Finding an Affordable Last-Minute Solo or Couples Getaway
These are the sites and tools I use to find the best destination, flights, and accommodations for each trip.

It’s no secret that I like to travel inexpensively, and often. That doesn’t mean “roughing it,” which I had to leave behind in my 20s and 30s. These old bones aren’t sleeping in hammocks or riding buses around the countryside anymore.
The good news is there are plenty of affordable adventures to be had, especially if you have location-independent work and can continue producing an income while you’re on the road. Today, I’ll share a sneak peek at how I score budget-friendly flights and uncover the perfect accommodations for trips a few weeks or months ahead.
If you’re like me, planning is half the fun 😁. I’m sure everyone has their own system, but this is a combination of sites I like to use, and a research process that incorporates flights, accommodations, and cost of living/existing in various locations.
Disclosure: Midlife Nomads often refers and links to websites, apps, and products/services I actually use. Sometimes, I receive compensation if readers sign up or make a purchase. A girl’s gotta eat – and travel! ✈️
1. Go to Google Flights > Explore.
Set your home airport and destination Anywhere. Set your dates or be flexible for even better pricing.
2. Set filters.
Add any filters that matter to you: direct flights or no more than one stop; under $800, etc.
My typical filters are:
Stops > One stop or fewer
Airlines > Star Alliance (gotta get those points)
Price > Under $1000 CDN round-trip
Keep in mind that these prices typically don’t include additional options like seat selection and checked baggage. I’ve gotten really good at doing 2-3 week trips with just a backpack for this reason. You can do it!
I’ve used these packing cubes for years, and you can save a ton of room by rolling your clothes inside one of the large and one small (which is what you fit in a backpack.
Keep your dirty clothes in a travel laundry bag so they stay separate from your clean ones until you hit a washing machine (or the bathroom sink, in a pinch).
3. Check out your long list.
Get your list of destinations that have cheap flights and meet whatever needs/wants you have (big city, by the ocean, in the mountains, what have you).
From Toronto, looking just one week out, I have plenty of options including Miami, San Diego, Lisbon, London, and Aruba:
Some results are popped open into those visual cards you see above, but there are plenty more results, too. Hover over any city with a blue plane icon and the card pops up – those are your matches.
4. Filter down to a shortlist.
There’s quite a bit here, so I can take the budget down even further and see what’s available for under $600 CDN.
That takes European destinations out, so if you have your heart set on that just scale back up again. At this price point, we have:
5. Evaluate flights.
Now, check out the routes and schedules to make sure they’re workable for you. Click on each destination card to see the recommended flights.
If I see things like an 11-hour stopover in Chicago, that’s probably not a great choice for me. However, 24 hours stopover in Miami is something I’d consider.
Next – and this is important – click on your flights of choice and make sure it’s actually available via the airline. You’ll want to book direct with the airline and avoid third-party booking sites like CheapO Air, GoToGate, etc.
It can be very difficult to get customer support if needed when you’ve used a third-party booking site, and you don’t need them. Even if you’re using two airlines, one each direction, you can just book directly with each one.
Be prepared for at least a 3-4 hour stopover if you’re changing airlines. Sometimes you can check in online and stay security-side, but not always – you may have to exit to do customs, for example, and certainly will have to recheck your bag if you’re carrying checked luggage.
Carrying an iPad lets you to read books, watch movies, play games and even get some work done while you’re waiting out stopovers, waiting for buses, etc. You don’t need (or even want) a brand new one for this, either. Find an older generation iPad or even used/refurbished one you won’t feel paranoid about losing or having stolen while you travel. I’ve come to love my travel days, as I get some alone time to chill and binge on movies and podcasts.
Because I travel with my work laptop, I do make sure my travel insurance covers loss or theft of devices (cell phone, laptops, tablets). WorldNomads offers an additional layer of coverage with their ‘Explorer’ level plans, so you may want to check that out. You can get your medical, travel interruption/cancellation, and device coverage all in one place.
6. Price out your options on the airline site.
Google Flights is showing you the rock bottom rates available, but you might choose to upgrade slightly. For example, I don’t want non-refundable fares. I usually like to pick my own seat, too, and may need a checked bag depending on the destination.
