Research says the anticipation of a trip may have a greater impact on happiness than the trip itself.

But when it comes to booking a trip with rewards it’s not that easy.

When I started booking reward flights, I made mistakes. But these mistakes led me to create a process for each trip I booked. A process that gets me from idea to vacation in the shortest and most efficient way possible.

If you’re looking to book a flight or hotel using rewards, here’s a step-by-step guide to ensure you’re getting the best deal.

Step #1: Set a Goal

If you’re brand new to booking reward trips, it’s difficult to understand what exactly you can and can’t do.

Is round-trip airfare for a family of four to Hawaii possible? A first class international flight for two? A 5-night stay at a 5-star hotel?

Within reason, there’s very little you can’t do.

So, think big. 

Pick a goal that’s worth your time and effort.

Your goal should fall into one of the three following categories:

  • Airfare
  • Accommodations
  • Both

If there’s a specific time you’d like to take the trip, include that in as well.

Still unsure? Check out my post on the best family vacation ideas.

A few notes:

  • I prefer to use reward points on airfare. This is where I find the best value for my travel goals.
  • Depending on your circumstances, it may make sense to use your rewards to only book a hotel. Reasons may include: driving to your destination, cheaper flights, or a specific hotel that is on your bucket list.
  • If you’re trying to book both a hotel and flight, you’ll likely have to apply for two credit cards. That means hitting two minimum spend limits. Plan accordingly.

This post is part of a mini-series on travel hacking. You can get the entire free series, delivered in order, by entering your email address below.


Researching Your Travel Goal

The aim here is to find the most efficient way of booking your trip.

To do that, I want to share with a goal from a potential upcoming trip of my own:

Roundtrip airfare from Chicago to Bermuda and a 5-Night stay at a minimum four-star hotel in January of 2019.

Finding Programs & Partners

Let’s start with the flight.

My goal is to get from Chicago to Bermuda in January of 2019.

I plan on flying economy. For first class, a good rule is to double the number of points needed.

I like to start my search with a visit to AwardHacker. Here I can see the different options to get to my destination of choice using rewards.

By typing in Chicago to Bermuda, here’s the top search results:

Travel Hacking 101: Options to Bermuda

Using AwardHacker, there are a few things we now know:

  • The airlines, programs, and transfer partners of the airlines that go from Chicago to Bermuda
  • The price per round-trip ticket.

Sign up for Loyalty Programs & Verify Availability

No award search engine is 100% accurate. Next is to sign up for the individual loyalty programs to verify the information.

In my case, I’ll sign up for:

Here’s what you’re looking for when you search for the flight in each loyalty program:

  • Are the dates indeed available for your flight
  • If your travel dates are flexible, is there a better time to fly
  • What’s the total travel time of the flight, # of stops, etc.
  • How much that flight will cost in points
  • What are the total fees involved

All airlines loyalty programs are free to join. So, this it’s a matter of signing up for the top 3-4 loyalty programs you found via AwardHacker to confirm the details.

Repeat for Hotels

If I was looking to book only a flight, I’d move on to Step # 2. But since I’m also looking to book a hotel with points, I need to find a place to stay.

To do that, I like to start my search at Hotel Hustle.

Just as AwardHacker allows you to search for award flight availability, Hotel Hustle allows you to search for Hotel availability.

And when I search for award availability in Bermuda, here’s what I get:

Award Availability in Bermuda

That’s right, nothing!

Hotel Hustle searches Radisson, Hyatt, Hilton, Comfort Inn, IHG, Wyndham, SPG, and Marriott rewards programs. So, these programs are out.

But there are other options.

One is to see if I can find a hotel directly through a credit card company’s travel portal. The downside here is you must already have a credit card open.

As an American Express Cardholder, here’s an option I get when I search for Bermuda hotels through

Travel Hacking 101: Trip to Bermuda

As a Chase cardholder, here’s what I get when I search for award availability through Chase Ultimate Rewards.

Chase Ultimate Rewards Bermuda

For 13,203 points per night or 66,015 total Chase Ultimate Reward points, I can stay at the Cambridge Beaches Resort & Spa. A quick look at TripAdvisor and the hotel has some great reviews.

