Affording To Travel - In Your 20s and 30s

Affording To Travel - In Your 20s and 30s

"Seriously, you're travelling again? How do you manage to afford it?"

I literally get asked this question a few times a week. So here are a few of my @gringosontherun not so secret tips to affording flights, accommodation and eating while on the run. 

1. Being Flexible

The only way you're going to find cheap flights is to make your travel schedule as flexible as possible. I know this is almost impossible for anyone who has a full time job, so below I've added some avenues to try out when searching for more specific dates. For the most part though consider rethinking the timing of your travel, such as going to destinations just before or after high season. This way you will still get the great weather, just without the crowds and high prices. 

2. Sign Up For Travel Blogs Based In Your City

Finding an active travel blogger in your city can really save you a lot of the time and hassle of searching for a cheap flight.

My go to guy is @ChrisMyden at his blog 

YOW Deals - Ottawa Flight Deals & Travel Specials

Ottawa - Bangkok $731 CAD Roundtrip including taxes--- NEW RECORD! 


This guy is the man. Sign up for his email list, and I promise you won't regret it. He will only email you if there is a ridiculous deal out of YOW (Ottawa international airport). I have pretty much booked everyone one of the flight deals he has posted. He even runs you through where and how to book the flight. 

Examples of deals: Above Ottawa-Bangkok $731.00 (roundtrip), Ottawa-Santiago, Chile $690 (roundtrip), Ottawa-Azores islands, Portugal $418.00 (roundtrip) the list goes on!!!

Tip: He also runs deal websites for every big city in Canada. Just type in the 3 letters representing your closest international airport followed by to find it. I'm signed up for the cities below as well just to see crazy deals that may be worth the drive.

i.e. (Montreal), (Toronto) and so on.... 

3. United Flex-Fare

When searching for flights, go on (make sure your in Canadian dollars before booking). When entering your travel destination and dates there is an option that says "My dates are Flexible", select this and choose the amount of days you want to travel for. This gives you options from 1 day to 90 days. Click search and the entire month in which you want to travel will pop up showing all the flight prices to your destination throughout the month, allowing you to choose the cheapest! For people with full time jobs, try maybe using this 6 months pre-travel, that way you can give your employer tons of warning and still get the best deal. 

Tip: Play with the length of your trip. Sometimes changing your trip from 12 days to 11 can drastically alter the price in your favour! 

4. Sign up for Aeroplan! 


Don't have an Aeroplan card yet? Get one. Its free and takes 5 minutes to sign up for. Once you have your Aeroplan number always try to fly with a Star Alliance Member. The Star Alliance is a group of 20 Airlines including Air Canada, United, TAM, SAS etc which pretty much cover every continent. If you book a flight via United FlexFare like I recommended above it will automatically search all 20 partners flight paths and prices giving you the best deal.

***Go to for a full list of partner airlines***. 

Why fly with Star Alliance partners? For starters every time you fly with them you gain valuable Aeroplan points. More or less the equation is 1 point = 2.7 cents (CAD). So 15000 points will get you a short haul flight (Ottawa - NYC), 25000 will get you a long haul (anywhere in North America) and 60000-90000 will get you anywhere in the world. 

Tip, doubling up: Using my Aeroplan Infinite Privilege credit card which gives me 1.25 Aeroplan points/Dollar I spend, I booked a flight to Bangkok via united flexfare for $730.00. Which gave me 1825 Aeroplan points (because I also booked my friends ticket as well). Then because we were flying long haul flight with United to Asia we received a total of 14 284 points (each!) for our flights. 

So basically I got 16109 points or x2.7 cents = $434.43 in points. 

or a short haul flight (15000) , or it was like I paid $730 for the initial flight, minus$ 434.00 = $294.00 for a roundtrip to Asia!

So please, utilize the Aeroplan redemption into your flight company selection. i.e. you will not get this with airlines like Sun wing, WestJet, American airlines...

Enroll via this link:

5. Airbnb -

If you haven't used Airbnb yet, you should. It's like the the Uber of accommodation. One of the principal investors is Ashton Kutcher and it reflects his online savviness. We just recently used it in Copenhagen over the weekend and it was amazing and cheap in an otherwise astronomically expensive city. We paid $60.00/night and had a huge room with a super comfy bed in a massive apartment right in the centre of the city. The other tenants in the apartment were down to hang and gave us great local tips on where to go and what to eat that we would have never gotten from a hotel reception, or even the Lonely Planet. It's all about who you know in any location and staying with a bunch of local like-minded people will only help your cause,  especially if your social. Airbnb also offers an array of rentals at great prices, so its really up to you and your budget...or whether you're in the mood for a couch or a private rooftop penthouse.

I hope these pointers give you a baseline for your next trip search. Remember: these are very broad pointers, I could ramble on for days about this stuff so please, if you have any questions feel free to comment and I will get back to you ASAP. 

And ladies... don't leave on any Vacation without your Soulstice Swim Kini ;)


Jesse Delgrosse

Follow Jesse's adventures via Instagram @jdegrosse or @gringosontherun and @soulsticeswim.