So in this case, I’ve clicked through to the United site and it’s telling me there’s an upgrade from Basic Economy to Economy which would allow me to choose a seat. After that upgrade, we’re still looking at a return flight from Toronto to Las Vegas for under $400 CDN:
Here are a few examples from other destinations that came up in these same Google Flights search results for round-trip flights from Toronto, Dec 9 to 16 (one week away from time of search), under $600 with one stop or less. I removed the “Star Alliance” filter here as that may not matter to you.
So, we have some options now for round-trip flights under $600 – Aruba, Maui, Cancun, Barbados, and the U.S. Virgin Islands.
7. Check out costs of living, internet availability, safety, etc.
I like NomadList for digging into the info that matters to me. How’s the internet? What are the average temps this time of year? Are groceries and restaurants affordable? Is it a walkable destination?
NomadList used to be open and now requires a login, but it’s still free to use many features. You can dig into different cities and see how NomadList members feel about the place, whether it’s good for families, how much standard items cost in the local currency, pros and cons, and a lot more.
I sometimes use NomadList for inspiration, and often as I’m closer to making a decision about places on my shortlist.
8. Check out rooms.
Now, we’re going to search for hostels with private rooms and ensuites in your shortlist cities.
I’ve always had good experiences with Airbnb, but prices are now often just as expensive as hotels in many locations and cleaning fees have gotten out of control. If you do decide to try Airbnb, make sure you understand the full cost with local taxes and cleaning fees, and never choose a property without a solid history of good ratings.
Because I’m a Marriott loyalty member, they’re often the first place I check. Marriott includes brands like Courtyard, Residence Inn, and TownePlace Suites, where I can often find a good deal. At the higher end, they have Westin, Delta, Sheraton and even Ritz-Carlton if you feel like a splurge.
It doesn’t have to be Marriott, but if you plan on traveling more than 10-14 days this coming year, it’s worth looking into a hotel loyalty plan. You can get perks like late check-out, free premium internet, and free breakfasts, which I love as a business/digital nomad traveler. Check out different chains and see who has the most affordable options in the destinations you want to hit up.
Google and Expedia are good places to look for hotels, too. Book direct with the property whenever possible. Not only are there sometimes perks for booking direct (because the property saves on a booking fee), but the hotel can’t help in a lot of cases if something goes wrong and you’ve booked with a third-party like Expedia or Booking.com.
Now, if hotels are out of your price range, try hostels. Hostels typically come with kitchen access, some kind of coworking space, and laundry facilities. They often offer tours and social activities. I just don’t want to share a room or washroom – and the good news is, you don’t have to.
I like Hostelworld.com as a search engine and booking agent. I’ve used them several times and they haven’t led me astray; that’s not an endorsement, but my personal preference. You can filter results for any location to include only those hostels with private rooms:
Now, make sure you click through and check the property out on the website. “Private rooms” don’t necessarily include ensuite private baths, so you want to make sure that’s what you’re getting if you don’t want to share.
If budget is a consideration, Maui is probably getting crossed off the list. Accommodations are quite expensive, and even a hostel private is close to $200 a night.
Saint Thomas didn’t return any results, so that’s coming off my list for now.
Cancun has several great options; here are just a couple:
From here, I’m going to start comparing features and also cross-referencing these reviews with Google Reviews to make sure I have a pretty good idea of the experiences others are having at these properties.
Now make a decision. That’s the hard part.
I’ll often repeat these searches over a period of days or weeks, and you can expect pricing will change. That’s part of the fun – for me, at least, because as I said, I love the planning part.
If you don’t want to come back to this several times, be prepared to sit down for one marathon research session and take the leap to booking when you find the right combo.
The fun part is that you really can’t get it wrong, and if you don’t have “the perfect trip,” you can do it all over again. You haven’t spent your entire annual trip budget to sit on one beach at one resort. (I know not everyone can afford a $2,000-$5,000 pp annual vacation but I also know many people who are doing it, then ask how I travel so much!).
Once you know where you’re going, I like GetYourGuide for reliable, interesting tour options. You’ll find guided hikes, food tours, city adventures, sunset cruises and a whole lot more.
So, my question to you is – what’s on your shortlist?
And what’s stopping you? 😉