This looks like a winner but we must figure out if it’s possible to earn enough points to book those rewards.

Step #2: Earning Enough Points

The aim of phase # 1 was to figure out:

  • At least two ways to travel to my destination of choice using rewards
  • At least two places to stay using rewards

Now we’ll find the best way to earn the points necessary to book the trip.

Let’s start with booking the flight:

Identifying The Best Travel Rewards Credit Card for Free Flights

With AwardHacker, I have a good idea of the rewards needed to book a reward flight and trip. I can then search the current top travel cards on the market with this in mind.

Again, here are my top four options:

Travel Hacking 101: Options to Bermuda

Option #1 – JAL Mileage Bank

At 21K points for one round-trip ticket, Japanese Airlines looks like the lowest cost option.

After some research, I find that there’s a JAL Mileage Bank Credit Card through First National Bank of Omaha. But the signup bonus is low.

Fortunately, under transfer partners, I see that SPG (Starwood’s Preferred Guest) is a transfer partner to JAL Mileage Bank. But there’s no current sign-up bonus for Starwoods cards.

Since points are difficult to accumulate, we’re moving on to option # 2.

Option #2 – Iberia Plus

At 23K points for a round-trip ticket according to AwardHacker, Iberia Plus is the next lowest option.

A quick search shows that there’s a current offer for a Chase Iberia Plus credit card that could be enough to book the trip.

Before moving on to option # 3, AwardHacker lists American Express as a transfer partner for Iberia Plus.

American Express has many good offers on the market right now, especially if you run a business. So, it’s worthwhile to see if there’s a card that might better fit your needs. Then, transfer American Express points to your Iberia Plus account.

Compare current American Express credit card offers.

On another note, while AwardHacker doesn’t list it, Chase Ultimate Rewards recently become a transfer partner of Iberia Plus. So, it’s worthwhile to check out the top offers from Chase too.

Compare current travel rewards card offers.

Last, it’s important to pay attention to fees when booking your flight. To check what your fees would be, you’d go through the booking process without confirming the flight.

Here’s what I get with Iberia Plus.

Iberia Plus Fees

Option #3 – American Airlines

The final option I want to check out is American Airlines. With American Airlines I can book award flights for 25K points round-trip, according to AwardHacker.

Searching the top airline reward cards, I see there’s a good sign up bonus right now available through Citi to earn AAdvantage points.

Compare top airline rewards cards currently available

Knowing this, I head over to AAdvantage to see what my options are for booking the flight. Surprise! Come January it looks like the lowest cost option is 30K points round trip.

Also, I check on the fees when booking with American.

AAdvantage Bermuda: Travel Hacking 101

Choosing the Optimal Flight

Choosing which credit card to go with here depends largely on my situation.

The American Airlines Card, American Express, and Iberia Plus card are good choices. So, it comes down to picking the right card for me and optimizing my spending to earn enough points.

One rule of thumb I stick to is to always do what’s best for my long-term credit.

A few of the American Express cards available right now I can see myself holding on to.

On the other hand, I’m not sure the long-term value of holding on to the Chase Iberia Plus Card. If I held on to the card long-term, I’d continue to earn only Chase Iberia Plus points. My preference would be to earn transferable points.

One such option is Platinum Card from American Express has a signup bonus large enough to book two round-trip tickets.

While the $550 annual fee is hard to swallow, I can earn up to $200 in Uber Credit and $200 in airline fee credits a year. Plus, I get access to The Centurion Lounge.

Compare current American Express credit card offers.

Another option which makes sense for those who fly American Airlines (or another airline with a hub in your city) is the Citi AAdvantage card. With the first checked bag free for you and up to four people, the annual fee can certainly pay for itself for frequent American Airline flyers.

In theory, I’d now apply for the card that’s ideal for me and reach the minimum spend requirements. Once then I have enough points in my account, I’ll transfer to Iberia Plus (if necessary) and book the flight.

Step #3: Research Hotels

Bermuda is small. As such, I don’t have a lot of options when it comes to hotels.

