetBlue challenge to get 350,000 points (value of 5950 CAD to UNLIMITED).
I have done 11 of 20 destinations, and on this trip, I booked 5 more in 4 days. I could have done more, but honestly, it was a bit intense in September with 13 flights in 13 days, so I chose to take it easier. It will be easy to do the other 4 in November and December, despite my many trips.
Context of my fall trip to the United States
I’m sharing a bit more details about my situation, so you can learn a bit more about how we plan our trips if you’re interested.
So it was certain that I was attending both weekends for these events. It’s been literally 1 year in the planning. That’s not nothing for someone who’s become extremely last-minute with their trips! 😅
I could have, of course, done 2 separate roundtrips (for each weekend).
But it only costs 3 more nights of accommodation to stay between the 2, because I would have left Vegas on Monday and I had to be in Chicago Thursday evening (because I’m also hosting one of the new optional masterclasses on Friday before the main event from Friday evening to Sunday evening).
So, with the JetBlue flights I had to do, it made so much more sense to do some there. And the JetBlue flight from Vegas is overnight, so that saves 1 night in accommodation costs (but it’s disgusting and I hate it and I would have avoided it if there was any decent way).
My return flight from Vegas lets me do 2 JetBlue destinations for cheaper than it would have already cost me to return from Vegas to Canada. My outbound to Chicago lets me do 3 destinations, and even by making a detour to Florida (kingdom of cheap flights), it comes out to almost the same price as I would’ve paid anyway from Canada to Chicago.
So it only costs me an extra 2 nights of accommodation.
By the way, speaking of accommodation, without being a reason for the trip (it’s more of a collateral effect), it will also allow me to complete my requalification for Marriott Bonvoy Titanium elite status. Yes, in October! Incredible.
It will be by far the earliest in the year that I’ll finish that, in my 7 years with this status. It’s thanks to the doubled elite nights promotion this winter; it’s the first time I really maximized it by being savvy and planning a trip to Asia accordingly. Do the same thing this winter if you want a higher elite status!
In short, I would have traveled a lot this fall in any case.
But the 2 flight challenges made this a very intense sequence of trips from August to December, possibly one of the most intense of my life (which says a lot):
- Left 23 days for the 6 continents challenge
- Returned 5 hours
- Left 3 days with my girlfriend to Toronto
- Returned 23 days
- Left 13 days for the JetBlue challenge
- Returned 6 days
- Left 11 days to do a real trip to Europe
- Returned 1 day
- Left 10 days for the United States (this trip)
- I’ll return for 4 days
- I’ll leave 9 days with my girlfriend for a vacation
- I’ll return for 3 days
- I’ll leave 12 days to review Marriott hotels in Mexico
- I’ll return for 3 days
- I’ll leave 3 days with my girlfriend for a short getaway
- I’ll return for 2 days
- I’ll leave 5 days for my annual trip to Miami Art Week
Ah, the addiction to points. And to luxurious business class especially…
Fortunately, I really hadn’t traveled much in the first 7 months of 2025 (a day in Ottawa, a few days in British Columbia, 3 weeks in Asia, a week in Florida… and 3 weeks in Europe but that doesn’t count because I was with my girlfriend at least).
Itinerary for my fall trip to the United States
I’m sharing the general itinerary of my trip, so you can follow me.
Here’s my itinerary on a map.
Obviously, it’s another itinerary that makes no sense, other than to do as many JetBlue flights as possible at the lowest price possible between my events in Las Vegas and Chicago. Florida is the key; as I already explained, the price of plane tickets has nothing to do with distance. It’s always just the price that people are willing to pay, and Florida is a leisure destination (not business), so it’s not expensive.
Here are the cities I’ll visit during my trip (so connections are excluded):
- Las Vegas, Nevada
- 2 nights
- For the WWWY festival
- Tampa, Florida
- 1 night
- For the JetBlue challenge
- New York, New York
- 1 night
- For the JetBlue challenge
- Chicago, Illinois
- 4 nights
- For the Chicago Seminars
I was really looking forward to the 2 events, but honestly, really not to the part between the 2. Especially not with a terrible red-eye (overnight) flight in economy class. I’m starting to look forward to this challenge being over, honestly! 😂
Booking transportation for my fall trip to the United States
I’m sharing the details of how I planned my trip, so you can learn about transportation as it’s obviously always the aspect to design a trip around.
