Calling Reconsideration Lines

Sometimes, you may not get approved right away. Instead, you get some version of "sorry, not right now." If you get that, call the reconsideration department for that issuer.

Here is a short list of known reconsideration lines for the card issuers:

Ok, assuming everything has gone your way, and you're approved, you can expect to receive your new card in the mail in the next 5-10 business days.

What To Do When You Receive The Card

You're going to have a few things you need to do when you receive your card:

• Activate: You'll need to activate the card, either online or by calling an automated number.
• Register: Create an online account with that card issuer if you haven't already done so. If you already have an online account, make sure the new card has been added to that account.
• Link: Connect your credit card to the checking account you'll be using to pay off the statements.
• Automate: Set up autopay so you never miss a payment–but make sure you have the funds in the checking account to draw from.
• Choose: Select benefits, if any, such as with some of the premium cards from American Express.
• Download: Download the mobile app of your card issuer.

Staying Organized (A Little Goes A Long Way)

The key to winning the travel rewards game is being organized.

There are few things more tragic than jumping through all the hoops to get approved for a card, then not getting the signup bonus because you either confused the amount of the minimum spend or messed up on the deadline.

Or, forgetting to pay off your statement in full, and getting hit with either a late fee, or significant interest expense, or both.

The ounce of prevention here is the ability to get a little organized.

You'll Want To Know The Following Pieces Of Information About Each Card:

1. Name of the card.
2. Date the card was approved–this is when the countdown starts for the minimum spend to be met.
3. How much time do you have to meet the spend? Most issuers give you three months from the approval date, but some banks may only have a two-month window. An easy way to know for sure is to send a “secure message” through your online login to get the exact date you need to hit the spending requirement.
4. The amount of the minimum spend.
5. The amount of the bonus.
6. How much the annual fee is, if any.
7. If the card has an annual fee, note the date you should be considering calling in for a retention offer.

While we recommend using a Google Sheet or Microsoft Excel for keeping track of this info, if you use a pen-and-paper approach, that’s cool too. Just make sure you have all that information stored in a place you can locate quickly.

As discussed previously, make sure you set up all your cards for auto-pay with a bank account that always has enough money to cover your spending.

Make a note in your calendar to check all your credit card accounts once every 2 to 4 weeks. You can use Todoist, Google calendar, or Microsoft Outlook, among others.

You want to verify that your card is paid off and that your cumulative spending is on track.

Passwords

You're going to want to avoid having the same password for all your credit card accounts. In fact, when you set up your travel rewards accounts with the airlines and hotels, you should have different passwords as well.

If you are unable to keep track of all these passwords, you can:

1. Let your browser (like Chrome) suggest strong passwords, then have it save the login details. Make sure your personal computer is protected by a login password, though.
2. Better yet: sign up for a password manager like BitWarden

Key Points

There you have it; that's the whole application and activation process. It takes a little time and organization, but it'll be well worth it when you're traveling for almost free with your family.

Just because you've applied for your first card doesn't mean you're done. We've still got quite a bit to cover. The next section will be all about business credit cards, which are vital to the travel rewards world.

Why Business Credit Cards Are So Valuable

They Are Not Included In Chase's 5/24 Rule

In the world of Chase's 5/24 rule, most business credit cards are not included in your 5/24 number. There are exceptions: The business cards from Capital One and a few others do show up, so stay away from these until you have all the Chase cards you can get within 5/24.

Who Can Apply For A Small Business Credit Card?

If you have a business, you can apply for a business card. Your business doesn't have to be registered or licensed–and you don't have to have an EIN. Side hustles totally count!

Here are some examples of common businesses, but the list is endless:

• Rental Properties
• Drive for Uber or Lyft
• Babysitting or dogsitting
• Deliver food or packages
• Do freelance writing or design work
• Work as a handyman/woman
• Sell your handmade stuff on Etsy

Here’s what you do not need to have to be a small business owner:

• Significant amounts of income
• A registered business
• An office
• Employees
• You do not even need an Employer Identification Number (EIN), although that does make applications a little less tricky.