As we found out through Hotel Hustle the big hotel loyalty programs don’t have a hotel in Bermuda.

In most destinations Hotel Hustle will provide award availability for a number of hotels. So if something did pop up on the search, I’d repeat the process I did with flights.

Next, I would sign up for the free hotel loyalty programs and confirm the details. To see an example, view this post on Travel Hacking Hawaii.

Another option is to book hotels right through the credit card travel portal.

When doing my search, I found that the Chase Ultimate Rewards travel portal offered the best deal–for 13,203 points per night or 66,015 total points, I can stay at the Cambridge Beaches Resort & Spa

I’m seeing this offer only because I have the Chase Sapphire Reserve Card. With this card, I can redeem points for 1.5 cents each towards the cost of travel.

Other popular Chase cards, Chase Sapphire Preferred Card or Ink Business Preferred Credit Card, you’d only be able to redeem for 1.25 cents towards the cost of travel. As such, this award would be closer to 16,000 points per night or around 80,000 total points.

As we learned in booking our flight, not all programs offer big signup bonuses. The next step then is reviewing the top travel rewards credit card offers to see if there’s a fit.

We’re in luck. There are a few cards which allow me to get the sign up bonus with my current level of spending.

These are the:

I’d then take a closer look at the benefits of each of these cards. 

The Ink Business Preferred Credit Card sounds like a great fit. However, that’s only available to someone who has a business.

Then, there’s the Chase Sapphire Reserve Card. This is the card that allows me to redeem points for 1.5 cents each towards the cost of travel.

While there’s a $450 annual fee, with a $300 travel credit that fee is more like $150 a year.

Note: If a signup bonus is under the number of points I need to book, I can either wait a few months until I earn enough points or Chase allows you to pay with points and cash.

As I’m a business owner, I decide to go with the Ink Business Preferred Credit Card.

The card is a great fit for me as I can earn 3X the points when I spend in select business categories.

The thing to realize here is that there’s no single best card for everyone. Do your research and find the card that fits you best.

To build credit it’s best to keep accounts open. Think long-term and apply for the cards you plan on keeping.

If you’re interested in learning more about the Sapphire Preferred and Sapphire Reserve, I reviewed and compared the two cards here.

Step #4: Hitting Minimum Spends

Let’s review what we’ve done:

  • I set my goal of going to Bermuda in January for a five-night stay, using points to pay for both airfare and a hotel
  • I found the airline where I could book my flight, then applied for a credit card that allowed me to earn enough points.
  • I found a hotel in Bermuda to stay at, then applied for a credit card that allowed me to earn enough points.

Unfortunately, when you apply for the card, the points don’t hit your account. There’s a minimum spend amount you need to hit.

The two credit cards I choose to sign up for in this example were the:

As both accounts require a minimum spend, it’s important to plan this aspect out. Depending on where I’m at with my business and personal expenses, it may make sense to space out these applications.

Ideally, I’d hit these bonuses without impacting my budget. And if I had to overspend, I wouldn’t apply for these cards in the first place.

Once I do hit the minimum spend, the points still take some time to hit my account. Typically, it’s when the next billing cycle occurs. So, I plan around 4 months after account opening to be safe.

Once they do, I can finally go ahead and book my flight and hotel.

Credit Card Reward Travel 101: Key Takeaways

This example may seem complex. However, when it comes to booking reward travel this is pretty much what to expect.

For now, here are the key takeaways:

  • Plan ahead. Don’t expect to take your first award trip in a matter of weeks. From the day you apply for a card, plan at least six months out.
  • Think long-term. If you’re just starting out, don’t destroy your credit. Excellent credit score turns reward travel into a lifelong hobby, rather than a one time experience. Two common mistakes that could hurt your credit score are: 1) Applying for a card where the minimum spend exceeds your budget 2) Applying for too many cards at one time
  • Always verify trip details. Award search engines like AwardHacker and HotelHustle are a great place to start with. Nonetheless, they are not always 100% accurate. Always make sure to check directly with the travel program for up to the minute offers.

Ready to get started?

Compare current top travel rewards card offers


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