Here’s the transportation during my trip:
- Flights: Montreal—Toronto—Las Vegas
- Air Canada and Air Canada Rouge
- Flights: Las Vegas—Boston—Philadelphia
- JetBlue (destinations #12 and #13)
- Train: Philadelphia—Newark
- Amtrak
- Flight: Newark—Tampa
- JetBlue (destination #14)
- Flight: Tampa—New York-LaGuardia
- JetBlue (destination #15)
- Flight: New York-Kennedy—Chicago
- JetBlue (destination #16)
- Flight: Chicago—Québec City
- American Airlines (American Eagle)
- Bus: Québec City—Trois-Rivières
- Orléans Express
I’m sharing details on each.
Flights: Montreal—Toronto—Las Vegas
To get from Montreal to Las Vegas, Air Canada had an excellent price in cash by buying in advance… and I waited too long because I was hesitating about how much buffer to leave myself after my arrival from İstanbul on Friday. It’s rare that I miss a deal, honestly.
I ended up paying a bit more, but in Aeroplan points, because it was a rare good redemption on Air Canada rather than on partner airlines. It was a good redemption because the prices in cash were obviously expensive 4 days before the flight, when I finally booked.
That’s the basics of the more lucrative type of points: they can often be great when prices are expensive, including (but not only) in luxurious business class.
I managed to do well, considering it was 4 days in advance and I had no flexibility on the date (I had my Turkish flight Friday evening and the festival Sunday morning). Thanks to a connection in Toronto (the key to saving; it’s so simple).
I love Air Canada in part thanks to the elite status they kindly offer me as a content creator, which gives me extra legroom seats for free. And thanks to another little-known tip that everyone can benefit from, but that nobody knows. I just used it on Saturday; to be continued.
I would have obviously wanted to fly JetBlue to be efficient (as I did to get to Toronto in September, via New York and Buffalo), but since I had very little time after my arrival from İstanbul, I just couldn’t go to the United States.
Flights: Las Vegas—Boston—Philadelphia
Then, flying JetBlue from Las Vegas to Boston was expensive because it’s a direct flight. Adding the flight to Philadelphia lowered the price by a lot, as is often the case. Basics of flight prices.
As with JFK (the other JetBlue hub), to do the challenge for cheaper, you have to do Boston as a connection, not as a destination itself!
It’s a terrible red-eye flight, but it was the only way to fly JetBlue, and I decided to endure it, and I bitterly regret it now (like every time I take an 8 AM flight to save a few dollars).
Train: Philadelphia—Newark
By the way, the Philly airport (PHL) is the only one that scored lower than Montreal in a ranking we told you about recently. At least PHL has a train that connects it to the city, like any respectable city does.
It takes you to the Amtrak station directly, actually. I’ve already done that Amtrak—PHL connection, so I know it’s easy and efficient. And Amtrak has a station directly at the Newark airport, so it’s even simpler on the other end.
All this is a bit tight in terms of time, though, but it will be okay if all goes well (like for the 15 flights to do for the round-the-world trip last fall, the 6 flights for all continents this summer, and the 11 JetBlue flights to date).
This is really the key to minimizing the cost of the JetBlue challenge: do all the airports from which you can then easily get to another airport without having to take a flight again, so especially in the Northeast like that. My priority, as it often logically is as someone who wants to travel more, was to do all this at the lowest price possible.
Flight: Newark—Tampa
Even better, I even added this flight from Newark to Tampa on the same booking as Las Vegas—Boston—Philadelphia, with the multi-city booking trick.
It lowered the total price even more: 274 USD for the 3 JetBlue destinations (don’t forget the promotion excludes the basic economy fare class). Only 91 USD per destination on average, that’s excellent.
Flight: Tampa—New York-LaGuardia
I then booked from Tampa to LaGuardia for 98 USD to complete another airport in the New York area.