Applying For Your First Business Credit Card

Just as with your personal credit application, a business card will be approved or declined based partly on your personal credit score.

Other factors would be your personal income and annual business income to date.

And just as with your personal credit card applications, you should be candid about your business revenue to date, even if it is not yet significant.

Every new business goes through a start-up stage, and many depend on a line of credit to keep the finances organized and separated from personal accounts.

With any type of side hustle, you shouldn’t feel weird applying for a business credit card. It’s every bit as normal as applying for a personal credit card.

When applying for the first business card, many people report the business as a sole proprietorship and use their Social Security number as the tax ID number on the application.

Some use an Employer Identification Number (EIN) from the IRS instead. It’s basically a tax ID for businesses. All kinds of businesses can get one, even sole proprietorships, and it can be done in less than 10 minutes online.

You can apply for an EIN here. It's free and only takes a few minutes.

Anecdotally, we've heard that if you have a business with a track record, use the EIN. If you are just starting with a new business, use your Social Security Number.

Key Points

Don't think you can't apply for a business credit card just because you don't have a registered business. Most people with side-hustles can, even if you don't make a ton of money yet.

So, whether or not you own your own store or just write a few freelance articles on weekends, a business card can go a long way in earning you travel rewards.

In the next section, we're going to be talking about how to meet minimum spends on credit cards. Business cards have them too if you want to earn a huge signup bonus.

Consolidate Your Spending

Put all your everyday spending on the card you are working on. Gas, groceries, dining out, utilities, and so on.

Then, think about all the things you're not using credit cards to pay for and figure out if you can use credit cards (preferably without transaction charges).

If you can use a credit card instead of cash, check, or bank transfers - do that.

Pre-Pay Your Bills

If you already have recurring payments like subscriptions or utilities set up to pay with credit cards, you should avoid messing with those.

It would be pretty painful to have to reset everything each time you get a new card.

But you can use the new card to make extra payments. That way, you transfer the spend from the credit card you have on file to the one you are trying to meet the minimum spend.

Paying For Work-Related Expenses

If you're employed, see if your employer will let you pay using your own card, then reimburse you for it. If you are one of the lucky ones that get to choose and pay for your flights and lodging, congratulations!

If you run your own business or have a side hustle, use your new card to pay for business expenses.

Less Optimal Options

Third-Party Payment Services

Use third-party payment services to pay for things you would usually write a check for, such as rent, mortgage, or tuition.

This is not the best option because there is usually a fee (~2.5%) involved, but if you need to meet spend, then know this option is out there. You'll still get more value from the bonus points than the cost of the fee, but clearly, it's a less optimal way to meet spend.

Pre-pay Your Estimated Taxes

Another sub-optimal option is to pre-pay your estimate federal and state taxes.

Again, there is always a transaction fee. If you go down this path, expect the fee to be between 1.96% to 1.99% from the IRS-approved service providers.

You can find out more about using your credit card to pay estimated taxes here.

Enlist A Partner

If you have a spouse or partner who has no interest in the logistics of earning free travel, see if they might be open to helping out by putting their spending on your card.

Make it super easy for them to help, though. Give them just one card to use at the beginning, and label it so they know where to use the card.

Rinse and repeat if there is another card to work on.

What's A Category Bonus?

Great question!

Aside from the initial signup bonus, many cards also give a multiplier on points or miles earned based on the spend category.

Some of these categories include:

• Travel
• Dining
• Groceries
• Office supplies
• Gas
• Drug stores
• Home Improvement & Furnishings
• Online Shopping

The multiplier varies between 2x through 5x. Occasionally, it may go as high as 10x for specific promotions, but those are usually temporary.

Some of the cards provide the bonus category year-round, and any multiplier is applied automatically. Other cards have categories that rotate every three months, and you have to activate them ahead of time.

Category bonuses are a neat way to continue earning accelerated points and miles when you are in between new minimum spending.

Key Points

Signup bonuses are common with most credit cards these days, and luckily they don't have to be difficult to earn.

As long as you're only spending on purchases you were already going to make (think of everything from utilities to groceries and gas), you can easily make the minimum spend requirement.

