Do You Plan the Trip First or Follow the Deal? Here’s How I Plan Our Vacations

Written By Angie Green Terry

One of the questions I get the most usually goes like this—

“Do you choose where you want to go first, or do you just wait for a deal to pop up and plan around that?”

The answer is both! Sometimes we’re working toward a dream destination, and other times we book a trip we didn’t even know we wanted because the deal was too good to pass up.

So if you’re planning a trip and wondering how to get started, here’s exactly what I do — whether I’m chasing a destination or chasing a deal.

If You Already Have a Destination in Mind

Let’s say you’re dreaming of Hawaii, or Paris. or Disney with your kids. Here’s what I’d do step-by-step:

1. Use FlightConnections to check airline options

Start with FlightConnections.com to see which airlines fly to your destination — either from your home airport or from one nearby. Check out my post on positioning flights to see why airports nearby could make all the difference. I look for nonstop flights first (especially with kids), or at least routes with good layover times. If you HAVE to have a layover, make sure you are holding one of my favorite premium cards to get lounge access. That makes those layovers actually enjoyable.

2. Open Google Flights

Even if I plan to use points, I check Google Flights to see cash prices and flight schedules. I look at which airlines offer the best times and connections, and I keep those cash prices in mind for comparison.

3. Check award availability with flexible points

Once I know which airlines I want to fly, I start checking if those flights can be booked with points. Here are some of my favorite cards to earn to start using those points. I usually search:

This is where transferable points come in handy — you can often move them to different partners to get a better deal. If you need help understanding how that works, check out my post:

How to Transfer Credit Card Points to Travel Partners (And Why It’s Worth It)

4. Search for hotels next — with family-friendly space in mind

We’re a family of six, so I look for hotels that offer rooms that fit us, or book two rooms using points. I love using Max My Point to set alerts for hotel availability using points — it saves a ton of time when I’m trying to grab popular properties. You can also use staywithpoints.com and pointsyeah.com to check points prices.

If you’re booking with points, I like starting with brands that still use an award chart (it’s usually better value). If not, I check cash prices and compare to the value I’d get from using points.

5. Build out a realistic itinerary

Once the flights and hotel are set, I start planning what we’ll actually do. One main activity a day is usually plenty — especially for younger kids. We always build in buffer time for downtime, snacks, or naps by the pool. I try to balance things we want to do with what’s actually going to work with our energy levels and travel days. Depending on where you are going, there are many people who post itineraries online for trips they have taken. I usually look at a few of them and see what the common factors are. That usually tells me what the best activities are and the best places to go.

Need help deciding where to stay?

Mom’s Guide to Hyatt for Families

Favorite Marriott Stays for Families

Best Hyatt Hotels in Hawaii for Families of 5+

If You’re Open to Going Wherever the Deal Takes You

This is one of my favorite ways to travel — letting the deals lead the way. This can open up a whole realm of possibilities you had never considered, as long as you can be flexible! If you can be a little more spontaneous, either in dates or destination, here’s how I do it:

1. Subscribe to flight deal alerts

I use Thrifty Traveler Premium to find amazing airfare deals — both cash and points. These include mistake fares, wide-open award availability, and deals I wouldn’t find on my own. You can use code Rewardsmom for $10 off your first year.

2. Check Google Flights to verify

When a deal hits my inbox, I hop on Google Flights to check dates, routing, and price trends. Even if I’m using points, I always like to see if the cash price is worth paying (especially for cheap economy flights).

3. See if you can use points instead

If I decide to book with points, I search with the airline or through my card’s travel portal. All of these cards have great options through their travel portal, and you get more points when you book through them! Win, win. I also check if it’s a good redemption value by comparing it to cash price. To learn more on how to do that, check out How to Calculate the Value of a Point.

4. Check hotel options and award space

If the flight deal is amazing, I want to make sure lodging won’t kill the budget. I’ll check award availability using Max My Point and compare hotel points vs. cash pricing. You can also use staywithpoints.com and pointsyeah.com. If points work, great. If not, we might pivot — or use one of our free night certificates to cover a night or two.

5. Book fast — then figure out the rest

With flight deals, you have to move quickly. I often book the flights first (especially with a flexible cancellation policy), and then I fill in the hotel and itinerary later. This method has taken us to places like Kauai, Cancun, and even Europe for way less than you’d expect.

What If You’re Paying Cash?

Even though I use points for most of our travel, I always keep my eye on cash deals too — especially for cheap domestic flights, positioning flights, or vacation rentals. Here’s how I keep costs lower:

  • I use Capital One’s travel portal with one of their cards to earn or redeem points. Oftentimes booking through a travel portal you will be rewarded by the credit card company by 2x, 5x, or even 10x the points by booking through their portal.

  • I stack cash-back with Rakuten or other shopping portals when booking

  • I compare hotels across booking sites and often find discounts with programs like Walmart+ Travel or by calling the hotel directly

  • If we’re booking an Airbnb or VRBO, I check if we can offset it by booking part of the trip with points and part with cash—Booking Vacation Rentals with Points.

Need a Quick Recap?

Chasing a Destination?

  • Use FlightConnections to see your options

  • Compare flights + prices with Google Flights

  • Search award flights and hotel points availability

  • Build an itinerary that works with your family’s energy

  • Use points where you can — spend where it makes sense

Chasing a Deal?

  • Sign up for Thrifty Traveler Premium

  • When you see a deal, check it fast on Google Flights

  • Compare points vs. cash and act quickly

  • Backfill the hotel + plan the details once the flight is locked in

Want more tips like this each week?

Come join the community — this is what I help moms with every single day.

And if you’re ready to get started with points…

These are my favorite beginner cards for families

Editorial Disclosure:

Opinions, reviews, analyses & recommendations are the author’s alone, and have not been reviewed, endorsed or approved by any of these entities.

Advertiser Disclosure:

The Rewards Mom has partnered with CardRatings for our coverage of credit card products. The Rewards Mom and CardRatings may receive a commission from card issuers.

Angie Green Terry
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