That’s convenient because then I can easily leave from JFK, the hub from which everything is cheap. And changing airports obviously doesn’t matter if you’re staying overnight, because it obviously doesn’t make any difference to go from one airport to your accommodation and then from there to a different airport.
It’s the most expensive of all my 7 JetBlue flights between Florida and the Northeast, but it’s still quite affordable. I had no choice because of my date restrictions.
Flight: New York-Kennedy—Chicago
I booked from New York to Chicago at the last minute, so a bit more expensive at 124 USD. The thing is, I hesitated for a long time: I could have done 2 more JetBlue destinations quite easily, or at least one more.
But it would have been an extremely packed schedule, specifically 8 flights in 4 days (instead of my 5 flights in 4 days). And the schedules were disgusting. I chose not to maximize, or rather to maximize my sanity and my sleep! For once!
Flight: Chicago—Québec City
Traveling for less is so simple: you literally just have to take the time to compare everything. Obviously, knowing how to compare and what to compare helps. And Flytrippers is here for that. But it’s really not more complicated than that, for real. Compare!
This is a good example to illustrate that, even if it only applies to those who live in Québec City or nearby. Flights at the Québec City airport are almost always more expensive than Montreal. But I always check anyway! It literally takes 30 seconds.
And magic! The direct Chicago-Québec City flight on American Airlines on my specific non-flexible date was 72 USD! Cheaper than Montreal! It’s rare, but it happens! I’ll even be able to take advantage of it to grab a coffee with a Québec City friend between the airport and the bus station.
Bus: Québec City—Trois-Rivières
That’s the story of my life; taking a bus at the beginning and end of each trip. That’s the price to pay for living where my girlfriend and I grew up, where the quality of life is very good, and where having my house built cost me half the price especially! 😂
I actually found a loophole to save 50% (!!!) on the Orléans Express price for all my summer and fall trips, I’ll share that separately.
Booking accommodations for my fall trip to the United States
I’m sharing the details of where I’ll be staying during my trip, so you can learn about the other important aspect of the travel budget.
Here’s the accommodation during my trip:
- Las Vegas
- The ENGLiSH Hotel, Las Vegas, a Tribute Portfolio Hotel (Marriott)
- AC Hotel Las Vegas Symphony Park (Marriott)
- Tampa
- To be determined
- New York
- To be determined
- Chicago
- To be determined
Okay, honestly, this section is often going to look like this with me. I very often love booking hotels at the last minute. The exception is for peak periods (I obviously try to avoid them like the plague anyway) or during a major event (hence my existing bookings in Vegas, with 150,000+ people attending the festival).
To be very clear, I obviously looked at prices, and I even continue to follow prices. As always. I even have fully-refundable bookings made to have a plan B. As always. I just haven’t decided yet. I’ll try to do better, but I can’t make promises.
Las Vegas
I booked a Marriott Bonvoy hotel as soon as their calendar opened up that far, so in November 2024. Prices become completely crazy because of the festival.
I actually already wrote a detailed post about my booking at the AC Hotel Las Vegas Symphony Park, because it was an excellent concrete example of the tip to recheck accommodations. I’ll even be able to do another post for the follow-up to the tip, something else happened.
So I was able to change my initial hotel to this new, cheaper hotel. To my great pleasure, because it was much better in addition to being cheaper, and because it’s not on the Strip. The Las Vegas Arts District is infinitely better. And plus, the festival is nearby.
I ended up also staying at The ENGLiSH Hotel, Las Vegas, a Tribute Portfolio Hotel, a luxurious Marriott Bonvoy hotel that recently opened, which I wanted to try but was always way too expensive for me. It wasn’t planned. A first happened to me, after hundreds of hotel nights. Quite an adventure. I’ll tell you about it.
Tampa, New York, Chicago
To be continued.
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Summary
I’m currently on a fall trip to the United States. It’s a short 10-day trip to be a speaker at a travel rewards event, attend my favorite music festival, and continue the JetBlue challenge between the 2. The 2 ends of the trip will be extremely enjoyable, while the middle will really not be.
What would you like to know about my fall trip to the United States? 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: Reasons for my trip (photo credit: Andrew D’Amours/Flytrippers)