Next section, we get into the nitty-gritty details of using your rewards to earn almost-free travel. Stay tuned!

✈️ The ChooseFI Travel Rewards Redemption Starter List

To make it on our go-to starter list, these redemptions have to meet a few key criteria:

🛠️ Criteria for Choosing Redemptions:

1. Points/Miles Are Easy to Accumulate
   Big bonuses on one or two cards, or multiple smaller bonuses that can be earned and combined.

2. Ample Award Availability
   Plan 6-9 months ahead and you'll find plenty of award seats, both on the airline’s own flights and on partner flights.

3. Online Redemption
   No phone calls required! You should be able to redeem these awards on the airline's website or mobile app.

   📝 Note: Most travel rewards experts expect phone calls as part of the process, but we’ve cut that step out to make things easier.

⚠️ Best Value? Not Always...

Are these going to be the absolute best “value” for your points and miles in terms of dollars saved off the sticker price?

No.

But that’s not our primary goal. If you’re aiming for financial independence, your focus is likely on maximizing the number of free trips while minimizing the time spent chasing the perfect deal.

We’ve kept this balance as our guiding principle for these recommendations.

💡 Maximizing Your Redemptions

Here are three strategies to help you get great value from your points and miles:

1. Leverage Airline Partners for Cheaper Awards
   Sometimes, redeeming a flight on an airline through its partner can cost you fewer miles.
   For example:

   • Redeem Delta Airlines flights using Virgin Atlantic miles.
   • Redeem United flights using Singapore Airlines Krisflyer miles.

   (We’ll dive into these examples later on.)

2. Stack Destinations with Free Stopovers
   Get more value by adding stopovers to your itinerary at little or no extra cost. Imagine visiting two cities for the price of one flight!

3. Fly in Style with Luxury Business or First-Class Flights
   If you prefer luxury, use your miles for business or first-class flights.
   ⚠️ Caveat: While you'll enjoy style and comfort, these redemptions require more points, meaning fewer trips overall.

🎯 Starting Point for Great Redemptions

We'll begin by exploring some excellent domestic redemption options and, in the following section, we’ll take you through the best international itineraries.

💬 Pro Tip: Always compare different airline partners to see where your miles can stretch the farthest. Just because an airline offers a redemption doesn’t mean it’s the best deal out there!

Southwest Airlines Rapid Rewards

No Restrictions

The Southwest Rapid Rewards Program may not have universal appeal, but it is a favorite for many people.

Unlike just about every other airline, Southwest does not restrict award space on its flights. If you find a seat that you can pay cash for, you can also book that same seat with points. The cash price will vary based on capacity and various promotions, but if you can pay cash for it, you can pay points for it. Just toggle between “$” or “Points” for your preference. No ifs, ands, or buts.

No Cancellation Fee

Another way that Southwest makes it easy to redeem flights is that there is no cancellation fee up to 10 minutes before the flight’s departure. So, book as many flights as you have points for, even if you aren’t sure if you will be flying.

If you change your mind for any reason, you can cancel the booking and get your points and fees refunded.

This means you can book first, then see if your Southwest flight is really the best redemption compared to Delta, United, American, Alaska Airlines, etc…

Even better: if the cost of your Southwest booking drops, book a new seat on the same flight to nab the savings, then cancel the original one.

Easy-To-Use Mobile App

Another bonus: it’s just as easy to make a redemption on the mobile app as it is on the website. This isn’t always the case for all programs!

Companion Pass

If you love the Southwest program, you should double down and shoot for the Companion Pass. That’ll allow you to bring someone with you for just a $5.60 airport security fee for each one-way domestic flight.

How To Stash Southwest Points:

Transfer Partner Programs:

• Chase Ultimate Rewards
• Marriott Bonvoy

Co-Branded cards:

• Chase Southwest cards

Alaska Airlines Mileage Plan

Another favorite for folks is Alaska Airlines because of how generous their program is with its stopovers. You get one free stopover for every one-way flight, and one of the itinerary segments can even include a partner airline.

You can choose to stop over for as long as you want on an Alaska Airlines redemption, sometimes even on partner American Airlines too.

An Example Of A Stopover

If you live in Atlanta and want to make a trip out to Honolulu, you could throw in a stopover in Seattle for weeks, even months, for as low as 25,000 total points one-way.

That’s the same cost you would pay for Atlanta-Honolulu without the stopover.

Stopovers Get Better If You Live In One Of Alaska Airline’s Hubs

The stopover benefit becomes a super benefit if you live in one of Alaska Airlines’s hubs like Seattle, Portland (Oregon), San Francisco, and Los Angeles because now you can get really creative.

Let’s say you live in Seattle. And you’ve always wanted to go to Honolulu and Cancun. Here’s what you can do to get the biggest bang for your buck/points:

1. Book a one-way to Honolulu on any airline for your vacation, maybe using the British Airways redemption we discuss later. This can be an award redemption or a paid flight. You can plan to stay for as long as you want, as long as there is award availability when you are ready to leave.
2. Redeem on Alaska Airlines this itinerary: Honolulu-Seattle-Cancun, with a “stayover” (what we call a long stopover) in Seattle, where you’re actually back home. Then, when the time comes, jet off to Cancun for your next vacation.

This is what the numbers looked like when we checked in Nov 2021: the HNL-SEA-CUN redemption can be had for as low as 22.5k points. Booked separately, HNL-SEA was 20k points, and SEA-CUN is another 15k points. That’s a total of 35k points compared to 22.5K, which means a savings of 12.5k points!

Now, figure out your next destination–maybe it’s Anchorage? If so, your return flight from Cancun may take you back to Seattle for another lengthy “stopover”, then onwards to Anchorage months later.

Again, you’re going to save a bunch of points: Cancun to Seattle is 17.5k points, while Seattle to Anchorage is 10k, for a total of 27.5k points. In contrast, Cancun-Seattle-Anchorage is available for as low as 17.5k points, which means you basically got the Seattle to Anchorage segment for free.

Rinse and repeat for your next trip.

For folks living in an Alaska Airlines hub, this is quite possibly the best way to get the biggest bang for your buck for domestic travel. It’s also a great way to get great value for international travel, but more on that later.

How To Stash Alaska Airline Miles:

Transfer Partner Programs:

• Marriott Bonvoy

Co-Branded cards:

• Bank of America

British Airways Executive Club

The BA Executive Club program is good for specific kinds of redemptions–non-stop flights on partner airlines within 2,000 miles, at least within the US.

If that sounds incredibly specific, well, there are reasons for that.

Non-Stop Flights

When redeeming British Airways miles (called Avios), each flight segment is treated as a separate redemption. So, if you have a redemption for Seattle to New York’s La Guardia, but the itinerary has you changing planes in Chicago, you’ll be making two redemptions that look like this: SEA-ORD, ORD-LGA.

Refer to the table on this page for Avios points needed for redemptions if you want to follow along. Note that this is not an actual redemption we want since it isn’t non-stop; we are just using it to illustrate why you want non-stop flights when using your Avios points.

So instead of 12,500 Avios for a direct flight, you’re now paying 20,750, as well as two separate security fees for the same ultimate journey from Seattle to NYC.

If you redeem your Avios for international flights on British Airways metal, chances are, they fly through London, and those usually come with some exorbitant taxes and ‘fuel surcharges’ (junk fees) that effectively defeat the whole purpose of using points.

These charges are usually far more reasonable on partner flights that aren’t flying through London.

How To Stash British Airlines Avios:

Transfer Partner Programs:

• Chase Ultimate Rewards
• American Express Member Rewards
• Marriott Bonvoy

Co-Branded cards:

• Chase

Key Points

Your first trip using your travel rewards should be an easy one, so stick to domestic flights. You'll find tons of ways to redeem domestic flights. If you can be flexible with your travel, there's a deal to be had on nearly every airline.

In part 4, we'll tackle how to do all of this again, but with a focus on international redemptions, since plenty of you are likely getting into this pursuit to take deluxe vacations to other countries.